Tyrosine-derived stimuli responsive, fluorescent amino acids

Pradeep Cheruku, Jen Huang Huang, Hung Ju Yen, Rashi S. Iyer, Kirk D. Rector, Jennifer S. Martinez, Hsing Lin Wang

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

A series of fluorescent unnatural amino acids (UAAs) bearing stilbene and meta-phenylenevinylene (m-PPV) backbone have been synthesized and their optical properties were studied. These novel UAAs were derived from protected diiodo-l-tyrosine using palladium-catalyzed Heck couplings with a series of styrene analogs. Unlike the other fluorescent UAAs, whose emissions are restricted to a narrow range of wavelengths, these new amino acids display the emission peaks at broad range wavelengths (from 400-800 nm); including NIR with QY of 4% in HEPES buffer. The incorporation of both pyridine and phenol functional groups leads to distinct red, green, and blue (RGB) emission, in its basic, acidic and neutral states, respectively. More importantly, these amino acids showed reversible pH and redox response showing their promise as stimuli responsive fluorescent probes. To further demonstrate the utility of these UAAs in peptide synthesis, one of the amino acids was incorporated into a cell penetrating peptide (CPP) sequence through standard solid phase peptide synthesis. Resultant CPP was treated with two different cell lines and the internalization was monitored by confocal fluorescence microscopy.

Original languageEnglish (US)
Pages (from-to)1150-1158
Number of pages9
JournalChemical Science
Volume6
Issue number2
DOIs
StatePublished - Feb 1 2015
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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