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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. [ABSTRACT FROM PUBLISHER]

Abstract: Porphyrin-containing polyaspartamide ligands (APTSPP–PHEA–DTPA) were synthesized by the incorporation of diethylenetriaminepentaacetic acid (DTPA) and 5-(4′-aminophenyl)-10,15,20-tris(4′-sulfonatophenyl) porphyrin, trisodium salt (APTSPP) into poly-α,β-[N-(2-hydroxyethyl)-l-aspartamide] (PHEA). These ligands were further reacted with gadolinium chloride to produce macromolecule-gadolinium complexes (APTSPP–PHEA–DTPA–Gd). Experimental data of 1H NMR, IR, UV and elemental analysis evidenced the formation of the polyaspartamide ligands and gadolinium complexes. In vitro and in vivo property tests indicated that APTSPP–PHEA–DTPA–Gd possessed noticeably higher relaxation effectiveness, less toxicity to HeLa cells, and significantly higher enhanced signal intensities (SI) of the VX2 carcinoma in rabbits with lower injection dose requirement than that of Gd–DTPA. Moreover, APTSPP–PHEA–DTPA–Gd was found to greatly enhance the contrast of MR images of the VX2 carcinoma, providing prolonged intravascular duration, and distinguished the VX2 carcinoma and normal tissues in rabbits according to MR image signal enhancements. These porphyrin-containing polyaspartamide gadolinium complexes can be used as the candidates of contrast agents for targeted MRI to tumors. [Copyright &y& Elsevier]

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 (a N 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. [Copyright &y& Elsevier]

Targeted tumor imaging in vivo has been one of the main challenges in the early stage of cancer diagnosis and therapy. However, few contrast probes are available to specifically respond to tumor environments. The aim was to investigate porphyrin‐1,8‐naphthalimide derivative (APTSPP‐2NI) as a potential tumor‐targeting fluorescent probe in vitro and in vivo. A tumor‐targeting APTSPP‐2NI was synthesized by the incorporation of water‐soluble 5‐(4'‐aminophenyl)‐10,15,20‐tris(4'‐sulfonato‐phenyl) porphyrin (APTSPP) as a tumor‐targeting group into N‐butyl‐4‐ethyldiamino‐1,8‐naphthalene imide (NI) fluorescence molecule herein. The derivative was further characterized and its properties in vitro and in vivo including the cell cytotoxicity, cell uptake of tumor cells and fluorescent imaging were also evaluated. Experiment results indicated that APTSPP‐2NI possessed the low cell cytotoxicity and good tumor‐targeting property to the B16F10 melanoma cells. Moreover, APTSPP‐2NI can be taken up highly by B16F10 melanoma tumors and then achieve the good green and red fluorescent imaging in B16F10 melanoma tumors. Therefore APTSPP‐2NI can be considered as a potential tumor‐targeting dual‐mode enhanced probe in fluorescent imaging in vitro and in vivo. [ABSTRACT FROM AUTHOR]

A water-soluble fullerenol containing porphyrin and isoindoline nitroxide groups APTSPP-C60(OH)10-(TMIO)3was synthesized by the incorporation of 5-(4-amino-phenyl)-10,15,20-tris(4-sulfonatophenyl)-porphyrin (APTSPP) as a tumor-targeting group and 5-formyl-1,1,3,3-tetramethylisoindolin-2-yloxyl (FTMIO) into fullerenol C60(OH)11. This nonmaterial was further characterized by FT-IR, UV, MS, TEM, fluorescence, etc. and its properties in vitro were also evaluated. Electrochemical experiments indicated that APTSPP-C60(OH)10-(TMIO)3retained similar electrochemical properties and redox reaction mechanisms as 5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl (CTMIO). Electron paramagnetic resonance (EPR) spectra of APTSPP-C60(OH)10-(TMIO)3exhibited the hyperfine splittings and characteristic spectra of CTMIO, with typical nitroxide g-values and nitrogen isotropic hyperfine coupling constants. In vitro cytotoxicity assay showed APTSPP-C60(OH)10-(TMIO)3possessed low cytotoxicities to human renal tubular epithelial 293T cells and HepG-2 cells. Therefore APTSPP-C60(OH)10-(TMIO)3may be considered as a potential candidate for novel biological spin probe using EPR spectroscopy. [ABSTRACT FROM AUTHOR]