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Synthesis of a Sialyl Lewis X Mimetic Conjugated with DTPA, Potential Ligand of New Contrast Agents for Medical Imaging
Author(s) -
Fu Yanjun,
Laurent Sophie,
Muller Robert N.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200212)2002:23<3966::aid-ejoc3966>3.0.co;2-p
Subject(s) - chemistry , moiety , conjugated system , phenylacetic acid , ligand (biochemistry) , amide , stereochemistry , selectin , sialic acid , alkyl , biochemistry , organic chemistry , adhesion , receptor , polymer
The structure of a mimetic of sialyl Lewis X , namely 3‐[2‐(α‐ D ‐mannopyranosyloxy)phenyl]phenylacetic acid, was coupled to diethylenetriaminepentaacetic acid (DTPA) via a flexible alkyl spacer and the amide linkage. The overall yield of the eleven‐step synthesis starting from 3‐bromophenylacetic acid was 4−8%. This new ligand is expected to target inflammation sites through specific interactions with selectins, the adhesion molecules expressed on the vascular endothelium in pathological conditions. In particular, complexation of the DTPA moiety with gadolinium or radionuclides could produce contrast agents for medical imaging. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)