Synthesis and assessment of a maleimide functionalized BF2 azadipyrromethene near-infrared fluorochrome

Dan Wu; Shane Cheung; Marc Devocelle; Li-Jun Zhang; Zhi-Long Chen; Donal F. O'Shea

doi:10.1039/C5CC06137G

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Synthesis and assessment of a maleimide functionalized BF₂ azadipyrromethene near-infrared fluorochrome†

Dan Wu,^a Shane Cheung,^a Marc Devocelle,^a Li-Jun Zhang,^b Zhi-Long Chen^b and Donal F. O'Shea ‡*^ac

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* Corresponding authors

^a Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland
E-mail: donalfoshea@rcsi.ie

^b Department of Pharmaceutical Science & Technology, College of Chemistry and Biology, Donghua University, Shanghai 201620, China

^c School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland

Abstract

The first water soluble maleimide bearing NIR BF₂-azadipyrromethene (NIR-AZA) fluorochrome has been synthesised which is capable of rapid thiol conjugations in water with peptides such as glutathione, the cell penetrating peptide (CPP) C(β-A)SKKKKTKV-NH₂ and a thiol substituted cRGD. NIR fluorescence imaging showed rapid cellular delivery of the CPP conjugate and effective in vivo tumour localization for the cRGD conjugate.

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Article information

DOI: https://doi.org/10.1039/C5CC06137G
Article type: Communication
Submitted: 22 Jul 2015
Accepted: 24 Sep 2015
First published: 24 Sep 2015

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Chem. Commun., 2015,51, 16667-16670

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Synthesis and assessment of a maleimide functionalized BF₂ azadipyrromethene near-infrared fluorochrome

D. Wu, S. Cheung, M. Devocelle, L. Zhang, Z. Chen and D. F. O'Shea, Chem. Commun., 2015, 51, 16667 DOI: 10.1039/C5CC06137G

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