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Synthesis and properties of novel porphyrin spin probes containing isoindoline nitroxides

By Guo-Ping Yan, Daniel J. Bischa and Steven E. Bottle

Abstract

We report the synthesis of novel spin-labeled porphyrins containing isoindoline nitroxides (TMIO-APTPP and TMIO-APTSPP) and their manganese complexes (Mn-TMIO-APTPP and Mn-TMIO-APTSPP). These compounds represent potential new tools for electron paramagnetic resonance (EPR) as well as novel spin probes. Both TMIO-APTPP and TMIO-APTSPP have characteristic UV absorption peaks of free base porphyrin, while the characteristic absorption peaks of their manganese complexes Mn-TMIO-APTPP and Mn-TMIO-APTSPP shifted to shorter wavelengths. Electron paramagnetic resonance (EPR) spectroscopy indicated that these compounds all exhibit hyperfine splittings characteristic of EPR spectra of tetramethylisoindoline nitroxides, the typical nitroxide g values of approximately 2.006, and nitrogen isotropic hyperfine coupling constants (aN values) of about 14 G (293 K). The observed linewidths (La) for TMIO-APTSPP (0.73 G) and Mn-TMIO-APTSPP (0.65 G) in distilled water are significantly narrower than for TMIO-APTPP (1.475 G) and Mn-TMIO-APTPP (1.55 G) in chloroform

Topics: 030505 Physical Organic Chemistry, 030503 Organic Chemical Synthesis, Electron paramagnetic resonance (EPR), Porphyrin, Nitroxide, Isoindoline, Spin probe
Publisher: Elsevier
Year: 2007
DOI identifier: 10.1016/j.freeradbiomed.2007.03.032
OAI identifier: oai:eprints.qut.edu.au:14862

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