Oligomycin A | CAS#579-13-5 | ATP synthase inhibitor

MedKoo Cat#: 329825 | Name: Oligomycin A

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Description:

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

Oligomycin A, also known as MCH 32, is an inhibitor of ATP synthase. Oligomycin A inhibits ATP synthase by blocking its proton channel (Fo subunit), which is necessary for oxidative phosphorylation of ADP to ATP (energy production). The inhibition of ATP synthesis by oligomycin A will significantly reduce electron flow through the electron transport chain; however, electron flow is not stopped completely due to a process known as proton leak or mitochondrial uncoupling. This process is due to facilitated diffusion of protons into the mitochondrial matrix through an uncoupling protein such as thermogenin, or UCP1.

Chemical Structure

Oligomycin A

CAS#579-13-5

Theoretical Analysis

MedKoo Cat#: 329825

Name: Oligomycin A

CAS#: 579-13-5

Chemical Formula: C45H72O11

Exact Mass: 788.5075

Molecular Weight: 789.06

Elemental Analysis: C, 68.50; H, 9.20; O, 22.30

Price and Availability

Size	Price	Availability
25mg	USD 750.00	2 Weeks
50mg	USD 1,250.00	2 Weeks
100mg	USD 2,250.00	2 Weeks
200mg	USD 3,950.00	2 Weeks

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Related CAS #

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Synonym

Oligomycin A; MCH 32; MCH 32; MCH 32.

IUPAC/Chemical Name

(1S,2'R,4E,5'R,6R,6'S,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,28R,29S)-22-ethyl-3',4',5',6'-tetrahydro-7,11,14,15-tetrahydroxy-6'-[(1Z)-2-hydroxy-1-propen-1-yl]-5',6,8,10,12,14,16,28,29-nonamethyl-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,9,13-trione

InChi Key

STEWZSZUSBALCS-HQBODTQXSA-N

InChi Code

InChI=1S/C45H72O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,24-27,29-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-23H2,1-11H3/b14-13+,17-15+,21-18+,28-24-/t25-,26-,27+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m1/s1

SMILES Code

O=C(/C=C/[C@@H](C)[C@H](O)[C@@H](C)C([C@@H](C)[C@H](O)[C@H]1C)=O)O[C@]([C@H]2C)([H])[C@@H](C)[C@]3(CC[C@@H](C)[C@@H](/C=C(O)/C)O3)O[C@]2([H])CC[C@H](CC)/C=C/C=C/C[C@H](C)[C@@H](O)[C@](C)(O)C1=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

>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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C23M05C08

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Oligomycin A (MCH 32), created by Streptomyces, acts as a mitochondrial F0F1-ATPase inhibitor, with a Ki of 1 μM.

In vitro activity:

Incubation of boar spermatozoa in a capacitation medium with oligomycin A, a specific inhibitor of the F0 component of the mitochondrial ATP synthase, induced an immediate and almost complete immobilisation of cells. Oligomycin A also inhibited the ability of spermatozoa to achieve feasible in vitro capacitation (IVC), as measured through IVC-compatible changes in motility patterns, tyrosine phosphorylation levels of the acrosomal p32 protein, membrane fluidity and the ability of spermatozoa to achieve subsequent, progesterone-induced in vitro acrosome exocytosis (IVAE). Both inhibitory effects were caused without changes in the rhythm of O2 consumption, intracellular ATP levels or mitochondrial membrane potential (MMP). IVAE was accompanied by a fast and intense peak in O2 consumption and ATP levels in control spermatozoa. Oligomycin A also inhibited progesterone-induced IVAE as well as the concomitant peaks of O2 consumption and ATP levels. Reference: Reprod Fertil Dev. 2014;26(6):883-97. https://pubmed.ncbi.nlm.nih.gov/25319379/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	126.73
	Ethanol	100.0	126.73

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 789.06 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.

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. Ramió-Lluch L, Yeste M, Fernández-Novell JM, Estrada E, Rocha L, Cebrián-Pérez JA, Muiño-Blanco T, Concha II, Ramírez A, Rodríguez-Gil JE. Oligomycin A-induced inhibition of mitochondrial ATP-synthase activity suppresses boar sperm motility and in vitro capacitation achievement without modifying overall sperm energy levels. Reprod Fertil Dev. 2014;26(6):883-97. doi: 10.1071/RD13145. PMID: 25319379. 2. He L, Jang JH, Choi HG, Lee SM, Nan MH, Jeong SJ, Dong Z, Kwon YT, Lee KS, Lee KW, Chung JK, Ahn JS, Kim BY. Oligomycin A enhances apoptotic effect of TRAIL through CHOP-mediated death receptor 5 expression. Mol Carcinog. 2013 Feb;52(2):85-93. doi: 10.1002/mc.21831. Epub 2011 Nov 15. PMID: 23335397.

In vitro protocol:

In vivo protocol:

TBD

1: Lysenkova LN, Saveljev OY, Grammatikova NE, Tsvetkov VB, Bekker OB, Danilenko VN, Dezhenkova LG, Bykov EE, Omelchuk OA, Korolev AM, Shchekotikhin AE. Verification of oligomycin A structure: synthesis and biological evaluation of 33-dehydrooligomycin A. J Antibiot (Tokyo). 2017 Jul;70(8):871-877. doi: 10.1038/ja.2017.48. Epub 2017 Apr 19. PubMed PMID: 28420869. 2: Han S, Pham TV, Kim JH, Lim YR, Park HG, Cha GS, Yun CH, Chun YJ, Kang LW, Kim D. Structural Analysis of the Streptomyces avermitilis CYP107W1-Oligomycin A Complex and Role of the Tryptophan 178 Residue. Mol Cells. 2016 Mar;39(3):211-6. doi: 10.14348/molcells.2016.2226. Epub 2016 Feb 16. PubMed PMID: 26883908; PubMed Central PMCID: PMC4794603. 3: Han S, Pham TV, Kim JH, Lim YR, Park HG, Cha GS, Yun CH, Chun YJ, Kang LW, Kim D. Functional characterization of CYP107W1 from Streptomyces avermitilis and biosynthesis of macrolide oligomycin A. Arch Biochem Biophys. 2015 Jun 1;575:1-7. doi: 10.1016/j.abb.2015.03.025. Epub 2015 Apr 4. PubMed PMID: 25849761. 4: Serrill JD, Tan M, Fotso S, Sikorska J, Kasanah N, Hau AM, McPhail KL, Santosa DA, Zabriskie TM, Mahmud T, Viollet B, Proteau PJ, Ishmael JE. Apoptolidins A and C activate AMPK in metabolically sensitive cell types and are mechanistically distinct from oligomycin A. Biochem Pharmacol. 2015 Feb 1;93(3):251-65. doi: 10.1016/j.bcp.2014.11.015. Epub 2014 Dec 12. PubMed PMID: 25511868. 5: Ramió-Lluch L, Yeste M, Fernández-Novell JM, Estrada E, Rocha L, Cebrián-Pérez JA, Muiño-Blanco T, Concha II, Ramírez A, Rodríguez-Gil JE. Oligomycin A-induced inhibition of mitochondrial ATP-synthase activity suppresses boar sperm motility and in vitro capacitation achievement without modifying overall sperm energy levels. Reprod Fertil Dev. 2014;26(6):883-97. doi: 10.1071/RD13145. PubMed PMID: 25319379. 6: Lysenkova LN, Turchin KF, Korolev AM, Danilenko VN, Bekker OB, Dezhenkova LG, Shtil AA, Preobrazhenskaya MN. Study on retroaldol degradation products of antibiotic oligomycin A. J Antibiot (Tokyo). 2014 Feb;67(2):153-8. doi: 10.1038/ja.2013.92. Epub 2013 Oct 2. PubMed PMID: 24084683. 7: Palmer RA, Ladd M, Howlin B, Lisgarten DR. X-ray structures of two forms of the antibiotic oligomycin A: an inhibitor of ATP synthase. Future Med Chem. 2013 May;5(8):881-93. doi: 10.4155/fmc.13.68. PubMed PMID: 23682566. 8: Lysenkova LN, Turchin KF, Korolev AM, Dezhenkova LG, Bekker OB, Shtil AA, Danilenko VN, Preobrazhenskaya MN. Synthesis and cytotoxicity of oligomycin A derivatives modified in the side chain. Bioorg Med Chem. 2013 Jun 1;21(11):2918-24. doi: 10.1016/j.bmc.2013.03.081. Epub 2013 Apr 6. PubMed PMID: 23623676. 9: He L, Jang JH, Choi HG, Lee SM, Nan MH, Jeong SJ, Dong Z, Kwon YT, Lee KS, Lee KW, Chung JK, Ahn JS, Kim BY. Oligomycin A enhances apoptotic effect of TRAIL through CHOP-mediated death receptor 5 expression. Mol Carcinog. 2013 Feb;52(2):85-93. doi: 10.1002/mc.21831. Epub 2011 Nov 15. PubMed PMID: 23335397. 10: Lysenkova LN, Turchin KF, Korolev AM, Bykov EE, Danilenko VN, Bekker OB, Trenin AS, Elizarov SM, Dezhenkova LG, Shtil AA, Preobrazhenskaya MN. A novel acyclic oligomycin A derivative formed via retro-aldol rearrangement of oligomycin A. J Antibiot (Tokyo). 2012 Aug;65(8):405-11. doi: 10.1038/ja.2012.38. Epub 2012 May 23. PubMed PMID: 22617550. 11: Lysenkova LN, Turchin KF, Korolev AM, Danilenko VN, Bekker OB, Trenin AS, Shtil AA, Preobrazhenskaya MN. Synthesis and properties of a novel brominated oligomycin A derivative. J Antibiot (Tokyo). 2012 Apr;65(4):223-5. doi: 10.1038/ja.2012.4. Epub 2012 Feb 8. PubMed PMID: 22318333. 12: Lysenkova LN, Turchin KF, Danilenko VN, Korolev AM, Preobrazhenskaya MN. The first examples of chemical modification of oligomycin A. J Antibiot (Tokyo). 2010 Jan;63(1):17-22. doi: 10.1038/ja.2009.112. Epub 2009 Nov 13. PubMed PMID: 19911026. 13: Lin X, Wen Y, Li M, Chen Z, Guo J, Song Y, Li J. A new strain of Streptomyces avermitilis produces high yield of oligomycin A with potent anti-tumor activity on human cancer cell lines in vitro. Appl Microbiol Biotechnol. 2009 Jan;81(5):839-45. doi: 10.1007/s00253-008-1684-y. Epub 2008 Sep 20. PubMed PMID: 18810431. 14: Tettamanti G, Malagoli D, Ottaviani E, de Eguileor M. Oligomycin A and the IPLB-LdFB insect cell line: actin and mitochondrial responses. Cell Biol Int. 2008 Feb;32(2):287-92. Epub 2007 Nov 12. Erratum in: Cell Biol Int. 2008 Nov;32(11):1464. PubMed PMID: 18093849. 15: Tettamanti G, Malagoli D, Marchesini E, Congiu T, de Eguileor M, Ottaviani E. Oligomycin A induces autophagy in the IPLB-LdFB insect cell line. Cell Tissue Res. 2006 Oct;326(1):179-86. Epub 2006 Jun 10. PubMed PMID: 16767407. 16: Laatsch H, Kellner M, Wolf G, Lee YS, Hansske F, Konetschny-Rapp S, Pessara U, Scheuer W, Stockinger H. Oligomycin F, a new immunosuppressive homologue of oligomycin A. J Antibiot (Tokyo). 1993 Sep;46(9):1334-41. PubMed PMID: 8226311. 17: Nakakita Y, Nakagawa M, Sakai H. Isolation of oligomycin A as a result of screening for antagonists of lipids. J Antibiot (Tokyo). 1980 May;33(5):514-6. PubMed PMID: 7429975. 18: Roberton AM, Holloway CT, Knight IG, Beechey RB. A comparison of the effects of NN'-dicyclohexylcarbodi-imide, oligomycin A and aurovertin on enrgy-linked reactions in mitochondria and submitochondrial particles. Biochem J. 1968 Jul;108(3):445-56. PubMed PMID: 4299126; PubMed Central PMCID: PMC1198830. 19: Beechey RB, Williams V, Holloway CT, Knight IG, Roberton AM. Estimation of the molecular weights and molecular formulae of oligomycin-A, rutamycin & aurovertin by mass spectrometry. Biochem Biophys Res Commun. 1967 Feb 8;26(3):339-41. PubMed PMID: 6034358. 20: SMITH RM, PETERSON WH, McCOY E. Oligomycin, a new antifungal antibiotic. Antibiot Chemother (Northfield). 1954 Sep;4(9):962-70. PubMed PMID: 24543225.