Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission

J Org Chem. 2010 Mar 5;75(5):1799-802. doi: 10.1021/jo9026947.

Abstract

In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H(2)[pz(A(4-n);C(n))], n = 1, and 2 (trans-), where "A" represents peripheral heteroatom (S- and O-) R-groups and "C" is a fused, beta,beta'-diisopropyloxynaphtho group. The sulfide appended trans-H(2)[pz(A(2);C(2))] pz (7) has the longest wavelength absorption, approximately 874 nm (log epsilon = 4.53), and S(1) fluorescence at approximately 927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.

Publication types

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

MeSH terms

  • Absorption
  • Fluorescence
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Hydrogen-Ion Concentration
  • Molecular Structure
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Spectrum Analysis

Substances

  • Heterocyclic Compounds
  • Porphyrins