Porphyrin with amino acid moieties: A tumor photosensitizer

Chemico-Biological Interactions

Volumn 172, Issue 2, 2008, Pages 154-158

  Wang, H M ^a   Jiang, J Q ^b   Xiao, J H ^a   Gao, R L ^a   Lin, F Y ^b   Liu, X Y ^b  

^a Beijing Institute of Pharmaceutical Chemistry   (China)

^b JIANGNAN UNIVERSITY   (China)

Author keywords

Cell; Photodynamic therapy; Porphyrin; Valine

Indexed keywords

AMINO ACID DERIVATIVE; LACTIC ACID; PHOTOSENSITIZING AGENT; PORPHYRIN DERIVATIVE; TETRAKIS(4 NITROPHENYL)PORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; BREAST TUMOR; CATALYST; CELL STRAIN MCF 7; CELL SURVIVAL; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PHOTODYNAMIC THERAPY; PHOTOSENSITIZATION; PHOTOTOXICITY;

TETRA;

EID: 40149085529     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2007.11.016     Document Type: Article

References (29)

1. A. Jasat D. Dolphin Expanded porphyrins and their heterologs Chem. Rev. 97 1997 2267 2340
2. N. Kashiwagi T. Akeda T. Morimoto T. Ishizuka H. Furuta Synthesis and isomerization of imino-fused n-confused porphyrin Org. Lett. 9 2007 1733 1736
3. + Inorg. Chem. 46 2007 3889 3902
4. P. Kubat K. Lang P. Cigler M. Kozisek P. Matejicek P. Janda Z. Zelinger K. Prochazka V. Kral Tetraphenylporphyrin-cobalt(III) bis(1,2-dicarbollide) conjugates: from the solution characteristics to inhibition of HIV protease J. Phys. Chem. B 111 2007 4539 4546
5. H.P. Li Study on synthesis and biological activity of a galactosylated piperazinyl porphyrin Bioorg. Med. Chem. Lett. 16 2006 6298 6301
6. H.P. He T. Tian P. Wang L. Wu J.J. Xu X. Zhou X.L. Zhang X.P. Cao X.J. Wu Porphyrin-DNA cross-linking agent hybrids: chemical synthesis and biological studies Bioorg. Med. Chem. Lett. 14 2004 3013 3016
7. Y.S. Kim R. Song C.O. Lee Y.S. Sohn Synthesis and biological activity of novel platinum(II) complexes of glutamate tethered to hydrophilic hematoporphyrin derivatives Bioorg. Med. Chem. Lett. 14 2004 2889 2892
8. B. Di Stasio C. Frochot D. Dumas P. Even J. Zwier A. Muller J. Didelon F. Guillemin M.L. Viriot M. Barberi-Heyob The 2-aminoglucosamide motif improves cellular uptake and photodynamic activity of tetraphenylporphyrin Eur. J. Med. Chem. 40 2005 1111 1122
9. C.N. Lunardi A.C. Tedesco Synergic photosensitizers: a new trend in photodynamic therapy Curr. Org. Chem. 9 2005 813 821
10. O. Ongayi V. Gottumukkala F.R. Fronczek M.G.H. Vicente Synthesis and characterization of a carboranyl-tetrabenzoporphyrin Bioorg. Med. Chem. Lett. 15 2005 1665 1668
11. M. Kwitniewski D. Kunikowska B. Dera-Tomaszewska E. Tokarska-Pietrzak H. Dziadziuszko A. Graczyk R. Glosnicka Influence of diamino acid derivatives of protoporphyrin IX on mouse immunological system: preliminary results J. Photochem. Photobiol. B-Biol. 81 2005 129 135
12. G. Di Venosa H. Fukuda A. Batlle A. MacRobert A. Casas Photodynamic therapy: regulation of porphyrin synthesis and hydrolysis from ala esters J. Photochem. Photobiol. B-Biol. 83 2006 129 136
13. G. Kramer-Marek C. Serpa A. Szurko M. Widel A. Sochanik M. Snietura P. Kus R.M.D. Nunes L.G. Arnaut A. Ratuszna Spectroscopic properties and photodynamic effects of new lipophilic porphyrin derivatives: efficacy, localisation and cell death pathways J. Photochem. Photobiol. B-Biol. 84 2006 1 14
14. V. Sol V. Chaleix Y. Champavier R. Granet Y.M. Huang P. Krausz Glycosyl bis-porphyrin conjugates: synthesis and potential application in PDT Bioorg. Med. Chem. 14 2006 7745 7760
15. S. Banfi E. Caruso S. Caprioli L. Mazzagatti G. Canti R. Ravizza M. Gariboldi E. Monti Photodynamic effects of porphyrin and chlorin photosensitizers in human colon adenocarcinoma cells Bioorg. Med. Chem. 12 2004 4853 4860
16. V. Gottumukkala O. Ongayi D.G. Baker L.G. Lomax M.G.H. Vicente Synthesis, cellular uptake and animal toxicity of a tetra(carboranylphenyl)-tetrabenzoporphyrin Bioorg. Med. Chem. 14 2006 1871 1879
17. I. Laville S. Pigaglio J.C. Blais B. Loock P. Maillard D.S. Grierson J. Blais A study of the stability of tri(glucosyloxyphenyl)chlorin, a sensitizer for photodynamic therapy, in human colon tumoural cells: a liquid chromatography and MALDI-TOF mass spectrometry analysis Bioorg. Med. Chem. 12 2004 3673 3682
18. Y. You S.L. Gibson R. Hilf S.R. Davies A.R. Oseroff I. Roy T.Y. Ohulchanskyy E.J. Bergey M.R. Detty Water soluble, core-modified porphyrins. 3. Synthesis, photophysical properties, and in vitro studies of photosensitization, uptake, and localization with carboxylic acid-substituted derivatives J. Med. Chem. 46 2003 3734 3747
19. R. Schneider L. Tirand C. Frochot R. Vanderesse N. Thomas J. Gravier F. Guillemin M. Barberi-Heyob Recent improvements in the use of synthetic peptides for a selective photodynamic therapy Anti-Cancer Agent Med. Chem. 6 2006 469 488
20. G.L. Liang L. Wang Z.M. Yang H. Koon N. Mak C.K. Chang B. Xu Using enzymatic reactions to enhance the photodynamic therapy effect of porphyrin dityrosine phosphates Chem. Commun. 2006 5021 5023
21. I. Laville S. Pigaglio J.C. Blais F. Doz B. Loock P. Maillard D.S. Grierson J. Blais Photodynamic efficiency of diethylene glycol-linked glycoconjugated porphyrins in human retinoblastoma cells J. Med. Chem. 49 2006 2558 2567
22. M.G. Alvarez C. Prucca M.E. Milanesio E.N. Durantini V. Rivarola Photodynamic activity of a new sensitizer derived from porphyrin-c-60 dyad and its biological consequences in a human carcinoma cell line Int. J. Biochem. Cell Biol. 38 2006 2092 2101
23. M.E. Milanesio M.G. Alvarez V. Rivarola J.J. Silber E.N. Durantini Porphyrin-fullerene c-60 dyads with high ability to form photoinduced charge-separated state as novel sensitizers for photodynamic therapy Photochem. Photobiol. 81 2005 891 897
24. N. Malatesti K. Smith H. Savoie J. Greenman R.W. Boyle Synthesis and in vitro investigation of cationic 5,15-diphenyl porphyrin-monoclonal antibody conjugates as targeted photodynamic sensitisers Int. J. Oncol. 28 2006 1561 1569
25. G.M. Di Venosa A.G. Casas S. Battah P. Dobbin H. Fukuda A.J. MacRobert A. Batlle Investigation of a novel dendritic derivative of 5-aminolaevulinic acid for photodynamic therapy Int. J. Biochem. Cell Biol. 38 2006 82 91
26. B. Pegaz E. Debefve F. Borle J.P. Ballini H. van den Bergh Y.N. Kouakou-Konan Encapsulation of porphyrins and chlorins in biodegradable nanoparticles: the effect of dye lipophilicity on the extravasation and the photothrombic activity. A comparative study J. Photochem. Photobiol. B-Biol. 80 2005 19 27
27. H.W. Gu K.M. Xu Z.M. Yang C.K. Chang B. Xu Synthesis and cellular uptake of porphyrin decorated iron oxide nanoparticles—a potential candidate for bimodal anticancer therapy Chem. Commun. 2005 4270 4272
28. A. Bettelheim B.A. White S.A. Raybuck R.W. Murray Electrochemical polymerization of amino-, pyrrole-, and hydroxy-substituted tetraphenylporphyrins Inorg. Chem. 26 1987 1009 1017
29. X.M. Jin J. Wu Synthesis of amino acid porphyrins J. Zhejiang Univ. (Sci. Ed.) 30 2003 180 183