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Seocalcitol

CAS No.:
134404-52-7
Catalog Number:
AG009CEQ
Molecular Formula:
C30H46O3
Molecular Weight:
454.6844
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$255
- +
5mg
≥98%
1 week
United States
$890
- +
Product Description
Catalog Number:
AG009CEQ
Chemical Name:
Seocalcitol
CAS Number:
134404-52-7
Molecular Formula:
C30H46O3
Molecular Weight:
454.6844
MDL Number:
MFCD00871599
IUPAC Name:
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,3E,5E)-7-ethyl-7-hydroxynona-3,5-dien-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
InChI:
InChI=1S/C30H46O3/c1-6-30(33,7-2)18-9-8-11-21(3)26-15-16-27-23(12-10-17-29(26,27)5)13-14-24-19-25(31)20-28(32)22(24)4/h8-9,11,13-14,18,21,25-28,31-33H,4,6-7,10,12,15-17,19-20H2,1-3,5H3/b11-8+,18-9+,23-13+,24-14-/t21-,25-,26-,27+,28+,29-/m1/s1
InChI Key:
LVLLALCJVJNGQQ-SEODYNFXSA-N
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
UNII:
Q0OZ0D9223
Properties
Complexity:
812  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
4  
Exact Mass:
454.345g/mol
Formal Charge:
0
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
454.695g/mol
Monoisotopic Mass:
454.345g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
60.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.8  
Literature
Title Journal
Motor neuron-like NSC-34 cells as a new model for the study of vitamin D metabolism in the brain. The Journal of steroid biochemistry and molecular biology 20160401
MNU-induced mammary gland carcinogenesis: chemopreventive and therapeutic effects of vitamin D and Seocalcitol on selected regulatory vitamin D receptor pathways. Toxicology letters 20111110
Vitamin D inhibits CEACAM1 to promote insulin/IGF-I receptor signaling without compromising anti-proliferative action. Laboratory investigation; a journal of technical methods and pathology 20110101
Expression and vitamin D3 regulation of long-chain fatty-acid-CoA ligase 3 in human prostate cancer cells. Prostaglandins, leukotrienes, and essential fatty acids 20110101
1{alpha},25-Dihydroxyvitamin D3 inhibits growth of VCaP prostate cancer cells despite inducing the growth-promoting TMPRSS2:ERG gene fusion. Endocrinology 20100401
Vitamin D3 affects expression of thyroid hormone receptor alpha and deiodinase activity in liver of MNU-treated Sprague-Dawley rats. General physiology and biophysics 20091201
EB1089 inhibits the parathyroid hormone-related protein-enhanced bone metastasis and xenograft growth of human prostate cancer cells. Molecular cancer therapeutics 20090701
Characterization of the vitamin D endocrine system in human sebocytes in vitro. The Journal of steroid biochemistry and molecular biology 20090101
EB1089 induces Skp2-dependent p27 accumulation, leading to cell growth inhibition and cell cycle G1 phase arrest in human hepatoma cells. Cancer investigation 20090101
Prostate-derived Ets transcription factor as a favorable prognostic marker in ovarian cancer patients. International journal of cancer 20080915
Vitamin D derivatives induce apoptosis and downregulate ICAM-1 levels in peripheral blood mononuclear cells of inflammatory bowel disease patients. Inflammatory bowel diseases 20080501
The calcitriol analogue EB1089 impairs alveolarization and induces localized regions of increased fibroblast density in neonatal rat lung. Experimental lung research 20080501
Vitamin D3 analogue EB1089 inhibits the proliferation of human laryngeal squamous carcinoma cells via p57. Molecular cancer therapeutics 20080501
Differential regulation of apolipoprotein A-I gene expression by vitamin D receptor modulators. Biochimica et biophysica acta 20080201
Inhibition of hepatocellular cancer by EB1089: in vitro and in vive study. Anticancer research 20080101
Antioxidants and doxorubicin supplementation to modulate CD14 expression and oxidative stress induced by vitamin D3 and seocalcitol in HL60 cells. Oncology reports 20071201
Vitamin D receptor-dependent inhibition of mammary tumor growth by EB1089 and ultraviolet radiation in vivo. Endocrinology 20071001
Increased expression of corepressors in aggressive androgen-independent prostate cancer cells results in loss of 1alpha,25-dihydroxyvitamin D3 responsiveness. Molecular cancer research : MCR 20070901
Bioavailability of seocalcitol III. Administration of lipid-based formulations to minipigs in the fasted and fed state. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20070501
Potentiating effects of nonactive/active vitamin D analogues and ketoconazole in parathyroid cells. Clinical endocrinology 20070301
The inhibition of Wnt/beta-catenin signalling by 1alpha,25-dihydroxyvitamin D3 is abrogated by Snail1 in human colon cancer cells. Endocrine-related cancer 20070301
Control of macroautophagy by calcium, calmodulin-dependent kinase kinase-beta, and Bcl-2. Molecular cell 20070126
In vitro comparison of the vitamin D endocrine system in 1,25(OH)2D3-responsive and -resistant melanoma cells. Cancer biology & therapy 20070101
Bioavailability of seocalcitol IV: evaluation of lymphatic transport in conscious rats. Pharmaceutical research 20061101
Potentiation of radiation sensitivity in breast tumor cells by the vitamin D3 analogue, EB 1089, through promotion of autophagy and interference with proliferative recovery. Molecular cancer therapeutics 20061101
Bioavailability of seocalcitol II: development and characterisation of self-microemulsifying drug delivery systems (SMEDDS) for oral administration containing medium and long chain triglycerides. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20060601
Multiple mechanisms underlie the aberrant expression of the human kallikrein 6 gene in breast cancer. Biological chemistry 20060601
Vitamin D receptor is a novel drug target for ovarian cancer treatment. Current cancer drug targets 20060501
Prostate cancer cell type-specific involvement of the VDR and RXR in regulation of the human PTHrP gene via a negative VDRE. Steroids 20060201
Investigation of the mechanisms by which EB1089 abrogates apoptosis induced by 9-cis retinoic acid in pancreatic cancer cells. Pancreas 20060101
EB1089, a vitamin D receptor agonist, reduces proliferation and decreases tumor growth rate in a mouse model of hormone-induced mammary cancer. Cancer letters 20051118
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 of endocrinological investigation 20051101
Vitamin D analog EB1089 triggers dramatic lysosomal changes and Beclin 1-mediated autophagic cell death. Cell death and differentiation 20051001
1alpha,25-Dihydroxyvitamin D3 targets PTEN-dependent fibronectin expression to restore thyroid cancer cell adhesiveness. Molecular endocrinology (Baltimore, Md.) 20050901
Bioavailability of seocalcitol I: Relating solubility in biorelevant media with oral bioavailability in rats--effect of medium and long chain triglycerides. Journal of pharmaceutical sciences 20050801
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. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050701
Nuclear BAG-1 expression inhibits apoptosis in colorectal adenoma-derived epithelial cells. Apoptosis : an international journal on programmed cell death 20050301
A near-infrared Fourier transform Raman spectroscopy of epidermal keratinocytes: changes in the protein-DNA structure following malignant transformation. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20050101
Growth suppression of ovarian cancer xenografts in nude mice by vitamin D analogue EB1089. Clinical cancer research : an official journal of the American Association for Cancer Research 20050101
Effects of calcitriol, seocalcitol, and medium-chain triglyceride on a canine transitional cell carcinoma cell line. Anticancer research 20050101
25-Hydroxyvitamin D3 1alpha-hydroxylase expression in breast cancer and use of non-1alpha-hydroxylated vitamin D analogue. Breast cancer research : BCR 20050101
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. The Journal of steroid biochemistry and molecular biology 20041201
[Effects of vitamin D analogue EB1089 on proliferation and apoptosis of hepatic carcinoma cells]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20041101
The transcription factor SNAIL represses vitamin D receptor expression and responsiveness in human colon cancer. Nature medicine 20040901
Modifications of cellular autofluorescence emission spectra under oxidative stress induced by 1 alpha,25dihydroxyvitamin D(3) and its analog EB1089. Technology in cancer research & treatment 20040801
Differential skeletal responses of hindlimb unloaded rats on a vitamin D-deficient diet to 1,25-dihydroxyvitamin D3 and its analog, seocalcitol (EB1089). Bone 20040701
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. Breast cancer research and treatment 20040501
The tissue-specific distribution of 3H-seocalcitol (EB 1089) and 3H-calcitriol in rats. The Journal of steroid biochemistry and molecular biology 20040501
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 of medicinal chemistry 20040408
Vitamin D analogs as therapeutic agents: a clinical study update. Current opinion in investigational drugs (London, England : 2000) 20040301
[Regulatory mechanism of EB1089 for hepatocarcinoma cell proliferation]. Wei sheng yan jiu = Journal of hygiene research 20040301
Role of 24-hydroxylase in vitamin D3 growth response of OVCAR-3 ovarian cancer cells. International journal of cancer 20040120
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. Acta oto-laryngologica 20040101
Inhibition of MG-63 cell cycle progression by synthetic vitamin D3 analogs mediated by p27, Cdk2, cyclin E, and the retinoblastoma protein. Biochemical pharmacology 20030801
Effects of Seocalcitol (EB1089) on nitrosomethyl urea-induced rat mammary tumors. Breast cancer research and treatment 20030801
A phase II study of the vitamin D analogue Seocalcitol in patients with inoperable hepatocellular carcinoma. British journal of cancer 20030721
Prostate cancer cell type-specific regulation of the human PTHrP gene via a negative VDRE. Molecular and cellular endocrinology 20030630
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. Clinical cancer research : an official journal of the American Association for Cancer Research 20030601
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. Blood 20030401
Inhibition of F-Box protein p45(SKP2) expression and stabilization of cyclin-dependent kinase inhibitor p27(KIP1) in vitamin D analog-treated cancer cells. Endocrinology 20030301
Characterization of mammary tumor cell lines from wild type and vitamin D3 receptor knockout mice. Molecular and cellular endocrinology 20030227
Efficacy of Vitamin D compounds to modulate estrogen receptor negative breast cancer growth and invasion. The Journal of steroid biochemistry and molecular biology 20030201
Vitamin D receptor is expressed in pancreatic cancer cells and a vitamin D3 analogue decreases cell number. Pancreatology : official journal of the International Association of Pancreatology (IAP) ... [et al.] 20030101
Significant experimental decrease of the hepatocellular carcinoma incidence in C3H/Sy mice after long-term administration of EB1089, a vitamin D analogue. Oncology research 20030101
[Differential effect of vitamin D analogues on the proliferation of vascular smooth muscle cells]. Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia 20030101
1alpha,25-dihydroxyvitamin D3 inhibits anti-CD40 plus IL-4-mediated IgE production in vitro. European journal of immunology 20021201
Vitamin D receptor-dependent antitumour effects of 1,25-dihydroxyvitamin D3 and two synthetic analogues in three in vivo models of prostate cancer. BJU international 20021001
Preclinical activity of ketoconazole in combination with calcitriol or the vitamin D analogue EB 1089 in prostate cancer cells. The Journal of urology 20021001
Vitamin D and its analog EB1089 induce p27 accumulation and diminish association of p27 with Skp2 independent of PTEN in pituitary corticotroph cells. Brain pathology (Zurich, Switzerland) 20021001
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. Bone 20020901
Calcium and calpain as key mediators of apoptosis-like death induced by vitamin D compounds in breast cancer cells. The Journal of biological chemistry 20020823
Expression profiling in squamous carcinoma cells reveals pleiotropic effects of vitamin D3 analog EB1089 signaling on cell proliferation, differentiation, and immune system regulation. Molecular endocrinology (Baltimore, Md.) 20020601
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. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20020601
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. Biological & pharmaceutical bulletin 20020501
A phase II trial of the vitamin D analogue Seocalcitol (EB1089) in patients with inoperable pancreatic cancer. British journal of cancer 20020304
The induction of apoptosis by a combined 1,25(OH)2D3 analog, EB1089 and TGF-beta1 in NCI-H929 multiple myeloma cells. International journal of oncology 20020301
Synergistic inhibitory effect of cyclosporin A and vitamin D derivatives on T-lymphocyte proliferation in active ulcerative colitis. The American journal of gastroenterology 20020301
Synergistic effect of vitamin D derivatives and retinoids on C2C12 skeletal muscle cells. IUBMB life 20020301
Sensitive analysis of 1alpha,25-dihydroxyvitamin D3 in biological fluids by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A 20011123
Autocrine TGFbeta signaling mediates vitamin D3 analog-induced growth inhibition in breast cells. Journal of cellular physiology 20010901
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. Bioorganic & medicinal chemistry 20010901
Polyclonal antibodies to EB1089 (seocalcitol), an analog of 1alpha,25-dihydroxyvitamin D(3)*. Steroids 20010701
Regulation of gene Expression by 1alpha,25-dihydroxyvitamin D3 and Its analog EB1089 under growth-inhibitory conditions in squamous carcinoma Cells. Molecular endocrinology (Baltimore, Md.) 20010701
Vitamin D and cancer: effects of 1,25(OH)2D3 and its analogs on growth control and tumorigenesis. Frontiers in bioscience : a journal and virtual library 20010701
1alpha,25-Dihydroxyvitamin D3 and its analogues, EB1089 and CB1093, profoundly inhibit the in vitro proliferation of the human hepatoblastoma cell line HepG2. ANZ journal of surgery 20010701
Action of low calcemic 1alpha,25-dihydroxyvitamin D3 analogue EB1089 in head and neck squamous cell carcinoma. Journal of the National Cancer Institute 20010516
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. Cancer research 20010515
Amphiregulin is a vitamin D3 target gene in squamous cell and breast carcinoma. Biochemical and biophysical research communications 20010309
Anti-oestrogen resistant human breast cancer cell lines are more sensitive towards treatment with the vitamin D analogue EB1089 than parent MCF-7 cells. British journal of cancer 20010301
Suppressive effect of 1,25-dihydroxyvitamin D3 and its analogues EB 1089 and KH 1060 on T lymphocyte proliferation in active ulcerative colitis. Biochemical pharmacology 20010201
Examination of structurally selective derivatization of vitamin D(3) analogues by electrospray mass spectrometry. Journal of mass spectrometry : JMS 20010101
Effects of 1,25(OH)2D3, EB1089, and analog V on PTHrP production, PTHrP mRNA expression and cell growth in SCC 2/88. Anticancer research 20010101
Inhibition of endothelial cell activation by nitric oxide donors. The Journal of pharmacology and experimental therapeutics 20001101
Apoptosis induced by vitamin D compounds in breast cancer cells is inhibited by Bcl-2 but does not involve known caspases or p53. Cancer research 19991001
A phase I study of the vitamin D analogue EB 1089 in patients with advanced breast and colorectal cancer. British journal of cancer 19980701
Apoptotic regression of MCF-7 xenografts in nude mice treated with the vitamin D3 analog, EB1089. Endocrinology 19980401
Cytotoxic effects of 1 alpha,25-dihydroxyvitamin D3 and synthetic vitamin D3 analogues on a glioma cell line. Cancer letters 19960227
Studies on two new vitamin D analogs, EB 1089 and KH 1060: effects on bone resorption and osteoclast recruitment in vitro. Bone 19951001
Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3. Endocrinology 19950101
EB1089: a new vitamin D analogue that inhibits the growth of breast cancer cells in vivo and in vitro. Biochemical pharmacology 19921215
Properties