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Bioorg Med Chem. 2013 Nov 1;21(21):6292-302. doi: 10.1016/j.bmc.2013.08.064. Epub 2013 Sep 11.

A novel pH sensitive water soluble fluorescent nanomicellar sensor for potential biomedical applications.

Author information

  • 1Department of Organic Synthesis, University of Chemical Technology and Metallurgy, 8 Kliment Ohridsky Blvd., 1756 Sofia, Bulgaria.

Abstract

Herein we report on the synthesis and sensor activity of a novel pH sensitive probe designed as highly water-soluble fluorescent micelles by grafting of 1,8-naphthalimide-rhodamine bichromophoric FRET system (RNI) to the PMMA block of a well-defined amphiphilic diblock copolymer-poly(methyl methacrylate)-b-poly(methacrylic acid) (PMMA48-b-PMAA27). The RNI-PMMA48-b-PMAA27 adduct is capable of self-assembling into micelles with a hydrophobic PMMA core, containing the anchored fluorescent probe, and a hydrophilic shell composed of PMAA block. Novel fluorescent micelles are able to serve as a highly sensitive pH probe in water and to internalize successfully HeLa and HEK cells. Furthermore, they showed cell specificity and significantly higher photostability than that of a pure organic dye label such as BODIPY. The valuable properties of the newly prepared fluorescent micelles indicate the high potential of the probe for future biological and biomedical applications.

KEYWORDS:

1,8-Naphthalimide/rhodamine 6G bichromophore; Fluorescent micelles; Fluorescent resonance energy transfer (FRET); Living cells; Well-defined PMMA–PMAA block copolymer; pH sensor

PMID:
24075142
DOI:
10.1016/j.bmc.2013.08.064
[PubMed - indexed for MEDLINE]
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