4.7 Article

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

Journal

BIOORGANIC & MEDICINAL CHEMISTRY
Volume 21, Issue 21, Pages 6292-6302

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2013.08.064

Keywords

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

Funding

  1. Bulgarian National Science Fund [DDVU-02/97]
  2. University of Chemical Technology and Metallurgy, Sofia, Bulgaria
  3. Scientific Funds for Scientific Research (F.R.S-FNRS), Bruxelles, Belgium

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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) (PMMA(48)-b-PMAA(27)). The RNI-PMMA(48)-b-PMAA(27) 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. (C) 2013 Elsevier Ltd. All rights reserved.

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