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MedKoo Cat#: 591400 | Name: Agosterol A

Description:

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

Agosterol A is extracted from marine sponge Spongia.

Chemical Structure

Agosterol A
Agosterol A
CAS#213549-32-7

Theoretical Analysis

MedKoo Cat#: 591400

Name: Agosterol A

CAS#: 213549-32-7

Chemical Formula: C33H52O8

Exact Mass: 576.3662

Molecular Weight: 576.77

Elemental Analysis: C, 68.72; H, 9.09; O, 22.19

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Agosterol A;
IUPAC/Chemical Name
Cholest-7-ene-3,4,6,11,22-pentol, 3,4,6-triacetate, (3beta,4beta,5alpha,6alpha,11alpha,22R)-
InChi Key
SUIRSZOPEPPNGJ-JGEDILIOSA-N
InChi Code
InChI=1S/C33H52O8/c1-17(2)9-12-25(37)18(3)23-10-11-24-22-15-28(40-20(5)35)30-31(41-21(6)36)27(39-19(4)34)13-14-32(30,7)29(22)26(38)16-33(23,24)8/h15,17-18,23-31,37-38H,9-14,16H2,1-8H3/t18-,23+,24-,25+,26+,27-,28-,29+,30-,31-,32+,33+/m0/s1
SMILES Code
CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@@]2([H])C3=C[C@H](OC(C)=O)[C@@]4([H])[C@@H](OC(C)=O)[C@@H](OC(C)=O)CC[C@]4(C)[C@@]3([H])[C@H](O)C[C@]12C
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 576.77 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: Abraham I, El Sayed K, Chen ZS, Guo H. Current status on marine products with reversal effect on cancer multidrug resistance. Mar Drugs. 2012 Oct;10(10):2312-21. doi: 10.3390/md10102312. Epub 2012 Oct 19. Review. PubMed PMID: 23170086; PubMed Central PMCID: PMC3497025. 2: Ren XQ, Furukawa T, Yamamoto M, Aoki S, Kobayashi M, Nakagawa M, Akiyama S. A functional role of intracellular loops of human multidrug resistance protein 1. J Biochem. 2006 Sep;140(3):313-8. Epub 2006 Jul 21. PubMed PMID: 16861249. 3: Noguchi T, Ren XQ, Aoki S, Igarashi Y, Che XF, Nakajima Y, Takahashi H, Mitsuo R, Tsujikawa K, Sumizawa T, Haraguchi M, Kobayashi M, Goto S, Kanehisa M, Aikou T, Akiyama S, Furukawa T. MRP1 mutated in the L0 region transports SN-38 but not leukotriene C4 or estradiol-17 (beta-D-glucuronate). Biochem Pharmacol. 2005 Oct 1;70(7):1056-65. PubMed PMID: 16098482. 4: Ren XQ, Furukawa T, Nakajima Y, Takahashi H, Aoki S, Sumizawa T, Haraguchi M, Kobayashi M, Chijiiwa K, Akiyama S. GSH inhibits trypsinization of the C-terminal half of human MRP1. J Biol Chem. 2005 Feb 18;280(7):6231-7. Epub 2004 Dec 3. PubMed PMID: 15579473. 5: Mitsuo M, Noguchi T, Nakajima Y, Aoki S, Ren XQ, Sumizawa T, Haraguchi M, Kobayashi M, Baba M, Nagata Y, Akiyama S, Furukawa T. Binding site(s) on P-glycoprotein for a newly synthesized photoaffinity analog of agosterol A. Oncol Res. 2003;14(1):39-48. PubMed PMID: 14552590. 6: Ren XQ, Furukawa T, Aoki S, Sumizawa T, Haraguchi M, Che XF, Kobayashi M, Akiyama S. Localization of the GSH-dependent photolabelling site of an agosterol A analog on human MRP1. Br J Pharmacol. 2003 Apr;138(8):1553-61. PubMed PMID: 12721111; PubMed Central PMCID: PMC1573804. 7: Ren XQ, Furukawa T, Aoki S, Sumizawa T, Haraguchi M, Nakajima Y, Ikeda R, Kobayashi M, Akiyama S. A positively charged amino acid proximal to the C-terminus of TM17 of MRP1 is indispensable for GSH-dependent binding of substrates and for transport of LTC4. Biochemistry. 2002 Dec 3;41(48):14132-40. PubMed PMID: 12450376. 8: Che XF, Nakajima Y, Sumizawa T, Ikeda R, Ren XQ, Zheng CL, Mukai M, Furukawa T, Haraguchi M, Gao H, Sugimoto Y, Akiyama S. Reversal of P-glycoprotein mediated multidrug resistance by a newly synthesized 1,4-benzothiazipine derivative, JTV-519. Cancer Lett. 2002 Dec 10;187(1-2):111-9. PubMed PMID: 12359358. 9: Aoki S, Chen ZS, Higasiyama K, Setiawan A, Akiyama S, Kobayashi M. Reversing effect of agosterol A, a spongean sterol acetate, on multidrug resistance in human carcinoma cells. Jpn J Cancer Res. 2001 Aug;92(8):886-95. PubMed PMID: 11509122; PubMed Central PMCID: PMC5926837. 10: Murakami N, Sugimoto M, Morita M, Kobayashi M. Total synthesis of agosterol A: an MDR-modulator from a marine sponge. Chemistry. 2001 Jun 18;7(12):2663-70. PubMed PMID: 11465457. 11: Chen ZS, Aoki S, Komatsu M, Ueda K, Sumizawa T, Furukawa T, Okumura H, Ren XQ, Belinsky MG, Lee K, Kruh GD, Kobayashi M, Akiyama S. Reversal of drug resistance mediated by multidrug resistance protein (MRP) 1 by dual effects of agosterol A on MRP1 function. Int J Cancer. 2001 Jul 1;93(1):107-13. PubMed PMID: 11391629. 12: Ren XQ, Furukawa T, Aoki S, Nakajima T, Sumizawa T, Haraguchi M, Chen ZS, Kobayashi M, Akiyama S. Glutathione-dependent binding of a photoaffinity analog of agosterol A to the C-terminal half of human multidrug resistance protein. J Biol Chem. 2001 Jun 22;276(25):23197-206. Epub 2001 Apr 11. PubMed PMID: 11301332. 13: Murakami N, Sugimoto M, Morita M, Akiyama S, Kobayashi M. Synthesis and evaluation of 4-deacetoxyagosterol A as an MDR-modulator. Bioorg Med Chem Lett. 2000 Nov 20;10(22):2521-4. PubMed PMID: 11086720.