A 80915A

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

MedKoo CAT#: 571210

CAS#: 127875-60-9

Description: A 80915A is A semi-naphthoquinone antibiotic produced by Streptomyces aculeolatus. It is a potent inhibitor of gastric (H(+)-K+)-ATPase, the enzyme responsible for acid secretion in the stomach. Inhibition by A80915A is dependent on the conformation of gastric (H(+)-K+)-ATPase and that potassium slows the rate of inhibition by converting the enzyme to a conformation where the drug binding site is not as accessible.


Price and Availability

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A 80915A is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571210
Name: A 80915A
CAS#: 127875-60-9
Chemical Formula: C26H31Cl3O5
Exact Mass: 528.1237
Molecular Weight: 529.88
Elemental Analysis: C, 58.94; H, 5.90; Cl, 20.07; O, 15.10


Synonym: A 80915A; A-80915A; A80915A;

IUPAC/Chemical Name: 2H-Naphtho(2,3-b)pyran-5,10-dione, 3,4a-dichloro-10a-((3-chloro-2,2-dimethyl-6-methylenecyclohexyl)methyl)-3,4,4a,10a-tetrahydro-6,8-dihydroxy-2,2,7-trimethyl-

InChi Key: JCIYFFNGTHMEDE-UHFFFAOYSA-N

InChi Code: InChI=1S/C26H31Cl3O5/c1-12-7-8-17(27)23(3,4)15(12)10-26-21(32)14-9-16(30)13(2)20(31)19(14)22(33)25(26,29)11-18(28)24(5,6)34-26/h9,15,17-18,30-31H,1,7-8,10-11H2,2-6H3

SMILES Code: O=C(C1(Cl)C2(CC3C(C)(C)C(Cl)CCC3=C)OC(C)(C)C(Cl)C1)C4=C(C2=O)C=C(O)C(C)=C4O


Technical Data

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).

Harmonized System Code:
293490


References

1: Haste NM, Farnaes L, Perera VR, Fenical W, Nizet V, Hensler ME. Bactericidal kinetics of marine-derived napyradiomycins against contemporary methicillin-resistant Staphylococcus aureus. Mar Drugs. 2011;9(4):680-9. doi: 10.3390/md9040680. Epub 2011 Apr 21. PubMed PMID: 21731557; PubMed Central PMCID: PMC3124980.

2: Ono S, Guntupalli J, DuBose TD Jr. Role of H(+)-K(+)-ATPase in pHi regulation in inner medullary collecting duct cells in culture. Am J Physiol. 1996 May;270(5 Pt 2):F852-61. PubMed PMID: 8928848.

3: Dantzig AH, Minor PL, Garrigus JL, Fukuda DS, Mynderse JS. Studies on the mechanism of action of A80915A, a semi-naphthoquinone natural product, as an inhibitor of gastric (H(+)-K+)-ATPase. Biochem Pharmacol. 1991 Oct 24; 42(10):2019-26. PubMed PMID: 1683772.

4: Armitage FE, Wingo CS. Luminal acidification in K-replete OMCDi: inhibition of bicarbonate absorption by K removal and luminal Ba. Am J Physiol. 1995 Jul;269(1 Pt 2):F116-24. PubMed PMID: 7631825.

5: Armitage FE, Wingo CS. Luminal acidification in K-replete OMCDi: contributions of H-K-ATPase and bafilomycin-A1-sensitive H-ATPase. Am J Physiol. 1994 Sep; 267(3 Pt 2):F450-8. PubMed PMID: 8092259.

6: Zhou X, Xia SL, Wingo CS. Chloride transport by the rabbit cortical collecting duct: dependence on H,K-ATPase. J Am Soc Nephrol. 1998 Dec;9(12):2194-202. PubMed PMID: 9848773.