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MedKoo Cat#: 534834 | Name: Muristerone A
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Description:

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

Muristerone A is a phytoecdysteroid.

Chemical Structure

Muristerone A
Muristerone A
CAS#38778-30-2

Theoretical Analysis

MedKoo Cat#: 534834

Name: Muristerone A

CAS#: 38778-30-2

Chemical Formula: C27H44O8

Exact Mass: 496.3036

Molecular Weight: 496.64

Elemental Analysis: C, 65.30; H, 8.93; O, 25.77

Price and Availability

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1mg USD 405.00 2 Weeks
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Related CAS #
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Synonym
Muristerone A
IUPAC/Chemical Name
Cholest-7-en-6-one, 2,3,5,11,14,20,22-heptahydroxy-, (2beta,3beta,5beta,11alpha,22R)-
InChi Key
LRJUYAVTHIEHAI-LHBNDURVSA-N
InChi Code
InChI=1S/C27H44O8/c1-14(2)6-7-20(31)25(5,33)19-8-9-26(34)15-10-21(32)27(35)13-17(29)16(28)11-24(27,4)22(15)18(30)12-23(19,26)3/h10,14,16-20,22,28-31,33-35H,6-9,11-13H2,1-5H3/t16-,17+,18+,19-,20+,22+,23+,24+,25+,26+,27+/m0/s1
SMILES Code
CC(C)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC([C@]4(O)C[C@@H](O)[C@@H](O)C[C@]4(C)[C@@]3([H])[C@H](O)C[C@]12C)=O
Appearance
Solid powder
Purity
>95% (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
>3 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Muristerone A is a phytoecdysteroid analog of ecdysone and a potent agonist of ecdysteroid receptor with a Kd of 1 nM.
In vitro activity:
Inhibition of Fas ligand- and TNF-related apoptosis-inducing ligand-induced apoptosis by muristerone A occurs at the level of caspase-8 activation and is neutralized by phosphatidylinositol-3-kinase/Akt, protein kinase C and mitogen-activated protein kinase inhibitors. Microarray, Northern and Western blot analysis revealed that incubation of RKO cells with muristerone A leads to changes in gene expression levels, including an upregulation of bcl-x(L) mRNA and protein levels. Reference: Cell Death Differ. 2006 Feb;13(2):189-201. https://pubmed.ncbi.nlm.nih.gov/16082389/
In vivo activity:
In this study, human dermal fibroblasts (hDFBs) were genetically modified to release human nerve growth factor (NGF) using an ecdysone-inducible system. When transfected hDFBs in the presence of Muristerone A were placed in vivo in nude rats, NGF levels reach 2074 +/- 257 pg/mL and 1620 +/- 132 pg/mL at 24 and 48 h, respectively. These levels were significantly higher than negative control and wound fluid levels. Reference: Tissue Eng. 2001 Jun;7(3):303-11. https://pubmed.ncbi.nlm.nih.gov/11429150/

Preparing Stock Solutions

The following data is based on the product molecular weight 496.64 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
Formulation protocol:
1. Nieva C, Spindler-Barth M, Azoitei A, Spindler KD. Influence of hormone on intracellular localization of the Drosophila melanogaster ecdysteroid receptor (EcR). Cell Signal. 2007 Dec;19(12):2582-7. doi: 10.1016/j.cellsig.2007.08.007. Epub 2007 Aug 23. PMID: 17884338. 2. Oehme I, Bösser S, Zörnig M. Agonists of an ecdysone-inducible mammalian expression system inhibit Fas Ligand- and TRAIL-induced apoptosis in the human colon carcinoma cell line RKO. Cell Death Differ. 2006 Feb;13(2):189-201. doi: 10.1038/sj.cdd.4401730. PMID: 16082389. 3. Patrick CW Jr, Zheng B, Wu X, Gurtner G, Barlow M, Koutz C, Chang D, Schmidt M, Evans GR. Muristerone A-induced nerve growth factor release from genetically engineered human dermal fibroblasts for peripheral nerve tissue engineering. Tissue Eng. 2001 Jun;7(3):303-11. doi: 10.1089/10763270152044161. PMID: 11429150. 4. Liu CJ, Wang H, Lengyel P. The interferon-inducible nucleolar p204 protein binds the ribosomal RNA-specific UBF1 transcription factor and inhibits ribosomal RNA transcription. EMBO J. 1999 May 17;18(10):2845-54. doi: 10.1093/emboj/18.10.2845. PMID: 10329630; PMCID: PMC1171365.
In vitro protocol:
1. Nieva C, Spindler-Barth M, Azoitei A, Spindler KD. Influence of hormone on intracellular localization of the Drosophila melanogaster ecdysteroid receptor (EcR). Cell Signal. 2007 Dec;19(12):2582-7. doi: 10.1016/j.cellsig.2007.08.007. Epub 2007 Aug 23. PMID: 17884338. 2. Oehme I, Bösser S, Zörnig M. Agonists of an ecdysone-inducible mammalian expression system inhibit Fas Ligand- and TRAIL-induced apoptosis in the human colon carcinoma cell line RKO. Cell Death Differ. 2006 Feb;13(2):189-201. doi: 10.1038/sj.cdd.4401730. PMID: 16082389.
In vivo protocol:
1. Patrick CW Jr, Zheng B, Wu X, Gurtner G, Barlow M, Koutz C, Chang D, Schmidt M, Evans GR. Muristerone A-induced nerve growth factor release from genetically engineered human dermal fibroblasts for peripheral nerve tissue engineering. Tissue Eng. 2001 Jun;7(3):303-11. doi: 10.1089/10763270152044161. PMID: 11429150. 2. Liu CJ, Wang H, Lengyel P. The interferon-inducible nucleolar p204 protein binds the ribosomal RNA-specific UBF1 transcription factor and inhibits ribosomal RNA transcription. EMBO J. 1999 May 17;18(10):2845-54. doi: 10.1093/emboj/18.10.2845. PMID: 10329630; PMCID: PMC1171365.
1: Constantino S, Santos R, Gisselbrecht S, Gouilleux F. The ecdysone inducible gene expression system: unexpected effects of muristerone A and ponasterone A on cytokine signaling in mammalian cells. Eur Cytokine Netw. 2001 Apr- Jun;12(2):365-7. PMID: 11399528. 2: Patrick CW Jr, Zheng B, Wu X, Gurtner G, Barlow M, Koutz C, Chang D, Schmidt M, Evans GR. Muristerone A-induced nerve growth factor release from genetically engineered human dermal fibroblasts for peripheral nerve tissue engineering. Tissue Eng. 2001 Jun;7(3):303-11. doi: 10.1089/10763270152044161. PMID: 11429150. 3: Xie J, Nair A, Hermiston TW. A comparative study examining the cytotoxicity of inducible gene expression system ligands in different cell types. Toxicol In Vitro. 2008 Feb;22(1):261-6. doi: 10.1016/j.tiv.2007.08.019. Epub 2007 Sep 6. PMID: 17928190. 4: Yam JW, Chan KW, Hsiao WL. Suppression of the tumorigenicity of mutant p53-transformed rat embryo fibroblasts through expression of a newly cloned rat nonmuscle myosin heavy chain-B. Oncogene. 2001 Jan 4;20(1):58-68. doi: 10.1038/sj.onc.1203982. PMID: 11244504. 5: Ling T, Lang WH, Maier J, Quintana Centurion M, Rivas F. Cytostatic and Cytotoxic Natural Products against Cancer Cell Models. Molecules. 2019 May 26;24(10):2012. doi: 10.3390/molecules24102012. PMID: 31130671; PMCID: PMC6571673. 6: Mhashilkar AS, Vankayala SL, Liu C, Kearns F, Mehrotra P, Tzertzinis G, Palli SR, Woodcock HL, Unnasch TR. Identification of Ecdysone Hormone Receptor Agonists as a Therapeutic Approach for Treating Filarial Infections. PLoS Negl Trop Dis. 2016 Jun 14;10(6):e0004772. doi: 10.1371/journal.pntd.0004772. PMID: 27300294; PMCID: PMC4907521. 7: Gao H, Sellin LK, Pütz M, Nickel C, Imgrund M, Gerke P, Nitschke R, Walz G, Kramer-Zucker AG. A short carboxy-terminal domain of polycystin-1 reorganizes the microtubular network and the endoplasmic reticulum. Exp Cell Res. 2009 Apr 15;315(7):1157-70. doi: 10.1016/j.yexcr.2009.01.027. Epub 2009 Feb 10. PMID: 19331813. 8: Beatty JM, Smagghe G, Ogura T, Nakagawa Y, Spindler-Barth M, Henrich VC. Properties of ecdysteroid receptors from diverse insect species in a heterologous cell culture system--a basis for screening novel insecticidal candidates. FEBS J. 2009 Jun;276(11):3087-98. doi: 10.1111/j.1742-4658.2009.07026.x. Epub 2009 Apr 22. PMID: 19490110. 9: Davis EM, Musch mW, Goldstein L. Transfection of an inducible trout anion exchanger (AE1) into HEK-EcR cells. J Exp Zool. 2002 Jun 15;293(1):46-57. doi: 10.1002/jez.10111. PMID: 12115918. 10: Nieva C, Spindler-Barth M, Azoitei A, Spindler KD. Influence of hormone on intracellular localization of the Drosophila melanogaster ecdysteroid receptor (EcR). Cell Signal. 2007 Dec;19(12):2582-7. doi: 10.1016/j.cellsig.2007.08.007. Epub 2007 Aug 23. PMID: 17884338. 11: Zhang Q, Tian L, Mansouri A, Korapati AL, Johnson TJ, Claret FX. Inducible expression of a degradation-resistant form of p27Kip1 causes growth arrest and apoptosis in breast cancer cells. FEBS Lett. 2005 Jul 18;579(18):3932-40. doi: 10.1016/j.febslet.2005.06.012. PMID: 15996662; PMCID: PMC1366489. 12: Henrich VC, Burns E, Yelverton DP, Christensen E, Weinberger C. Juvenile hormone potentiates ecdysone receptor-dependent transcription in a mammalian cell culture system. Insect Biochem Mol Biol. 2003 Dec;33(12):1239-47. doi: 10.1016/j.ibmb.2003.08.002. PMID: 14599496. 13: Lüers GH, Jess N, Franz T. Reporter-linked monitoring of transgene expression in living cells using the ecdysone-inducible promoter system. Eur J Cell Biol. 2000 Sep;79(9):653-7. doi: 10.1078/0171-9335-00086. PMID: 11043406. 14: Olson DL, Norcross JA, O'Neil-Johnson M, Molitor PF, Detlefsen DJ, Wilson AG, Peck TL. Microflow NMR: concepts and capabilities. Anal Chem. 2004 May 15;76(10):2966-74. doi: 10.1021/ac035426l. PMID: 15144211. 15: Cole SL, Schindler M, Sellers LA, Humphrey PP. Titrating the expression of a Gi protein-coupled receptor using an ecdysone-inducible system in CHO-K1 cells. Receptors Channels. 2001;7(4):289-302. PMID: 11697234. 16: Duquesne F, Florent M, Roué G, Troussard X, Sola B. Ectopic expression of cyclin D1 impairs the proliferation and enhances the apoptosis of a murine lymphoid cell line. Cell Death Differ. 2001 Jan;8(1):51-62. doi: 10.1038/sj.cdd.4400768. PMID: 11313703. 17: Timmer RT, Gunn RB. Inducible expression of erythrocyte band 3 protein. Am J Physiol. 1999 Jan;276(1):C66-75. doi: 10.1152/ajpcell.1999.276.1.C66. PMID: 9886921. 18: Bielska K, Seliga J, Wieczorek E, Kędracka-Krok S, Niedenthal R, Ożyhar A. Alternative sumoylation sites in the Drosophila nuclear receptor Usp. J Steroid Biochem Mol Biol. 2012 Nov;132(3-5):227-38. doi: 10.1016/j.jsbmb.2012.05.011. Epub 2012 Jun 4. PMID: 22676916. 19: Alexander HK, Booy EP, Xiao W, Ezzati P, Baust H, Los M. Selected technologies to control genes and their products for experimental and clinical purposes. Arch Immunol Ther Exp (Warsz). 2007 May-Jun;55(3):139-49. doi: 10.1007/s00005-007-0025-7. Epub 2007 Jun 8. PMID: 17557142. 20: Tarrant AM, Behrendt L, Stegeman JJ, Verslycke T. Ecdysteroid receptor from the American lobster Homarus americanus: EcR/RXR isoform cloning and ligand- binding properties. Gen Comp Endocrinol. 2011 Sep 1;173(2):346-55. doi: 10.1016/j.ygcen.2011.06.010. Epub 2011 Jun 22. PMID: 21722641.