TABLE 18.

Azidonucleotides

Name	Molecular formula	Other names	Inhibitory potency (reference)
8-Azido-ATP	C10H15N8O13P3	8-Azidoadenosine 5′-triphosphate	1 mMb (bovine heart SMP, phosphorylation) (371); 1 mMb (bovine heart SMP-ATPase) (371); 88% inhibition at 1.7 mM (bovine heart MF1-ATPase) (419); complete inhibition at 2 inhibitor bound mol/mol F1 (bovine heart MF1-ATPase) (110, 420)
8-Azido-ADP	C10H14N8O10P2	8-Azidoadenosine 5′-diphosphate	86% inhibition at 1.7 mM (bovine heart MF1-ATPase) (419); full inhibition at 1.9-2 mol bound inhibitor/mol F1 (134, 419)
2-Azido-ATP	C10H15N8O13P3	2-Azidoadenosine 5′-triphosphate	52% inhibition at 1.8 (0.8 covalent) inhibitor mol/mol F1 (EF1-ATPase) (425); complete inhibition at 0.92 inhibitor bound mol/mol F1 (bovine heart MF1-ATPase) (408)
2-Azido-ADP	C10H14N8O10P2	2-Azidoadenosine 5′-diphosphate; 1-azidoadenosine-3′,5′-bisphosphate	5 μMc in the dark (bovine heart MF1-ATPase) (45); full inhibition at 1.9-2 mol bound inhibitor/mol F1 (45, 134)
2-Azido-TNP-ATP	C17H20N11O18P3	2-N3-TNP-ATP
ANA-ADP	C21H17N8O11P2	3′-O-[5-Azidonaphthoyl]-ADP	11 μMb in the dark (bovine heart MF1-ATPase) (240); total inactivation at 2 mol/mol F1 (bovine heart MF1-ATPase) (240)
8-Azido-FSBA	C17H15FN8O7S	5′-p′-Fluorosulfonylbenzoyl-8-azidoadenosine; 8-N3-FSBA	0.47 mMc in the dark (bovine heart MF1-ATPase) (453)
2-Azido-AMP-PNP	C10H15N9O12P3	2-Azidoadenyl-5′-yl imidodiphosphate	4 μMb (bovine heart MF1-ATPase) (109)
8-Azido-AMP-PNP	C10H15N9O12P3	8-Azidoadenyl-5′-yl imidodiphosphate	460 μMb (bovine heart MF1-ATPase) (109)
NAP4-ADP	C20H24N10O13P2	N-4-Azido-2-nitrophenyl-γ−aminobutyryl-ADP	2.0 μMa (bovine heart SMP-oxidative phosphorylation) (355); 0.6 mMb in the dark (bovine heart MF1-ATPase) (244); 0.5 μMb (bovine heart SMP-oxidative phosphorylation) (355)
NAP4-AMP-PNP	C20H23N11O15P3	Nap4-PPNHP; NAP4-AdoPP[NH]P; N-4-azido-2-nitrophenyl γ−aminobutyryl-5-adenylyl imidodiphosphate; N-4-Azido-2-nitrophenyl-γ-aminobutyryl-AdoPP[NH]P	3 μMc in the dark (bovine heart MF1-ATPase) (247)
NAP3-ATP	C19H23N10O16P3	3′-O-{3-[N-(4-Azido-2-nitrophenyl) amino]propionyl}adenosine 5′-triphosphate; arylazido aminopropionyl ATP	43% maximum inhibition at 36 μM with 15 min photoreaction (bovine heart MF1-ATPase) (341)
NAP3-ADP	C19H22N10O13P2	3′-O-[3-[N-(Azido-2-nitrophenyl) amino]propionyl]adenosine 5′-diphosphate; arylazido-β-alanyl-ADP; arylazido aminopropionyl ADP	80% inhibition at 50 μM in the dark (pig heart MF1-ATPase) (117)
NAB-ATP	C17H18N9O16P3	3′(2′)-O-(2-Nitro-4-azidobenzoyl)adenosine 5′-triphosphate	Km of 0.85 mM, maximal 40-45% modification (bovine heart MF1-ATPase) (216)
NAB-GTP	C17H18N9O17P3	3′(2′)-O-(2-Nitro-4-azidobenzoyl)guanosine 5′-triphosphate	Maximal 40-45% modification (bovine heart MF1-ATPase) (216)
ANP-ADP	C19H27N9O13P2	3′-O-[3-(4-Azido-2-nitrophenyl)propionyl]-ADP	1.3 μMa (bovine heart SMP-oxidative phosphorylation) (355); 50 μMb (bovine heart MF1-ATPase) (426); 0.2 μMb (bovine heart SMP-oxidative phosphorylation) (355, 426); full inhibition at 3 mol/mol F1 (bovine heart MF1-ATPase) (426)

^aI₅₀.

^bK_i.

^cK_d.