Home Aldehydes 90141-22-3
90141-22-3,MFCD00017352
Catalog No.:AA00GTY9

90141-22-3 | [2,2'-Binaphthalene]-8,8'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)-

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00GTY9
Chemical Name:
[2,2'-Binaphthalene]-8,8'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)-
CAS Number:
90141-22-3
Molecular Formula:
C30H30O8
Molecular Weight:
518.5544
MDL Number:
MFCD00017352
SMILES:
CC1=C(C(=C2C(=C1)C(=C(C(=C2C=O)O)O)C(C)C)O)C3=C(C=C4C(=C3O)C(=C(C(=C4C(C)C)O)O)C=O)C
Properties
Computed Properties
 
Complexity:
780  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
38  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
5  
XLogP3:
6.9  

Literature

Title: Synthesis and biological evaluation of water-soluble derivatives of chiral gossypol as HIV fusion inhibitors targeting gp41.

Journal: Bioorganic & medicinal chemistry letters 20180101

Title: Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships.

Journal: Chemico-biological interactions 20150605

Title: Molecular screening of insecticides with sigma glutathione S-transferases (GST) in cotton aphid Aphis gossypii using docking.

Journal: Bioinformation 20140101

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: Stability and antioxidant activity of gossypol derivative immobilized on N-polyvinylpyrrolidone.

Journal: International journal of biological macromolecules 20121201

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Gossypol-enhanced P450 gene pool contributes to cotton bollworm tolerance to a pyrethroid insecticide.

Journal: Molecular ecology 20120901

Title: Alleviation of reproductive toxicity of gossypol using selenium supplementation in rams.

Journal: Journal of animal science 20120901

Title: Action of db-cAMP on the bystander effect and chemosensitivity through connexin 43 and Bcl-2-mediated pathways in medulloblastoma cells.

Journal: Oncology reports 20120901

Title: Effects of different sources and levels of dietary gossypol on gossypol residues in plasma and milk of lactating cows.

Journal: Journal of dairy science 20120901

Title: Insect P450s: mounted for battle in their war against toxins.

Journal: Molecular ecology 20120901

Title: The role of COX-2/PGE2 in gossypol-induced apoptosis of colorectal carcinoma cells.

Journal: Journal of cellular physiology 20120801

Title: Structure-based design of rhodanine-based acylsulfonamide derivatives as antagonists of the anti-apoptotic Bcl-2 protein.

Journal: Bioorganic & medicinal chemistry 20120715

Title: Randomized phase II trial of docetaxel plus prednisone in combination with placebo or AT-101, an oral small molecule Bcl-2 family antagonist, as first-line therapy for metastatic castration-resistant prostate cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20120701

Title: Pretreatment with AT-101 enhances tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis of breast cancer cells by inducing death receptors 4 and 5 protein levels.

Journal: Journal of cancer research and clinical oncology 20120701

Title: A validated HPLC assay for the determination of R-(-)-gossypol in human plasma and its application in clinical pharmacokinetic studies.

Journal: Journal of pharmaceutical and biomedical analysis 20120701

Title: Sabutoclax, a Mcl-1 antagonist, inhibits tumorigenesis in transgenic mouse and human xenograft models of prostate cancer.

Journal: Neoplasia (New York, N.Y.) 20120701

Title: Mcl-1 Phosphorylation defines ABT-737 resistance that can be overcome by increased NOXA expression in leukemic B cells.

Journal: Cancer research 20120615

Title: Amino acid derivatives of the (-) enantiomer of gossypol are effective fusion inhibitors of human immunodeficiency virus type 1.

Journal: Antiviral research 20120601

Title: Enhanced delivery of mda-7/IL-24 using a serotype chimeric adenovirus (Ad.5/3) in combination with the Apogossypol derivative BI-97C1 (Sabutoclax) improves therapeutic efficacy in low CAR colorectal cancer cells.

Journal: Journal of cellular physiology 20120501

Title: Gossypol exhibits a strong influence towards UDP-glucuronosyltransferase (UGT) 1A1, 1A9 and 2B7-mediated metabolism of xenobiotics and endogenous substances.

Journal: Molecules (Basel, Switzerland) 20120427

Title: [Effects of gossypol acetate on apoptosis in primary cultured cells from patients with lymphoid leukemia and its synergy with dexamethasone].

Journal: Zhongguo shi yan xue ye xue za zhi 20120401

Title: Inhibitory effects of gossypol, gossypolone, and apogossypolone on a collection of economically important filamentous fungi.

Journal: Journal of agricultural and food chemistry 20120314

Title: Hemigossypol, a constituent in developing glanded cottonseed (Gossypium hirsutum).

Journal: Journal of agricultural and food chemistry 20120314

Title: Evaluating the value of number of cycles of docetaxel and prednisone in men with metastatic castration-resistant prostate cancer.

Journal: European urology 20120201

Title: Re: Gregory R. Pond, Andrew J. Armstrong, Brian A. Wood, et al. Evaluating the value of number of cycles of docetaxel and prednisone in men with metastatic castration-resistant prostate cancer. Eur Urol 2012;61:363-9.

Journal: European urology 20120201

Title: Vibrational spectra, structure and antioxidant activity of gossypol imine derivatives.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120201

Title: Dietary intake of cottonseed toxins is hypothesized to be a partial cause of Alzheimer's disorder.

Journal: Medical hypotheses 20120201

Title: Metronomic dosing of BH3 mimetic small molecule yields robust antiangiogenic and antitumor effects.

Journal: Cancer research 20120201

Title: Sorafenib sensitizes (-)-gossypol-induced growth suppression in androgen-independent prostate cancer cells via Mcl-1 inhibition and Bak activation.

Journal: Molecular cancer therapeutics 20120201

Title: Synthesis and antiviral activities of novel gossypol derivatives.

Journal: Bioorganic & medicinal chemistry letters 20120201

Title: Proapoptotic protein Smac mediates apoptosis in cisplatin-resistant ovarian cancer cells when treated with the anti-tumor agent AT101.

Journal: The Journal of biological chemistry 20120102

Title: Bcl-2 inhibitors: emerging drugs in cancer therapy.

Journal: Current medicinal chemistry 20120101

Title: Involvement of Smac, p53, and caspase pathways in induction of apoptosis by gossypol in human retinoblastoma cells.

Journal: Molecular vision 20120101

Title: Small molecule inhibition of the steroid receptor coactivators, SRC-3 and SRC-1.

Journal: Molecular endocrinology (Baltimore, Md.) 20111201

Title: Novel O-glycosidic gossypol isomers and their bioactivities.

Journal: Carbohydrate research 20111018

Title: Valproic acid synergistically enhances the cytotoxicity of gossypol in DU145 prostate cancer cells: an iTRTAQ-based quantitative proteomic analysis.

Journal: Journal of proteomics 20110906

Title: In vitro and in vivo studies on antitumor effects of gossypol on human stomach adenocarcinoma (AGS) cell line and MNNG induced experimental gastric cancer.

Journal: Biochemical and biophysical research communications 20110812

Title: Environmental inhibitors of 11β-hydroxysteroid dehydrogenase type 2.

Journal: Toxicology 20110729

Title: Quercetin downregulates Mcl-1 by acting on mRNA stability and protein degradation.

Journal: British journal of cancer 20110712

Title: Cotton plants expressing CYP6AE14 double-stranded RNA show enhanced resistance to bollworms.

Journal: Transgenic research 20110601

Title: Drug synergistic antifertility effect of combined administration of low-dose gossypol with steroid hormones in rats.

Journal: Chinese medical journal 20110601

Title: [Gossypol acetic acid induces DNA double-strand breaks in human mucoepidermoid carcinoma cell MEC-1].

Journal: Sheng li xue bao : [Acta physiologica Sinica] 20110425

Title: Gossypol decreases tumor necrosis factor-α-induced intercellular adhesion molecule-1 expression via suppression of NF-κB activity.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110401

Title: Double-blind, placebo-controlled, randomized phase 2 study of the proapoptotic agent AT-101 plus docetaxel, in second-line non-small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110401

Title: Inhibitory effects of gossypol-related compounds on growth of Aspergillus flavus.

Journal: Letters in applied microbiology 20110401

Title: Mechanisms of drug sensitization to TRA-8, an agonistic death receptor 5 antibody, involve modulation of the intrinsic apoptotic pathway in human breast cancer cells.

Journal: Molecular cancer research : MCR 20110401

Title: Discovery of N-hydroxyindole-based inhibitors of human lactate dehydrogenase isoform A (LDH-A) as starvation agents against cancer cells.

Journal: Journal of medicinal chemistry 20110324

Title: Mirabamides E-H, HIV-inhibitory depsipeptides from the sponge Stelletta clavosa.

Journal: Journal of natural products 20110225

Title: Evidence for a trianion intermediate in the metalation of 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid. Methodology and application to racemic 5,5'-didesisopropyl-5,5'-dialkylapogossypol derivatives.

Journal: The Journal of organic chemistry 20110121

Title: Apogossypolone targets mitochondria and light enhances its anticancer activity by stimulating generation of singlet oxygen and reactive oxygen species.

Journal: Chinese journal of cancer 20110101

Title: Fitness cost of resistance to Bt cotton linked with increased gossypol content in pink bollworm larvae.

Journal: PloS one 20110101

Title: Suppression of jasmonic acid-dependent defense in cotton plant by the mealybug Phenacoccus solenopsis.

Journal: PloS one 20110101

Title: Transcriptional responses underlying the hormetic and detrimental effects of the plant secondary metabolite gossypol on the generalist herbivore Helicoverpa armigera.

Journal: BMC genomics 20110101

Title: The influence of protonation on molecular structure and physico-chemical properties of gossypol Schiff bases.

Journal: Organic & biomolecular chemistry 20101221

Title: Spermatotoxicity, biochemical changes and histological alteration induced by gossypol in testicular and hepatic tissues of male rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20101201

Title: Effects of combined administration of low-dose gossypol with steroid hormones on the mitotic phase of spermatogenesis of rat.

Journal: Journal of experimental zoology. Part A, Ecological genetics and physiology 20101201

Title: Expression of anti-apoptosis genes determines the response of adrenal cancer to apoptosis-inducing chemotherapy.

Journal: Anticancer research 20101201

Title: Aromatase expression in leptin-pretreated human breast pre-adipocytes is enhanced by zeranol and suppressed by (-)-gossypol.

Journal: Anticancer research 20101201

Title: Synthesis and biological evaluation of Apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins.

Journal: Journal of medicinal chemistry 20101125

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Gossypol inhibits phosphorylation of Bcl-2 in human leukemia HL-60 cells.

Journal: European journal of pharmacology 20101025

Title: Toward the development of innovative bifunctional agents to induce differentiation and to promote apoptosis in leukemia: clinical candidates and perspectives.

Journal: Journal of medicinal chemistry 20101014

Title: Phase I/II study of AT-101 with topotecan in relapsed and refractory small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20101001

Title: Comparison of XTT and Alamar blue assays in the assessment of the viability of various human cancer cell lines by AT-101 (-/- gossypol).

Journal: Toxicology mechanisms and methods 20101001

Title: Spermatotoxicity of a protein isolated from the root of Achyranthes aspera: a comparative study with gossypol.

Journal: Contraception 20101001

Title: Combining cytotoxic and targeted therapies for lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20101001

Title: Apogossypolone, a novel inhibitor of antiapoptotic Bcl-2 family proteins, induces autophagy of PC-3 and LNCaP prostate cancer cells in vitro.

Journal: Asian journal of andrology 20100901

Title: Effects of silymarin on gossypol toxicosis in divergent lines of chickens.

Journal: Poultry science 20100901

Title: The Bcl-2 homology domain 3 mimetic gossypol induces both Beclin 1-dependent and Beclin 1-independent cytoprotective autophagy in cancer cells.

Journal: The Journal of biological chemistry 20100813

Title: A novel water-soluble gossypol derivative increases chemotherapeutic sensitivity and promotes growth inhibition in colon cancer.

Journal: Journal of medicinal chemistry 20100812

Title: Modulation of apoptosis by natural products for cancer therapy.

Journal: Planta medica 20100801

Title: AT-101 (R-(-)-gossypol acetic acid) enhances the effectiveness of androgen deprivation therapy in the VCaP prostate cancer model.

Journal: Journal of cellular biochemistry 20100801

Title: [Effect of testosterone on the expression of CMTM family of the male spermatogenesis suppression rats].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20100801

Title: The pan-Bcl-2 inhibitor (-)-gossypol triggers autophagic cell death in malignant glioma.

Journal: Molecular cancer research : MCR 20100701

Title: Gossypol exerts its cytotoxic effect on HL-60 leukemic cell line via decreasing activity of protein phosphatase 2A and interacting with human telomerase reverse transcriptase activity.

Journal: Hematology (Amsterdam, Netherlands) 20100601

Title: BI-97C1, an optically pure Apogossypol derivative as pan-active inhibitor of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins.

Journal: Journal of medicinal chemistry 20100527

Title: BH3 response profiles from neuroblastoma mitochondria predict activity of small molecule Bcl-2 family antagonists.

Journal: Cell death and differentiation 20100501

Title: Inhibition of proliferation of prostate cancer cell line, PC-3, in vitro and in vivo using (-)-gossypol.

Journal: Asian journal of andrology 20100501

Title: AT-101, a pan-Bcl-2 inhibitor, leads to radiosensitization of non-small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20100501

Title: Preclinical studies of apogossypolone, a novel pan inhibitor of bcl-2 and mcl-1, synergistically potentiates cytotoxic effect of gemcitabine in pancreatic cancer cells.

Journal: Pancreas 20100401

Title: Overcoming drug resistance in hormone- and drug-refractory prostate cancer cell line, PC-3 by docetaxel and gossypol combination.

Journal: Molecular biology reports 20100301

Title: Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20100202

Title: Inhibition of calcineurin by quercetin in vitro and in Jurkat cells.

Journal: Journal of biochemistry 20100201

Title: (-)-Gossypol containing hen sera and a myosin (-)-gossypol conjugate reduces the proliferation of MCF-7 cells.

Journal: Anticancer research 20100201

Title: Temperature control of spermatogenesis and prospect of male contraception.

Journal: Frontiers in bioscience (Scholar edition) 20100101

Title: [Synthesis, structures, and acute toxicity of gossypol nonsymmetrical aldehyde derivatives].

Journal: Bioorganicheskaia khimiia 20100101

Title: The effect of racemic gossypol and at-101 on angiogenic profile of ovcar-3 cells: a preliminary molecular framework for gossypol enantiomers.

Journal: Experimental oncology 20091201

Title: [Apoptosis of multiple myeloma cells induced by gossypol acetic acid in vitro and its mechanism].

Journal: Zhongguo shi yan xue ye xue za zhi 20091201

Title: Mutual anti-oxidative effect of gossypol acetic acid and gossypol-iron complex on hepatic lipid peroxidation in male rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20091101

Title: Targeting apoptosis in the hormone- and drug-resistant prostate cancer cell line, DU-145, by gossypol/zoledronic acid combination.

Journal: Cell biology international 20091101

Title: Mitogenic activity of zeranol in human breast cancer cells is enhanced by leptin and suppressed by gossypol.

Journal: Anticancer research 20091101

Title: Structure-activity relationship and molecular mechanisms of ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4h-chromene-3-carboxylate (sha 14-1) and its analogues.

Journal: Journal of medicinal chemistry 20091008

Title: [Effect of gossypol acetate on proliferation and apoptosis in Raji lymphoblastoid cell line].

Journal: Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae 20091001

Title: Combined gossypol and zoledronic acid treatment results in synergistic induction of cell death and regulates angiogenic molecules in ovarian cancer cells.

Journal: European cytokine network 20090901

Title: Mcl1 downregulation sensitizes neuroblastoma to cytotoxic chemotherapy and small molecule Bcl2-family antagonists.

Journal: Cancer biology & therapy 20090801

Title: The immobilization of gossypol derivative on N-polyvinylpyrrolidone increases its water solubility and modifies membrane-active properties.

Journal: Journal of medicinal chemistry 20090723

Title: Gossypol, a polyphenolic aldehyde from cotton plant, interferes with swine granulosa cell function.

Journal: Domestic animal endocrinology 20090701

Title: Endofacial competitive inhibition of the glucose transporter 1 activity by gossypol.

Journal: American journal of physiology. Cell physiology 20090701

Title: Efficacy of signal pathway inhibitors alone and in combination with Cisplatin varies between human non-small cell lung cancer lines.

Journal: The Journal of surgical research 20090601

Title: Gossypol induced apoptosis of polymorphonuclear leukocytes and monocytes: involvement of mitochondrial pathway and reactive oxygen species.

Journal: Immunopharmacology and immunotoxicology 20090601

Title: Spermatotoxic effects of Cananga odorata (Lam): a comparison with gossypol.

Journal: Fertility and sterility 20090501

Title: The immunosuppressive effect of gossypol in mice is mediated by inhibition of lymphocyte proliferation and by induction of cell apoptosis.

Journal: Acta pharmacologica Sinica 20090501

Title: An open-label, multicenter, phase I/II study of single-agent AT-101 in men with castrate-resistant prostate cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090501

Title: Antifungal activity of alkyl and heterocyclic aza-derivatives of gossypol as well as their complexes with NaClO4 against Fusarium oxysporum f. sp. lupini.

Journal: Bioorganic & medicinal chemistry letters 20090401

Title: Design and synthesis of a gossypol derivative with improved antitumor activities.

Journal: Archiv der Pharmazie 20090401

Title: Bcl-2 inhibitors: targeting mitochondrial apoptotic pathways in cancer therapy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090215

Title: The (+)- and (-)-gossypols potently inhibit human and rat 11beta-hydroxysteroid dehydrogenase type 2.

Journal: The Journal of steroid biochemistry and molecular biology 20090201

Title: Total and percent atropisomers of gossypol and gossypol-6-methyl ether in seeds from pima cottons and accessions of Gossypium barbadense L.

Journal: Journal of agricultural and food chemistry 20090128

Title: Non-peptidic small molecule inhibitors against Bcl-2 for cancer therapy.

Journal: Journal of cellular physiology 20090101

Title: AT-101 induces apoptosis in CLL B cells and overcomes stromal cell-mediated Mcl-1 induction and drug resistance.

Journal: Blood 20090101

Title: ApoG2 induces cell cycle arrest of nasopharyngeal carcinoma cells by suppressing the c-Myc signaling pathway.

Journal: Journal of translational medicine 20090101

Title: Enhancement of taxane-induced cytotoxicity and apoptosis by gossypol in human breast cancer cell line MCF-7.

Journal: Journal of B.U.ON. : official journal of the Balkan Union of Oncology 20090101

Title: AT-101, a small molecule inhibitor of anti-apoptotic Bcl-2 family members, activates the SAPK/JNK pathway and enhances radiation-induced apoptosis.

Journal: Radiation oncology (London, England) 20090101

Title: Cinnamyl-3,4-dihydroxy-alpha-cyanocinnamate and nordihydroguaiaretic acid inhibit human Kv1.5 currents independently of lipoxygenase.

Journal: European journal of pharmacology 20081214

Title: Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein.

Journal: Phytochemistry 20081201

Title: Synergistic antitumoral activity and induction of apoptosis by novel pan Bcl-2 proteins inhibitor apogossypolone with adriamycin in human hepatocellular carcinoma.

Journal: Acta pharmacologica Sinica 20081201

Title: Interaction of kendomycin and semi-synthetic analogues with the anti-apoptotic protein Bcl-xl.

Journal: Bioorganic & medicinal chemistry letters 20081101

Title: Bcl-2 family members as molecular targets in cancer therapy.

Journal: Biochemical pharmacology 20081015

Title: Effect of racemic, (+)- and (-)-gossypol on survival and development of Heliothis virescens larvae.

Journal: Environmental entomology 20081001

Title: Gossypol, a BH3 mimetic, induces apoptosis in chronic lymphocytic leukemia cells.

Journal: Blood 20080901

Title: Gossypol affects ion transport in the isolated intestine of the seawater adapted eel, Anguilla anguilla.

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20080901

Title: Gossypol disrupts embryo development in heifers.

Journal: Journal of dairy science 20080801

Title: [Determination of gossypol in feeds by HPLC].

Journal: Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20080801

Title: Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.

Journal: Journal of medicinal chemistry 20080724

Title: Energy metabolism transition in multi-cellular human tumor spheroids.

Journal: Journal of cellular physiology 20080701

Title: Cytotoxic and antibacterial sesquiterpenes from Thespesia populnea.

Journal: Journal of natural products 20080701

Title: Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa.

Journal: Molecular cancer therapeutics 20080701

Title: [Progress in small-molecule inhibitors of Bcl-2 family proteins].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20080701

Title: Targeting Bcl-2 family members with the BH3 mimetic AT-101 markedly enhances the therapeutic effects of chemotherapeutic agents in in vitro and in vivo models of B-cell lymphoma.

Journal: Blood 20080601

Title: New targets for lymphoma treatment.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20080601

Title: Reproductive toxicologic effects of gossypol on male rabbits: biochemical, enzymatic, and electrolytic properties of seminal plasma.

Journal: Fertility and sterility 20080501

Title: R-(-)-gossypol (AT-101) activates programmed cell death in multiple myeloma cells.

Journal: Experimental hematology 20080501

Title: Anti-oxidant treatment enhances anti-tumor cytotoxicity of (-)-gossypol.

Journal: Cancer biology & therapy 20080501

Title: HPLC preparation of the chiral forms of 6-methoxy-gossypol and 6,6'-dimethoxy-gossypol.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080501

Title: Acylpyrogallols as inhibitors of antiapoptotic Bcl-2 proteins.

Journal: Journal of medicinal chemistry 20080227

Title: Rat testicular germ cell type(s) targeted by anti-spermatogenic agents in vivo and their recovery on withdrawal of treatment--a flow cytometric study.

Journal: Animal reproduction science 20080115

Title: Comparison of pharmacokinetic and metabolic profiling among gossypol, apogossypol and apogossypol hexaacetate.

Journal: Cancer chemotherapy and pharmacology 20080101

Title: Synergistic cytotoxicity of Bcl-xL inhibitor, gossypol and chemotherapeutic agents in non-Hodgkin's lymphoma cells.

Journal: Cancer biology & therapy 20080101

Title: Inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.

Journal: Current medicinal chemistry 20080101

Title: Preclinical studies of Apogossypolone: a new nonpeptidic pan small-molecule inhibitor of Bcl-2, Bcl-XL and Mcl-1 proteins in Follicular Small Cleaved Cell Lymphoma model.

Journal: Molecular cancer 20080101

Title: [Male antifertility drugs and cell apoptosis].

Journal: Zhonghua nan ke xue = National journal of andrology 20080101

Title: -(-)Gossypol promotes the apoptosis of bladder cancer cells in vitro.

Journal: Pharmacological research 20080101

Title: N-Nitrosodimethylamine changes the expression of glutathione S-transferase in the liver of male mice: The role of antioxidants.

Journal: Journal of biochemical and molecular toxicology 20080101

Title: The in vitro effect of gossypol and its interaction with salts on conidial germination and viability of Fusarium oxysporum sp. vasinfectum isolates.

Journal: Journal of applied microbiology 20071201

Title: In vivo evaluation of AT-101 (R-(-)-gossypol acetic acid) in androgen-independent growth of VCaP prostate cancer cells in combination with surgical castration.

Journal: Neoplasia (New York, N.Y.) 20071201

Title: Spermatoprotective activity of the leaf extract of Psidium guajava Linn.

Journal: The Nigerian postgraduate medical journal 20071201

Title: (-)Gossypol and its combination with imatinib induce apoptosis in human chronic myeloid leukemic cells.

Journal: Leukemia & lymphoma 20071101

Title: Silencing a cotton bollworm P450 monooxygenase gene by plant-mediated RNAi impairs larval tolerance of gossypol.

Journal: Nature biotechnology 20071101

Title: Gossypol reduction of tumor growth through ROS-dependent mitochondria pathway in human colorectal carcinoma cells.

Journal: International journal of cancer 20071015

Title: [The effect of gossypol, praziquantel and artemether on recombinant lactate dehydrogenase from Schistosoma japonicum].

Journal: Zhongguo ji sheng chong xue yu ji sheng chong bing za zhi = Chinese journal of parasitology & parasitic diseases 20071001

Title: Therapeutic window for melanoma treatment provided by selective effects of the proteasome on Bcl-2 proteins.

Journal: Cell death and differentiation 20070901

Title: Preparation of an edible cottonseed protein concentrate and evaluation of its functional properties.

Journal: International journal of food sciences and nutrition 20070901

Title: Design, synthesis, and biological evaluation of Plasmodium falciparum lactate dehydrogenase inhibitors.

Journal: Journal of medicinal chemistry 20070809

Title: The absence of expression of the three isoenzymes of the inositol 1,4,5-trisphosphate 3-kinase does not prevent the formation of inositol pentakisphosphate and hexakisphosphate in mouse embryonic fibroblasts.

Journal: Cellular signalling 20070701

Title: Determining larval host plant use by a polyphagous lepidopteran through analysis of adult moths for plant secondary metabolites.

Journal: Journal of chemical ecology 20070601

Title: Radiosensitization of tumour cell lines by the polyphenol Gossypol results from depressed double-strand break repair and not from enhanced apoptosis.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20070601

Title: Current status and future perspectives in male contraception.

Journal: Minerva ginecologica 20070601

Title: Engineering Escherichia coli for production of functionalized terpenoids using plant P450s.

Journal: Nature chemical biology 20070501

Title: Gossypol induces apoptosis in human PC-3 prostate cancer cells by modulating caspase-dependent and caspase-independent cell death pathways.

Journal: Life sciences 20070130

Title: Gossypol inhibits calcineurin phosphatase activity at multiple sites.

Journal: European journal of pharmacology 20070126

Title: Modulation of multidrug resistance gene expression in human breast cancer cells by (-)-gossypol-enriched cottonseed oil.

Journal: Anticancer research 20070101

Title: Gossypol with methyltestosterone and ethinylestradiol male does not affect rat spermatogonial stem cell differentiation.

Journal: Archives of andrology 20070101

Title: Plant secondary metabolites.

Journal: Methods in molecular biology (Clifton, N.J.) 20070101

Title: Bax activators potentiate coated-platelet formation.

Journal: Journal of thrombosis and haemostasis : JTH 20061201

Title: Quantitative determination of apogossypol, a pro-apoptotic analog of gossypol, in mouse plasma using LC/MS/MS.

Journal: Journal of pharmaceutical and biomedical analysis 20061116

Title: Structure-based design of potent small-molecule inhibitors of anti-apoptotic Bcl-2 proteins.

Journal: Journal of medicinal chemistry 20061019

Title: Multinuclear magnetic resonance, electrospray ionization-mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2-thiophenecarbohydrazide as well as its complexes with LI+, Na+, K+, RB+, and Cs+ cations.

Journal: Biopolymers 20061015

Title: Effect of selected fungi on the reduction of gossypol levels and nutritional value during solid substrate fermentation of cottonseed meal.

Journal: Journal of Zhejiang University. Science. B 20060901

Title: 1H- and 13C-NMR, FTIR, UV-VIS, ESI-MS, and PM5 studies as well as emission properties of a new Schiff base of gossypol with 5-methoxytryptamine and a new hydrazone of gossypol with dansylhydrazine.

Journal: Biopolymers 20060805

Title: American Society of Clinical Oncology--42nd annual meeting. Poster presentations on leukemia and cytotoxic chemotherapy. 2-6 June 2006, Atlanta, GA, USA.

Journal: IDrugs : the investigational drugs journal 20060801

Title: Molecular cloning and characterization of a novel lactate dehydrogenase gene from Clonorchis sinensis.

Journal: Parasitology research 20060601

Title: Embryo survival from gossypol-fed heifers after transfer to lactating cows treated with human chorionic gonadotropin.

Journal: Journal of dairy science 20060601

Title: Effect of racemic and (+)- and (-)-gossypol on the survival and development of Helicoverpa zea larvae.

Journal: Journal of chemical ecology 20060501

Title: Dissecting the behavior of a promiscuous solvate former.

Journal: Angewandte Chemie (International ed. in English) 20060320

Title: The peroxidative coupling of hemigossypol to (+)- and (-)-gossypol in cottonseed extracts.

Journal: Phytochemistry 20060201

Title: Effect of antispermatogenic agents on cell marker enzymes of rat Sertoli cells in vitro.

Journal: Contraception 20060101

Title: Proteinaceous diet inhibits gossypol-induced spermatotoxicity.

Journal: European journal of histochemistry : EJH 20060101

Title: Epididymis-specific pathologic disorders in rats exposed to gossypol from weaning through puberty.

Journal: Toxicologic pathology 20060101

Title: Nonpeptidic small-molecule inhibitor of Bcl-2 and Bcl-XL, (-)-Gossypol, enhances biological effect of genistein against BxPC-3 human pancreatic cancer cell line.

Journal: Pancreas 20051101

Title: A fluorescence-based coupling reaction for monitoring the activity of recombinant human NAD synthetase.

Journal: Assay and drug development technologies 20051001

Title: Relative toxicity of gossypol enantiomers in broilers.

Journal: Poultry science 20050901

Title: Mapping the binding site for gossypol-like inhibitors of Plasmodium falciparum lactate dehydrogenase.

Journal: Molecular and biochemical parasitology 20050801

Title: Development of competitive direct ELISA for gossypol analysis.

Journal: Journal of agricultural and food chemistry 20050713

Title: Synthesis of gossypol atropisomers and derivatives and evaluation of their anti-proliferative and anti-oxidant activity.

Journal: Bioorganic & medicinal chemistry 20050701

Title: Reversal of cisplatin resistance with a BH3 mimetic, (-)-gossypol, in head and neck cancer cells: role of wild-type p53 and Bcl-xL.

Journal: Molecular cancer therapeutics 20050701

Title: Schiff bases of gossypol: an NMR and DFT study.

Journal: Magnetic resonance in chemistry : MRC 20050401

Title: Study on structure and characterization of inclusion complex of gossypol/beta cyclodextrin.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20050401

Title: Nutrient content of whole cottonseed.

Journal: Journal of dairy science 20050401

Title: Reversal of a full-length mutant huntingtin neuronal cell phenotype by chemical inhibitors of polyglutamine-mediated aggregation.

Journal: BMC neuroscience 20050101

Title: Preclinical studies of a nonpeptidic small-molecule inhibitor of Bcl-2 and Bcl-X(L) [(-)-gossypol] against diffuse large cell lymphoma.

Journal: Molecular cancer therapeutics 20050101

Title: (-)-Gossypol acts directly on the mitochondria to overcome Bcl-2- and Bcl-X(L)-mediated apoptosis resistance.

Journal: Molecular cancer therapeutics 20050101

Title: Control of spermatogenesis in primate and prospect of male contraception.

Journal: Archives of andrology 20050101

Title: In vitro effects of the BH3 mimetic, (-)-gossypol, on head and neck squamous cell carcinoma cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041115

Title: [Determination of anti-nutrients in genetically modified crops].

Journal: Wei sheng yan jiu = Journal of hygiene research 20041101

Title: A combined regimen of gossypol plus methyltestosterone and ethinylestradiol as a contraceptive induces germ cell apoptosis and expression of its related genes in rats.

Journal: Contraception 20041001

Title: Determination of gossypol enantiomer ratio in cotton plants by chiral higher-performance liquid chromatography.

Journal: Journal of agricultural and food chemistry 20040922

Title: An alpha-proteobacterial type malate dehydrogenase may complement LDH function in Plasmodium falciparum. Cloning and biochemical characterization of the enzyme.

Journal: European journal of biochemistry 20040901

Title: Combined administration of low-dose gossypol acetic acid with desogestrel/mini-dose ethinylestradiol/testosterone undecanoate as an oral contraceptive for men.

Journal: Contraception 20040901

Title: Involvement of reactive oxygen species-independent mitochondrial pathway in gossypol-induced apoptosis.

Journal: Archives of biochemistry and biophysics 20040815

Title: Identification of Babesia bovis L-lactate dehydrogenase as a potential chemotherapeutical target against bovine babesiosis.

Journal: Molecular and biochemical parasitology 20040801

Title: The schiff base of gossypol with 3,6,9,12,15,18,21,24-octaoxa-pentacosylamine complexes and monovalent cations studied by electrospray ionization-mass spectrometry, (1)H nuclear magnetic resonance, Fourier transform infrared, as well as PM5 semiempirical methods.

Journal: Biopolymers 20040701

Title: Cytotoxicity of enantiomers of gossypol Schiff's bases and optical stability of gossypolone.

Journal: European journal of medicinal chemistry 20040701

Title: Sertoli cell junctional proteins as early targets for different classes of reproductive toxicants.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20040501

Title: Characterization of GaWRKY1, a cotton transcription factor that regulates the sesquiterpene synthase gene (+)-delta-cadinene synthase-A.

Journal: Plant physiology 20040501

Title: Effects of cottonseed cake-based diets supplemented with blood meal, alone or with lysine, on the growth of pigs.

Journal: Tropical animal health and production 20040501

Title: An evaluation of the use of cottonseed cake in the diet of growing pigs.

Journal: Tropical animal health and production 20040401

Title: Schiff base of gossypol with 3,6,9-trioxa-decylamine complexes with monovalent cations studied by mass spectrometry, (1)H-NMR, FTIR, and PM5 semiempirical methods.

Journal: Biopolymers 20040301

Title: An optimized gossypol high-performance liquid chromatography assay and its application in evaluation of different gland genotypes of cotton.

Journal: Journal of biosciences 20040301

Title: Monoclonal antibodies for the analysis of gossypol in cottonseed products.

Journal: Journal of agricultural and food chemistry 20040225

Title: Effect of gossypol in association with chromium protoporphyrin on heme metabolic enzymes.

Journal: Artificial cells, blood substitutes, and immobilization biotechnology 20040201

Title: Trypanocidal constituents in plants 3. Leaves of Garcinia intermedia and heartwood of Calophyllum brasiliense.

Journal: Biological & pharmaceutical bulletin 20040101

Title: Apoptosis and nitric oxide release induced by thalidomide, gossypol and dexamethasone in cultured human chronic myelogenous leukemic K-562 cells.

Journal: Cell biology international 20040101

Title: The inhibitory effects of gossypol on human prostate cancer cells-PC3 are associated with transforming growth factor beta1 (TGFbeta1) signal transduction pathway.

Journal: Anticancer research 20040101

Title: [Immunomodulating effect of the novel water-soluble gossypol derivative Mebavin in adjuvant arthritis].

Journal: Eksperimental'naia i klinicheskaia farmakologiia 20040101

Title: Mechanism of drug and toxic actions of gossypol: focus on reactive oxygen species and electron transfer.

Journal: Current medicinal chemistry 20031201

Title: Irradiation effects on embryotoxicity and oxidative properties of gossypol dissolved in methanol.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20031001

Title: Effect of gossypol on intracellular Ca2+ regulation in human hepatoma cells.

Journal: The Chinese journal of physiology 20030930

Title: Discovery, characterization, and structure-activity relationships studies of proapoptotic polyphenols targeting B-cell lymphocyte/leukemia-2 proteins.

Journal: Journal of medicinal chemistry 20030925

Title: 8-Hydroxy-(+)-delta-cadinene is a precursor to hemigossypol in Gossypium hirsutum.

Journal: Phytochemistry 20030901

Title: Aldose reductase inhibitors from the nature.

Journal: Current medicinal chemistry 20030801

Title: The gossypol-cyclododecanone (1/2) inclusion complex.

Journal: Acta crystallographica. Section C, Crystal structure communications 20030701

Title: Gossypol activates pancreatic polyamine catabolism in normal rats and induces acute pancreatitis in transgenic rats over-expressing spermidine/spermine N1-acetyltransferase.

Journal: Scandinavian journal of gastroenterology 20030701

Title: Preparation of enantiomeric gossypol by crystallization.

Journal: Chirality 20030601

Title: New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents.

Journal: Bioorganic & medicinal chemistry 20030501

Title: Effects of demethylzeylasteral and celastrol on spermatogenic cell Ca2+ channels and progesterone-induced sperm acrosome reaction.

Journal: European journal of pharmacology 20030307

Title: Novel pharmacophore-based methods reveal gossypol as a reverse transcriptase inhibitor.

Journal: Journal of molecular graphics & modelling 20030301

Title: Type of cottonseed and level of gossypol in diets of lactating dairy cows: plasma gossypol, health, and reproductive performance.

Journal: Journal of dairy science 20030301

Title: Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism.

Journal: Chirality 20030201

Title: Modulatory influence of tin-protoporphyrin on gossypol-induced alterations of heme oxygenase activity in male Wistar rats.

Journal: European journal of drug metabolism and pharmacokinetics 20030101

Title: [Anti-inflammatory activity of the novel water soluble gossipol derivative mebavine].

Journal: Eksperimental'naia i klinicheskaia farmakologiia 20030101

Title: Effects of immunosuppressants, calcineurin inhibition, and blockade of endoplasmic reticulum calcium channels on free fatty acid efflux from the ischemic/reperfused rat cerebral cortex.

Journal: Brain research 20021206

Title: Effects of gossypol from cottonseed on hematological responses and plasma alpha-tocopherol concentration of dairy cows.

Journal: Journal of dairy science 20021201

Title: Toxicity of (+)- and (-)-gossypol to the plant pathogen, Rhizoctonia solani.

Journal: Journal of agricultural and food chemistry 20021120

Title: Effects of gossypol from cottonseed meal and dietary vitamin E on the reproductive characteristics of superovulated beef heifers.

Journal: Journal of animal science 20020901

Title: Gossypol, a component in cottonseed, induced increases in cytosolic Ca2+ levels in Chang liver cells.

Journal: Toxicon : official journal of the International Society on Toxinology 20020701

Title: Regulation of cytokine mRNAs by interferon and interferon inducers.

Journal: Russian journal of immunology : RJI : official journal of Russian Society of Immunology 20020701

Title: Gossypol and gossypolone enantiomers in tissues of rainbow trout fed low and high levels of dietary cottonseed meal.

Journal: Journal of agricultural and food chemistry 20020508

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Fermentation of cottonseed and other feedstuffs in cattle rumen fluid.

Journal: Journal of agricultural and food chemistry 20020410

Title: Inhibition of T-type Ca(2+) currents in mouse spermatogenic cells by gossypol, an antifertility compound.

Journal: European journal of pharmacology 20020405

Title: [Determination of gossypol in cotton root bark by HPLC].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20020301

Title: Spectroscopic studies and PM3 semiempirical calculations of Schiff bases of gossypol with L-amino acid methyl esters.

Journal: Biopolymers 20020101

Title: Inhibition of 11beta-hydroxysteroid dehydrogenase in guinea pig kidney by three bioflavonoids and their interactions with gossypol.

Journal: Acta pharmacologica Sinica 20020101

Title: Postweaning exposure to gossypol results in epididymis-specific effects throughout puberty and adulthood in rats.

Journal: Journal of andrology 20020101

Title: The (-)-enantiomer of gossypol possesses higher anticancer potency than racemic gossypol in human breast cancer.

Journal: Anticancer research 20020101

Title: Effects of gossypol on O2 consumption and CO2 production in human prostate cancer cells.

Journal: Anticancer research 20020101

Title: [The effect of Kagocel on herpes virus reproduction].

Journal: Voprosy virusologii 20020101

Title: [Effect of interferon inductors on infection induced by hepatitis C virus and activity of mRNA cytokines in cell cultures SW-13 and MT-4].

Journal: Voprosy virusologii 20020101

Title: Reversible inhibition of calcineurin by the polyphenolic aldehyde gossypol.

Journal: The Journal of biological chemistry 20011221

Title: The kinetic properties and sensitivities to inhibitors of lactate dehydrogenases (LDH1 and LDH2) from Toxoplasma gondii: comparisons with pLDH from Plasmodium falciparum.

Journal: Molecular and biochemical parasitology 20011101

Title: Selective active site inhibitors of human lactate dehydrogenases A4, B4, and C4.

Journal: Biochemical pharmacology 20010701

Title: Tissue distribution of gossypol enantiomers in broilers fed various cottonseed meals.

Journal: Poultry science 20010701

Title: Reproductive efficiency and maternal-offspring transfer of gossypol in rainbow trout (Oncorhynchus mykiss) fed diets containing cottonseed meal.

Journal: Journal of animal science 20010601

Title: The performance of broiler chicks fed diets containing extruded cottonseed meal supplemented with lysine.

Journal: Poultry science 20010601

Title: Use of expander cottonseed meal in broiler diets formulated on a digestible amino acid basis.

Journal: Poultry science 20010601

Title: Oral gossypol in the treatment of patients with refractory metastatic breast cancer: a phase I/II clinical trial.

Journal: Breast cancer research and treatment 20010401

Title: Gossypol inhibits follicle-stimulating hormone- and epidermal growth factor-stimulated expansion of oocyte-cumulus complexes from porcine preovulatory follicles.

Journal: Physiological research 20010101

Title: Trypanocidal activity of 4 isopropyl salicylaldehyde and 4-isopropyl salicylic acid on Trypanosoma cruzi.

Journal: Revista latinoamericana de microbiologia 20010101

Title: Low dose gossypol for male contraception.

Journal: Asian journal of andrology 20001201

Title: Gossypol as a male antifertility agent--why studies should have been continued.

Journal: International journal of andrology 19980201

Title: Synthesis and anti-HIV activity of 1,1'-dideoxygossypol and related compounds.

Journal: Journal of medicinal chemistry 19950623

Title: Comparison of the antiviral activities of 3'-azido-3'-deoxythymidine (AZT) and gossylic iminolactone (GIL) against clinical isolates of HIV-1.

Journal: Pharmacological research 19950101

Title: Comparative in vitro study of contraceptive agents with anti-HIV activity: gramicidin, nonoxynol-9, and gossypol.

Journal: Contraception 19940201

Title: Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema.

Journal: British journal of pharmacology 19931201

Title: Anti-HIV-1 activity and cellular pharmacology of various analogs of gossypol.

Journal: Biochemical pharmacology 19930720

Title: Inhibition of human immunodeficiency virus type I replication by derivatives of gossypol.

Journal: Pharmacological research 19911201

Title: Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.

Journal: Journal of natural products 19910101

Title: Selective inhibition of human immunodeficiency virus type 1 replication by the (-) but not the (+) enantiomer of gossypol.

Journal: Antimicrobial agents and chemotherapy 19891201

Title: Inactivation of human immunodeficiency virus in vitro by gossypol.

Journal: Contraception 19890601

Title: Prolactin-dependent mitogenesis in Nb 2 node lymphoma cells: effects of immunosuppressive cyclopeptides.

Journal: Journal of immunology (Baltimore, Md. : 1950) 19870101

Title: Resolution of racemic gossypol and interaction of individual enantiomers with serum albumins and model peptides.

Journal: Biochimica et biophysica acta 19860619

Title: Monkey lactate dehydrogenase-C4 as a model for the interaction of enzymes with gossypol.

Journal: Contraception 19860601

Title: Screening for new compounds with antiherpes activity.

Journal: Antiviral research 19841001

Title: Oliver CL, et al. In vitro effects of the BH3 mimetic, (-)-Gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res. 2004 Nov 15;10(22):7757-63.

Title: Sun Y, et al. Apogossypolone, a nonpeptidic small molecule inhibitor targeting Bcl-2 family proteins, effectively inhibits growth of diffuse large cell lymphoma cells in vitro and in vivo. Cancer Biol Ther. 2008 Sep;7(9):1418-26.

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Tags:90141-22-3 Molecular Formula|90141-22-3 MDL|90141-22-3 SMILES|90141-22-3 [2,2'-Binaphthalene]-8,8'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)-