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Proceedings Paper

Synthesis and evaluation of two NIR fluorescent cyclic RGD penta-peptides for targeting integrins
Author(s): Yunpeng Ye; Sharon Bloch; Baogang Xu; Samuel Achilefu
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Paper Abstract

Interest in novel RGD peptides has been increasingly growing as the interactions between RGD peptides and integrins are the basis for a variety of cellular functions and medical applications such as modulation of cell adhesion, invasion, tumor angiogenesis, and metastasis. In particular, we have been interested in novel NIR fluorescent RGD peptides as potential optical contrast agents for in vivo tumor optical imaging. Therefore, two cyclic RGD penta-peptides conjugated with a NIR fluorescent carbocyanine (Cypate), i.e. lactam-based cyclo[RGDfK(Cypate)] (1) and disulfide-containing Cypate-cyclo(CRGDC)-NH2 (2), were designed and synthesized. The competitive binding assay between the purified αvβ3 integrin and the peptide ligands using 125I-echistatin as a tracer showed that 1 had a higher receptor binding affinity (IC50~10-7 M) than 2 (IC50~10-6 M). Furthermore, the internalization of 1 in A549 cells in vitro was less than 2, as revealed by fluorescence microscopy. These results suggest that both the lactam- and disulfide-based cyclic RGD penta-peptides should be further studied structurally and functionally to elucidate the advantages of each class of compounds.

Paper Details

Date Published: 10 February 2006
PDF: 7 pages
Proc. SPIE 6097, Optical Molecular Probes for Biomedical Applications, 609707 (10 February 2006); doi: 10.1117/12.648105
Show Author Affiliations
Yunpeng Ye, Washington Univ. School of Medicine, St. Louis (United States)
Sharon Bloch, Washington Univ. School of Medicine, St. Louis (United States)
Baogang Xu, Washington Univ. School of Medicine, St. Louis (United States)
Samuel Achilefu, Washington Univ. School of Medicine, St. Louis (United States)

Published in SPIE Proceedings Vol. 6097:
Optical Molecular Probes for Biomedical Applications
Samuel I. Achilefu; Darryl J. Bornhop; Ramesh Raghavachari, Editor(s)

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