Synthesis of Phthalocyanines-ALA Conjugates: Water-Soluble Compounds with Low Aggregation

被引:41
作者
de Oliveira, Kleber T. [1 ,2 ]
de Assis, Francisco F. [1 ]
Ribeiro, Anderson O. [2 ]
Neri, Claudio R. [1 ]
Fernandes, Adjaci U. [1 ,3 ]
Baptista, Mauricio S. [3 ]
Lopes, Norberto P. [4 ]
Serra, Osvaldo A. [1 ]
Iamamoto, Yassuko [1 ]
机构
[1] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, BR-14040901 Ribeirao Preto, SP, Brazil
[2] Univ Fed ABC UFABC, Ctr Ciencias Nat & Humanas, BR-09210170 Santo Andre, SP, Brazil
[3] Univ Sao Paulo, Dept Bioquim, Inst Quim, BR-05508000 Sao Paulo, Brazil
[4] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Quim & Fis, BR-14040901 Ribeirao Preto, SP, Brazil
关键词
PHOTODYNAMIC THERAPY; UPDATE; 2006; PHOTOSENSITIZERS; PORPHYRINS; ZINC(II); METALLOPHTHALOCYANINES; ELECTROSPRAY; DERIVATIVES; IONIZATION; GENERATION;
D O I
10.1021/jo901633a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of two water-soluble phthalocyanines (Pc) containing 5-aminolevulinic acid (ALA) linked to the core structure are described. These compounds were prepared by using original functionalizations, and they present remarkable structural and photophysical features, indicating that they could be applied to photodynamic therapy (PDT).
引用
收藏
页码:7962 / 7965
页数:4
相关论文
共 71 条
[41]   Photodynamic therapy of skin cancer: controlled drug delivery of 5-ALA and its esters [J].
Lopez, RFV ;
Lange, N ;
Guy, R ;
Bentley, MVLB .
ADVANCED DRUG DELIVERY REVIEWS, 2004, 56 (01) :77-94
[42]   The synthesis and characterization of zincphthalocyanines bearing functionalized bulky phenoxy substituents [J].
Makhseed, Saad ;
Samuel, Jacob .
DYES AND PIGMENTS, 2009, 82 (01) :1-5
[43]   Photodynamic activity of water-soluble phthalocyanine zinc(II) complexes against pathogenic microorganisms [J].
Mantareva, Vanya ;
Kussovski, Veselin ;
Angelov, Ivan ;
Borisova, Ekaterina ;
Avramov, Latchezar ;
Schnurpfeil, Guenter ;
Woehrle, Dieter .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (14) :4829-4835
[44]   Supramolecular phthalocyanine dimers based on the secondary dialkylammonium cation/dibenzo-24-crown-8 recognition motif [J].
Martínez-Díaz, MV ;
Rodríguez-Morgade, MS ;
Feiters, MC ;
van Kan, PJM ;
Nolte, RJM ;
Stoddart, JF ;
Torres, T .
ORGANIC LETTERS, 2000, 2 (08) :1057-1060
[45]   Synthesis of novel push-pull unsymmetrically substituted alkynyl phthalocyanines [J].
Maya, EM ;
García, C ;
García-Frutos, EM ;
Vázquez, P ;
Torres, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (09) :2733-2739
[46]   The self-ordering properties of novel phthalocyanines with out-of-plane alkyl substituents [J].
McKeown, Neil B. ;
Helliwell, Madeleine ;
Hassan, Bashir M. ;
Hayhurst, David ;
Li, Hong ;
Thompson, Neil ;
Teat, Simon L. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (01) :228-234
[47]   Bis(2-pyridylimino)isoindole (BPI) ligands with novel linker units:: Synthesis and characterization of their palladium and platinum complexes [J].
Meder, M ;
Galka, CH ;
Gade, LH .
MONATSHEFTE FUR CHEMIE, 2005, 136 (10) :1693-1706
[48]   Photodynamic therapy: Porphyrins and phthalocyanines as Photosensitizers [J].
Moreira, Leonardo Marmo ;
dos Santos, Fabio Vieira ;
Lyon, Juliana Pereira ;
Maftoum-Costa, Maira ;
Pacheco-Soares, Cristina ;
da Silva, Newton Soares .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (10) :741-754
[49]   Guidelines for topical photodynamic therapy: update [J].
Morton, C. A. ;
McKenna, K. E. ;
Rhodes, L. E. .
BRITISH JOURNAL OF DERMATOLOGY, 2008, 159 (06) :1245-1266
[50]   Crown ether substituted monomeric and cofacial dimeric metallophthalocyanines. 1. Photophysical studies of the free base, zinc(II), and copper(II) variants [J].
Nikolaitchik, AV ;
Korth, O ;
Rodgers, MAJ .
JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (38) :7587-7596