Molecular structure of Oligomycin, CAS Number: 1404-19-9
Oligomycin (CAS 1404-19-9)
See product citations (18)
Alternate Names:
Oligomycin is also known as Oligomycin a, b, c mixture.
Application:
Oligomycin is an oxidative phosphorylation blocker and specific inhibitor of the mitochondrial ATP-synthase.
CAS Number:
1404-19-9
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 is a macrolide that acts as a specific inhibitor of the mitochondrial ATP-synthase and blocks oxidative phosphorylation. It is a mixture of isomers A (sc-201551), B (sc-202262), and C (sc-202263). Cancer cell studies show that Oligomycin does not activate the hypoxia-induced factor. Further studies report that it enhances the bioenergetic adaptation of heterogeneous bioenergetically organized cells. Additionally, it can decrease cyclin D1 protein expression levels.
Oligomycin (CAS 1404-19-9) References
- Structure-activity relationships within a family of selectively cytotoxic macrolide natural products. | Salomon, AR., et al. 2001. Org Lett. 3: 57-9. PMID: 11429871
- Oligomycin induced the proteasomal degradation of cyclin D1 protein. | Kanai, M., et al. 2009. J Antibiot (Tokyo). 62: 425-9. PMID: 19575044
- Oligomycin-induced bioenergetic adaptation in cancer cells with heterogeneous bioenergetic organization. | Hao, W., et al. 2010. J Biol Chem. 285: 12647-54. PMID: 20110356
- Oligomycin frames a common drug-binding site in the ATP synthase. | Symersky, J., et al. 2012. Proc Natl Acad Sci U S A. 109: 13961-5. PMID: 22869738
- 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
- Retraction: Oligomycin, an F1FO-ATPase inhibitor, protects against ischemic acute kidney injury in male but not in female rats. | . 2014. J Pharmacol Sci. 126: 291. PMID: 25409749
- Synthesis, antimicrobial and antiproliferative properties of epi-oligomycin A, the (33S)-diastereomer of oligomycin A. | Lysenkova, LN., et al. 2020. Nat Prod Res. 34: 3073-3081. PMID: 31075992
- Oligomycin-induced proton uncoupling. | Hearne, A., et al. 2020. Toxicol In Vitro. 67: 104907. PMID: 32502624
- A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium. | Saito, S., et al. 2020. Beilstein J Org Chem. 16: 1100-1110. PMID: 32550925
- Oligomycin A promotes radioresistance in HT29 colorectal cancer cells and its mechanisms. | Li, X., et al. 2021. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 46: 113-120. PMID: 33678646
- Glucose starvation greatly enhances antiproliferative and antiestrogenic potency of oligomycin A in MCF-7 breast cancer cells. | Scherbakov, AM., et al. 2021. Biochimie. 186: 51-58. PMID: 33872751
- Stereochemistries and Biological Properties of Oligomycin A Diels-Alder Adducts. | Omelchuk, OA., et al. 2021. J Org Chem. 86: 7975-7986. PMID: 34043357
- A dataset describing glycolytic inhibitors overcoming the underestimation of maximal mitochondrial oxygen consumption rate in oligomycin-treated cells. | Ruas, JS., et al. 2022. Data Brief. 40: 107739. PMID: 35005137
- Oligomycin toxicity in intact rats. | Kramar, R., et al. 1984. Agents Actions. 15: 660-3. PMID: 6532186
- Mitochondrial respiratory chain inhibitors induce apoptosis. | Wolvetang, EJ., et al. 1994. FEBS Lett. 339: 40-4. PMID: 8313978
Inhibitor of:
1190007I07Rik, 1810026J23Rik, 1810043H04Rik, 2900010M23Rik, acetyl-CoA acyltransferase 2 (ACAA2), ACOT9, ACSF3, AI-BP, AK1, apoO, apoOL, ARMCX4, ASCL5, ATAD3C, ATP10A, ATP10D, ATP11B, ATP5, ATP5ATP5L2, ATP5C1, ATP5E, ATP5G3, ATP5H, ATP5I, ATP5J2, ATP5S, ATP8, ATP8B (P-type ATPases), ATP8B1, ATPAF1, BCS1L, BOLA3, BRP44L, C10orf88, C11orf83, C20orf7, C3orf60, C7orf44, C7orf55, C7orf73, C8orf38, CCDC44, CHCHD8, CKMT1A, Clpb, CLS1, CNTNAP3, COA5, COX14, COX6a2, COX7a2L, COX7b2, creatine kinase-B, Cyclophilin F, cytochrome b561, Cytochrome c oxidase (COX), D10Jhu81e, Dbil5, DNAH5, EF-G2, EG546368, EG623286, ERAL1, ETHE1, EXTL1, FAHD1, FAM173A, FAM173B, FASTKD1, FASTKD2, FASTKD3, FDX1L, GCDH, Grim19, GrpEL2, GTPBP3, HAO2, HARS2, HCCR-1, HCCS, HDMCP, HGTD-P, HIGD1B, HPPDL, HRPAP20, HSP 75, IARS2, ICK, ICT1, IMMP1L, LIPT1, LOC147646, LOC283398, LONP2, LRP130, LYCAT, LYRM2, MAMSTR, MCART2, MCEE, MDH1B, ME3, Mecr, Metaxin 3, Mimp, MIPEP, MiRP1, Misato, Mitochondrial ATP synthase (ATP5G), Mitochondrial Inner Membrane, Mitochondrial Marker, Mitofilin, MMAA, Mot1, MPV17L2, MRP-L33, MT-ND (mitochondrial NADH dehydrogenase), MTCH1, MTERFD2, MTFmt, MTG1, MTHFD2L, Mtif3, MTMR12, mtp110, MTRF1, MTRF1L, ND4, ND6, NDUFB2, NDUFB6, NDUFB7, NDUFB9, NIMP, NUBPL, Oma1, OPA3, ORNT2, OSAP, OSCP, OSCP1, P117, p60 Mitochondrial Marker, PET100, Pma1p, PMPCB, PRELI, PRELID2, PRH2, PTCD1, PTCD3, PYROXD2, Ribosomal Protein S26, RPUSD1, RPUSD2, SBDS, SCaMC-1, SDHC, SerRSmt, SFXN2, SFXN3, SFXN4, SFXN5, SLC10A3, SLC25A14, SLC25A21, SLC25A22, SLC25A33, SLC25A34, SLC25A36, SLC25A40, SLC25A42, SLC25A43, SLC25A44, SLC25A48, SLC43A3, SR-α, Sval1, Syntaphilin, TAMM41, TaR-1, TBC1D20, TCEANC, TCP-1 ε, TDRD9, TFB2M, THAP6, Tim13A/B, Tim17A, Tim22, TMEM126A, TMEM33, TMEM60, Tom34, Tomm5, TSGA2, TSHZ2, UNQ9438, UQCRC2, UQCRH, V1RH10, VDAC3, VWCE, WDR93, XylT-I, Yfh1, and ZBTB24.Activator of:
4930420K17Rik, 4930468A15Rik, 4933412E24Rik, AFG3L2, AK2, AMPKα1, ATP5D, ATPAF1, C20orf7, COX4, Cstad, cytochrome c1, EG545802, EXOSC4, FASTKD3, GHITM, Hrnbp3, KIAA0664, KILLIN, LETM2, LOC100131244, LOC100131781, LOC100132288, LOC100132292, LOC100132418, LOC645202, LSm2, MARCH5, MCJ, METTL21A, Mitoferrin, MPC1L, MRP-L15, MRP-L22, MRP-S18B, NDUFA1, NTT4, OPA3, PGAM5, PISD, Pma2, PPA2, Pramel, RBM15, RIP3, SLC25A3, SLC25A45, SUCLG2, TaR-1, TGase5, Tim22, Tim8B, TMEM39B, TMEM60, Tomm20l, TRAP-1, UCRC, UQCRB, V-ATPase A2, V-ATPase F, and WDR34.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Oligomycin, 10 mg | sc-203342 | 10 mg | $146.00 | |||
Oligomycin, 1 g | sc-203342C | 1 g | $12250.00 |