Synthesis of Cationic and Zwitterionic Cy7 Dyes for Antibody Conjugation and Bio-distribution Studies in Mice

Authors

• V Coble
• C Li
• M Schnermann
• O Vasalatiy
• R Swenson

Abstract

Cy7 dyes are a crucial component of biomedical imaging technologies. Recent work by Dr. Frangioni’s group expounded the superior imaging properties (higher extinction coefficient and quantum yield; low nonspecific binding and organ uptake; and exclusive clearance by the kidneys) of neutral, geometrically balanced, zwitterionic cy7 dyes. Furthermore, they showed that these properties persisted even after conjugation to a peptide or antibody. Recently, Dr. Schnermann’s group synthesized a similar but anionic cy7 dye (FNIR-774) utilizing an electrophile induced N to O rearrangement. They showed that antibody conjugates of the dye showed higher tumor uptake than conjugates of IR800CW in tumor bearing mice. Herein we report the synthesis of a series of zwitterionic cy7 dyes and their cationic counterparts (IPDC-Probes 1-4). The dyes were synthesized in 5-7 steps starting from commercially available starting materials. The physiochemical properties of this series of dyes will be tested in tumor bearing mice.

Scientific Focus Area: Research Support Services

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