Synthesis and photophysical studies of a chlorin sterically designed to prevent self-aggregation

Dyes and Pigments

Volumn 98, Issue 1, 2013, Pages 153-159

  De Assis, Francisco F ^a   De Souza, Juliana M ^a   Assis, Beatriz H K ^a   Brocksom, Timothy J ^a   De Oliveira, Kleber T ^a  

^a FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

Author keywords

1,3 dipolar cycloaddition; Chlorin; Non aggregation; PDT; Porphyrin; Synthesis

Indexed keywords

SCAFFOLDS; SYNTHESIS (CHEMICAL);

1 ,3-DIPOLARCYCLOADDITION; AGGREGATION IN SOLUTIONS; AZOMETHINE YLIDES; CHLORINS; MOLECULAR SCAFFOLDS; NON-AGGREGATION; PHOTOPHYSICAL PROPERTIES; PHOTOPHYSICAL STUDIES;

PORPHYRINS;

EID: 84874939090     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.02.011     Document Type: Article

References (23)

1. Mikroyannidis JA, Charalambidis G, Coutsolelos AG, Balraju P, Sharma GD. Novel zinc porphyrin with phenylenevinylene meso-substituents: synthesis and application in dye-sensitized solar cells. J Power Sources 2011;196: 6622-8.
2. Fackler P, Huber SM, Bach T. Enantio- and regioselective epoxidation of olefinic double bonds in quinolones, pyridones, and amides catalyzed by a ruthenium porphyrin catalyst with a hydrogen bonding site. J Am Chem Soc 2012;134:12869-78.
3. Morales-Espinoza EG, Lijanova IV, Morales-Saavedra OG, Torres-Zuñiga V, Hernandez-Ortega S, Martínez-García M. Synthesis of porphyrin-dendrimers with a pyrene in the periphery and their cubic nonlinear optical properties. Molecules 2011;16:6950-68.
4. Bischoff R, Bischoff G, Hoffmann S. Scanning force microscopy observation of tumor cells treated with hematoporphyrin IX derivatives. Ann Biomed Eng 2001;29:1092-9.
5. Ethirajan M, Chen Y, Joshi P, Pandey RK. The role of porphyrin chemistry in tumour imaging and photodynamic therapy. Chem Soc Rev 2011;40:340-62.
6. Inada NM, da Costa MM, Guimarães OCC, Ribeiro ES, Kuracho C, Quintana SM, et al. Photodiagnosis and treatment of condyloma acuminatum using 5- aminolevulinic acid and homemade devices. Photodiagnosis Photodyn Ther 2012;9:60-8.
7. Gois MM, Kurachi C, Santana EJB, Mima EGO, Spolidório DMP, Pelino JEP, et al. Susceptibility of Staphylococcus aureus to porphyrin-mediated photodynamic antimicrobial chemotherapy: an in vitro study. Lasers Med Sci 2010;23:391-5.
8. Mima EG, Vergani CE, Machado AL, Massucato EMS, Colombo AL, Bagnato VS, et al. Comparison of photodynamic therapy versus conventional antifungal therapy for the treatment of denture stomatitis: a randomized clinical trial. Clin Microbiol Infect 2012;18:E380-8.
9. de Oliveira KT, de Assis FF, Ribeiro AO, Neri CR, Fernandes AU, Baptista MS, et al. Synthesis of phthalocyanines-ALA conjugates: water-soluble compounds with low aggregation. J Org Chem 2009;74:7962-5.
10. Li K, Guo C, Chen Q. Efficient one-pot regioselective synthesis of 2, 3-dibromo- 5, 10, 15, 20-tetraarylporphyrins from 5, 10, 15, 20-tetraarylchlorins. Synlett 2009:2867-71.
11. You H, Yoon H, Yoon J, Ko H, Kim Y. Synthesis of pheophorbide-a conjugates with anticancer drugs as potential cancer diagnostic and therapeutic agents. Bioorg Med Chem 2011;19:5383-91.
12. de Oliveira KT, Silva AMS, Tomé AC, Neves MGPMS, Neri CR, Garcia VS, et al. Synthesis of new amphiphilic chlorin derivatives from protoporphyrin-IX dimethyl ester. Tetrahedron 2008;64:8709-15.
13. Gaeüzowski M, Gryko DT. Synthesis of locked meso-β-substituted chlorins via 1, 3-dipolar cycloaddition. J Org Chem 2006;71:5942-50.
14. Silva AMG, Tomé AC, Neves MGPMS, Silva MAS, Cavaleiro JAS. meso-Tetraarylporphyrins as dipolarophiles in 1, 3-dipolar cycloaddition reactions. Chem Commun 1999:1767-8.
15. Wyrebek P, Mikus A, Ostrowski S. 1, 3-Dipolar cycloaddition reaction in porphyrin systems with functionalized alkyl nitrile oxides - synthesis of isoxazoline-fused chlorins. Heterocycles 2012;85:57-64.
16. Uchoa AF, de Oliveira KT, Baptista MS, Bortoluzzi AJ, Iamamoto Y, Serra OA. Chlorin photosensitizers sterically designed to prevent self-aggregation. J Org Chem 2011;76:8824-32.
17. Armarego WLF, Perrin DD. Purification of laboratory chemicals. 4th ed. Oxford: Butterworth-Heinemann; 2000.
18. Roitman L, Ehrenberg B, Kobayashi N. Spectral properties and absolute determination of singlet oxygen production by naphthaloporphyrins. J Photochem Photobiol A Chem 1994;77:23-8.
19. Nas A, Fandakli S, Kantekin H, Demirbas A, Durmus M. Novel organosoluble metal-free and metallophthalocyanines bearing triazolemoieties: microwave assisted synthesis and determination of photophysical and photochemical properties. Dyes Pigment 2012;95:8-17.
20. Arnold DP, Nitschinsk LJ, Kennard CHL, Smith G. Preparation of some pyrrole- 3, 4-dicarboxylic acid derivatives and the crystal structure of 2-methylpyrrolo[3, 4-c]pyrrole-1, 3(H2, 5H)-dione. Aust J Chem 1991;44:323-30.
21. Uno H, Inoue K, Inoue T, Ono N. Oligocyclization of 2-(hydroxymethyl) pyrroles with electron withdrawing groups at β-positions: formation and structural elucidation of porphyrinogens and hexaphyrinogens. Org Biomol Chem 2003;1:3857-65.
22. Lindsey JS, Hsu HC, Schereiman IC. Synthesis of tetraphenylporphyrins under very mild conditions. Tetrahedron Lett 1986;27:4969-70.
23. Tomé JPC, Neves MGPMS, Tomé AC, Cavaleiro JAS, Mendonça AF, Pegado IN, et al. Synthesis of glycoporphyrin derivatives and their antiviral activity against herpes simplex virus types 1 and 2. Bioorg Med Chem 2005;13:3878-88.