Synthesis of [3(R)-amino-2(S)-sulfhydryl-5-sulfonate]-pentanoyl-(S)-3-[125I]-iodotyrosyl-(S)-aspartic acid: a radiolabelled inhibitor of aminopeptidase A

Christelle David-Basei (1) , Laurent Bischoff (1) , Marie-Claude Fournie-Zaluski (1) , Bernard P. Roques (1)

1 Pharmacochimie moléculaire et structurale

In order to investigate the localization of aminopeptidase A in the central nervous system and peripheral organs, we have synthesized the first radiolabelled inhibitor of this enzyme. This molecule, [3(R)‐amino‐2(S)‐sulfhydryl‐5‐sulfonate]‐pentanoyl‐(S)‐3‐[125I]‐iodotyrosyl‐(S)‐aspartic acid, exhibited a Ki value of 4.8 nM for aminopeptidase A. A high purity was obtained with a specific activity of about 2,000 Ci/mmol at the end of the synthesis.

Keywords: Thiol compounds/125I/Aminopeptidase A/Inhibitors

Domains: Chemical Sciences; Organic chemistry; Medicinal Chemistry; Radiochemistry; Material chemistry; Inorganic chemistry; Catalysis

Christelle David-Basei, Laurent Bischoff, Marie-Claude Fournie-Zaluski, Bernard P. Roques. Synthesis of [3(R)-amino-2(S)-sulfhydryl-5-sulfonate]-pentanoyl-(S)-3-[125I]-iodotyrosyl-(S)-aspartic acid: a radiolabelled inhibitor of aminopeptidase A. Journal of Labelled Compounds and Radiopharmaceuticals, 2001, 44 (1), pp.89-98. ⟨10.1002/jlcr.445⟩. ⟨hal-02385512⟩