ABSTRACT
Two novel axially substituted phthalocyanines, namely bis(4-(4-acetylpiperazine)phenoxy)phthalocyaninatosilicon (IV) (1) and its N-methylated derivative 2, have been synthesized. The dicationic phthalocyanine 2 is non-aggregated in water and exhibits good photophysical properties. The non-covalent BSA conjugates of these compounds have also been prepared. Compound 2 and the conjugate 2-BSA show extremely high photodynamic activities toward B16 melanoma cancer cell lines. The corresponding 50% growth-inhibitory (IC50) ratios are 33 and 38 nM, respectively.
Subject(s)
Indoles/chemical synthesis , Indoles/pharmacology , Organosilicon Compounds/chemical synthesis , Organosilicon Compounds/pharmacology , Photosensitizing Agents/chemical synthesis , Photosensitizing Agents/pharmacology , Serum Albumin, Bovine/chemistry , Animals , Cattle , Cell Line, Tumor , Cell Proliferation/drug effects , Drug Screening Assays, Antitumor , In Vitro Techniques , Indoles/chemistry , Mice , Molecular Structure , Organosilicon Compounds/chemistry , Photosensitizing Agents/chemistry , StereoisomerismABSTRACT
A new silicon phthalocyanine axially substituted by Nipagin, i.e. bis(4-methoxycarboxyl phenoxy)phthalocyaninatosilicon, has been synthesized and characterized by IR, NMR, HPLC and elemental analysis. Its electronic absorption spectra and fluorescence spectra in different solvents were investigated. It was found that the compound existed in the form of monomer in a saline solution containing 2% (phi) Cremophor EL and 20% (phi) propanediol. The electronic absorption spectra of the compound in the above saline solution were typical for non-aggregated phthalocyanines, showing an intense and sharp Q band at 683 nm with a molar absorption coefficient of 7.47 x 10(4) mol(-1) x L x cm(-1). The compound exhibited a relatively strong fluorescence emission at 690 nm with a quantum yield of 0.34 and with a fluorescence lifetime of 4.7 ns. The primary in vitro assay showed the compound had photodynamic killing activities against B16 melanoma cells with a LD50(half lethal dose) of 1.2 x 10(-4) mol x L(-1).
Subject(s)
Indoles/analysis , Mass Spectrometry/methods , Organosilicon Compounds/analysis , Parabens/chemistry , Photochemical Processes , Chromatography, High Pressure Liquid , Indoles/chemistry , Molecular Structure , Organosilicon Compounds/chemistryABSTRACT
This paper reported the syntheses of amphiphilic substituted metal phthalocyanines containig sulfonic acid groups and phthalimidomethyl groups (MPcSP, M=Zn or Al(OH), S=-SO(3)(-), P=phthalimidomethyl). We have selected zinc phthalocyanine (Zn-D) as the one with better cell killing potential by an in vitro cell survival assay. Over 90 % tumor cells were killed with 10 mg/L Zn-D, after they were exposed to 12 J/cm(2) red light.
