Synthesis and spectroelectrochemistry of N-cobaltacarborane porphyrin conjugates

Bioconjugate Chemistry

Volumn 19, Issue 11, 2008, Pages 2171-2181

  Hao, Erhong ^a   Zhang, Min ^b   Wenbo, E ^b   Kadish, Karl M ^b   Fronczek, Frank R ^a   Courtney, Brandy H ^a   Vicente, M Graça H ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

^b University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE QUENCHING; SPECTROELECTROCHEMISTRY; SUBSTITUTION REACTIONS;

BIOCHEMICAL PROCESS; DEGREE OF DISTORTION; ELECTROCHEMICALS; FLUORESCENCE QUENCHING; HYBRIDISATION; MACROCYCLES; MODEL COMPOUND; PORPHYRIN MACROCYCLE; SPECTROELECTROCHEMICAL PROPERTIES; X-RAY STRUCTURE;

PORPHYRINS;

5 (N COBALTACARBORANEPHENYL) 10,15,20 TRIPHENYLPORPHYRIN; 5 (N,N DICOBALTACARBORANEPHENYL) 10,15,20 TRIPHENYLPORPHYRIN; CARBORANE DERIVATIVE; COBALT; COBALTACARBORANYLPORPHYRIN DERIVATIVE; N COBALTACARBORANE OCTAETHYLPORPHYRIN; N COBALTACARBORANE TETRAPHENYLPORPHYRIN; N,N DICOBALTACARBORANE OCTAETHYLPORPHYRIN; N,N DICOBALTACARBORANE TETRAPHENYLPORPHYRIN; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELECTRON TRANSPORT; FLUORESCENCE; OXIDATION; REDUCTION KINETICS; SPECTROSCOPY;

EID: 56749106158     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800265w     Document Type: Article

References (49)

1. Kadish, K. M., Smith, K. M., Guilard, R. Eds. (2000) The Porphyrin Handbook, Academic Press, Boston.
2. McLaughlin, G. M. (1974) Crystal and molecular structure of anon-metallo N-substituted porphyrin 21 ethoxycarbonylmethyl-2, 3,7,8,12,13,17,18- octaethylporphyrin. J. Chem. Soc., Perkin Trans. 2, 136-139.
3. Lavallee, D. K., Kopelove, A. G., and Anderson, O. P. (1978) Structures and properties of N-memyltetraphenylporphyrin complexes. The crystal and molecular structure of chloro-N-methyl.alpha.,.beta.,.gamma.,.delta.- tetraphenylporphinatozinc(II) and the chelate effect of zinc(II), cobalt(II), and cadmium(II) N-methylporphyrin complexes. J. Am. Chem. Soc. 100, 3025-3033.
4. Lavallee, D. K. (1987) The Chemistry and Biochemistry of N-Substituted Porphyrins, VCH Publishers, Weinheim.
5. Venkateshrao, S., Yin, J., Jarzecki, A. A., Schultz, P. G., and Spiro, T. G. (2004) Porphyrin distortion during affinity maturation of a ferrochelatase antibody, monitored by resonance raman spectroscopy. J. Am. Chem. Soc. 126, 16361-16367.
6. Jarzecki, A. A., and Spiro, T. G. (2005) Porphyrin distortion from resonance raman intensities of out-of-plane modes: computation and modeling of N-methylmesoporphyrin, a ferrochelatase transition state analog. J. Phys. Chem. A 109, 421-430.
7. Cochran, A. G., and Schultz, P. G. (1990) Antibody-catalyzed porphyrin metallation. Science 249, 781-783.
8. Dailey, H. A. (1996) Mechanisms of Metallocenter Assembly (Eichorn, G. L., Marzilh, L. G., and Hausinger, R. P. Eds.) pp 77-89, VCH, New York.
9. Ito, A., Konishi, K., and Aida, T. (1996) Free bases of chiral N-substituted porphyrins as catalysts for asymmetric reaction. Tetrahedron Lett. 37, 2585-2588.
10. Konishi, K., Yahara, K., Toshishige, H., Aida, T., and Inoue, S. (1994) A novel anion-binding chiral receptor based on a metalloporphyrin with molecular asymmetry. Highly enantioselective recognition of amino acid derivatives. J. Am. Chem. Soc. 116, 1337-1344.
11. Setsune, J.-I., and Takeda, H. (1995) Synthesis of N,N′- (trimethylene)-linked porphyrin-cyclen composite. Tetrahedron Lett. 33, 5903-5904.
12. Lavallee, D. K., Xu, Z., and Pina, R. (1993) Synthesis and properties of new cationic-periphery porphyrins, tetrakis(p-(aminomethyl)phenyl)porphyrin and N-methyltetrakis(p-(aminomethyl)phenyl)porphyrin. J. Org. Chem. 58, 6000-6008.
13. Tsukahara, K., Sawai, N., Hamada, S., Koji, K., Onoue, Y., Nakazawa, T., Nakagaki, R., Nozaki, K., and Ohno, T. (1999) Photophysical and photochemical properties of viologen-linked N-Alkylporphyrin diads and their metal complexes. J. Phys. Chem. B 103, 2867-2877.
14. Vicente, M. G. H. (2000) Reactivity and functionalization of b-substituted porphyrins and chlorins. In The Porphyrin Handbook, (Kadish, K. M., Smith, K. M., Guilard, R. Eds.) pp 149-199, Chapter 4, Volume 1: Synthesis and Organic Chemistry, Academic Press, Boston.
15. Ishimaru, Y., Sumida, S., and Iida, T. (2001) Regio- and stereoselective reduction of intramolecular N-strapped porphyrins to phlorins. Tetrahedron Lett. 42, 419-421.
16. (a) Ruppert, R., Jeandon, C., Sgambati, A., and Callot, H. L. (1999) Reduction of N-arylporphyrins to N-arylphlorins: opposite stereochemical courses as a function of the reducing agent. Chem. Commun. 2123-2124.
17. (b) Krattinger, B., and Callot, H. J. (1999) Alkylation and reduction of porphyrins and N-substituted porphyrins: new routes to chlorins and phlorins. Eur. J. Org. Chem. 1857-1867.
18. (c) Smith, K. M., Pandey, P. K., and Snow, K. M. (1986) Nickel(II)-promoted rearrangements of some N-substituted porphyrins. J. Chem. Soc., Chem. Comm. 1498-1499.
19. Paolesse, R., Nardis, S., Stefanelli, M., Fronczek, F. R., and Vicente, M. G. H. (2005) Hemiporphycene from expansion of a corrole ring. Angew. Chem., Int. Ed. 44, 3047-3050.
20. 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.
21. Renner, M. W., Miura, M., Easson, M. W., and Vicente, M. G. H. (2006) Recent progress in the syntheses and biological evaluation of boronated porphyrins for boron neutron-capture therapy. Curr. Med. Chem. Anti-Cancer Agents 6, 145-158.
22. Sivaev, I. B., and Bregadze, V. I. (1999) Chemistry of cobalt bis(discarbollides). A review. Collect. Czech. Chem. Commun. 64, 783-805.
23. (a) Hao, E., and Vicente, M. G. H. (2005) Expeditious synthesis of porphyrin-cobaltacarborane conjugates. Chem. Commun. 1306-1308.
24. (b) 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.
25. (c) Sibrian-Vazquez, M., Hao, E., Jensen, T. J., and Vicente, M. G. H. (2006) Enhanced cellular uptake with a cobaltacarborane-porphyrin-HIV-1 Tat 48-60 conjugate. Bioconjugate Chem. 17, 928-934.
26. (d) Hao, E., Sibrian-Vazquez, M., Fronczek, F. R., Garno, J., and Vicente, M. G. H. (2007) Syntheses, aggregation and cellular studies of porphyrin-cobaltacarborane conjugates. Chem. Eur. J. 32, 9035-9042.
27. Lin, X. Q., and Kadish, K. M. (1985) Vacuum-tight thin-layer spectroelectrochemical cell with a doublet platinum gauze working electrode. Anal. Chem. 57, 1498-1501.
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. Otwinowski, Z., Minor, W. (1997) Processing of X-ray diffraction data collected in oscillation mode (Carter, C. W., Jr., and Sweet, R. M. Eds.) Macromolecular Crystallography, Part A, Methods in Enzymology Volume 276, pp 307-326, Academic Press, New York.
30. Sheldrick, G. M. SHELXL97. University of Göttingen, Germany, 1997.
31. Plešek, J., Heømánek, S., Franken, A., Cisarova, I., and Nachtigal, C. (1997) Dimethyl sulfate induced nucleophilic substitution of the [bis(l,2-dicarbollido)-3-cobalt(1-)]ate ion. Syntheses, properties and structures of its 8,8′-μ-sulfato, 8-phenyl and 8-dioxane derivatives. Collect. Czech. Chem. Commun. 62, 47-56.
32. - in coordination, generation of the highly uncommon S(thioether)-Na bond. Organometallics 22, 3414-3423.
33. Plešek, J., Heømánek, S., Baše, K., Todd, L., and Wright, W. F. (1976) Zwitterionic compounds of the 8,8′-R-3-commo-3- cobaltabis(1,2-dicarba-closo-dodecaborane(11). Collect. Czech. Chem. Commun. 41, 3509-3515.
34. 2Co. Z. Kristallogr. 144, 139-141.
35. b-dimethyletioporhyrin I triiodide. Tetrahedron 36, 1857-1868.
36. Lavallee, D. K., and Anderson, O. P. (1982) Crystal and molecular structure of a free-base N-Methylporphyrin: N-Methyl-5,10,15,20-tetrakis(p- bromophenyl)porphyrin. J. Am. Chem. Soc. 104, 4707-4708.
37. 3,8]-dodecane, the 2:1 condensation product of formaldehyde and 1,2-diaminoethane, and the conformation of this system. J. Chem. Soc., Perkin Trans. 2, 136-140.
38. Al-Hazimi, H. M. G., Jackson, A. H., Johnson, A. W., and Winter, M. (1977) N-methylated tetraphenylporphins. J. Chem. Soc. Perkin I 98-103.
39. Senge, M. O., Kalisch, W. W., and Runge, S. (1997) N-Methyl derivatives of highly substituted porphyrins - the combined influence of both core and peripheral substitution on the porphyrin conformation. Liebigs Ann. Recueil 1345-1352.
40. Stolzenberg, A. M., Simerly, S. W., Steffey, B. D., and Haymond, G. S. (1997) The synthesis, properties, and reactivities of free-base and Zn(II)-N-methyl hydroporphyrin compounds. The unexpected selectivity of the direct methylation of free-base hydroporphyrin compounds. J. Am. Chem. Soc. 119, 11843-11854.
41. (a) Broadhurst, M. L., Grigg, R., and Shelton, G. (1970) N-Alkylation of porphins and related macrocycles. J. Chem. Soc., Chem. Comm. 231-233.
42. (b) Grigg, R., Shelton, G., Sweeney, A., and Johnson, A. W. (1972) N-methylation and electrophilic substitution reactions of octa-alkyl-porphins, octaethylchlorin, and metalloporphins. J. Chem. Soc. Perkin I 1789-1799.
43. Rudakov, D. A., Shirokii, V. L., Knizhnikov, V. A., Bazhanov, A. V., Vecher, E. I., Maier, N. A., Potkin, V. I., Ryabtsev, A. N., Petrovskii, P. V., Sivaev, I. B., Bregadze, V. I., and Eremenko, I. L. (2004) Electrochemical synthesis of halogen derivatives of bis(1,2-dicarbollyl)cobalt(III). Russ. Chem. Bull. 53, 2554-2557.
44. Kadish, K. M., Caemelbecke, E. V., Royal, G. (1999) Electrochemistry of metalloporphyrins in nonaqueous media. The Porphyrin Handbook, Volume 8: Electron Transfer (Kadish, K. M., Smith, K. M., and Guilard, R. Eds.) pp 1-97, Chapter 55, Academic Press, Boston.
45. Kadish, K. M., Royal, G., Caemelbecke, E. V., Gueletti, L. (1999) Metalloporphyrins in nonaqueous media: database of redox potentials. The Porphyrin Handbook Volume 9: Database of Redox Potentials and Binding Constants (Kadish, K. M., Smith, K. M., and Guilard, R. Eds.) pp 90-117, Chapter 59, Academic Press, Boston.
46. Kadish, K. M. (1986) The electrochemistry of metalloporphyrins in nonaqueous media. In Progress in Inorganic Chemistry. Volume 34 (Lippard, S. J. Ed.) pp 435-605, John Wiley, New York.
47. Malinski, T., Chang, D., Bottomley, L. A., and Kadish, K. M. (1982) Substituent effects on the redox reactions of parasubstituted tetraphenylporphyrin complexes of ruthenium(II). Inorg. Chem. 21, 4248-4253.
48. Bettelheim, A., White, B. A., Raybuck, S. A., and Murray, R. W. (1987) Electrochemical polymerization of amino-, pyrrole-, and hydroxy-substituted tetraphenylporphyrins. Inorg. Chem. 26, 1009-1017.
49. 4. New J. Chem. 16, 815-820.