8-Azidoadenosine-5'-O-diphosphate sodium salt

8-Azido-ADP (disodium) is a covalent-binding inhibitor of mitochondrial adenine nucleotide translocation. 8-Azido-ADP (disodium) causes irreversible inhibition of adenine nucleotide exchange in a light-dependent reaction. 8-Azido-ADP (disodium) inhibits the normal state 4 → 3 transitions of mitochondrial respiration induced by ADP[1]. 8-Azido-ADP (disodium) is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.

[1] SchHafer G, et al. 8-azido-ADP, a covalent-binding inhibitor of mitochondrial adenine nucleotide translocation. FEBS Lett. 1976 Apr 15;64(1):185-9. DOI:10.1016/0014-5793(76)80279-7
[2] J N DHOLAKIA. Photoaffinity labeling of the rabbit reticulocyte guanine nucleotide exchange factor and eukaryotic initiation factor 2 with 8-azidopurine nucleotides. Identification of GTP- and ATP-binding domains.[J]. The Journal of Biological Chemistry, 1989, 264 34: 20638-20642.
[3] S W CHO  H Y Y. Photoaffinity labeling of brain glutamate dehydrogenase isoproteins with an azido-ADP.[J]. The Journal of Biological Chemistry, 1999, 274 20: 13948-13953. DOI: 10.1074/jbc.274.20.13948