Synthesis and characterization of positively charged porphyrin-pep tide conjugates

Bioconjugate Chemistry

Volumn 16, Issue 4, 2005, Pages 852-863

  Sibrian Vazquez, Martha ^a   Jensen, Timothy J ^a   Fronczek, Frank R ^a   Hammer, Robert P ^a   Vicente, M Graça H ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; HYDROPHOBICITY; METAL IONS; METALS; PEPTIDES; SPECTROSCOPIC ANALYSIS;

AMINO-ACIDS; CHARGED AMINO ACIDS; IN-VITRO; ISOTHIOCYANATES; METALS IONS; POSITIVELY CHARGED; SPECTROSCOPIC METHOD; SYNTHESIS AND CHARACTERIZATIONS; TOTAL SYNTHESIS; X-RAY STRUCTURE;

PORPHYRINS;

4 [4 (10,15,20 TRIPHENYLPORPHYRIN 5 YL)PHENYLCARBAMOYL]BUTYRIC ACID; 5 (4 ISOTHIOCYANATOPHENYL) 10,15,20 TRIPHENYLPORPHYRIN; AMINO ACID DERIVATIVE; ARGININE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; MACROCYCLIC COMPOUND; METAL CHELATE; METAL ION; PEPTIDE DERIVATIVE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CELLULAR DISTRIBUTION; CONJUGATE; CRYSTAL STRUCTURE; DRUG ACCUMULATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; DRUG UPTAKE; HUMAN; HUMAN CELL; HYDROPHOBICITY; IC 50; IN VITRO STUDY; MOLECULAR INTERACTION; PROTEIN FOLDING; THEORETICAL STUDY;

EID: 22644434142     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc050057g     Document Type: Article

References (55)

1. Pandey, R. K., and Zheng, G. (2000). Porphyrins as photosensitizers in photodynamic therapy. The Porphyrin Handbook. Volume 6: Applications: past, present and future (Radish, K. M., Smith, K. M., and Guilard, R., Eds.) pp 157-230, Chapter 43, Academic Press, New York.
2. Vicente, M. G. H. (2001) Porphyrin-based sensitizers in the detection and treatment of cancer: Recent progress. Curr. Med. Chem. Anti-Cancer Agents 1, 175-194.
3. Rosenkranz, A. A., Jans, D. A., and Sobolev, A. S. (2000) Targeted intracellular delivery of photosensitizers to enhance photodynamic efficiency. Immunol. Cell Biol. 78, 452-464.
4. Kessel, D. (2004) Correlation between subcellular localization and photodynamic efficacy. J. Porphyrins Phthalocyanines 8, 1009-1014.
5. Kessel, D., and Luo, Y. (1998) Mitochondrial photodamage and PDT-induced apoptosis. J. Photochem. Photobiol. B: Biol. 42, 89-95.
6. Osterloh, J., and Vicente, M. G. H. (2002) Mechanisms of porphyrinoid localization in tumors. J. Porphyrins Phthalocyanines 6, 305-324.
7. Marzilli, L. G. (1990) Medical aspects of DNA-porphyrin interactions. New J. Chem. 14, 409-420.
8. Mettath, S., Munson, B. R., and Pandey, R. K. (1999) DNA interaction and photocleavage properties of porphyrins containing cationic substituents at the peripheral position. Bioconjugate Chem. 10, 94-102.
9. Bustamante, C., Gurrieri, S., Pasternack, R. F., Purrello, R., and Rizzarelli, E. (1994) Interaction of water-soluble porphyrins with single- and double-stranded polyribonucleotides. Biopolymers 34, 1099-1104.
10. Hamblin, M. R., O'Donnell, D. A., Murthy, N., Contag, C. H., and Hasan, T. (2002) Rapid control of wound infections by targeted photodynamic therapy monitored by in vivo bioluminescence imaging. Photochem. Photobiol. 75, 51-57.
11. Reddi, E., Ceccon, M., Valduga, G., Jori, G., Bommer, J. C., Elisei, F., Latterini, L., and Mazzucato, U. (2002) Photophysical properties and antibacterial activity of mesosubstituted cationic porphyrins. Photochem. Photobiol. 75, 462-470.
12. Sol, V., Branland, P., Chaleix, V., Granet, R., Guilloton, M., Lamarche, F., Verneuil, B., and Krausz, P. (2004) Amino porphyrins as photoinhibitors of gram-positive and -negative bacteria. Bioorg. Med. Chem. Lett. 14, 4207-4211.
13. Tome, J. P. C., Neves, M. G. P. M. S., Tome, A. C., Cavaleiro, J. A. S., Soncin, M., Magaraggia, M., Ferro, S., and Jori, G. (2004) Synthesis and antibacterial activity of new poly-S-lysine-porphyrin conjugates. J. Med. Chem. 47, 6649-6652.
14. Lazzeri, D., Rovera, M., Pascual, L., and Durantini, E. N. (2004) Photodynamic studies and photoinactivation of Escherichia coli using meso-substituted cationic porphyrin derivatives with asymmetric charge distribution. Photochem. Photobiol. 80, 286-293.
15. Matthews, J. L., Sogandares-Bernal, F., Judy, M., Gulliya, K., Newman, J., Chanh, T., and Marengo-Rowe, A. (1992) Inactivation of viruses with photoactive compounds. Blood Cells 18, 75-89.
16. Casteel, M. J., Jayaraj, K., Gold, A., Ball, L. M., and Sobsey, M. D. (2004) Photoinactivation of hepatitis A virus by synthetic porphyrins. Photochem. Photobiol. 80, 294-300.
17. Cavanaugh, P. G. (2002) Synthesis of chlorin e6-transferrin and demonstration of its light-dependent in vitro breast cancer cell killing ability. Breast Cancer Res. Treat. 72, 117-130.
18. Sutton, J. M., Clarke, O. J., Fernandez, N., and Boyle, R. W. (2002) Porphyrin, chlorin, and bacteriochlorin isothiocyanates: useful reagents for the synthesis of photoactive bioconjugates. Bioconjugate Chem. 13, 249-263.
19. Hamblin, M. R., Miller, J. L., and Ortel B. (2000) Scavenger receptor targeted photodynamic therapy. Photochem. Photobiol. 72, 533-540.
20. Nagae, T., Louie, A. Y., Aizawa, K., Ishimaru, S., and Wilson, S. E. (1998) Selective targeting and photodynamic destruction of intimal hyperplasia by scavenger-receptor mediated protein-chlorin e6 conjugates. J. Cardiovasc. Surg. (Torino) 39, 709-715.
21. Chaloin, L., Bigey, P., Loup, C., Marin, M., Galeotti, N., Piechaczyk, M., Heitz, F., and Meunier, B. (2001) Improvement of porphyrin cellular delivery and activity by conjugation to a carrier peptide. Bioconjugate Chem. 12, 691-700.
22. Rahimipour, S., Ben-Aroya, N., Ziv, K., Chen, A., Fridkin, M., and Koch, Y. (2003) Receptor-mediated targeting of a photosensitizer by its conjugation to gonadotropin-releasing hormone analogues. J. Med. Chem. 46, 3965-3974.
23. De Luca, S., Tesauro, D., Di Lello, P., Fattorusso, R., Saviano, M., Pedone, C., and Morelli, G. (2001) Synthesis and solution characterization of a porphyrin-CCK8 conjugate. J. Pept. Sci. 7, 386-394.
24. Bigey, P., Sonnichsen, S. H., Meunier, B., and Nielsen, P. E. (1997) DNA binding and cleavage by a cationic manganese porphyrin-peptide nucleic acid conjugate. Bioconjugate Chem. 8, 267-270.
25. Mestre, B., Pitie, M., Loup, C., Claparols, C., Pratviel, G., and Meunier, B. (1997) Influence of the nature of the porphyrin ligand on the nuclease activity of metalloporphyrin-oligonucleotide conjugates designed with cationic, hydrophobic or anionic metalloporphyrins. Nucleic Acid Res. 25, 1022-1027.
26. Vrouenraets, M. B., Visser, G. W. M., Loup, C., Meunier, B., Stigter, M., Oppelaar, H., Stewart, F. A., Snow, G. B., and van Dongen, G. A. M. S. (2000) Targeting of a hydrophilic photosensitizer by use of internalizing monoclonal antibodies: A new possibility for use in photodynamic therapy. Int. J. Cancer 88, 108-114.
27. Soukos, N. S., Hamblin, M. R., Keel, S., Fabian, R. L., Deutsch, T. F., and Hasan, T. (2001) Epidermal growth factor receptor-targeted immunophotodiagnosis and photoimmunotherapy of oral precancer in vivo. Cancer Res. 61, 4490-4496.
28. Luguya, R., Jaquinod, L., Fronczek, F. R., Vicente, M. G. H., and Smith, K. M. (2004) Synthesis and reactions of meso(p-nitrophenyl)porphyrins. Tetrahedron 60, 2757-2763.
29. Gradl, S. N., Felix, J. P., Isacoff, E. Y., Garcia, M. L., and Trauner, D. (2003) Protein surface recognition by rational design: nanomolar ligands for potassium channels. J. Am. Chem. Soc. 125, 12668-12669.
30. Xu, H., Kinsel, G. R., Zhang, J., Li, M., and Rudkevich, D. M. (2003) Calixarene amino acids; building blocks for calixarene peptides and peptide-dendrimers. Tetrahedron 59, 5837-5848.
31. Takeoka, S.; Mori, K., Ohkawa, H., Sou, K., and Tsuchida, E. (2000) Synthesis and assembly of poly(ethylene glycol)lipids with mono-, di- and tetra-acyl chains and a poly(ethylene glycol) chain of various molecular weights. J. Am. Chem. Soc. 122, 7927-7935.
32. Matthews, S. E., Pouton, C. W., and Threadgill, M. D. (1999) Synthesis of porphyrin α,ω-bis(methylamino)peptide constructs. New J. Chem. 23, 1087-1096.
33. Hermanson, G. T. (1996) Bioconjugate Techniques, pp 137, 303-307, Academic Press, New York.
34. Solladie, N., Hamel, A., and Gross, M. (2000) Synthesis of multiporphyrinic α-polypeptides: towards the study of the migration of an excited state for the mimicking of the natural light harvesting device. Tetrahedron Lett. 41, 6075-6078.
35. Hammer, R. P., Owens, C. V., Hwang, S. H., and Soper, S. A. (2002) Asymmetrical water-soluble phthalocyanine dyes for covalent labeling of oligonucleotides. Bioconjugate Chem. 13, 1244-1252.
36. ε-methylated lysine side products. Tetrahedron Lett. 33, 4301-4302.
37. Anantharamaiah, G. M., and Sivanandaiah, K. M. (1977) Transfer hydrogenation; a convenient method for removal of some commonly used protecting groups in peptide synthesis. J. Chem. Soc., Perkin Trans, 1 490-491.
38. Lott, R. S., Chauhan, V. S., and Stammer, C. H. (1979) Trimethylsilyl iodide as a peptide deblocking agent. J. Chem. Soc., Chem. Commun. 495-496.
39. Chaleix, V., Sol, V., Guilloton, M., Granet, R., and Krausz, P. (2004) Efficient synthesis of RGD-containing cyclic peptide-porphyrin conjugates by ring closing metathesis on solid support. Tetrahedron Lett. 45, 5295-5299.
40. Knorr, R., Trzeciak, A., Bannwarth, W., and Gillessen, D. (1989) New coupling reagents in peptide chemistry. Tetrahedron Lett. 30, 1927-1930.
41. Reid, G. E., and Simpson, R. J. (1992) Automatized solid-phase peptide synthesis: Use of 2-(LH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate for coupling of tert-butyloxycarbonyl amino acids. Anal. Biochem. 200, 301-309.
42. Liu, W., Jensen, T. J., Fronczek, F. R., Hammer, R. P., Smith, K. M., and Vicente, M. G. H. (2005) Synthesis and in vitro Studies of Nonaggregated Water-soluble Phthalocyanines. J. Med. Chem. 48, 1033-1041.
43. (a) Matthews, S. E., Pouton, C. W., and Threadgill, M. D. (1995) Monofunctional electrophilic and nucleophilic derivatives of meso-tetraphenylporphyrin for attachment to peptides. J. Chem. Soc., Chem. Commun. 1809-1811.
44. (b) Matthews, S. E., Pouton, C. W., and Threadgill, M. D. (1999) Synthesis of porphyrin α,ω-bis(methylamino)peptide constructs. New J. Chem. 23, 1087-1096.
45. Wender, P. A., Mitchell, D. J., Pattabiraman, K., Pelkey, E. T., Steinman, L., and Rothbard, J. B. (2000) The design, synthesis and evaluation of molecules that enable or enhance cellular uptake: Peptoid molecular transporters. Proc. Natl. Acad. Sci. 97, 13003-13008.
46. Futaki, S., Suzuki, T., Ohashi, W., Yagami, T., Tanaka, S., Ueda, K., and Sugiura, Y. (2001) Arginine-rich peptides. An abundant source of membrane-permeable peptides having potential as carriers for intracellular protein delivery. J. Biol. Chem. 276, 5836-5840.
47. Rothbard, J. B., Jessop, T. C., Lewis, R. S., Murray, B. A., and Wender, P. A. (2004) Role of membrane potential and hydrogen bonding in the mechanism of translocation of guanidinium-rich peptides into cells. J. Am. Chem. Soc. 126, 9506-9507.
48. Mitchell, D. J., Kim, D. T., Steinman, L., Fathman, C. G., and Rothbard, J. B. (2000) Polyarginine enters cells more efficiently than other polycationic homopolymers. J. Pept. Res. 56, 318-325.
49. Ricchelli, F., Franchi, L., Miotto, G., Borsetto, L., Gobbo, S., Nikolov, P., Bommer, J. C., and Reddi, E. (2005) Mesosubstituted tetra-cationic porphyrins photosensitize the death of human fibrosarcoma cells via lysosomal targeting. Int. J. Biochem. Cell Biol. 37, 306-319.
50. Pastrana-Rios, B. (2001) Mechanism of unfolding of a model helical peptide. Biochemistry 40, 9074-9081.
51. Eker, F., Cao, X., Nafie, L., and Schweitzer-Stenner, R. (2002) Tripeptides adopt stable structures in water. A combined polarized visible Raman, FTIR, and VCD spectroscopy study. J. Am. Chem. Soc. 124, 14330-14341.
52. 10-Helical transition. J. Am. Chem. Soc. 117, 5445-5452.
53. Sheraga, H. A. (1994) Treatment of Hydration in conformational energy calculations on polypeptides and proteins. In Structure and Reactivity in Aqueous Solution. Characterization of Chemical and Biological Systems (Cramer, C. J., and Truhlar, D. G. Eds.) ACS Symposium Series 568, pp 360-371, American Chemical Society, Washington, DC.
54. Arai, T., Inudo, M., Ishimatsu, T., Akamatsu, C., Tokusaki, Y., Sasaki, T., and Nishino, N. (2003) Self-assembling of the porphyrin-linked acyclic penta- and heptapeptides in aqueous trifluoroethanol. J. Org. Chem. 68, 5540-5549.
55. Dozzo, P., Koo, M.-S., Berger, S., Forte, T. M., and Kahl, S. B. (2005) Synthesis, characterization, and plasma lipoprotein association of a nucleus-targeted boronated porphyrin. J. Med. Chem. 48, 357-359.