Polyaspartamide spin probes containing isoindoline nitroxide and porphyrin groups

Abstract

Water-soluble polyaspartamide isoindoline nitroxides 5-(4′-aminophenyl)-10,15,20-tris (4′-sulfonatophenyl) porphyrin, trisodium salt–poly[α,β- N-(2-hydroxyethyl)-l-aspartamide]–5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl were synthesized by the incorporation of 5-(4′-aminophenyl)-10,15,20-tris(4′-sulfonatophenyl) porphyrin, trisodium salt, as a tumor-targeting group, and 5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl into poly[α,β- N-(2-hydroxyethyl)-l-aspartamide]. These compounds were characterized, and the in vitro properties were evaluated. The polyaspartamide isoindoline nitroxides had higher relaxation effectiveness and had greater toxicity to HeLa cells than that of 5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl. The polyaspartamide isoindoline nitroxides retained similar electrochemical properties and redox reaction mechanisms as the parent nitroxides. The electron paramagnetic resonance spectra of polyaspartamide isoindoline nitroxides exhibited characteristic hyperfine electron paramagnetic resonance spectra of tetramethyl isoindoline nitroxides, with typical nitroxide g-values and nitrogen isotropic hyperfine coupling constants. Therefore, the water-soluble 5-(4′-aminophenyl)-10,15,20-tris(4′-sulfonatophenyl) porphyrin, trisodium salt–poly[α,β- N-(2-hydroxyethyl)-l-aspartamide]–5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl is considered to be a novel potential spin probe for electron paramagnetic resonance.