Molecular structure of Oligomycin A, CAS Number: 579-13-5
Oligomycin A (CAS 579-13-5)
See product citations (26)
Alternate Names:
Oligomycin A is also known as Oligomycin A, Streptomyces.
Application:
Oligomycin A is a mitochondrial F1F0 ATP synthase inhibitor and uncoupler of oxidative phosphorylation, active in vivo and able to induce apoptosis in a variety of cell types.
CAS Number:
579-13-5
Purity:
>95%
Molecular Weight:
791.06
Molecular Formula:
C45H74O11
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Oligomycin A inhibits mitochondrial ATPases (F1F0) bound to the cell membrane. It stimulates lysosome acidification due to shunting of membrane potential at a concentration of 1.5-3 M. Oligomycin A has been observed to Induce apoptosis in a variety of cell types, along with inducing a switch from the apoptotic to necrotic pathway. It also exhibits broad nematocidal, antifungal, and antitumor activities. Oligomycin A has dissipated mitochondrial membrane potential, decreased cytoplasmic ATP contents, and disassembled metaphase II oocyte spindles when introduced to mouse oocytes. Oligomycin A is also known as MCH 32, (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, and Oligomycin A, Streptomyces.
Oligomycin A (CAS 579-13-5) References
- The BH3 domain is required for caspase-independent cell death induced by Bax and oligomycin. | Fitch, ME., et al. 2000. Cell Death Differ. 7: 338-49. PMID: 10773818
- Mitochondria in eosinophils: functional role in apoptosis but not respiration. | Peachman, KK., et al. 2001. Proc Natl Acad Sci U S A. 98: 1717-22. PMID: 11172017
- Inhibitors of the ATP synthethase system. | Linnett, PE. and Beechey, RB. 1979. Methods Enzymol. 55: 472-518. PMID: 156854
- Deficit of mitochondria-derived ATP during oxidative stress impairs mouse MII oocyte spindles. | Zhang, X., et al. 2006. Cell Res. 16: 841-50. PMID: 16983401
- A novel acyclic oligomycin A derivative formed via retro-aldol rearrangement of oligomycin A. | Lysenkova, LN., et al. 2012. J Antibiot (Tokyo). 65: 405-11. PMID: 22617550
- Oligomycin A enhances apoptotic effect of TRAIL through CHOP-mediated death receptor 5 expression. | He, L., et al. 2013. Mol Carcinog. 52: 85-93. PMID: 23335397
- Synthesis and cytotoxicity of oligomycin A derivatives modified in the side chain. | Lysenkova, LN., et al. 2013. Bioorg Med Chem. 21: 2918-24. PMID: 23623676
- X-ray structures of two forms of the antibiotic oligomycin A: an inhibitor of ATP synthase. | Palmer, RA., et al. 2013. Future Med Chem. 5: 881-93. PMID: 23682566
- Study on retroaldol degradation products of antibiotic oligomycin A. | Lysenkova, LN., et al. 2014. J Antibiot (Tokyo). 67: 153-8. PMID: 24084683
- Oligomycin A-induced inhibition of mitochondrial ATP-synthase activity suppresses boar sperm motility and in vitro capacitation achievement without modifying overall sperm energy levels. | Ramió-Lluch, L., et al. 2014. Reprod Fertil Dev. 26: 883-97. PMID: 25319379
- Apoptolidins A and C activate AMPK in metabolically sensitive cell types and are mechanistically distinct from oligomycin A. | Serrill, JD., et al. 2015. Biochem Pharmacol. 93: 251-65. PMID: 25511868
- Functional characterization of CYP107W1 from Streptomyces avermitilis and biosynthesis of macrolide oligomycin A. | Han, S., et al. 2015. Arch Biochem Biophys. 575: 1-7. PMID: 25849761
- Structural Analysis of the Streptomyces avermitilis CYP107W1-Oligomycin A Complex and Role of the Tryptophan 178 Residue. | Han, S., et al. 2016. Mol Cells. 39: 211-6. PMID: 26883908
- Verification of oligomycin A structure: synthesis and biological evaluation of 33-dehydrooligomycin A. | Lysenkova, LN., et al. 2017. J Antibiot (Tokyo). 70: 871-877. PMID: 28420869
- Acidification of rat liver lysosomes: quantitation and comparison with endosomes. | Van Dyke, RW. 1993. Am J Physiol. 265: C901-17. PMID: 8238315
Inhibitor of:
α-Amylase, from Bacillus amyloliquefaciens, 4921511M17Rik, 4921528O07Rik, 4930420K17Rik, 4930443G12Rik, 4932411G14Rik, 9430070O13Rik, ABCB7, ACAD-9, AFG3L1, AFG3L2, ALKBH7, AMCase, ANKRD13A, ANT3, ARMC3, ATAD3B, ATAD4, Ataxin-8, ATP-BL, ATP10B, ATP11A, ATP13A1, ATP13A5, ATP5, ATP5A, ATP5B, ATP5F1, ATP5G1, ATP5J, ATP5L2, ATP5SL, ATP6, ATP6E1, ATP8B5, ATPAF2, ATPIF1, BBS12, BTF3, C19orf12, C20orf72, Caytaxin, CCDC58, CHPPR, CIRH1A, CLPX, COA1, COX20, Cstad, DNALI1, DNTTIP2, EG628456, F1-ATPase, FAM113B, FAM96B, FARP2, FEV, FLJ22184, GABP-β1, GDAP1, GDAP1L1, Grpa, GTPBP10, GTPBP5, GTPBP8, GUF1, HIGD1A, HIGD2A, Hint2, IMMP2L, IMPA1, INTS5, Keg1, KIAA1143, LACE1, LACTB2, LOC100041282, LOC342541, LOC388564, LOC646037, LOC727745, LOC728730, LONP1, LYRM1, LYRM4, LYRM5, Magmas, MCART6, MFF, Midasin, Mimitin, MINOS1, Morc2b, MP68, MPC1L, MPV17, MRP-L46, MRPL28, MS4A6E, MSY4, Mtch2, MTERFD1, MTERFD3, MTO1, MTP18, MUL1, NARFL, NDUFA4L2, NDUFAF7, NUBP2, Olfr646, OXA1L, Paraplegin, PARL, PINK1, Psmg2, PTCD2, QIL1, RBM38, RBMY1B, RFX1, Rho T2, Ribosomal Protein L38, RMND1, RP24-329J6.2, Rpp14, RSPH9, RT1-Bβ, Sam 68, Sam50, SCAF1, Set1B, SFXN1, SH3TC2, SLC25A25, SLC25A29, SLC25A35, SLC25A41, SLC25A45, SLMO2, SMCR7L, Snurportin-1, SPAG7, SPANX-D, SPATA18, SPATA5L1, Spatacsin, StARD7, TEX10, TFB1M, Tim17B, Tim22, Tim50, TMEM11, TMEM135, TMEM150A, TMEM150B, TMEM39B, TMEM70, TMPPE, Tom40B, Tom7, Tom70, Trim12c, TTC23, TTC24, TTC34, TTI2_BC019943, uMtCK, UQCRB, USMG5, V-ATPase B2, WAC, WBSCR18, WDTC1, XYLB, YME1L1, and ZUFSP.Activator of:
2010309E21Rik, 4732471D19Rik, A130010J15Rik, AMPKγ3, ANKRD20A3, Annexin III, ATP6E1, ATP6V0E1, C030010C08Rik, CARD14, CD1A, CINP, ClpP, CMC1, COX7a2, CXorf66, cytochrome b, dinitrophenol, ENL, F1-ATPase, FAM21C, FUNDC1, gasdermin A3, gasdermin C, IgE, LACTB, LOC100130933, LONP2, Misato, MRP-L41, MRP-L49, MRRF, MTERF, Mtif3, ND1, OSCP, PADI2, PROS-30, RAIDD, RIBC2, RNase 9, RPS4Y1, SDHAF2, SLC25A18, SLC25A48, SUHW4, THAP5, Tim10, TMEM126A, TMEM37, UBE2B, Ubr4, UBTD2, UNC45B, V1RC23, V1RC25, V1RC27, V1rc29, V1RC32, V1rc5, V1rc8, V1RD10, V1RD12, V1RD14, ZNF37A, ZNF564, and ZNF628.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Oligomycin A, 5 mg | sc-201551 | 5 mg | $175.00 | |||
Oligomycin A, 25 mg | sc-201551A | 25 mg | $600.00 | |||
Oligomycin A, 100 mg | sc-201551B | 100 mg | $1179.00 | |||
Oligomycin A, 500 mg | sc-201551C | 500 mg | $5100.00 | |||
Oligomycin A, 1 g | sc-201551D | 1 g | $9180.00 |