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134404-52-7,MFCD00871599
Catalog No.:AA009CBY

134404-52-7 | Seocalcitol

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1mg
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  • Properties
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA009CBY
Chemical Name:
Seocalcitol
CAS Number:
134404-52-7
Molecular Formula:
C30H46O3
Molecular Weight:
454.6844
MDL Number:
MFCD00871599
SMILES:
CCC(/C=C/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C/1\C[C@@H](O)C[C@@H](C1=C)O)C)(CC)O
Properties
Computed Properties
 
Complexity:
812  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
4  
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
7  
XLogP3:
5.8  

Literature

Title: Motor neuron-like NSC-34 cells as a new model for the study of vitamin D metabolism in the brain.

Journal: The Journal of steroid biochemistry and molecular biology 20160401

Title: MNU-induced mammary gland carcinogenesis: chemopreventive and therapeutic effects of vitamin D and Seocalcitol on selected regulatory vitamin D receptor pathways.

Journal: Toxicology letters 20111110

Title: Vitamin D inhibits CEACAM1 to promote insulin/IGF-I receptor signaling without compromising anti-proliferative action.

Journal: Laboratory investigation; a journal of technical methods and pathology 20110101

Title: Expression and vitamin D3 regulation of long-chain fatty-acid-CoA ligase 3 in human prostate cancer cells.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20110101

Title: 1{alpha},25-Dihydroxyvitamin D3 inhibits growth of VCaP prostate cancer cells despite inducing the growth-promoting TMPRSS2:ERG gene fusion.

Journal: Endocrinology 20100401

Title: Vitamin D3 affects expression of thyroid hormone receptor alpha and deiodinase activity in liver of MNU-treated Sprague-Dawley rats.

Journal: General physiology and biophysics 20091201

Title: EB1089 inhibits the parathyroid hormone-related protein-enhanced bone metastasis and xenograft growth of human prostate cancer cells.

Journal: Molecular cancer therapeutics 20090701

Title: Characterization of the vitamin D endocrine system in human sebocytes in vitro.

Journal: The Journal of steroid biochemistry and molecular biology 20090101

Title: EB1089 induces Skp2-dependent p27 accumulation, leading to cell growth inhibition and cell cycle G1 phase arrest in human hepatoma cells.

Journal: Cancer investigation 20090101

Title: Prostate-derived Ets transcription factor as a favorable prognostic marker in ovarian cancer patients.

Journal: International journal of cancer 20080915

Title: Vitamin D derivatives induce apoptosis and downregulate ICAM-1 levels in peripheral blood mononuclear cells of inflammatory bowel disease patients.

Journal: Inflammatory bowel diseases 20080501

Title: The calcitriol analogue EB1089 impairs alveolarization and induces localized regions of increased fibroblast density in neonatal rat lung.

Journal: Experimental lung research 20080501

Title: Vitamin D3 analogue EB1089 inhibits the proliferation of human laryngeal squamous carcinoma cells via p57.

Journal: Molecular cancer therapeutics 20080501

Title: Differential regulation of apolipoprotein A-I gene expression by vitamin D receptor modulators.

Journal: Biochimica et biophysica acta 20080201

Title: Inhibition of hepatocellular cancer by EB1089: in vitro and in vive study.

Journal: Anticancer research 20080101

Title: Antioxidants and doxorubicin supplementation to modulate CD14 expression and oxidative stress induced by vitamin D3 and seocalcitol in HL60 cells.

Journal: Oncology reports 20071201

Title: Vitamin D receptor-dependent inhibition of mammary tumor growth by EB1089 and ultraviolet radiation in vivo.

Journal: Endocrinology 20071001

Title: Increased expression of corepressors in aggressive androgen-independent prostate cancer cells results in loss of 1alpha,25-dihydroxyvitamin D3 responsiveness.

Journal: Molecular cancer research : MCR 20070901

Title: Bioavailability of seocalcitol III. Administration of lipid-based formulations to minipigs in the fasted and fed state.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20070501

Title: Potentiating effects of nonactive/active vitamin D analogues and ketoconazole in parathyroid cells.

Journal: Clinical endocrinology 20070301

Title: The inhibition of Wnt/beta-catenin signalling by 1alpha,25-dihydroxyvitamin D3 is abrogated by Snail1 in human colon cancer cells.

Journal: Endocrine-related cancer 20070301

Title: Control of macroautophagy by calcium, calmodulin-dependent kinase kinase-beta, and Bcl-2.

Journal: Molecular cell 20070126

Title: In vitro comparison of the vitamin D endocrine system in 1,25(OH)2D3-responsive and -resistant melanoma cells.

Journal: Cancer biology & therapy 20070101

Title: Bioavailability of seocalcitol IV: evaluation of lymphatic transport in conscious rats.

Journal: Pharmaceutical research 20061101

Title: Potentiation of radiation sensitivity in breast tumor cells by the vitamin D3 analogue, EB 1089, through promotion of autophagy and interference with proliferative recovery.

Journal: Molecular cancer therapeutics 20061101

Title: Bioavailability of seocalcitol II: development and characterisation of self-microemulsifying drug delivery systems (SMEDDS) for oral administration containing medium and long chain triglycerides.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20060601

Title: Multiple mechanisms underlie the aberrant expression of the human kallikrein 6 gene in breast cancer.

Journal: Biological chemistry 20060601

Title: Vitamin D receptor is a novel drug target for ovarian cancer treatment.

Journal: Current cancer drug targets 20060501

Title: Prostate cancer cell type-specific involvement of the VDR and RXR in regulation of the human PTHrP gene via a negative VDRE.

Journal: Steroids 20060201

Title: Investigation of the mechanisms by which EB1089 abrogates apoptosis induced by 9-cis retinoic acid in pancreatic cancer cells.

Journal: Pancreas 20060101

Title: EB1089, a vitamin D receptor agonist, reduces proliferation and decreases tumor growth rate in a mouse model of hormone-induced mammary cancer.

Journal: Cancer letters 20051118

Title: The role of non-calcemic analogs of vitamin D in differentiation of cultured rat bone marrow into osteoblast-like cells: age and sex differences.

Journal: Journal of endocrinological investigation 20051101

Title: Vitamin D analog EB1089 triggers dramatic lysosomal changes and Beclin 1-mediated autophagic cell death.

Journal: Cell death and differentiation 20051001

Title: 1alpha,25-Dihydroxyvitamin D3 targets PTEN-dependent fibronectin expression to restore thyroid cancer cell adhesiveness.

Journal: Molecular endocrinology (Baltimore, Md.) 20050901

Title: Bioavailability of seocalcitol I: Relating solubility in biorelevant media with oral bioavailability in rats--effect of medium and long chain triglycerides.

Journal: Journal of pharmaceutical sciences 20050801

Title: Human cathelicidin antimicrobial peptide (CAMP) gene is a direct target of the vitamin D receptor and is strongly up-regulated in myeloid cells by 1,25-dihydroxyvitamin D3.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050701

Title: Nuclear BAG-1 expression inhibits apoptosis in colorectal adenoma-derived epithelial cells.

Journal: Apoptosis : an international journal on programmed cell death 20050301

Title: A near-infrared Fourier transform Raman spectroscopy of epidermal keratinocytes: changes in the protein-DNA structure following malignant transformation.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20050101

Title: Growth suppression of ovarian cancer xenografts in nude mice by vitamin D analogue EB1089.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050101

Title: Effects of calcitriol, seocalcitol, and medium-chain triglyceride on a canine transitional cell carcinoma cell line.

Journal: Anticancer research 20050101

Title: 25-Hydroxyvitamin D3 1alpha-hydroxylase expression in breast cancer and use of non-1alpha-hydroxylated vitamin D analogue.

Journal: Breast cancer research : BCR 20050101

Title: Potentiation of cell killing by fractionated radiation and suppression of proliferative recovery in MCF-7 breast tumor cells by the Vitamin D3 analog EB 1089.

Journal: The Journal of steroid biochemistry and molecular biology 20041201

Title: [Effects of vitamin D analogue EB1089 on proliferation and apoptosis of hepatic carcinoma cells].

Journal: Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20041101

Title: The transcription factor SNAIL represses vitamin D receptor expression and responsiveness in human colon cancer.

Journal: Nature medicine 20040901

Title: Modifications of cellular autofluorescence emission spectra under oxidative stress induced by 1 alpha,25dihydroxyvitamin D(3) and its analog EB1089.

Journal: Technology in cancer research & treatment 20040801

Title: Differential skeletal responses of hindlimb unloaded rats on a vitamin D-deficient diet to 1,25-dihydroxyvitamin D3 and its analog, seocalcitol (EB1089).

Journal: Bone 20040701

Title: Sequential versus combined treatment of human breast cancer cells with antiestrogens and the vitamin D analogue EB1089 and evaluation of predictive markers for vitamin D treatment.

Journal: Breast cancer research and treatment 20040501

Title: The tissue-specific distribution of 3H-seocalcitol (EB 1089) and 3H-calcitriol in rats.

Journal: The Journal of steroid biochemistry and molecular biology 20040501

Title: Crystal structures of the vitamin D nuclear receptor liganded with the vitamin D side chain analogues calcipotriol and seocalcitol, receptor agonists of clinical importance. Insights into a structural basis for the switching of calcipotriol to a receptor antagonist by further side chain modification.

Journal: Journal of medicinal chemistry 20040408

Title: Vitamin D analogs as therapeutic agents: a clinical study update.

Journal: Current opinion in investigational drugs (London, England : 2000) 20040301

Title: [Regulatory mechanism of EB1089 for hepatocarcinoma cell proliferation].

Journal: Wei sheng yan jiu = Journal of hygiene research 20040301

Title: Role of 24-hydroxylase in vitamin D3 growth response of OVCAR-3 ovarian cancer cells.

Journal: International journal of cancer 20040120

Title: Molecular analysis of p21 promoter activity isolated from squamous carcinoma cell lines of the head and neck under the influence of 1,25(OH)2 vitamin D3 and its analogs.

Journal: Acta oto-laryngologica 20040101

Title: Inhibition of MG-63 cell cycle progression by synthetic vitamin D3 analogs mediated by p27, Cdk2, cyclin E, and the retinoblastoma protein.

Journal: Biochemical pharmacology 20030801

Title: Effects of Seocalcitol (EB1089) on nitrosomethyl urea-induced rat mammary tumors.

Journal: Breast cancer research and treatment 20030801

Title: A phase II study of the vitamin D analogue Seocalcitol in patients with inoperable hepatocellular carcinoma.

Journal: British journal of cancer 20030721

Title: Prostate cancer cell type-specific regulation of the human PTHrP gene via a negative VDRE.

Journal: Molecular and cellular endocrinology 20030630

Title: The combination of a potent vitamin D3 analog, EB 1089, with ionizing radiation reduces tumor growth and induces apoptosis of MCF-7 breast tumor xenografts in nude mice.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20030601

Title: The vitamin D3 analog EB1089 induces apoptosis via a p53-independent mechanism involving p38 MAP kinase activation and suppression of ERK activity in B-cell chronic lymphocytic leukemia cells in vitro.

Journal: Blood 20030401

Title: Inhibition of F-Box protein p45(SKP2) expression and stabilization of cyclin-dependent kinase inhibitor p27(KIP1) in vitamin D analog-treated cancer cells.

Journal: Endocrinology 20030301

Title: Characterization of mammary tumor cell lines from wild type and vitamin D3 receptor knockout mice.

Journal: Molecular and cellular endocrinology 20030227

Title: Efficacy of Vitamin D compounds to modulate estrogen receptor negative breast cancer growth and invasion.

Journal: The Journal of steroid biochemistry and molecular biology 20030201

Title: Vitamin D receptor is expressed in pancreatic cancer cells and a vitamin D3 analogue decreases cell number.

Journal: Pancreatology : official journal of the International Association of Pancreatology (IAP) ... [et al.] 20030101

Title: Significant experimental decrease of the hepatocellular carcinoma incidence in C3H/Sy mice after long-term administration of EB1089, a vitamin D analogue.

Journal: Oncology research 20030101

Title: [Differential effect of vitamin D analogues on the proliferation of vascular smooth muscle cells].

Journal: Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia 20030101

Title: 1alpha,25-dihydroxyvitamin D3 inhibits anti-CD40 plus IL-4-mediated IgE production in vitro.

Journal: European journal of immunology 20021201

Title: Vitamin D receptor-dependent antitumour effects of 1,25-dihydroxyvitamin D3 and two synthetic analogues in three in vivo models of prostate cancer.

Journal: BJU international 20021001

Title: Preclinical activity of ketoconazole in combination with calcitriol or the vitamin D analogue EB 1089 in prostate cancer cells.

Journal: The Journal of urology 20021001

Title: Vitamin D and its analog EB1089 induce p27 accumulation and diminish association of p27 with Skp2 independent of PTEN in pituitary corticotroph cells.

Journal: Brain pathology (Zurich, Switzerland) 20021001

Title: Vector-averaged gravity-induced changes in cell signaling and vitamin D receptor activity in MG-63 cells are reversed by a 1,25-(OH)2D3 analog, EB1089.

Journal: Bone 20020901

Title: Calcium and calpain as key mediators of apoptosis-like death induced by vitamin D compounds in breast cancer cells.

Journal: The Journal of biological chemistry 20020823

Title: Expression profiling in squamous carcinoma cells reveals pleiotropic effects of vitamin D3 analog EB1089 signaling on cell proliferation, differentiation, and immune system regulation.

Journal: Molecular endocrinology (Baltimore, Md.) 20020601

Title: The G gamma / T-15 transgenic mouse model of androgen-independent prostate cancer: target cells of carcinogenesis and the effect of the vitamin D analogue EB 1089.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20020601

Title: Effects of 1,25-dihydroxyvitamin D3 [1,25(OH)2D3] and its analogues (EB1089 and analog V) on canine adenocarcinoma (CAC-8) in nude mice.

Journal: Biological & pharmaceutical bulletin 20020501

Title: A phase II trial of the vitamin D analogue Seocalcitol (EB1089) in patients with inoperable pancreatic cancer.

Journal: British journal of cancer 20020304

Title: The induction of apoptosis by a combined 1,25(OH)2D3 analog, EB1089 and TGF-beta1 in NCI-H929 multiple myeloma cells.

Journal: International journal of oncology 20020301

Title: Synergistic inhibitory effect of cyclosporin A and vitamin D derivatives on T-lymphocyte proliferation in active ulcerative colitis.

Journal: The American journal of gastroenterology 20020301

Title: Synergistic effect of vitamin D derivatives and retinoids on C2C12 skeletal muscle cells.

Journal: IUBMB life 20020301

Title: Sensitive analysis of 1alpha,25-dihydroxyvitamin D3 in biological fluids by liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. A 20011123

Title: Autocrine TGFbeta signaling mediates vitamin D3 analog-induced growth inhibition in breast cells.

Journal: Journal of cellular physiology 20010901

Title: A non-calcemic sulfone version of the vitamin D(3) analogue seocalcitol (EB 1089): chemical synthesis, biological evaluation and potency enhancement of the anticancer drug adriamycin.

Journal: Bioorganic & medicinal chemistry 20010901

Title: Polyclonal antibodies to EB1089 (seocalcitol), an analog of 1alpha,25-dihydroxyvitamin D(3)*.

Journal: Steroids 20010701

Title: Regulation of gene Expression by 1alpha,25-dihydroxyvitamin D3 and Its analog EB1089 under growth-inhibitory conditions in squamous carcinoma Cells.

Journal: Molecular endocrinology (Baltimore, Md.) 20010701

Title: Vitamin D and cancer: effects of 1,25(OH)2D3 and its analogs on growth control and tumorigenesis.

Journal: Frontiers in bioscience : a journal and virtual library 20010701

Title: 1alpha,25-Dihydroxyvitamin D3 and its analogues, EB1089 and CB1093, profoundly inhibit the in vitro proliferation of the human hepatoblastoma cell line HepG2.

Journal: ANZ journal of surgery 20010701

Title: Action of low calcemic 1alpha,25-dihydroxyvitamin D3 analogue EB1089 in head and neck squamous cell carcinoma.

Journal: Journal of the National Cancer Institute 20010516

Title: Correspondence re: S. E. Blutt, T. C. Polek, L. V. Stewart, M. W. Kattan, and N. L. Weigel, A calcitriol analogue, EB1089, inhibits the growth of LNCaP tumors in nude mice. Cancer Res., 60: 779-782, 2000.

Journal: Cancer research 20010515

Title: Amphiregulin is a vitamin D3 target gene in squamous cell and breast carcinoma.

Journal: Biochemical and biophysical research communications 20010309

Title: Anti-oestrogen resistant human breast cancer cell lines are more sensitive towards treatment with the vitamin D analogue EB1089 than parent MCF-7 cells.

Journal: British journal of cancer 20010301

Title: Suppressive effect of 1,25-dihydroxyvitamin D3 and its analogues EB 1089 and KH 1060 on T lymphocyte proliferation in active ulcerative colitis.

Journal: Biochemical pharmacology 20010201

Title: Examination of structurally selective derivatization of vitamin D(3) analogues by electrospray mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20010101

Title: Effects of 1,25(OH)2D3, EB1089, and analog V on PTHrP production, PTHrP mRNA expression and cell growth in SCC 2/88.

Journal: Anticancer research 20010101

Title: Inhibition of endothelial cell activation by nitric oxide donors.

Journal: The Journal of pharmacology and experimental therapeutics 20001101

Title: Apoptosis induced by vitamin D compounds in breast cancer cells is inhibited by Bcl-2 but does not involve known caspases or p53.

Journal: Cancer research 19991001

Title: A phase I study of the vitamin D analogue EB 1089 in patients with advanced breast and colorectal cancer.

Journal: British journal of cancer 19980701

Title: Apoptotic regression of MCF-7 xenografts in nude mice treated with the vitamin D3 analog, EB1089.

Journal: Endocrinology 19980401

Title: Cytotoxic effects of 1 alpha,25-dihydroxyvitamin D3 and synthetic vitamin D3 analogues on a glioma cell line.

Journal: Cancer letters 19960227

Title: Studies on two new vitamin D analogs, EB 1089 and KH 1060: effects on bone resorption and osteoclast recruitment in vitro.

Journal: Bone 19951001

Title: Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3.

Journal: Endocrinology 19950101

Title: EB1089: a new vitamin D analogue that inhibits the growth of breast cancer cells in vivo and in vitro.

Journal: Biochemical pharmacology 19921215

Title: Wiberg K, et al. Studies on two new vitamin D analogs, EB 1089 and KH 1060: effects on bone resorption and osteoclast recruitment in vitro. Bone. 1995 Oct;17(4):391-5.

Title: Roy S, et al. Comparative effects of 1,25-dihydroxyvitamin D3 and EB 1089 on mouse renal and intestinal 25-hydroxyvitamin D3-24-hydroxylase. J Bone Miner Res. 1995 Dec;10(12):1951-9

Title: Bondza-Kibangou P, et al. Antioxidants and doxorubicin supplementation to modulate CD14 expression and oxidative stress induced by vitamin D3 and seocalcitol in HL60 cells. Oncol Rep. 2007 Dec;18(6):1513-9.

Title: Ghous Z, et al. Inhibition of hepatocellular cancer by EB1089: in vitro and in vivo study. Anticancer Res. 2008 Nov-Dec;28(6A):3757-61.

Title: Ormerod AK, et al. The calcitriol analogue EB1089 impairs alveolarization and induces localized regions of increased fibroblast density in neonatal rat lung. Exp Lung Res. 2008 May;34(4):155-82.

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Tags:134404-52-7 Molecular Formula|134404-52-7 MDL|134404-52-7 SMILES|134404-52-7 Seocalcitol