Cell-Penetrating Peptide-Conjugated BF 2 -Oxasmaragdyrins as NIRF Imaging and Photothermal Agents”

Authors

Kandala Laxman, B. Pradeep K. Reddy, Andrea Robinson, Rohit Srivastava, Mangalampalli Ravikanth

Published ChemMedChem
Graphical abstract
Abstract

Cell-penetrating peptides (CPPs) are excellent cell internalizing agents for hydrophobic drug/dye moieties. We exploited this property of CPPs for the cell internalization of BF2-oxasmaragdyrin by constructing covalent conjugates of BF2-oxasmaragdyrin with CPPs (CRGDK and polyarginine (R9)) using a solid-phase peptide synthesis (SPPS) methodology. The CPP-conjugated BF2-oxasmaragdyrins were purified by reversed-phase HPLC and characterized by mass spectrometry. The CPP-conjugated BF2-oxasmaragdyrins were found to be photostable, absorb in the visible-NIR region (400–700 nm), emit in the NIR−I region (∼715–720 nm) with moderate quantum yields, and be biocompatible, with excellent cellular imaging potential in breast cancer cells (MDA-MB-231). The R9conjugate, being the first water-soluble BF2-oxasmaragdyrin, also possesses excellent photothermal transduction efficacy with 750 nm laser irradiation and is a potential theranostic agent.

Citation

K. Laxman, B. P. K. Reddy, A. Robinson, R. Srivastava, M. Ravikanth, “Cell-Penetrating Peptide-Conjugated BF 2 -Oxasmaragdyrins as NIRF Imaging and Photothermal Agents”, ChemMedChem, 2020, 15(19), 1783– 1787

Pdf  
Doi

https://doi.org/10.1002/cmdc.202000401

Keywords

BF2-oxasmaragdyrin, macrocycles, NIR fluorescence imaging, peptides, photothermal therapy

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