Cell-Penetrating Peptide-Conjugated BF2-Oxasmaragdyrins as NIRF Imaging and Photothermal Agents

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

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1783-1787
Number of pages5
JournalChemMedChem
Volume15
Issue number19
DOIs
Publication statusPublished - 5 Oct 2020

Keywords

  • BF-oxasmaragdyrin
  • macrocycles
  • NIR fluorescence imaging
  • peptides
  • photothermal therapy

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