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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/12/28 17:47:12」(JST)

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Oligomycins are macrolides created by Streptomyces that can be poisonous to other organisms.

Function[edit]

They have use as antibiotics.

Oligomycin A is an inhibitor of ATP synthase. In oxidative phosphorylation research, it is used to prevent state 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.^[1] This process is due to the facilitated diffusion of protons into the mitochondrial matrix through an uncoupling protein such as thermogenin, or UCP1.

Administering oligomycin to an individual can result in very high levels of lactate accumulating in the blood and urine.^{[citation needed]}

**Oligomycins**^[2]

	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

References[edit]

^ Jastroch M, Divakaruni AS, Mookerjee S, Treberg JR, Brand MD (2010). "Mitochondrial proton and electron leaks". Essays in biochemistry (47): 53–67. doi:10.1042/bse0470053. PMID 20533900.
^ Nakata, Masaya; Ishiyama, Takashi; Akamatsu, Shinichi; Hirose, Youichi; Maruoka, Hiroshi; Suzuki, Rika; Tatsuta, Kuniaki (1995). "Synthetic studies on oligomycins. Synthesis of the oligomycin B spiroketal and polypropionate portions". Bulletin of the Chemical Society of Japan 68 (3): 967–89. doi:10.1246/bcsj.68.967.

English Journal

Nuclear depletion of apurinic/apyrimidinic endonuclease 1 (Ape1/Ref-1) is an indicator of energy disruption in neurons.

Singh S, Englander EW.SourceDepartment of Surgery, University of Texas Medical Branch, 301 University Boulevard, Galveston, TX 77555, USA.
Free radical biology & medicine.Free Radic Biol Med.2012 Nov 1;53(9):1782-90. doi: 10.1016/j.freeradbiomed.2012.07.025. Epub 2012 Jul 27.
Apurinic/apyrimidinic endonuclease 1 (Ape1/Ref-1) is a multifunctional protein critical for cellular survival. Its involvement in adaptive survival responses includes key roles in redox sensing, transcriptional regulation, and repair of DNA damage via the base excision repair (BER) pathway. Ape1 is
PMID 22841870

Mitochondrial energy metabolism plays a critical role in the cardioprotection afforded by intermittent hypobaric hypoxia.

Wang ZH, Cai XL, Wu L, Yu Z, Liu JL, Zhou ZN, Liu J, Yang HT.SourceH.-T. Yang: Institute of Health Sciences, SIBS, CAS & SJTUSM, Room 613, Building 1, 225 Chongqing Nan Road, Shanghai 200025, China. htyang@sibs.ac.cn J. Liu: Institute of Mitochondrial Biology and Medicine, Xi'an Jiaotong University School of Life Science and Technology, Xi'an 710049, China. Email: j.liu@mail.xjtu.edu.cn.
Experimental physiology.Exp Physiol.2012 Oct;97(10):1105-18. Epub 2012 May 4.
Intermittent hypobaric hypoxia (IHH) is an effective protective strategy against myocardial ischaemia-reperfusion (I/R) injury, but the precise mechanisms are far from clear. To understand the overall effects of IHH on the myocardial proteins during I/R, we analysed functional performance and the pr
PMID 22562809

Japanese Journal

Neural cell adhesion molecule is a cardioprotective factor up-regulated by metabolic stress.

Nagao Kazuya,Ono Koh,Iwanaga Yoshitaka,Tamaki Yodo,Kojima Yoji,Horie Takahiro,Nishi Hitoo,Kinoshita Minako,Kuwabara Yasuhide,Hasegawa Koji,Kita Toru,Kimura Takeshi
Journal of molecular and cellular cardiology 48(6), 1157-1168, 2010-06
… To search for genes whose expression was enhanced by treatment with oligomycin, a mitochondrial-F(0)F(1) ATP synthase inhibitor, signal sequence trapping was performed in H9C2 rat cardiac myoblasts. … Lentivirus-mediated knockdown of NCAM decreased the cell growth and survival following oligomycin treatment in H9C2 cells. … In primary rat neonatal cardiac myocytes, NCAM was also found to be up-regulated and played a protective role following oligomycin treatment. …
NAID 120002381089

Antisense Expression of Mitochondrial ATP Synthase Subunits OSCP (ATP5) and γ(ATP3) Alters Leaf Morphology, Metabolism and Gene Expression in Arabidopsis

ROBISON Mary M.,LING Xingyuan,SMID Matthew P. L.,ZAREI Adel,WOLYN David J.
Plant and cell physiology 50(10), 1840-1850, 2009-10-01
NAID 10027343921

Na+/K+-ATPaseとオリゴマイシンの相互作用

誉田晴夫
杏林医学会雑誌 38(2/3), 29-36, 2007
Na+/K+-ATPaseは全ての動物細胞膜に存在する膜酵素である。そして，ATPの加水分解エネルギーを用いてNa+を細胞内から細胞外に，K+をその逆方向に能動輸送するポンプの働きをする。オリゴマイシンはNa+/K+-ATPaseへのNa+結合親和性を上げるがK+結合には影響しない。またNa+輸送を阻害するが，K+輸送にはほとんど影響しない。さらに，ATPase活性を阻害するが，その部分反応である …
NAID 130000135244

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★リンクテーブル★

リンク元	「電子伝達系」「オリゴマイシン」

「電子伝達系」

Oligomycin A
	IUPAC name (1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione
	Other names Oligomycin
Identifiers
CAS number	1404-19-9
PubChem	6450197
ChemSpider	21106358
EC number	215-767-9
MeSH	Oligomycins
RTECS number	RK3325000
Jmol-3D images	Image 1
	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 ;
	InChI 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 ; Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N ;
Properties
Molar mass	791.062 g/mol
Hazards
MSDS	MSDS at Fermentek
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	Infobox references

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英: electron transport chain, electron transport system, electron-transport system, electron-transfer system
関: 電子