Synthesis and evaluation of two NIR fluorescent cyclic RGD penta-peptides for targeting integrins

Yunpeng Ye; Sharon Bloch; Baogang Xu; Samuel Achilefu

doi:10.1117/12.648105

10 February 2006 Synthesis and evaluation of two NIR fluorescent cyclic RGD penta-peptides for targeting integrins

Yunpeng Ye, Sharon Bloch, Baogang Xu, Samuel Achilefu

Proceedings Volume 6097, Optical Molecular Probes for Biomedical Applications; 609707 (2006) https://doi.org/10.1117/12.648105
Event: SPIE BiOS, 2006, San Jose, California, United States

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 α_vβ₃ 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.

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Yunpeng Ye, Sharon Bloch, Baogang Xu, and Samuel Achilefu "Synthesis and evaluation of two NIR fluorescent cyclic RGD penta-peptides for targeting integrins", Proc. SPIE 6097, Optical Molecular Probes for Biomedical Applications, 609707 (10 February 2006); https://doi.org/10.1117/12.648105

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KEYWORDS

Near infrared

Receptors

Magnesium

Luminescence

In vivo imaging

Tumors

Analog electronics

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