Carbacyclic peptide mimetics as VCAM-VLA-4 antagonists.
Substitution of carbon for sulfur in a potent 13-membered cyclic disulfide containing peptide was accomplished via an intramolecular Wittig reaction and resulted in a series of 'carba' analogues. Potency in the VCAM-VLA-4 assay was sensitive to ring size and lower than that of the parent disulfide.
Tilley
J
J
Roche Research Center, Hoffmann-La Roche Inc, Nutley, NJ 07110, USA. jefferson.tilley@roche.com
Kaplan
G
G
Fotouhi
N
N
Wolitzky
B
B
Rowan
K
K
D039041:Integrin alpha4beta1; D016023:Integrins / Q000037:antagonists & inhibitors*; D018716:Molecular Mimicry; D010456:Peptides, Cyclic / Q000737:chemistry / Q000494:pharmacology*; D016201:Receptors, Lymphocyte Homing / Q000037:antagonists & inhibitors*; D019010:Vascular Cell Adhesion Molecule-1 / Q000187:drug effects*
D039041:Integrin alpha4beta1; D016023:Integrins; D010456:Peptides, Cyclic; D016201:Receptors, Lymphocyte Homing; D019010:Vascular Cell Adhesion Molecule-1