Synthesis, crystal structure and spectroscopic characterizations of porphyrin-based Mg(II) complexes - Potential application as antibacterial agent

被引:34
作者
Amiri, Nesrine [1 ]
Ben Taheur, Fadia [2 ]
Chevreux, Sylviane [3 ]
Wenger, Emmanuel [4 ]
Lemercier, Gilles [3 ]
Nasri, Habib [1 ]
机构
[1] Univ Monastir, Lab Physicochim Mat, Ave Environm, Monastir 5019, Tunisia
[2] Univ Monastir, Lab Anal Traitement & Valorisat Polluantes Enviro, Fac Pharm, Rue Avicenne, Monastir 5000, Tunisia
[3] Univ Reims, ICMR UMR CNRS 7312, BP 1039, F-51687 Reims 2, France
[4] Univ Lorraine, Lab Cristallog Resonance Magnet & Modelisat, Fac Sci & Technol, CNRS, BP 70239, F-54506 Vandoeuvre Les Nancy, France
关键词
Porphyrin; Magnesium complex; UV-Vis spectroscopy; Fluorescence spectroscopy; Antibacterial activity; MANGANESE-PORPHYRINS; HYDROGEN-PEROXIDE; MOLECULAR STEREOCHEMISTRY; EPOXIDATION; CELLS; HYDROXYLATION; IMIDAZOLE;
D O I
10.1016/j.tet.2017.10.029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We reported the synthesis, spectral and photophysical studies of H2TBrPP (5,10,15,20-tetrakis(4-bromophenyl)porphyrin), Mg(TBrPP), and the complex [Mg(TBrPP)(HIm)] (I) (Him = Imidazole). A detailed analysis of infrared, and proton nuclear magnetic resonance spectroscopies, mass spectrometry, and elemental analysis are in good agreement with the transformation of the free base porphyrin H2TBrPP to the porphyrinic Mg(II) complex and to the one involving a bonded imidazole ligand. The photophysical properties were investigated by UV-visible absorption, and emission spectroscopies. New complex 1 was also characterized by single crystal X-ray diffraction confirming the pentacoordination of the Mg(II) ion within a new meso-porphyrin complex, an imidazole molecule in an axial position completing the ligand sphere. Potential use of this complex as a novel antibacterial agent was also investigated. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7011 / 7016
页数:6
相关论文
共 47 条
[1]   A SIMPLIFIED SYNTHESIS FOR MESO-TETRAPHENYLPORPHIN [J].
ADLER, AD ;
LONGO, FR ;
FINARELLI, JD ;
GOLDMACH.J ;
ASSOUR, J ;
KORSAKOF.L .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) :476-+
[2]   Nitration of Halterman porphyrin: a new route for fine tuning chiral iron and manganese porphyrins with application in epoxidation and hydroxylation reactions using hydrogen peroxide as oxidant [J].
Amiri, Nesrine ;
Le Maux, Paul ;
Srour, Hassan ;
Nasri, Habib ;
Simonneaux, Gerard .
TETRAHEDRON, 2014, 70 (46) :8836-8842
[3]  
[Anonymous], MOL SPECTROSC
[4]  
[Anonymous], 1988, Purification of Organic Solvents
[5]  
[Anonymous], J PHOTOCHEM PHOTOB B
[6]   Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus [J].
Bahnous, Mebarek ;
Bouraiou, Abdelmalek ;
Chelghoum, Meryem ;
Bouacida, Sofiane ;
Roisnel, Thierry ;
Smati, Farida ;
Bentchouala, Chafia ;
Gros, Philippe C. ;
Belfaitah, Ali .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (05) :1274-1278
[7]   Synthesis, Spectroscopic, and Biological Studies on New Zirconium(IV) Porphyrins with Axial Ligand [J].
Bajju, Gauri D. ;
Devi, Gita ;
Katoch, Sapna ;
Bhagat, Madhulika ;
Deepmala ;
Ashu ;
Kundan, Sujata ;
Anand, Sunil Kumar .
BIOINORGANIC CHEMISTRY AND APPLICATIONS, 2013, 2013
[8]   EXTINCTION WITHIN LIMIT OF VALIDITY OF DARWIN TRANSFER EQUATIONS .1. GENERAL FORMALISMS FOR PRIMARY AND SECONDARY EXTINCTION AND THEIR APPLICATION TO SPHERICAL CRYSTALS [J].
BECKER, PJ ;
COPPENS, P .
ACTA CRYSTALLOGRAPHICA SECTION A, 1974, A 30 (MAR) :129-147
[9]   A Magnesium Porphyrin Bicarbonate Complex with CO2-Modulated Photosystem I Action [J].
Bhuyan, Jagannath ;
Sarkar, Rudra ;
Sarkar, Sabyasachi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (45) :10603-10607
[10]   Highly efficient porphyrin sensitizers for dye-sensitized solar cells [J].
Campbell, Wayne M. ;
Jolley, Kenneth W. ;
Wagner, Pawel ;
Wagner, Klaudia ;
Walsh, Penny J. ;
Gordon, Keith C. ;
Schmidt-Mende, Lukas ;
Nazeeruddin, Mohammad K. ;
Wang, Qing ;
Gratzel, Michael ;
Officer, David L. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2007, 111 (32) :11760-11762