Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission.
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.
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Evan R
ER
Trivedi
Sangwan
S
Lee
Hong
H
Zong
Carl M
CM
Blumenfeld
Anthony G M
AG
Barrett
Brian M
BM
Hoffman
D000042:Absorption; D005453:Fluorescence; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013057:Spectrum Analysis
D006571:Heterocyclic Compounds; D011166:Porphyrins