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Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

2005; American Chemical Society; Volume: 7; Issue: 3 Linguagem: Inglês

10.1021/ol0476974

1523-7060

Amos B. Smith, Adam K. Charnley, Eugen F. Mesaros, Osamu Kikuchi, Wenyong Wang, Andrew B. Benowitz, C.T. Chu, Jin-Jye Feng, Kuo-Hsin Chen, Atsui Lin, Fong‐Chi Cheng, Laurie L. Taylor, Ralph Hirschmann,

Neuroendocrine Tumor Research Advances

Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (d,l-mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the d,l-mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide β-turns.