Oligomycin Complex | CAS# 1404-19-9 | Macrolide

MedKoo Cat#: 574829 | Name: Oligomycin Complex

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Description:

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

Oligomycin Complex is a mixture of oligomycins A, B, and C. Oligomycin A is a selective inhibitor of mitochondrial F1FO-ATP synthase that induces apoptosis in a variety of cell types. Oligomycin B is a nonselective inhibitor of ATP synthases. Oligomycin B can reduce the rate of ATP depletion in myocardial ischemia and decrease calcium-induced calcium release oscillation frequency of rat sensory neurons. Oligomycin Complex is a mitochondria-related pathway inhibitor.

Chemical Structure

Oligomycin Complex

CAS#1404-19-9

Theoretical Analysis

MedKoo Cat#: 574829

Name: Oligomycin Complex

CAS#: 1404-19-9

Chemical Formula: C135H220O33

Exact Mass: 2369.5537

Molecular Weight: 2371.21

Elemental Analysis: C, 68.38; H, 9.35; O, 22.27

Price and Availability

Size	Price	Availability
1mg	USD 205.00	2 Weeks
5mg	USD 345.00	2 Weeks
10mg	USD 545.00	2 Weeks

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Synonym

Oligomycin Complex

IUPAC/Chemical Name

(1S,4E,5'R,6R,6'R,7S,8R,10S,11R,12R,14R,15R,16S,18E,20E,22S,25R,27S,28R,29S)-22-ethyl-7,11,15-trihydroxy-6'-((S)-2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-pyran]-4,18,20-triene-3,9,13-trione compound with (1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27R,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-((S)-2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-5',6'-dihydro-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-pyran]-4,18,20-triene-3,3',9,13(4'H)-tetraone and (1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,28R,29S)-22-ethyl-7,11,14,15-tetrahydroxy-6'-((S)-2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-pyran]-4,18,20-triene-3,9,13-trione (1:1:1)

InChi Key

YQXULOWIGKNTBK-BKROBWKBSA-N

InChi Code

InChI=1S/C45H72O12.C45H74O11.C45H74O10/c1-12-33-17-15-13-14-16-25(3)42(52)44(11,54)43(53)31(9)40(51)30(8)39(50)29(7)38(49)24(2)18-21-37(48)55-41-28(6)34(20-19-33)56-45(32(41)10)36(47)22-26(4)35(57-45)23-27(5)46;1-12-34-17-15-13-14-16-27(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;1-12-35-17-15-13-14-16-26(3)39(48)30(7)41(50)32(9)43(52)33(10)42(51)31(8)40(49)27(4)18-21-38(47)53-44-29(6)36(20-19-35)54-45(34(44)11)23-22-25(2)37(55-45)24-28(5)46/h13-15,17-18,21,24-35,38,40-42,46,49,51-52,54H,12,16,19-20,22-23H2,1-11H3;13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3;13-15,17-18,21,25-37,39-40,43-44,46,48-49,52H,12,16,19-20,22-24H2,1-11H3/b3*14-13+,17-15+,21-18+/t24-,25+,26-,27+,28+,29-,30-,31-,32-,33-,34-,35-,38+,40+,41+,42-,44+,45+;25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-;25-,26+,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,39-,40+,43-,44+,45-/m111/s1

SMILES Code

C[C@@H]1CC[C@]2([C@H](C)[C@@]([H])(OC(/C=C/[C@@H](C)[C@H](O)[C@H](C([C@@H](C)[C@@H]([C@H]3C)O)=O)C)=O)[C@@H](C)[C@@]([H])(CC[C@@](CC)([H])/C=C/C=C/C[C@H](C)[C@@H](O)[C@@](O)(C)C3=O)O2)O[C@]1([H])C[C@@H](O)C.C[C@@H]([C@](C[C@@H](O)C)([H])O[C@@]45[C@H](C)[C@@]([H])(OC(/C=C/[C@@H](C)[C@H](O)[C@H](C([C@@H](C)[C@@H]([C@H]6C)O)=O)C)=O)[C@@H](C)[C@@]([H])(CC[C@@](CC)([H])/C=C/C=C/C[C@H](C)[C@@H](O)[C@@](O)(C)C6=O)O5)CC4=O.C[C@@H]7CC[C@]8([C@H](C)[C@@]([H])(OC(/C=C/[C@@H](C)[C@H](O)[C@H](C([C@@H](C)[C@@H]([C@H]9C)O)=O)C)=O)[C@@H](C)[C@@]([H])(CC[C@@](CC)([H])/C=C/C=C/C[C@H](C)[C@@H](O)[C@@H](C)C9=O)O8)O[C@]7([H])C[C@@H](O)C

Appearance

Solid powder

Purity

≥95% (Mixture of A, B, C)

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

>3 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

Instruction

View handling instruction

Biological target:

Oligomycin, an antifungal antibiotic, is an inhibitor of H+-ATP-synthase.

In vitro activity:

Human chondrocytes were treated with oligomycin, an inhibitor of mitochondrial respiratory chain complex V. Mitochondrial dysfunction was induced by treatment with oligomycin, which significantly decreased mitochondrial membrane potential (ΔΨm). This was associated with increased production of reactive oxygen species and cell death. Autophagy activation, as reflected by LC3-II, was decreased in a time-dependent manner. To evaluate whether autophagy regulates mitochondrial function, chondrocytes were pretreated with rapamycin and torin 1 before oligomycin. Autophagy activation significantly protected against mitochondrial dysfunction. Reference: Arthritis Rheumatol. 2015 Apr;67(4):966-76. https://pubmed.ncbi.nlm.nih.gov/25605458/

In vivo activity:

Oligomycin was injected into the rat left knee joint on days 0, 2, and 5 before joint tissues were obtained on day 6. The macroscopic findings showed significantly greater swelling in oligomycin-injected knees than in control knees. Likewise, the histological score of synovial damage was also increased significantly. Immunohistochemical studies showed high expression of IL-8, coinciding with a marked infiltration of polymorphonuclears and CD68+ cells in the synovium. Mitochondrial mass was increased in the synovium of oligomycin-injected joints, as well as cellular and mitochondrial ROS production, and 4-HNE. Reference: BMC Musculoskelet Disord. 2017 Jun 12;18(1):254. https://pubmed.ncbi.nlm.nih.gov/28606072/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	8.43
	Ethanol	30.0	12.65

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 2,371.21 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. López de Figueroa P, Lotz MK, Blanco FJ, Caramés B. Autophagy activation and protection from mitochondrial dysfunction in human chondrocytes. Arthritis Rheumatol. 2015 Apr;67(4):966-76. doi: 10.1002/art.39025. PMID: 25605458; PMCID: PMC4380780. 2. Gong Y, Agani FH. Oligomycin inhibits HIF-1alpha expression in hypoxic tumor cells. Am J Physiol Cell Physiol. 2005 May;288(5):C1023-9. doi: 10.1152/ajpcell.00443.2004. PMID: 15840558. 3. Vaamonde-García C, Loureiro J, Valcárcel-Ares MN, Riveiro-Naveira RR, Ramil-Gómez O, Hermida-Carballo L, Centeno A, Meijide-Failde R, Blanco FJ, López-Armada MJ. The mitochondrial inhibitor oligomycin induces an inflammatory response in the rat knee joint. BMC Musculoskelet Disord. 2017 Jun 12;18(1):254. doi: 10.1186/s12891-017-1621-2. PMID: 28606072; PMCID: PMC5469149.

In vitro protocol:

In vivo protocol:

1. Vaamonde-García C, Loureiro J, Valcárcel-Ares MN, Riveiro-Naveira RR, Ramil-Gómez O, Hermida-Carballo L, Centeno A, Meijide-Failde R, Blanco FJ, López-Armada MJ. The mitochondrial inhibitor oligomycin induces an inflammatory response in the rat knee joint. BMC Musculoskelet Disord. 2017 Jun 12;18(1):254. doi: 10.1186/s12891-017-1621-2. PMID: 28606072; PMCID: PMC5469149.

1: He R, Li X, Zhang S, Liu Y, Xue Q, Luo Y, Yu B, Li X, Liu Z. Dexamethasone inhibits IL-8 via glycolysis and mitochondria-related pathway to regulate inflammatory pain. BMC Anesthesiol. 2023 Sep 18;23(1):317. doi: 10.1186/s12871-023-02277-9. PMID: 37723417; PMCID: PMC10506226. 2: Yang H, van der Stel W, Lee R, Bauch C, Bevan S, Walker P, van de Water B, Danen EHJ, Beltman JB. Dynamic Modeling of Mitochondrial Membrane Potential Upon Exposure to Mitochondrial Inhibitors. Front Pharmacol. 2021 Aug 19;12:679407. doi: 10.3389/fphar.2021.679407. PMID: 34489692; PMCID: PMC8416757. 3: Whigham CA, Hastie R, Hannan NJ, Brownfoot F, Pritchard N, Cannon P, Nguyen TV, Kandel M, Masci J, Tong S, Kaitu'u-Lino TJ. Placental growth factor is negatively regulated by epidermal growth factor receptor (EGFR) signaling. Placenta. 2021 Oct;114:22-28. doi: 10.1016/j.placenta.2021.08.002. Epub 2021 Aug 5. PMID: 34418751. 4: Byrnes J, Ganetzky R, Lightfoot R, Tzeng M, Nakamaru-Ogiso E, Seiler C, Falk MJ. Pharmacologic modeling of primary mitochondrial respiratory chain dysfunction in zebrafish. Neurochem Int. 2018 Jul;117:23-34. doi: 10.1016/j.neuint.2017.07.008. Epub 2017 Jul 18. PMID: 28732770; PMCID: PMC5773416. 5: Danilenko AN, Bibikova MV, Spiridonova IA, Grammatikova NE, Katlinskiĭ AV. [Physico-chemical properties and structure of oligomycin SC-II, produced by Streptomyces virginiae 17]. Antibiot Khimioter. 2012;57(11-12):3-7. Russian. PMID: 23700929. 6: Grammatikova NE, Bibikova MV, Spiridonova IA, Kabanov AE, Katlinskiĭ AV. Novyĭ produtsent antibiotikov oligomitsinovoĭ struktury Streptomyces griseolus No 182. Taksonomiia, fermentatsiia i vydelenie [Streptomyces griseolus # 182--a novel organism producing oligomycin antibiotics. Taxonomy, fermentation, and isolation]. Antibiot Khimioter. 2003;48(6):11-5. Russian. PMID: 14558413. 7: Jørgensen PL. Functional domains of Na,K-ATPase; conformational transitions in the alpha-subunit and ion occlusion. Acta Physiol Scand Suppl. 1992;607:89-95. PMID: 1333164. 8: Esmann M. Oligomycin interaction with Na,K-ATPase: oligomycin binding and dissociation are slow processes. Biochim Biophys Acta. 1991 Apr 26;1064(1):31-6. doi: 10.1016/0005-2736(91)90408-z. PMID: 1709053. 9: Taniguchi K, Sasaki T, Shinoguchi E, Kamo Y, Ito E. Conformational change accompanying formation of oligomycin-induced Na(+)-bound forms and their conversion to ADP-sensitive phosphoenzymes in Na+,K(+)-ATPase. J Biochem. 1991 Feb;109(2):299-306. PMID: 1650775. 10: Prouty WF, Schnoes HK, Strong FM. A molecular weight revision for compounds of the oligomycin complex. Biochem Biophys Res Commun. 1969 Feb 21;34(4):511-6. doi: 10.1016/0006-291x(69)90411-2. PMID: 5776396. 11: LARSON MH, PETERSON WH. Chromatographic study of the oligomycin complex produced under various conditions of fermentation. Appl Microbiol. 1960 May;8(3):182-9. doi: 10.1128/am.8.3.182-189.1960. PMID: 14414291; PMCID: PMC1057600.