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5578-73-4,MFCD00012126
Catalog No.:AA0038KI

5578-73-4 | [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (1:1)

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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0038KI
Chemical Name:
[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (1:1)
CAS Number:
5578-73-4
Molecular Formula:
C20H14ClNO4
Molecular Weight:
367.7825
MDL Number:
MFCD00012126
SMILES:
C[n+]1cc2c3OCOc3ccc2c2c1c1cc3OCOc3cc1cc2.[Cl-]
Properties
Computed Properties
 
Complexity:
530  
Covalently-Bonded Unit Count:
2  
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
5  

Literature

Title: Improved apoptotic cell death in drug-resistant non-small-cell lung cancer cells by tumor necrosis factor-related apoptosis-inducing ligand-based treatment.

Journal: The Journal of pharmacology and experimental therapeutics 20140301

Title: NQO1 involves in the imine bond reduction of sanguinarine and recombinant adeno-associated virus mediated NQO1 overexpression decreases sanguinarine-induced cytotoxicity in rat BRL cells.

Journal: Toxicology letters 20140210

Title: Sanguinarine induces apoptosis in human colorectal cancer HCT-116 cells through ROS-mediated Egr-1 activation and mitochondrial dysfunction.

Journal: Toxicology letters 20130704

Title: Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells.

Journal: Phytochemistry 20130701

Title: Sanguinarine inhibits growth of human cervical cancer cells through the induction of apoptosis.

Journal: Oncology reports 20121201

Title: Antibacterial activity of substituted 5-methylbenzo[c]phenanthridinium derivatives.

Journal: Bioorganic & medicinal chemistry letters 20121201

Title: In vitro antifungal activity of sanguinarine and chelerythrine derivatives against phytopathogenic fungi.

Journal: Molecules (Basel, Switzerland) 20121102

Title: Luminescence and binding properties of two isoquinoline alkaloids chelerythrine and sanguinarine with ctDNA.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120901

Title: The anti-inflammatory effects of sanguinarine and its modulation of inflammatory mediators from peritoneal macrophages.

Journal: European journal of pharmacology 20120815

Title: Molecular basis for differential glycine transporters sensitivity to sanguinarine.

Journal: Toxicology letters 20120803

Title: Investigation of sanguinarine and chelerythrine effects on LPS-induced inflammatory gene expression in THP-1 cell line.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20120715

Title: Spectroscopic, molecular modeling, and NMR-spectroscopic investigation of the binding mode of the natural alkaloids berberine and sanguinarine to human telomeric G-quadruplex DNA.

Journal: ACS chemical biology 20120615

Title: Induction of heme oxygenase-1 by Macleaya cordata extract and its constituent sanguinarine in RAW264.7 cells.

Journal: Fitoterapia 20120301

Title: The sequential exposure to jasmonate, salicylic acid and yeast extract promotes sanguinarine accumulation in Argemone mexicana cell cultures.

Journal: Biotechnology letters 20120201

Title: Microinjection of sanguinarine into the ventrolateral orbital cortex inhibits Mkp-1 and exerts an antidepressant-like effect in rats.

Journal: Neuroscience letters 20120111

Title: Inhibition of Stat3 activation by sanguinarine suppresses prostate cancer cell growth and invasion.

Journal: The Prostate 20120101

Title: Antitumor effects of the benzophenanthridine alkaloid sanguinarine in a rat syngeneic model of colorectal cancer.

Journal: Anti-cancer drugs 20120101

Title: Sanguinarine induces apoptosis of HT-29 human colon cancer cells via the regulation of Bax/Bcl-2 ratio and caspase-9-dependent pathway.

Journal: International journal of toxicology 20120101

Title: Establishment of a sanguinarine-producing cell suspension culture of Argemone mexicana L (Papaveraceae): induction of alkaloid accumulation.

Journal: Methods in molecular biology (Clifton, N.J.) 20120101

Title: Binding of the anticancer alkaloid sanguinarine with tRNA(phe): spectroscopic and calorimetric studies.

Journal: Journal of biomolecular structure & dynamics 20120101

Title: Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: binding aspects and implications for drug design.

Journal: Medicinal research reviews 20111101

Title: Chiral HPLC studies on chemical behavior of 6-methoxydihydrosanguinarine in alcoholic solvent system.

Journal: Journal of pharmaceutical and biomedical analysis 20111101

Title: Sanguinarine is an allosteric activator of AMP-activated protein kinase.

Journal: Biochemical and biophysical research communications 20110923

Title: Embryonic toxicity of sanguinarine through apoptotic processes in mouse blastocysts.

Journal: Toxicology letters 20110910

Title: Evaluation of anticancer activities of benzo[c]phenanthridine alkaloid sanguinarine in oral squamous cell carcinoma cell line.

Journal: Anticancer research 20110901

Title: In vitro potentiation of ampicillin, oxacillin, norfloxacin, ciprofloxacin, and vancomycin by sanguinarine against methicillin-resistant Staphylococcus aureus.

Journal: Foodborne pathogens and disease 20110801

Title: The mechanism of action of sanguinarine against methicillin-resistant Staphylococcus aureus.

Journal: The Journal of toxicological sciences 20110601

Title: X-Ray diffraction analyses of the natural isoquinoline alkaloids Berberine and Sanguinarine complexed with double helix DNA d(CGTACG).

Journal: Chemical communications (Cambridge, England) 20110507

Title: Differential effect of the benzophenanthridine alkaloids sanguinarine and chelerythrine on glycine transporters.

Journal: Neurochemistry international 20110501

Title: Identification of benzo[c]phenanthridine metabolites in human hepatocytes by liquid chromatography with electrospray ion-trap and quadrupole time-of-flight mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110501

Title: Structural modification of sanguinarine and chelerythrine and their antibacterial activity.

Journal: Natural product research 20110501

Title: Interaction of berberine, palmatine, coralyne, and sanguinarine to quadruplex DNA: a comparative spectroscopic and calorimetric study.

Journal: Biochimica et biophysica acta 20110401

Title: In vitro and in vivo evaluation of sanguinarine liposomes prepared by a remote loading method with three different ammonium salts.

Journal: Die Pharmazie 20110401

Title: [Study on the alkaloids from the stem of Zanthoxylum dissitum].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110401

Title: Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana.

Journal: Archives of biochemistry and biophysics 20110301

Title: The actions of benzophenanthridine alkaloids, piperonyl butoxide and (S)-methoprene at the G-protein coupled cannabinoid CB₁ receptor in vitro.

Journal: European journal of pharmacology 20110301

Title: Inclusion complex formation of sanguinarine alkaloid with cucurbit[7]uril: inhibition of nucleophilic attack and photooxidation.

Journal: Organic & biomolecular chemistry 20110221

Title: [Study on liver injury of Oncomelania hupensis caused by Eomecon chinanthe sanguinarine].

Journal: Zhongguo xue xi chong bing fang zhi za zhi = Chinese journal of schistosomiasis control 20110201

Title: Human telomere d[(TTAGGG)4] undergoes a conformational transition to the Na+-form upon binding with sanguinarine in presence of K+.

Journal: Biochemical and biophysical research communications 20110107

Title: Interaction of the anticancer plant alkaloid sanguinarine with bovine serum albumin.

Journal: PloS one 20110101

Title: Potentiation of tumour promotion by topical application of argemone oil/isolated sanguinarine alkaloid in a model of mouse skin carcinogenesis.

Journal: Chemico-biological interactions 20101205

Title: Distinct G-quadruplex structures of human telomeric DNA formed by the induction of sanguinarine and nitidine under salt-deficient condition.

Journal: Fitoterapia 20101201

Title: Fluorescence of sanguinarine: spectral changes on interaction with amino acids.

Journal: Physical chemistry chemical physics : PCCP 20101007

Title: Effect of sanguinarine from the leaves of Macleaya cordata against Ichthyophthirius multifiliis in grass carp (Ctenopharyngodon idella).

Journal: Parasitology research 20101001

Title: In vitro growth-inhibitory effect of plant-derived extracts and compounds against Paenibacillus larvae and their acute oral toxicity to adult honey bees.

Journal: Veterinary microbiology 20100928

Title: Sanguinarine induces apoptosis of human osteosarcoma cells through the extrinsic and intrinsic pathways.

Journal: Biochemical and biophysical research communications 20100827

Title: Metabolism of sanguinarine in human and in rat: characterization of oxidative metabolites produced by human CYP1A1 and CYP1A2 and rat liver microsomes using liquid chromatography-tandem mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20100708

Title: Fusarium oxysporum homogenates and jasmonate induce limited sanguinarine accumulation in Argemone mexicana cell cultures.

Journal: Biotechnology letters 20100701

Title: Binding of the anticancer alkaloid sanguinarine to double stranded RNAs: insights into the structural and energetics aspects.

Journal: Molecular bioSystems 20100701

Title: Interaction of sanguinarine and its dihydroderivative with the Na+/K+-ATPase. Complex view on the old problem.

Journal: Toxicology letters 20100616

Title: Structure and mechanism of sanguinarine reductase, an enzyme of alkaloid detoxification.

Journal: The Journal of biological chemistry 20100611

Title: [Identification of differentially expressed proteins in the liver of Oncomelania snails induced by Eomecon chinanthe sanguinarine].

Journal: Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20100601

Title: Study on the inclusion interaction of cucurbit[n]urils with sanguinarine by spectrofluorimetry and its analytical application.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20100201

Title: Racemization of 6-methoxydihydrosanguinarine in methanol investigated by enantioselective dynamic HPLC.

Journal: Journal of pharmaceutical and biomedical analysis 20100105

Title: Skin tumor promotion by argemone oil/alkaloid in mice: evidence for enhanced cell proliferation, ornithine decarboxylase, cyclooxygenase-2 and activation of MAPK/NF-kappaB pathway.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100101

Title: The cytotoxic agents NSC-95397, brefeldin A, bortezomib and sanguinarine induce apoptosis in neuroendocrine tumors in vitro.

Journal: Anticancer research 20100101

Title: Sanguinarine as a potent and specific inhibitor of protein phosphatase 2C in vitro and induces apoptosis via phosphorylation of p38 in HL60 cells.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Involvement of lipoxygenase in elicitor-stimulated sanguinarine accumulation in Papaver somniferum suspension cultures.

Journal: Plant physiology and biochemistry : PPB 20100101

Title: Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.

Journal: BMC plant biology 20100101

Title: Inactivation of the Ecs ABC transporter of Staphylococcus aureus attenuates virulence by altering composition and function of bacterial wall.

Journal: PloS one 20100101

Title: A mutant of SWAP-70, a phosphatidylinositoltrisphosphate binding protein, transforms mouse embryo fibroblasts, which is inhibited by sanguinarine.

Journal: PloS one 20100101

Title: Antiproliferative and antiangiogenic effects of the benzophenanthridine alkaloid sanguinarine in melanoma.

Journal: Biochemical pharmacology 20091201

Title: Sanguinarine sensitizes human gastric adenocarcinoma AGS cells to TRAIL-mediated apoptosis via down-regulation of AKT and activation of caspase-3.

Journal: Anticancer research 20091101

Title: Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding.

Journal: Bioorganic & medicinal chemistry letters 20091001

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: Phenotype of hepatic xenobiotic metabolizing enzymes and CYP450 isoforms of sanguinarine treated rats: effect of P450 inducers on its toxicity.

Journal: Toxicology mechanisms and methods 20091001

Title: Antifungal activity of the benzo[c]phenanthridine alkaloids from Chelidonium majus Linn against resistant clinical yeast isolates.

Journal: Journal of ethnopharmacology 20090925

Title: Fluorescence of sanguinarine: fundamental characteristics and analysis of interconversion between various forms.

Journal: Analytical and bioanalytical chemistry 20090901

Title: Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20090601

Title: Anti-invasive activity of sanguinarine through modulation of tight junctions and matrix metalloproteinase activities in MDA-MB-231 human breast carcinoma cells.

Journal: Chemico-biological interactions 20090515

Title: Food contamination.

Journal: Disease-a-month : DM 20090501

Title: Effect of argemone oil and argemone alkaloid, sanguinarine on Sertoli-germ cell coculture.

Journal: Toxicology letters 20090425

Title: Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.

Journal: Journal of chromatography. A 20090313

Title: Sanguinarine induces apoptosis in A549 human lung cancer cells primarily via cellular glutathione depletion.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20090301

Title: Sanguinarine interacts with chromatin, modulates epigenetic modifications, and transcription in the context of chromatin.

Journal: Chemistry & biology 20090227

Title: Plant defense responses in opium poppy cell cultures revealed by liquid chromatography-tandem mass spectrometry proteomics.

Journal: Molecular & cellular proteomics : MCP 20090101

Title: Sanguinarine cytotoxicity on mouse melanoma K1735-M2 cells--nuclear vs. mitochondrial effects.

Journal: Biochemical pharmacology 20081201

Title: Natural feed additive of Macleaya cordata: safety assessment in rats a 90-day feeding experiment.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20081201

Title: Ligand binding to tandem G quadruplexes from human telomeric DNA.

Journal: Chembiochem : a European journal of chemical biology 20081103

Title: Induction of hepatotoxicity by sanguinarine is associated with oxidation of protein thiols and disturbance of mitochondrial respiration.

Journal: Journal of applied toxicology : JAT 20081101

Title: Site-specific binding of chelerythrine and sanguinarine to single pyrimidine bulges in hairpin DNA.

Journal: Analytical and bioanalytical chemistry 20081001

Title: Production of hydrogen peroxide and redox cycling can explain how sanguinarine and chelerythrine induce rapid apoptosis.

Journal: Archives of biochemistry and biophysics 20080901

Title: Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).

Journal: Journal of medicinal chemistry 20080612

Title: Sanguinarine-induced apoptosis: generation of ROS, down-regulation of Bcl-2, c-FLIP, and synergy with TRAIL.

Journal: Journal of cellular biochemistry 20080601

Title: Macleaya cordata extract and Sangrovit genotoxicity. Assessment in vivo.

Journal: Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia 20080601

Title: Separation of sanguinarine and chelerythrine in Macleaya cordata (Willd) R. Br. based on methyl acrylate-co-divinylbenzene macroporous adsorbents.

Journal: Journal of chromatography. A 20080523

Title: A decisive role of mitochondria in defining rate and intensity of apoptosis induction by different alkaloids.

Journal: Toxicology letters 20080401

Title: Histopathologic findings and diagnostic difficulties posed with use of escharotic agents for treatment of skin lesions: a case report and review of the literature.

Journal: Journal of cutaneous pathology 20080401

Title: Sanguinarine-induced G1-phase arrest of the cell cycle results from increased p27KIP1 expression mediated via activation of the Ras/ERK signaling pathway in vascular smooth muscle cells.

Journal: Archives of biochemistry and biophysics 20080315

Title: Sanguinarine causes DNA damage and p53-independent cell death in human colon cancer cell lines.

Journal: Chemico-biological interactions 20080310

Title: Apoptogenic activity of two benzophenanthridine alkaloids from Chelidonium majus L. does not correlate with their DNA damaging effects.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20080301

Title: Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells.

Journal: Cell biology international 20080201

Title: Conventional protein kinase C isoenzymes undergo dephosphorylation in neutrophil-like HL-60 cells treated by chelerythrine or sanguinarine.

Journal: Cell biology and toxicology 20080101

Title: Sanguinarine.

Journal: Cardiovascular therapeutics 20080101

Title: Sanguinarine-induced apoptosis in human leukemia U937 cells via Bcl-2 downregulation and caspase-3 activation.

Journal: Chemotherapy 20080101

Title: Sanguinarine, a benzophenanthridine alkaloid, induces apoptosis in MDA-MB-231 human breast carcinoma cells through a reactive oxygen species-mediated mitochondrial pathway.

Journal: Chemotherapy 20080101

Title: Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives.

Journal: Medicinal research reviews 20070901

Title: Specific binding and self-structure induction to poly(A) by the cytotoxic plant alkaloid sanguinarine.

Journal: Biochimica et biophysica acta 20070901

Title: Induction of apoptosis by sanguinarine in C6 rat glioblastoma cells is associated with the modulation of the Bcl-2 family and activation of caspases through downregulation of extracellular signal-regulated kinase and Akt.

Journal: Anti-cancer drugs 20070901

Title: Berberine suppresses inflammatory agents-induced interleukin-1beta and tumor necrosis factor-alpha productions via the inhibition of IkappaB degradation in human lung cells.

Journal: Pharmacological research 20070901

Title: The plant alkaloid sanguinarine is a potential inhibitor of follicular angiogenesis.

Journal: The Journal of reproduction and development 20070601

Title: Sanguinarine induces apoptosis of human pancreatic carcinoma AsPC-1 and BxPC-3 cells via modulations in Bcl-2 family proteins.

Journal: Cancer letters 20070508

Title: Disposition of sanguinarine in the rat.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20070501

Title: Sanguinarine-dependent induction of apoptosis in primary effusion lymphoma cells.

Journal: Cancer research 20070415

Title: Antiplatelet effect of sanguinarine is correlated to calcium mobilization, thromboxane and cAMP production.

Journal: Atherosclerosis 20070401

Title: Variability in the yield of benzophenanthridine alkaloids in wildcrafted vs cultivated bloodroot (Sanguinaria canadensis L.).

Journal: Journal of agricultural and food chemistry 20070221

Title: Metabolism of sanguinarine: the facts and the myths.

Journal: Current drug metabolism 20070201

Title: Aurintricarboxylic acid inhibits protein synthesis independent, sanguinarine-induced apoptosis and oncosis.

Journal: Toxicologic pathology 20070201

Title: Induction of necrosis and apoptosis to KB cancer cells by sanguinarine is associated with reactive oxygen species production and mitochondrial membrane depolarization.

Journal: Toxicology and applied pharmacology 20070115

Title: Sanguinarine inhibits VEGF-induced Akt phosphorylation.

Journal: Annals of the New York Academy of Sciences 20070101

Title: Sanguinarine inhibits VEGF-induced angiogenesis in a fibrin gel matrix.

Journal: BioFactors (Oxford, England) 20070101

Title: Protective effect of sanguinarine on ultraviolet B-mediated damages in SKH-1 hairless mouse skin: implications for prevention of skin cancer.

Journal: Photochemistry and photobiology 20070101

Title: Chelerythrine and sanguinarine dock at distinct sites on BclXL that are not the classic BH3 binding cleft.

Journal: Journal of molecular biology 20061201

Title: Protective effect of bioantioxidants on argemone oil/sanguinarine alkaloid induced genotoxicity in mice.

Journal: Cancer letters 20061128

Title: The effect of chelerythrine on cell growth, apoptosis, and cell cycle in human normal and cancer cells in comparison with sanguinarine.

Journal: Cell biology and toxicology 20061101

Title: The prokaryotic cytoskeleton: a putative target for inhibitors and antibiotics?

Journal: Applied microbiology and biotechnology 20061101

Title: Cytotoxicity of sanguinarine in primary rat hepatocytes is attenuated by dioxin and phenobarbital.

Journal: Toxicology letters 20060910

Title: Quaternary benzo[c]phenathridine alkaloids sanguinarine and chelerythrine do not affect transcriptional activity of aryl hydrocarbon receptor: analyses in rat hepatoma cell line H4IIE.luc.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060901

Title: DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine.

Journal: Bioorganic & medicinal chemistry 20060815

Title: Sanguinarine overcomes P-glycoprotein-mediated multidrug-resistance via induction of apoptosis and oncosis in CEM-VLB 1000 cells.

Journal: Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20060801

Title: Sanguinarine downregulates AT1a gene expression in a hypertensive rat model.

Journal: Journal of cardiovascular pharmacology 20060801

Title: Effects of sanguinarine and chelerythrine on the cell cycle and apoptosis.

Journal: Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia 20060701

Title: Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine.

Journal: Cancer letters 20060608

Title: The benzophenanthridine alkaloid sanguinarine perturbs microtubule assembly dynamics through tubulin binding. A possible mechanism for its antiproliferative activity.

Journal: The FEBS journal 20060501

Title: The plant alkaloid Sanguinarine affects swine granulosa cell activity.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20060401

Title: Cyclooxygenase 2 rescues LNCaP prostate cancer cells from sanguinarine-induced apoptosis by a mechanism involving inhibition of nitric oxide synthase activity.

Journal: Cancer research 20060401

Title: Investigation of sanguinarine and chelerythrine effects on CYP1A1 expression and activity in human hepatoma cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060201

Title: Enhancement of UVB radiation-mediated apoptosis by sanguinarine in HaCaT human immortalized keratinocytes.

Journal: Molecular cancer therapeutics 20060201

Title: Sanguinarine reductase, a key enzyme of benzophenanthridine detoxification.

Journal: Plant, cell & environment 20060201

Title: A liquid chromatographic-mass spectrometric evidence of dihydrosanguinarine as a first metabolite of sanguinarine transformation in rat.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060102

Title: Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine.

Journal: BMC cell biology 20060101

Title: Analysis of secondary metabolites from eschscholtzia californica by high-performance liquid chromatography.

Journal: Phytochemical analysis : PCA 20060101

Title: Rapid determination of protopine, allocryptopine, sanguinarine and chelerythrine in fruits of Macleaya cordata by microwave-assisted solvent extraction and HPLC-ESI/MS.

Journal: Phytochemical analysis : PCA 20060101

Title: Site-specific binding of chelerythrine to single cytosine and thymine bulges in DNA hairpins.

Journal: Nucleic acids symposium series (2004) 20060101

Title: Sanguinarine blocks cytokinesis in bacteria by inhibiting FtsZ assembly and bundling.

Journal: Biochemistry 20051220

Title: Correlation of DNA damage in epidemic dropsy patients to carcinogenic potential of argemone oil and isolated sanguinarine alkaloid in mice.

Journal: International journal of cancer 20051210

Title: Randomized controlled clinical trials on agents used for chemical plaque control.

Journal: International journal of dental hygiene 20051101

Title: Effects of the limited analyte solubility on its mobility and zone shape: electrophoretic behavior of sanguinarine and chelerythrine around pH 7.

Journal: Electrophoresis 20050901

Title: Sanguinarine activates polycyclic aromatic hydrocarbon associated metabolic pathways in human oral keratinocytes and tissues.

Journal: Toxicology letters 20050814

Title: Sanguinarine activates polycyclic aromatic hydrocarbon associated metabolic pathways in human oral keratinocytes and tissues.

Journal: Toxicology letters 20050728

Title: Effects of sanguinaria in fluoride-containing dentifrices on the remineralisation of subsurface carious lesion in vitro.

Journal: International dental journal 20050601

Title: Study of the inhibition of alpha-amylase by the benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine.

Journal: Journal of enzyme inhibition and medicinal chemistry 20050601

Title: The benzo[c]phenanthridine alkaloid, sanguinarine, is a selective, cell-active inhibitor of mitogen-activated protein kinase phosphatase-1.

Journal: The Journal of biological chemistry 20050513

Title: Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment.

Journal: Plant physiology 20050501

Title: Immunohistochemical assessment of Viadent-associated leukoplakia.

Journal: Oral oncology 20050201

Title: In vivo DNA damaging potential of sanguinarine alkaloid, isolated from argemone oil, using alkaline Comet assay in mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20050101

Title: Induction of contracture and extracellular Ca2+ influx in cardiac muscle by sanguinarine: a study on cardiotoxicity of sanguinarine.

Journal: Journal of biomedical science 20050101

Title: [Effect of alkaloid sanguinarine and a pharmaceutical preparation ukrain on modulation of vesicular membrane fusion and actin cytoskeleton of macrophages].

Journal: Tsitologiia 20050101

Title: Aggregation and other intermolecular interactions of biological buffers observed by capillary electrophoresis and UV photometry.

Journal: Journal of chromatography. A 20041008

Title: Sanguinarine: an evaluation of in vivo cytogenetic activity.

Journal: Mutation research 20040912

Title: Sanguinarine causes cell cycle blockade and apoptosis of human prostate carcinoma cells via modulation of cyclin kinase inhibitor-cyclin-cyclin-dependent kinase machinery.

Journal: Molecular cancer therapeutics 20040801

Title: Involvement of cytochrome P450 1A in sanguinarine detoxication.

Journal: Toxicology letters 20040715

Title: Chelerythrine and other benzophenanthridine alkaloids block the human P2X7 receptor.

Journal: British journal of pharmacology 20040701

Title: Capillary electrophoretic studies of acid-base properties of sanguinarine and chelerythrine alkaloids.

Journal: Journal of chromatography. A 20040618

Title: Suppression of angiogenesis by the plant alkaloid, sanguinarine.

Journal: Biochemical and biophysical research communications 20040430

Title: Hairy root induction of Papaver somniferum var. album, a difficult-to-transform plant, by A rhizogenes LBA 9402.

Journal: Planta 20040301

Title: Quantitative liquid chromatographic determination of sanguinarine in cell culture medium and in rat urine and plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040125

Title: Sanguinarine is a potent inhibitor of oxidative burst in DMSO-differentiated HL-60 cells by a non-redox mechanism.

Journal: Chemico-biological interactions 20040115

Title: Sanguinarine and chelerythrine: assessment of safety on pigs in ninety days feeding experiment.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040101

Title: Local anti-infective therapy: pharmacological agents. A systematic review.

Journal: Annals of periodontology 20031201

Title: Electrophoretic investigation of interactions of sanguinarine and chelerythrine with molecules containing mercapto group.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20031125

Title: Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy.

Journal: Phytochemistry 20030901

Title: Activation of prodeath Bcl-2 family proteins and mitochondrial apoptosis pathway by sanguinarine in immortalized human HaCaT keratinocytes.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20030801

Title: Sanguinarine-induced apoptosis is associated with an early and severe cellular glutathione depletion.

Journal: Cancer chemotherapy and pharmacology 20030601

Title: Spectroscopic and thermodynamic studies on the binding of sanguinarine and berberine to triple and double helical DNA and RNA structures.

Journal: Journal of biomolecular structure & dynamics 20030401

Title: In vitro effect of sanguinarine alkaloid on binding of [3H]candesartan to the human angiotensin AT1 receptor.

Journal: European journal of pharmacology 20030105

Title: Quaternary benzo[c]phenanthridine alkaloids as inhibitors of dipeptidyl peptidase IV-like activity baring enzymes in human blood plasma and glioma cell lines.

Journal: Physiological research 20030101

Title: Sensitivity of lysosomal enzymes to the plant alkaloid sanguinarine: comparison with other SH-specific agents.

Journal: Cell biology international 20030101

Title: Influence of DNA structures on the conversion of sanguinarine alkanolamine form to iminium form.

Journal: Journal of biomolecular structure & dynamics 20021201

Title: Inhibitory activity on binding of specific ligands to the human angiotensin II AT(1) and endothelin 1 ET(A) receptors: bioactive benzo[c]phenanthridine alkaloids from the root of Bocconia frutescens.

Journal: Planta medica 20020901

Title: DNA adduct formation from quaternary benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine as revealed by the 32P-postlabeling technique.

Journal: Chemico-biological interactions 20020815

Title: [Effect of a fungal elicitor on levels of sanguinarine and polyphenoloxidase activity in a suspension culture of Papaver somniferum L].

Journal: Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 20020701

Title: The alkaloid sanguinarine is effective against multidrug resistance in human cervical cells via bimodal cell death.

Journal: Biochemical pharmacology 20020415

Title: Interaction of sanguinarine with double stranded RNA structures.

Journal: Indian journal of biochemistry & biophysics 20020401

Title: Quaternary benzo[c]phenanthridine alkaloids as inhibitors of aminopeptidase N and dipeptidyl peptidase IV.

Journal: Phytotherapy research : PTR 20020201

Title: Antisense RNA-mediated suppression of benzophenanthridine alkaloid biosynthesis in transgenic cell cultures of California poppy.

Journal: Plant physiology 20020201

Title: [Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood].

Journal: Zhurnal evoliutsionnoi biokhimii i fiziologii 20020101

Title: The association between Viadent use and oral leukoplakia--results of a matched case-control study.

Journal: Journal of public health dentistry 20020101

Title: White patch of maxillary vestibule. Sanguinarine-associated leukoplakia.

Journal: General dentistry 20020101

Title: Cytotoxicity of natural compounds in hepatocyte cell culture models. The case of quaternary benzo[c]phenanthridine alkaloids.

Journal: Toxicology letters 20011215

Title: The association between Viadent use and oral leukoplakia.

Journal: Epidemiology (Cambridge, Mass.) 20011101

Title: Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant.

Journal: Planta 20011001

Title: Argemone mexicana and epidemic dropsy: phytopharmacology and putative sequelae and therapy.

Journal: The Journal of the Association of Physicians of India 20011001

Title: Bax, Bcl-2, and NF-kappaB expression in sanguinarine induced bimodal cell death.

Journal: Experimental and molecular pathology 20010801

Title: Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain.

Journal: Phytotherapy research : PTR 20010301

Title: Influence of natural and synthetic compounds on cell surface expression of cell adhesion molecules, ICAM-1 and VCAM-1.

Journal: Planta medica 20010301

Title: Sanguinarine induces K+ outflow from yeast cells expressing mammalian sodium pumps.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20010201

Title: Mechanisms underlying the induction of vasorelaxation in rat thoracic aorta by sanguinarine.

Journal: Japanese journal of pharmacology 20010101

Title: Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells.

Journal: Cell biology and toxicology 20010101

Title: Molecular aspects on the interaction of sanguinarine with B-form, Z-form and HL-form DNA structures.

Journal: Indian journal of biochemistry & biophysics 20010101

Title: Sanguinarine induces bimodal cell death in K562 but not in high Bcl-2-expressing JM1 cells.

Journal: Pathology, research and practice 20010101

Title: Role of Bcl-2 family proteins and caspase-3 in sanguinarine-induced bimodal cell death.

Journal: Cell biology and toxicology 20010101

Title: Sanguinaria-related leukoplakia: epidemiologic and clinicopathologic features of a recently described entity.

Journal: General dentistry 20010101

Title: Relationship between oral pain and ethanol concentration in mouthrinses.

Journal: Journal of periodontal research 19950501

Title: Wang Y, Noninvasive bioluminescence imaging of the dynamics of sanguinarine induced apoptosis via activation of reactive oxygen species. Oncotarget. 2016 Apr 19;7(16):22355-67.

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SDS
Tags:5578-73-4 Molecular Formula|5578-73-4 MDL|5578-73-4 SMILES|5578-73-4 [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (1:1)