Synthesis of functionalized chlorins sterically-prevented from self-aggregation

Dyes and Pigments

Volumn 99, Issue 2, 2013, Pages 402-411

  Dos Santos, Fabiane A B ^a   Uchoa, Adjaci F ^b   Baptista, Mauricio S ^b   Iamamoto, Yassuko ^b   Serra, Osvaldo A ^b   Brocksom, Timothy J ^a   De Oliveira, Kleber T ^a  

^a FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Chlorin derivatives; Diels Alder; Non aggregation; PDT and amphiphilicity; Photosensitizers; Protoporphyrin IX

Indexed keywords

AMPHIPHILICITY; CHLORINS; DIELS-ALDER; NON-AGGREGATION; PROTOPORPHYRIN IX;

ESTERIFICATION; ESTERS; PHOTODYNAMIC THERAPY; PHOTOSENSITIZERS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

CYCLOADDITION;

EID: 84879493566     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.05.024     Document Type: Article

References (20)

1. A.R. Battersby Tetrapyrroles: the pigments of life Nat Prod Rep 17 2000 507 526 (Pubitemid 32013254)
2. V.Y. Pavlov Modern aspects of the chemistry of protoporphyrin IX Russ J Org Chem 43 2007 9 36
3. M. Ethirajan, Y. Chen, P. Joshi, and R.K. Pandey The role of porphyrin chemistry in tumor imaging and photodynamic therapy Chem Soc Rev 40 2011 340 362
4. K.T. de Oliveira, A.M.S. Silva, A.C. Tomé, M.G.P.M.S. Neves, C.R. Néri, and V.S. Garcia Synthesis of new amphiphilic chlorin derivatives from protoporphyrin-IX dimethyl ester Tetrahedron 64 2008 8709 8715
5. F.F. de Assis, J.M. de Souza, B.H.K. Assis, T.J. Brocksom, and K.T. de Oliveira Synthesis and photophysical studies of a chlorin sterically designed to prevent self aggregation Dyes Pigment 98 2013 153 159
6. A.F. Uchoa, K.T. de Oliveira, M.S. Baptista, A.J. Bortoluzzi, Y. Iamamoto, and O.A. Serra Chlorin photosensitizers sterically designed to prevent self-aggregation J Org Chem 76 2011 8824 8832
7. W.L.F. Armarego, and C.L.L. Chai Purification of laboratory chemicals Copyright © 2009 Elsevier Inc
8. L. Roitman, B. Ehrenberg, and N. Kobayashi Spectral properties and absolute determination of singlet oxygen production by naphthaloporphyrins J Photochem Photobiol A Chem 77 1994 23 28
9. A. Nas, S. FandaklI, H. Kantekin, A. Demirbas, and M. Durmus Novel organosoluble metal-free and metallophthalocyanines bearing triazolemoieties: microwave assisted synthesis and determination of photophysical and photochemical properties Dyes Pigment 95 2012 8 17
10. F.M. Engelmann, S.V.O. Rocha, H.E. Toma, K. Araki, and M.S. Baptista Determination of n-octanol/water partition and membrane binding of cationic porphyrins Int J Pharm 329 2007 12 18 (Pubitemid 44937517)
11. J. Lindsey, S. Prathapan, T.E. Johnson, and R.W. Wagner Porphyrin building blocks for modular construction of bioorganic model systems Tetrahedron 50 1994 8941 8968 (Pubitemid 24246797)
12. G.Z. Xu, J.H. Dong, and K.Y. Qiu Photopolymerization of N-substituted phenyl maleimide initiated with N, N-dimethyl-4-toluidine J Polym Sci A1 35 1997 643 650 (Pubitemid 127581394)
13. V.G. Manecke, and J. Klawitter "Zur ynthese von Makromolekulen aus Nitronen durch 1,3-dipolare cycloaddition" Die Makromol Chem 142 1971 253 257
14. D.M. Wallace, S.H. Leung, M.0 Senge, and K.M. Smith Rational tetraarylporphyrin syntheses: tetraarylporphyrins from the MacDonald route J Org Chem 58 1993 1245 1251
15. B. Karini, H. Seradj, and M.H. Tabaei N-Bromosuccinimide (NBS), an efficient reagent for the conversion of 1,3-oxathiolanes to carbonyl compounds Synlett 12 2000 1798 1800 (Pubitemid 32005606)
16. A.H. Jackson, K.R.N. Rao, and M. Wilkins Synthetic and biosynthetic studies of porphyrins. Part 11. The synthesis of meso oxygenated protoporphyrins J Chem Soc Perkin Trans I 1987 307 312
17. D.R. Adans, and F. Wilkinson Lifetime of singlet oxygen in liquid solution J Chem Soc Faraday Trans 2 68 1972 586 593
18. P.F.C. Menezes, C.A.S. Melo, V.S. Bagnato, H. Imasato, and J.R. Perussi Dark cytotoxicity of the photoproducts of the photosensitizer photogem after photobleaching induced by laser Laser Phys 15 2005 435 442 (Pubitemid 40538287)
19. M. Kepczynski, R.P. Pandian, K.M. Smith, and B. Ehrenberg Do liposome-binding constants of porphyrins correlate with their measured and predicted partitioning between octanol and water Photochem Photobiol 76 2002 127 134
20. A.B. Ormond, and H.S. Freeman Effects of substituents on the photophysical properties of symmetrical porphyrins Dyes Pigment 96 2013 440 448