title: Photochemical and Photophysical Properties of Phthalocyanines Modified with Optically Active Alcohols.
abstract: Three phthalocyanine derivatives were synthesized and characterized: one modified with a racemic mixture of 1-(4-bromophenyl)ethanol and two other macrocycles modified with each one of the enantioenriched isomers (R)-1-(4-bromophenyl)ethanol and (S)-1-(4-bromophenyl)ethanol. The compounds were characterized by 1H-NMR spectroscopy, mass spectrometry, UV-Vis absorption, and excitation and emission spectra. Additionally, partition coefficient values and the quantum yield of the generation of oxygen reactive species were determined. Interestingly, the phthalocyanine containing a (R)-1-(4-bromophenyl)ethoxy moiety showed higher quantum yield of reactive oxygen species generation than other compounds under the same conditions. In addition, the obtained fluorescence microscopy and cell viability results have shown that these phthalocyanines have different interactions with mammary MCF-7 cells. Therefore, our results indicate that the photochemical and biological properties of phthalocyanines with chiral ligands should be evaluated separately for each enantiomeric species.
authors.affiliation: Centro de Ciências Naturais e Humanas-CCNH, Universidade Federal do ABC-UFABC, Avenida dos Estados, 5005, Bairro Bangu, Santo André-SP 09210-190, Brasil. linearamos@gmail.com.
authors.forename: Aline A
authors.initials: AA
authors.lastname: Ramos
authors.affiliation: Centro de Ciências Naturais e Humanas-CCNH, Universidade Federal do ABC-UFABC, Avenida dos Estados, 5005, Bairro Bangu, Santo André-SP 09210-190, Brasil. francisco.comunic@gmail.com.
authors.forename: Francisco B
authors.initials: FB
authors.lastname: Nascimento
authors.affiliation: Centro de Ciências Naturais e Humanas-CCNH, Universidade Federal do ABC-UFABC, Avenida dos Estados, 5005, Bairro Bangu, Santo André-SP 09210-190, Brasil. thaizamenegassi@gmail.com.
authors.forename: Thaiza F M
authors.initials: TF
authors.lastname: de Souza
authors.affiliation: Centro de Ciências Naturais e Humanas-CCNH, Universidade Federal do ABC-UFABC, Avenida dos Estados, 5005, Bairro Bangu, Santo André-SP 09210-190, Brasil. alvaro.omori@ufabc.edu.br.
authors.forename: Alvaro T
authors.initials: AT
authors.lastname: Omori
authors.affiliation: Centro de Ciências Naturais e Humanas-CCNH, Universidade Federal do ABC-UFABC, Avenida dos Estados, 5005, Bairro Bangu, Santo André-SP 09210-190, Brasil. tania.manieri@gmail.com.
authors.forename: Tânia M
authors.initials: TM
authors.lastname: Manieri
authors.affiliation: Centro de Ciências Naturais e Humanas-CCNH, Universidade Federal do ABC-UFABC, Avenida dos Estados, 5005, Bairro Bangu, Santo André-SP 09210-190, Brasil. gicerchiaro@gmail.com.
authors.forename: Giselle
authors.initials: G
authors.lastname: Cerchiaro
authors.affiliation: Centro de Ciências Naturais e Humanas-CCNH, Universidade Federal do ABC-UFABC, Avenida dos Estados, 5005, Bairro Bangu, Santo André-SP 09210-190, Brasil. anderson.ribeiro@ufabc.edu.br.
authors.forename: Anderson O
authors.initials: AO
authors.lastname: Ribeiro
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D054833:Isoindoles; D061986:MCF-7 Cells; D009369:Neoplasms / Q000188:drug therapy*; D010778:Photochemotherapy; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000438:Alcohols; D000970:Antineoplastic Agents; D007211:Indoles; D054833:Isoindoles; C013647:phthalocyanine
keywords: chiral phthalocyanines; dyes; enzymatic resolution; photodynamic therapy; photosensitizer