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Cell-Penetrating Peptide-Conjugated BF2-Oxasmaragdyrins as NIRF Imaging and Photothermal Agents |
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| Authors: | Dr Kandala Laxman B Pradeep K Reddy Prof Andrea Robinson Prof Rohit Srivastava Prof Mangalampalli Ravikanth |
| Affiliation: | 1. Department of Chemistry, Indian Institute of Technology, Bombay, Powai, Mumbai, 400076 India
School of Chemistry, Monash University, Clayton, Melbourne, Australia IITB-Monash Research Academy, IIT Bombay, Powai, Mumbai, India;2. Department of Biosciences and Bioengineering, IIT Bombay Powai, Mumbai, India;3. School of Chemistry, Monash University, Clayton, Melbourne, Australia;4. Department of Chemistry, Indian Institute of Technology, Bombay, Powai, Mumbai, 400076 India |
| 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 R9 conjugate, being the first water-soluble BF2-oxasmaragdyrin, also possesses excellent photothermal transduction efficacy with 750 nm laser irradiation and is a potential theranostic agent. |
| Keywords: | BF2-oxasmaragdyrin macrocycles NIR fluorescence imaging peptides photothermal therapy |