Enhanced cellular uptake with a cobaltacarborane-porphyrin-HIV-1 Tat 48-60 conjugate

Bioconjugate Chemistry

Volumn 17, Issue 4, 2006, Pages 928-934

  Sibrian Vazquez, Martha ^a   Hao, Erhong ^a   Jensen, Timothy J ^a   Vicente, M Graça H ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL PROLIFERATION; DISEASES; PEPTIDES; POLYETHYLENE GLYCOLS;

2-GROUP; CELLULAR UPTAKE; HEP-2 CELLS; HIV-1 TAT; INTRACELLULAR LOCALIZATION; LOW MOLECULAR WEIGHT; PEG SPACERS; PEPTIDE SEQUENCES; PORPHYRIN MACROCYCLE; SYNTHESISED;

PORPHYRINS;

CARBORANE DERIVATIVE; COBALT DERIVATIVE; COBALTABISDICARBOLLIDE ANION; COBALTACARBORANE; MACROCYCLIC COMPOUND; MACROGOL; PORPHYRIN; TRANSACTIVATOR PROTEIN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CELL PROLIFERATION; CELLULAR DISTRIBUTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG CONJUGATION; DRUG SYNTHESIS; DRUG UPTAKE; HEP 2 CELL; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; INTERNALIZATION; LYSOSOME; MOLECULAR WEIGHT;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 33746752105     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060047v     Document Type: Article

References (52)

1. 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.
2. Osterloh, J., and Vicente, M. G. H. (2002) Mechanisms of porphyrinoid localization in tumors. J. Porphyrins Phthalocyanines 6, 305-324.
3. Hudson, R., and Boyle, R. W. (2004) Strategies for selective delivery of photodynamic sensitizers to biological targets. J. Porphyrins Phthalocyanines 8, 954-975.
4. Soloway, A. H., Tjarks, W., Barnum, B. A., Rong, F. G., Barth, R. F., Codogni, I. M., and Wilson, J. G. (1998) The chemistry of neutron capture therapy. Chem. Rev. 98, 1515-1562.
5. Hawthorne, M. F. (1993) The role of chemistry in the development of boron neutron-capture therapy of cancer. Angew. Chem., Int. Ed. Engl. 32, 950-984.
6. Barth, R. F., Coderre, J. A., Vicente, M. G. H., and Blue, T. E. (2005) Boron neutron capture therapy of cancer: Current status and future prospects. Clin. Cancer Res. 11, 3987-4002.
7. Dougherty, T. J., Gomer, C. J., Henderson, B. W., Jori, G., Kessel, D., Korbelik, M., Moan, I., and Peng, Q. (1998) Photodynamic therapy. J. Natl Cancer Inst. 90, 889-905.
8. Pandey, R. K., and Zheng, G. (2000). Porphyrins as photosensitizers in photodynamic therapy. The Porphyrin Handbook. Applications: Past, present and future (Kadish, K. M., Smith, K. M., Guilard, R., Eds.) Vol. 6, Chapt. 43, pp 157-230, Academic Press, New York.
9. Kessel, D. (2004) Correlation between subcellular localization and photodynamic efficacy. J. Porphyrins Phthalocyanines 8, 1009-1014.
10. Rosenkranz, A. A., Jans, D. A., and Sobolev, A. S. (2002) Targeted intracellular delivery of photosensitizers to enhance photodynamic efficiency. Immunol. Cell Biol. 78, 452-464.
11. 10B neutron capture therapy: Enhancement of tumor dose via beam filtration and dose rate, and the effects of these parameters on minimum boron content: a theoretical evaluation. Int. J. Radiat. Oncol., Biol., Phys. 11, 831-840.
12. 7Li reaction in cells and tissue and its implication for boron neutron capture therapy. Radiat. Res. 111, 14-25.
13. (a) Hartman, T., and Carlsson, J. (1994) Radiation dose heterogeneity in receptor and antigen mediated boron neutron capture therapy. Radiother. Oncol. 31, 61-75.
14. (b) Hartman, T., Lundqvist, H., Westlin, J.-E., and Carlsson, J. (2000) Radiation doses to the cell nucleus in single cells and cells in micrometastases in targeted therapy with 1-131 labeled ligands or antibodies. Int. J. Radiat. Oncol., Biol., Phys. 46, 1025-1036.
15. Bregadze, V. I., Sivaev, I. B., Gabel, D., and Wohrle, D. (2001) Polyhedral boron derivatives of porphyrins and phthalocyanines. J. Porphyrins Phthalocyanines 5, 767-781.
16. Renner, M. W., Miura, M., Basson, M. W., and Vicente, M. G. H. (2006) Recent progress in the syntheses and biological evaluation of boronated porphyrins for boron neutron capture therapy. Anti-Cancer Agents Med. Chem. 6, 145-158.
17. Rosenthal, M. A., Kavar, B., Hill, J. S., Morgan, D. J., Nation, R. L., Stylli, S. S., Basser, R. L., Uren, S., Geldard, H., Green, M. D., Kahl, S. B., and Kaye, A. H. (2001) Phase I and pharmacokinetic study of photodynamic therapy for high-grade gliomas using a novel boronated porphyrin. J. Clin. Oncol 19, 519-524.
18. Vicente, M. G. H., Nurco, D. J., Shetty, S. J., Osterloh, J., Ventre, E., Hegde, V., and Deutsch, W. A. (2002) Synthesis, dark toxicity and induction of in vitro DNA photodamage by a tetra(4-nidocarboranylphenyl)porphyrin. J. Photochem. Photobiol. B: Biol. 68, 123-132.
19. (a) Fabris, C., Jori, G., Giuntini, F., and Roncucci, G. (2001) Photosensitizing properties of a boronated phthalocyanine: studies at the molecular and cellular level. J. Photochem. Photobiol., B 64, 1-7.
20. (b) Giuntini, F., Raoul, Y., Dei, D., Municchi, M., Chiti, G., Fabris, C., Colautti, P., Jori, G., and Roncucci, G. (2005) Synthesis of tetrasubstituted Zn(II)-phthalocyanines carrying four carboranyl-units as potential BNCT and PDT agents. Tetrahedron Lett. 46, 2979-2982.
21. Miura, M., Micca, P. L., Fisher, C. D., Gordon, C. R., Heinrichs, J. C., and Slatkin, D. N. (1998) Evaluation of carborane-containing porphyrins as tumour targeting agents for boron neutron capture therapy. Br. J. Radiol. 71, 773-781.
22. Miura, M., Morris, G. M., Micca, P. L., Lombardo, D. T., Youngs, K. M., Kalef-Ezra, J. A., Hoch, D. A., Slatkin, D. N., Ma, R., and Coderre, J. A. (2001) Boron neutron capture therapy of a murine mammary carcinoma using a lipophilic carboranyltetraphenylporphyrin. Radiat. Res. 155, 603-610.
23. 10B-enriched carboranyl-containing phthalocyanine as a radio- and photo-sensitising agent for boron neutron capture therapy and photodynamic therapy of tumours: In vitro and in vivo studies. Photochem. Photobiol. Sci. 1, 39-50.
24. Frixa, C., Mahon, M. F., Thompson, A. S., and Threadgill, M. D. (2003) Synthesis of meso-substituted porphyrins carrying carboranes and oligo(ethylene glycol) units for potential applications in boron neutron capture therapy. Org. Biomol. Chem. 1, 306-317.
25. 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.
26. Vives, E. (2003) Cellular uptake of the Tat peptide: An endocytosis mechanism following ionic interactions. J. Mol. Recognit. 16, 265-271.
27. (a) Futaki, S., Ohashi, W., Suzuki, T., Niwa, M., Tanaka, S., Ueda, K., Harashima, H., and Sugiura, Y. (2001) Stearylated arginine-rich peptides: A new class of transfection systems. Bioconj. Chem. 12, 1005-1011.
28. (b) Rothbard, J. B., Garlington, S., Lin, Q., Kirschberg, T., Kreider, E., McGrane, P. L., Wender, P. A., and Khavari, P. A. (2000) Conjugation of arginine oligomers to cyclosporin A facilitates topical delivery and inhibition of inflammation. Nat. Med. 6, 1253-1257.
29. (c) Kirschberg, T. A., VanDeusen, C. L., Rothbard, J. B., Yang, M., and Wender, P. A. (2003) Arginine-based molecular transporters: the synthesis and chemical evaluation of releasable taxol-transporter conjugates. Org. Lett. 5, 3459-3462.
30. (d) Wadia, J. S., Stan, R. V., and Dowdy, S. F. (2004) Transductible TAT-HA fusogenic peptides enhances escape of TAT fusion proteins after lipid raft macropinocytosis. Nat. Med. 10, 310-315.
31. (a) Efthymiadis, A., Briggs, L. J., and Jans, D. A. (1996) The HTV-1 Tat nuclear localization sequence confers novel nuclear import properties. J. Biol. Chem. 273, 1623-1628.
32. (b) Vives, E. (2003) Cellular uptake of the Tat peptide: an endocytosis mechanism following ionic interactions. J. Mol Recognit. 16, 265-271.
33. (c) Dietz, G. P., and Bahr, M. (2004) Delivery of bioactive molecules into the cell: The Trojan horse approach. Mol Cell. Neurosci. 27, 85-131.
34. Vives, E. (2005) Present and future of cell-penetrating peptide mediated delivery systems: "Is the Trojan horse to wild to go only to Troy?" J. Controlled Release 109, 77-85.
35. Sibrian-Vazquez, M., Jensen, T. J., Hammer, R. P., and Vicente, M. G. H. (2006) Peptide-mediated cell transport of water soluble porphyrin conjugates. J. Med. Chem. 49, 1364-1372.
36. Kawabata, S., Barth, R. F., Yang, W., Wu, G., Binns, P. J., Riley, K. J., Gottumukkala, V., and Vicente, M. G. H. (2005) Evaluation of the carboranylporphyrin H2TCP as a delivery agent for boron neutron capture therapy (BNCT). Proceedings of the 13th World Congress of Neurological Surgery. (Khamlichi, A., Ed.) pp 975-979.
37. Hao, E., and Vicente, M. G. H. (2005) Expeditious synthesis of porphyrin-cobaltacarborane conjugates. Chem. Commun. (Cambridge) 1306-1308.
38. Hao, E., Jensen, T. J., Courtney, B. H., and Vicente, M. G. H. (2005) Synthesis and cellular studies of porphyrin-cobaltacarborane conjugates. Bioconjugate Chem. 16, 1495-1502.
39. Weinkauf, J. R., Cooper, S. W., Schweiger, A., and Wamser, C. C. (2003) Substituent and solvent effects on the hyperporphyrin spectra of diprotonated tetraphenylporphyrins. J. Phys. Chem. A 107, 3486-3496.
40. 11)(2)](-) in coordination. Generation of the highly uncommon S(thioether)-Na bond. Organometallics 22, 3414-3423.
41. (a) Greenwald, R. B. (2001) PEG drugs: An overview. J. Controlled Release 74, 159-171.
42. (b) Greenwald, R. B., Choe, Y. H., McGuire, J., and Conover, C. D. (2003) Effective drug delivery by PEGylated drug conjugates. Adv. Drug Delivery Rev. 55, 217-250.
43. Schwartz, J. J., and Zhang, S. (2000) Peptide-mediated cellular delivery. Curr. Opin. Mol. Ther. 2, 162-167.
44. Lundberg, P., and Langel, U. (2003) A brief introduction to cell-penetrating peptides. J. Mol. Recognit. 16, 227-233.
45. Richard, J. P., Melikov, K., Vives, E., Ramos, C., Verbeure, B., Gait, M. J., Chemomordik, L. V., and Lebleu, B. (2003) Cell-penetrating peptides: A reevaluation of the mechanism of cellular uptake. J. Biol. Chem. 278, 585-590.
46. Futaki, S., Goto, S., Suzuki, T., Nakase, I., and Sugiura, Y. (2003) Structural variety of membrane permeable peptides. Curr. Protein Pept. Sci. 4, 87-96.
47. Deshayes, S., Morris, M. C., Divita, G., and Heitz, F. (2005) Cell-penetrating peptides: Tools for intracellular delivery of therapeutics. Cell. Mol. Life Sci. 1839-1849.
48. Nguyen, T., Brownell, G. L., Holden, S. A., Kahl, S., Miura, M., and Teicher, B. A. (1993) Subcellular distribution of various boron compounds and implications of their efficacy in boron neutron capture therapy by Monte Carlo simulations. Radiat. Res. 133, 33-40.
49. Vicente, M. G. H., Edwards, B. F., Shetty, S. J., Hou, Y., and Boggan, J. E. (2002) Synthesis and preliminary biological studies of four tetra(nido-carboranylmethylphenyl)porphyrins. Bioorg. Med. Chem. 70, 481-492.
50. 2OCP) for Application in BNCT. Bioorg. Med. Chem. 13, 1633-1640.
51. Gottumukkala, V., Ongayi, O., Baker, D. G., Lomax, L. G., and Vicente, M. G. H. (2006) Synthesis, cellular uptake and animal toxicity of a tetra(carboranylphenyl)-tetrabenzoporphyrin. Bioorg. Med. Chem. 14, 1871-1879.
52. Ye, S.-J. (1999) Monte Carlo based protocol for cell survival and tumor control probability in BNCT. Phys. Med. Biol. 44, 447-461.