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MedKoo Cat#: 581178 | Name: Deacylcortivazol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Deacylcortivazol (DAC), a potent glucocorticoid, contains a phenyl-pyrazole moiety fused to the 2--3 position of the traditional steroid nucleus. When incubated with glucocorticoid-resistant mutants derived from the glucocorticoid-sensitive human leukemic cell line CEM-C7, DAC caused significant growth inhibition. The cytotoxicity of DAC at concentrations higher than necessary for glucocorticoid receptor saturation is not mediated by glucocorticoid receptors. Thus, DAC may be a bifunctional compound having both steroid receptor-mediated and receptor-independent cytotoxicity.

Chemical Structure

Deacylcortivazol
Deacylcortivazol
CAS#4906-84-7

Theoretical Analysis

MedKoo Cat#: 581178

Name: Deacylcortivazol

CAS#: 4906-84-7

Chemical Formula: C30H36N2O4

Exact Mass: 488.2675

Molecular Weight: 488.63

Elemental Analysis: C, 73.74; H, 7.43; N, 5.73; O, 13.10

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
Deacylcortivazol; DAC; NSC 325316; NSC-325316; NSC325316;
IUPAC/Chemical Name
1-((1R,2R,3aS,3bS,10aR,10bS,11S,12aS)-1,11-dihydroxy-2,5,10a,12a-tetramethyl-7-phenyl-1,2,3,3a,3b,7,10,10a,10b,11,12,12a-dodecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-yl)-2-hydroxyethan-1-one
InChi Key
FKAINCOIINXAOK-UFVJYOHBSA-N
InChi Code
InChI=1S/C30H36N2O4/c1-17-10-21-23-11-18(2)30(36,26(35)16-33)29(23,4)14-25(34)27(21)28(3)13-19-15-31-32(24(19)12-22(17)28)20-8-6-5-7-9-20/h5-10,12,15,18,21,23,25,27,33-34,36H,11,13-14,16H2,1-4H3/t18-,21+,23+,25+,27-,28+,29+,30+/m1/s1
SMILES Code
C[C@@H]1C[C@H]2[C@@H]3C=C(C4=Cc5c(cnn5c6ccccc6)C[C@@]4([C@H]3[C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 488.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Suino-Powell K, Xu Y, Zhang C, Tao YG, Tolbert WD, Simons SS Jr, Xu HE. Doubling the size of the glucocorticoid receptor ligand binding pocket by deacylcortivazol. Mol Cell Biol. 2008 Mar;28(6):1915-23. Epub 2007 Dec 26. PubMed PMID: 18160712; PubMed Central PMCID: PMC2268401. 2: Mrigank, Kothekar V. Computer stimulation of interaction of deacylcortivazol with d(TGTTCT)2. J Theor Biol. 1993 Jul 7;163(1):33-50. PubMed PMID: 8412241. 3: Harmon JM, Schmidt TJ, Thompson EB. Deacylcortivazol acts through glucocorticoid receptors. J Steroid Biochem. 1981 Mar;14(3):273-9. PubMed PMID: 6111624. 4: Harmon JM, Schmidt TJ, Thompson EB. Non-glucocorticoid receptor-mediated effects of the potent glucocorticoid deacylcortivazol. Cancer Res. 1982 Jun;42(6):2110-4. PubMed PMID: 6951631. 5: Thompson EB, Simons SS Jr, Harmon JM. Deacylcortivazol, a potent glucocorticoid with unusual structure and unusual anti-leukemic cell activity. Adv Exp Med Biol. 1981;138:315-24. PubMed PMID: 6123225. 6: Lee GS, Simons SS Jr. Ligand binding domain mutations of the glucocorticoid receptor selectively modify the effects with, but not binding of, cofactors. Biochemistry. 2011 Jan 25;50(3):356-66. Epub 2010 Dec 30. PubMed PMID: 21142156; PubMed Central PMCID: PMC3123670. 7: Hurt DE, Suzuki S, Mayama T, Charmandari E, Kino T. Structural Analysis on the Pathologic Mutant Glucocorticoid Receptor Ligand-Binding Domains. Mol Endocrinol. 2016 Feb;30(2):173-88. doi: 10.1210/me.2015-1177. Epub 2016 Jan 8. PubMed PMID: 26745667; PubMed Central PMCID: PMC4792232. 8: Burollaud T, Danzé PM, Tbarka N, Formstecher P, Dautrevaux M. Binding of RU486 and deacylcortivazol to the glucocorticoid receptor is insensitive to sulfhydryl-modifying agents. J Steroid Biochem Mol Biol. 1993 Mar;44(3):217-25. PubMed PMID: 8461255. 9: Sun Y, Tao YG, Kagan BL, He Y, Simons SS Jr. Modulation of transcription parameters in glucocorticoid receptor-mediated repression. Mol Cell Endocrinol. 2008 Nov 25;295(1-2):59-69. doi: 10.1016/j.mce.2008.05.008. Epub 2008 May 21. PubMed PMID: 18583028; PubMed Central PMCID: PMC2662735. 10: Gagne D, Labhilili M, Pons M. Description and analysis of differential sensitivity to glucocorticoids in Fao cells. J Steroid Biochem. 1988 Dec;31(6):917-25. PubMed PMID: 2904511. 11: Tao YG, Xu Y, Xu HE, Simons SS Jr. Mutations of glucocorticoid receptor differentially affect AF2 domain activity in a steroid-selective manner to alter the potency and efficacy of gene induction and repression. Biochemistry. 2008 Jul 22;47(29):7648-62. doi: 10.1021/bi800472w. Epub 2008 Jun 26. PubMed PMID: 18578507; PubMed Central PMCID: PMC2678802. 12: Lamontagne N, Mercier L, Pons M, Thompson EB, Simons SS Jr. Glucocorticoid versus antiglucocorticoid activity: can a single functional group modification of glucocorticoid steroids always convey antiglucocorticoid activity? Endocrinology. 1984 Jun;114(6):2252-63. PubMed PMID: 6547091. 13: Chávez S, Candau R, Truss M, Beato M. Constitutive repression and nuclear factor I-dependent hormone activation of the mouse mammary tumor virus promoter in Saccharomyces cerevisiae. Mol Cell Biol. 1995 Dec;15(12):6987-98. PubMed PMID: 8524266; PubMed Central PMCID: PMC230954. 14: Huang Y, Simons SS Jr. Functional analysis of R651 mutations in the putative helix 6 of rat glucocorticoid receptors. Mol Cell Endocrinol. 1999 Dec 20;158(1-2):117-30. PubMed PMID: 10630412. 15: Schlechte JA, Simons SS Jr, Lewis DA, Thompson EB. [3H]cortivazol: a unique high affinity ligand for the glucocorticoid receptor. Endocrinology. 1985 Oct;117(4):1355-62. PubMed PMID: 4029081. 16: Simons SS Jr, Miller PA. Affinity-labeling steroids as biologically active probes of antiglucocorticoid hormone action. J Steroid Biochem. 1986 Jan;24(1):25-32. PubMed PMID: 3754598. 17: Milhon J, Kohli K, Stallcup MR. Genetic analysis of the N-terminal end of the glucocorticoid receptor hormone binding domain. J Steroid Biochem Mol Biol. 1994 Oct;51(1-2):11-9. PubMed PMID: 7947345. 18: Miller AL, Webb MS, Copik AJ, Wang Y, Johnson BH, Kumar R, Thompson EB. p38 Mitogen-activated protein kinase (MAPK) is a key mediator in glucocorticoid-induced apoptosis of lymphoid cells: correlation between p38 MAPK activation and site-specific phosphorylation of the human glucocorticoid receptor at serine 211. Mol Endocrinol. 2005 Jun;19(6):1569-83. Epub 2005 Apr 7. PubMed PMID: 15817653. 19: Sarlis NJ, Bayly SF, Szapary D, Simons SS Jr. Quantity of partial agonist activity for antiglucocorticoids complexed with mutant glucocorticoid receptors is constant in two different transactivation assays but not predictable from steroid structure. J Steroid Biochem Mol Biol. 1999 Feb;68(3-4):89-102. PubMed PMID: 10369406. 20: Mercier L, Thompson EB, Simons SS Jr. Dissociation of steroid binding to receptors and steroid induction of biological activity in a glucocorticoid-responsive cell. Endocrinology. 1983 Feb;112(2):601-9. PubMed PMID: 6129134.

View History

PD 125967

PD 125967

MSD-D

MSD-D

MB4280

MB4280

MB4253

MB4253

DPC AJ1951

DPC AJ1951

Trocimine

Trocimine