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  • Title: Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission.
    Author: Trivedi ER, Lee S, Zong H, Blumenfeld CM, Barrett AG, Hoffman BM.
    Journal: J Org Chem; 2010 Mar 05; 75(5):1799-802. PubMed ID: 20136100.
    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.
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