. 2008 Dec;72(4):590–641. doi: 10.1128/MMBR.00016-08

TABLE 24.

Miscellaneous inhibitors

Name or abbreviation	Molecular formula	Other names	Inhibitory potency (reference)
Dicarbopolyborate	C₂B₉H₁₁ (Dicarbononaborate)		Mercapto and chloro derivatives of dicarbononaborates, ∼95% inhibition at 500-800 μM (rat liver MF₁-ATPase) (104); dichlorodicarbononaborate, 170 μM^b (rat liver MF₁-ATPase) (104)
Almitrine	C₂₆H₂₉F₂N₇	6-(4-(Bis(4-fluorphenyl)methyl)-1-piperazinyl)-N,N′-di-2-propenyl-1,3,5-triazin-2,4-diamin; 2,4-bis(allylamino)-6-(4-(bis(p-fluorophenyl)methyl)-1-piperazinyl)-s-triazine	30 μM^a (S. cerevisiae mitochondria, ATPase) (336)
5-Hydroxy-1,2-naphthalene dicarboxylic anhydride	C₁₂H₆O₄	6-Hydroxynaphtho(1,2-c)furan-1,3-dione; 5-hydroxynaphthalenedicarboxylic anhydride	Complete inhibition of ATPase induced by gramicidin at 30 μM (rat liver SMP-ATPase) (165)
R207910	C₃₂H₃₁BrN₂O₂	1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol; TMC207; compound J	2.5 nM^a (M. smegmatis membrane vesicles, ATP synthesis) (215); 99% inhibition in the range of 0.03-0.12 μg/ml (M. tuberculosis, growth) (15)
Spegazzinine	C₂₁H₂₈N₂O₃		18.5-24 μg inhibitor/mg protein^a (S. pombe ATPase activity of cell extracts) (234); 100 μM^a (spinach CF₁-ATPase) (10); 80 μM^a (spinach chloroplasts, photophosphorylation) (10)
n-Butanol	C₄H₁₀O	1-Butanol; propyl carbinol; n-butyl alcohol; 1-hydroxybutane; butyl hydroxide; Hemostyp; methylolpropane; propylcarbinol; propylmethanol	160 mM^a (bovine heart MF₁-ATPase) (406)
TCS	C₁₃H₇Cl₄NO₂	TCSA; tetrachlorosalicylanilide; 3,3′,4′,5-tetrachlorosalicylanilide; 3,5-dichlorosalicyl 3,4-dichloroanilide; 3,5-dichloro-N-(3,4-dichlorophenyl)-2-hydroxy-benzamide	9-10 μM^a (F₀F₁-ATPase from V. parahaemolyticus) (290); 71% inhibition at 25 μM (V. parahaemolyticus F₁-ATPase) (344)
Dihydrostreptomycin	C₂₁H₄₁N₇O₁₂	Abiocine; Vibriomycin	38 mM^b (bovine heart SMP- and isolated MF_1-ATPase) (161)
Suramin	C₅₁H₄₀N₆O₂₃S₆	Belganyl; Naganol	40 μM^a (rat liver MF₁-ATPase) (28); 0.7 μg/ml^a (C. fasciculata MF₁-ATPase) (173)
Bz-423	C₂₇H₂₁ClN₂O₂	Bz-48	5 μM^a (Ramos cells, ATP synthesis) (193)
DMSO	C₂H₆OS	Dimethyl sulfoxide	> 95% inhibition at 40% DMSO (vol/vol) (EF₁-ATPase) (9); ∼60% inhibition at 50% DMSO (TF₁-ATPase) (440)
Hypochlorous acid	HOCl		75% inhibition at 125 μM HOCl/g cells (EF₁-ATPase) (167); 50 μmol inhibitor/g cells^a (EF₁-ATPase) (29)
DDT	C₁₄H₉C_l5	4, 4′-Dichlorodiphenyltri-chloroethane; 4, 4′-DDT; p,p′-DDT; 1,1′-(2,2,2-trichloroethylidene)bis (4-chlorobenzene); Agritan; Chlorophenothan; 1,1,1-trichloro-2,2-bis(4,4′-dichlorodiphenyl) ethane; Detoxan	50% lethal dose of 11 μg/mg (A. melllifera)
Diazoxide	C₈H₇ClN₂O₂S	7-Chloro-3-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide; Eudemine; Hyperstat; Hypertonalum	K_d of IF₁ to F₁, 250 nM with 1 diazoxide equivalent/F₁ from 760 nM without diazoxide (bovine MF₁-ATPase) (80)
HNB	C₇H₆BrNO₃	2-Hydroxy-5-nitrobenzyl bromide; Koshland's reagent I; 2-bromomethyl-4-nitrophenol; α-bromo-4-nitro-o-cresol	2.5 mM^a (bovine heart MF₁-ATPase) (27)
N-Sulfonyl or N-alkyl-substituted tetrahydrobenzodiazepine derivatives	C₂₈H₃₀N₄O₃S	1-(1H-Imidazol-4-ylmethyl)-4-[(4-methoxyphenyl)sulfonyl]-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine	77 nM^a (bovine heart MF₀F₁-ATPase) (166)
	C₂₂H₂₃F₃N₄O₂S	1-(1H-Imidazol-4-ylmethyl)-2-(2-phenylethyl)-4-[(trifluoromethyl)sulfonyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine	77 nM^a (bovine heart MF₀F₁-ATPase) (166)
	C₃₁H₃₆N₄O₂S	4-[(4-tert-Butylphenyl)sulfonyl]-1-(1H-imidazol-4-ylmethyl)-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine	8 nM^a (bovine heart MF₀F₁-ATPase) (166)
	C₃₂H₃₈N₄O₂S	4-[(4-tert-Butylphenyl)sulfonyl]-1-[(5-methyl-1H-imidazol-4-yl)methyl]-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine	77 nM^a (bovine heart MF₀F₁-ATPase) (166)
	C₂₈H₂₈Cl₂N₄O₂S	4-[(3,4-Dichlorophenyl)sulfonyl]-1-[(5-methyl-1H-imidazol-4-yl)methyl]-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine	22 nM^a (bovine heart MF₀F₁-ATPase) (166)
4-(N-Arylimidazole)-substituted benzopyran derivatives	C₂₂H₂₁ClN₄O₂	4-[(4-Chlorophenyl)(1H-imidazol-2-ylmethyl)amino]-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbonitrile	3R, 4S enantiomer, 0.48 μM^a (rat heart MF₀F₁-ATPase) (21) and 4 μM^a (rat heart SMP-ATP synthesis) (21); 3S, 4R enantiomer, 0.24 μM^a (rat heart SMP-ATPase) (21) and 3.8 μM^a (rat heart SMP-ATP synthesis) (21);
	C₂₆H₃₁ClN₄O₄S	4-[(4-Chlorophenyl)(1H-imidazol-2-ylmethyl)amino]-2,2-dimethyl-6-(piperidin-1-ylsulfonyl)-3,4-dihydro-2H-chromen-3-ol	3R, 4S enantiomer (BMS-199264), 0.48 μM^a (rat heart SMP-ATPase) (21), 18 μM^a (rat heart SMP-ATP synthesis) (21); ∼42% inhibition at 3 μM (ischemic rat heart SMP-ATPase) (156)
N-[1-Aryl-2-(1-imidazolo)ethyl]-cyanoguanidine	C₁₉H₁₄Cl₄N₆	2-Cyano-1-(2,4-dichlorophenyl)-3-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl]guanidine	0.6 μM^a (bovine MF₀F₁-ATPase) (20)
derivatives	C₂₁H₁₄Cl₂F₆N₆	1-{1-[2,5-Bis(trifluoromethyl)phenyl]-2-(1H-imidazol-1-yl)ethyl}-2-cyano-3-(2,4-dichlorophenyl)guanidine	0.71 μM^a (bovine MF₀F₁-ATPase) (20)
N-[1-Aryl-2-(1-imidazolo)ethyl]-acylguanidine derivatives	C₂₆H₁₉Cl₃N₆O	N-[(Z)-[(4-Chlorophenyl)amino]{[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl]amino}methylidene]-3-cyanobenzamide	Racemic mixture, 33 nM^a (bovine MF₀F_1-ATPase) (20); one enantiomer. 18 nM^a (bovine MF₀F_1-ATPase) (20); the other enantiomer, >100 nM^a (bovine MF₀F₁-ATPase) (20)
	C₂₅H₁₉Cl₄N₅O	4-Chloro-N-[(Z)-[(4-chlorophenyl)amino]{[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl]amino}methylidene]benzamide	Racemic mixture, 82 nM^a (bovine MF₀F_1-ATPase) (20)
O-[1-Aryl-2-(1-imidazolo)ethyl]-thiourethane derivatives	C₁₈H₁₄Cl₃N₃OS	O-[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl] (4-chlorophenyl)carbamothioate	0.43 μM^a (bovine heart MF₀F₁-ATPase) (20); >300 μM^a (bovine heart MF₀F₁, ATP synthesis) (20)
	C₁₈H₁₃Cl₄N₃OS	O-[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl] (2,4-dichlorophenyl)carbamothioate	30 nM^a (bovine heart MF₀F₁-ATPase) (20)
Dio-9 complex	Unknown (a mixture of at least 9 compounds)		0.7 μg inhibitor/mg protein^a (T. pyriformis SMP-ATPase) (404); ∼500 μg inhibitor/mg protein^a (S. faecalis F₁-ATPase) (169); 6.6 μg/mg protein^a (C. fasciculata SMP-ATPase) (439)
Ethanol	C₂H₅OH	Ethyl alcohol	60% inhibition at about 7 μM (V. parahaemolyticus F₀F₁-ATPase) (290)
Zinc	Zn²⁺		∼100 μM^a (V. parahaemolyticus F₀F₁-ATPase) (290)

I₅₀.

K_i.