Tuftsin analogs: synthesis, structure-function relationships, and implications for specificity of tuftsin's bioactivity

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Abstract
Thirteen analogues of the natural macrophage activator peptide tuftsin, ten of which are novel, were synthesized with the aim of exploring the relation between their biological potency and their capacity to attach specifically to cellular tuftsin''s receptors. The analogues representing modifications and chain extensions at various parts of the parent tuftsin molecule can be classified as (a) N-terminal analogues, (b) C-terminal analogues, (c) "within-chain" derivatives, or (d) dimers of tuftsin and retrotuftsin. The various synthetic routes employed to prepare the analogues are described. A direct correlation was found between the ability of analogues to inhibit [3H-Arg4]tuftsin specific binding to mice peritoneal macrophages and their capacity to enhance phagocytosis or to inhibit tuftsin mediated phagocytosis by the cells and to potentiate the cell''s immune response.

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