Oligomycin
{{short description|Group of chemical compounds}}
{{Chembox
| Watchedfields = changed
| verifiedrevid = 432936619
| Name = Oligomycin A
| ImageFile = Oligomycin A.png
| IUPACName = (1R,4E,5
| OtherNames = Oligomycin
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106358
| InChI = 1S/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1
| InChIKey = QBAMBSAJEFIQBK-GJHUHQBXBC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QBAMBSAJEFIQBK-GJHUHQBXSA-N
| InChIKey1 = QBAMBSAJEFIQBK-GJHUHQBXSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1404-19-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 14JVM0OHLV
| EINECS = 215-767-9
| PubChem = 6450197
| SMILES = C[C@](C)(O)C[C@H]1O[C@@]2(CC[C@H]1C)O[C@H]3CC[C@@H](CC)/C=C\C=C\C[C@H](C)[C@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@@H](C)[C@H](O)[C@H](C)/C=C/C(=O)O[C@H]([C@H]2C)[C@H]3C
| RTECS = RK3325000
| ChEBI = 28285
| MeSHName = Oligomycins
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
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|Section2={{Chembox Properties
| C=45 | H=74 | O=11
| MolarMass = 791.062 g/mol
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|Section3={{Chembox Structure
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|Section4={{Chembox Thermochemistry
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|Section5={{Chembox Pharmacology
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|Section6={{Chembox Explosive
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|Section7={{Chembox Hazards
| ExternalSDS = [http://www.fermentek.co.il/MSDS/oligomycin-MSDS.htm MSDS at Fermentek]
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|Section9={{Chembox Related
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Oligomycins are macrolides created by Streptomyces that are strong antibacterial agents but are often poisonous to other organisms, including humans.
Function
Oligomycins have use as antibiotics. However, in humans, they have limited or no clinical use due to their toxic effects on mitochondria and ATP synthase.{{cite journal | vauthors = Mackieh R, Al-Bakkar N, Kfoury M, Roufayel R, Sabatier JM, Fajloun Z | title = Inhibitors of ATP Synthase as New Antibacterial Candidates | journal = Antibiotics | volume = 12 | issue = 4 | pages = 650 | date = March 2023 | pmid = 37107012 | pmc = 10135114 | doi = 10.3390/antibiotics12040650 | doi-access = free }}
Oligomycin A is an inhibitor of ATP synthase. In oxidative phosphorylation research, it is used to prevent stage 3 (phosphorylating) respiration. 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.{{cite journal | vauthors = Jastroch M, Divakaruni AS, Mookerjee S, Treberg JR, Brand MD | title = Mitochondrial proton and electron leaks | journal = Essays in Biochemistry | volume = 47 | issue = 1 | pages = 53–67 | year = 2010 | pmid = 20533900 | pmc = 3122475 | doi = 10.1042/bse0470053 }} This process is due to facilitated diffusion of protons into the mitochondrial matrix through an uncoupling protein such as thermogenin, or UCP1.
Administering oligomycin to rats can result in very high levels of lactate accumulating in the blood and urine.{{cite journal | vauthors = Kramar R, Hohenegger M, Srour AN, Khanakah G | title = Oligomycin toxicity in intact rats | journal = Agents and Actions | volume = 15 | issue = 5–6 | pages = 660–663 | date = December 1984 | pmid = 6532186 | doi = 10.1007/BF01966788 | s2cid = 7837164 }}
| border="1" cellpadding="5" cellspacing="0" |
| colspan="6" | 200px |
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| R1 | R2 | R3 | R4 | R5 |
| Oligomycin A
| CH3 | H | OH | H,H | CH3 |
| Oligomycin B
| CH3 | H | OH | O | CH3 |
| Oligomycin C
| CH3 | H | H | H,H | CH3 |
| Oligomycin D (Rutamycin A) | H | H | OH | H,H | CH3 |
| Oligomycin E
| CH3 | OH | OH | O | CH3 |
| Oligomycin F
| CH3 | H | OH | H,H | CH2CH3 |
| Rutamycin B
| H | H | H | H,H | CH3 |
| 44-Homooligomycin A
| CH2CH3 | H | OH | H,H | CH3 |
| 44-Homooligomycin B
| CH2CH3 | H | OH | O | CH3 |
{{Clear}}