Bichromophoric fluorescent photolabile protecting group for alcohols and carboxylic acids

Photochem Photobiol Sci. 2012 Mar;11(3):518-21. doi: 10.1039/c1pp05317e. Epub 2011 Dec 21.

Abstract

Novel bichromophoric fluorescent photolabile protecting group, (5-dansyloxy-3-hydroxynaphthalen-2-yl)methyl (DNS-NQMP), allows for the independent photochemical release and fluorescent imaging of caged substrates. Irradiation of DNS-NQMP-caged alcohols and carboxylic acids with 300 or 350 nm light results in fast (k(release) ~ 10(5) s(-1)), efficient (Φ = 0.2), and quantitative release of the substrates. This uncaging chemistry is compatible with aqueous media and DNS-NQMP-protected hydroxy compounds are hydrolytically stable at neutral pH. Upon excitation with 400 nm light, caged compounds show intense green emission (λ(max) = 559 nm) with 21% fluorescence quantum yield. Fluorescent readout conducted using 400 nm or longer wavelengths does not cause substrate release. The DNS-NQMP chromophore retains its fluorescent properties after photo-uncaging reaction.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohols / chemistry*
  • Carboxylic Acids / chemistry*
  • Fluorescence*
  • Molecular Structure
  • Naphthalenes / chemical synthesis
  • Naphthalenes / chemistry*
  • Photolysis

Substances

  • (5-dansyloxy-3-hydroxynaphthalen-2-yl)methyl
  • Alcohols
  • Carboxylic Acids
  • Naphthalenes