The development of peptide-boron difluoride formazanate conjugates as fluorescence imaging agents

Neha Sharma; Stephanie M Barbon; Tyler Lalonde; Ryan R Maar; Mark Milne; Joe B Gilroy; Leonard G Luyt

doi:10.1039/d0ra02104k

The development of peptide-boron difluoride formazanate conjugates as fluorescence imaging agents

RSC Adv. 2020 May 19;10(32):18970-18977. doi: 10.1039/d0ra02104k. eCollection 2020 May 14.

Authors

Neha Sharma¹, Stephanie M Barbon¹, Tyler Lalonde¹, Ryan R Maar¹, Mark Milne², Joe B Gilroy¹, Leonard G Luyt^{1

2

3}

Affiliations

¹ Department of Chemistry, University of Western Ontario 1151 Richmond Street London Ontario N6A 5B7 Canada joe.gilroy@uwo.ca lluyt@uwo.ca.
² London Regional Cancer Program, Lawson Health Research Institute 800 Commissioners Road East London Ontario N6A 5W9 Canada.
³ Departments of Oncology and Medical Imaging, University of Western Ontario 1151 Richmond Street London Ontario N6A 5B7 Canada.

Abstract

Two new fluorescence imaging probes have been synthesized by incorporating a versatile alkyne-substituted boron difluoride formazanate precursor with peptides through copper-catalyzed alkyne-azide cycloaddition. The formazanate dye was appended to a C-terminal amino acid of ghrelin for imaging the growth hormone secretagogue receptor (GHSR-1a). To demonstrate versatile bioconjugation chemistry, the formazanate dye was added to the N-terminus of bombesin for targeting the gastrin releasing peptide receptor (GRPR). These are the first examples of using this emerging class of dyes, boron difluoride formazanates, for the labelling of biomolecules.