Microwave Synthesis, Basic Spectral and Biological Evaluation of Some Copper (II) Mesoporphyrinic Complexes

被引:25
作者
Boscencu, Rica [1 ]
Ilie, Mihaela [1 ]
Socoteanu, Radu [2 ,3 ]
Oliveira, Anabela Sousa [4 ]
Constantin, Carolina [5 ]
Neagu, Monica [5 ]
Manda, Gina [5 ]
Vieira Ferreira, Luis Filipe [3 ]
机构
[1] Carol Davila Univ Med & Pharm, Fac Pharm, Bucharest 020956, Romania
[2] Acad Romana, Ilie Murgulescu Inst Phys Chem, Bucharest 060021, Romania
[3] Inst Super Tecn, Inst Nanosci & Nanotechnol, Ctr Quim Fis Mol, P-1049001 Lisbon, Portugal
[4] Escola Super Tecnol & Gestao Portalegre, Inst Politecn Portalegre, P-7300901 Portalegre, Portugal
[5] Victor Babes Natl Inst Pathol & Biomed Sci, Bucharest 050096, Romania
关键词
copper (II) mesoporphyrinic complexes; FT-IR spectroscopy; solvatochromy; cytotoxicity; PHOTODYNAMIC THERAPY; ASSISTED SYNTHESIS; PORPHYRINS; PHOTOSENSITIZERS; PHTHALOCYANINES; LOCALIZATION; MECHANISMS; CHEMISTRY; LIPOSOMES; MTHPC;
D O I
10.3390/molecules15053731
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Cu(II) complexes with asymmetrical and symmetrical porphyrinic ligands were synthesized with superior yields using microwave irradiation. The paper presents the synthesis of 5-(3-hydroxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl)-21,23-Cu(II)-porphine in comparison to its symmetrical complex 5,10,15,20-meso-tetrakis-(4-carboxymethylphenyl)- 21,23-Cu(II) porphine. The two compounds were characterized by FT-IR, UV-Vis and EPR spectroscopy, which fully confirmed the structures. The spectral molecular absorption properties of the porphyrinic complexes were studied in organic solvents (methanol, ethanol, iso-propanol, dimethyl sulfoxide, dimethylformamide and methylene chloride), and the influence of the solvent polarity on the absorbance maxima is described. In order to establish their future potential in biomedical applications preliminary toxicological studies consisting of viability and proliferation of standard tumor cell lines (MCF7 and B16) testing was performed. The obtained results indicate a low toxicity for both compounds and further recommends them for testing in light activation protocols.
引用
收藏
页码:3731 / 3743
页数:13
相关论文
共 40 条
[1]   Microwave chemistry: Out of the kitchen [J].
Adam, D .
NATURE, 2003, 421 (6923) :571-572
[2]   Photodynamic effects of porphyrin and chlorin photosensitizers in human colon adenocarcinoma cells [J].
Banfi, S ;
Caruso, E ;
Caprioli, S ;
Mazzagatti, L ;
Canti, G ;
Ravizza, R ;
Gariboldi, M ;
Monti, E .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (18) :4853-4860
[3]   5-(3-CARBOXYMETHOXYPHENYL)-2-(4,5-DIMETHYLTHIAZOLYL)-3-(4-SULFOPHENYL)TETRAZOLIUM, INNER SALT (MTS) AND RELATED ANALOGS OF 3-(4,5-DIMETHYLTHIAZOLYL)-2,5-DIPHENYLTETRAZOLIUM BROMIDE (MTT) REDUCING TO PURPLE WATER-SOLUBLE FORMAZANS AS CELL-VIABILITY INDICATORS [J].
BARLTROP, JA ;
OWEN, TC ;
CORY, AH ;
CORY, JG .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (11) :611-&
[4]   Porphyrins in analytical chemistry. A review [J].
Biesaga, M ;
Pyrzynska, K ;
Trojanowicz, M .
TALANTA, 2000, 51 (02) :209-224
[5]  
BONNETT R, 2000, ADVANCED CHEM TEXTS, V1, P1
[6]  
Boscencu R, 2008, POL J CHEM, V82, P509
[7]   Studies on Zn(II) monohydroxyphenyl mesoporphyrinic complexes. Synthesis and characterization [J].
Boscencu, Rica ;
Socoteanu, Radu ;
Oliveira, Anabela S. ;
Ferreira, Luis Filipe Vieira .
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2008, 73 (07) :713-726
[8]   Efficient microwave-assisted synthesis of new sulfonylbenzimidazole-4,7-diones: heterocyclic quinones with potential antitumor activity [J].
Boufatah, N ;
Gellis, A ;
Maldonado, J ;
Vanelle, P .
TETRAHEDRON, 2004, 60 (41) :9131-9137
[9]   Structure and biodistribution relationships of photodynamic sensitizers [J].
Boyle, RW ;
Dolphin, D .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1996, 64 (03) :469-485
[10]   Nanoparticles in photodynamic therapy: An emerging paradigm [J].
Chatterjee, Dev Kumar ;
Fong, Li Shan ;
Zhang, Yong .
ADVANCED DRUG DELIVERY REVIEWS, 2008, 60 (15) :1627-1637