title: Sulfonated chloroaluminum phthalocyanine incorporates into human plasma lipoproteins: photooxidation of low-density lipoproteins.
abstract: The interactions of sulfonated chloroaluminum phthalocyanine (AlPcSn) with human low-density lipoproteins (LDL) were studied in vitro in human plasma and in an isolated LDL fraction, in order to understand the potential effects of the sensitizer against LDL. The AlPcSn added to plasma distributes in all lipoproteins as observed by the drastic color changes of the separated fractions by ultracentrifugation. In isolated LDL, incubation with AlPcSn causes fluorescence quenching of the apoprotein tryptophan residues. Furthermore, AlPcSn incorporates in liposomes, with a lipid composition similar to the external monolayer of human LDL, as indicated by absorbance spectroscopy. The photosensitizing properties of AlPcSn in LDL particles were studied on the basis of the fluorescence quenching of previously incorporated cis-parinaric acid (PnA), used as an oxidation probe, and of O2 consumption. The photooxidation of either PnA or LDL lipids is highly dependent on irradiation time and on the dye concentration. Moreover, photooxidation of LDL proceeds only during the illumination period. After stopping the illumination and upon addition of Cu2+ to the LDL solution, the oxidative rate is resumed, probably due to hydroperoxide cleavage and formation of species able to propagate the oxidative reaction. Thus, our data indicate that AlPcSn distributes in human plasma lipoproteins and, in isolated LDL, it can interact either with the lipid phase or the apoprotein. The photooxidation of LDL induced by AlPcSn seems to involve singlet oxygen as the main reactive species in the degradative process.
authors.affiliation: Laboratório de Bioquímica, Faculdade de Farmácia and Centro de Neurociências, Universidade de Coimbra, Portugal.
authors.forename: A E
authors.initials: AE
authors.lastname: Santos
authors.forename: J A
authors.initials: JA
authors.lastname: Laranjinha
authors.forename: L M
authors.initials: LM
authors.lastname: Almeida
mesh_terms: D006801:Humans; D007211:Indoles / Q000097:blood*; D008077:Lipoproteins, LDL / Q000097:blood* / Q000378:metabolism*; D009942:Organometallic Compounds / Q000097:blood*; D017319:Photosensitizing Agents / Q000097:blood*; D011485:Protein Binding; D013050:Spectrometry, Fluorescence
chemical_list: D007211:Indoles; D008077:Lipoproteins, LDL; D009942:Organometallic Compounds; D017319:Photosensitizing Agents; C099252:oxidized low density lipoprotein; C063071:aluminum(III) phthalocyanine trisulfonic acid; C064331:aluminum phthalocyanine disulfonate