Novel types of boronated chlorin e6 conjugates via 'click chemistry'

Applied Organometallic Chemistry

Volumn 23, Issue 9, 2009, Pages 370-374

  Bregadze, Vladimir I ^a   Semioshkin, Andrey A ^a   Las'kova, Julia N ^a   Berzina, Maria Ya ^a,b   Lobanova, Irina A ^a   Sivaev, Igor B ^a   Grin, Mikhail A ^b   Titeev, Rustam A ^b   Brittal, Dmitry I ^b   Ulybina, Olga V ^b   Chestnova, Anastasija V ^b,c   Ignatova, Anastasija A ^c,d   Feofanov, Alexey V ^c,d   Mironov, Andrey F ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b MIREA RUSSIAN TECHNOLOGICAL UNIVERSITY   (Russian Federation)

^c SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^d MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

BNCT; Boronated conjugates; Chlorin e6; PDT

Indexed keywords

BNCT; BORON NEUTRON CAPTURE THERAPY; BORONATED CONJUGATES; CANCER CELLS; CHLORIN E6; CHLORINS; CLICK CHEMISTRY; COBALT BIS(DICARBOLLIDE); HIGH YIELD; HUMAN LUNG ADENOCARCINOMA CELLS; IN-VITRO; INTRACELLULAR CONCENTRATION; PDT;

BORON; BORON COMPOUNDS; COBALT;

PHOTODYNAMIC THERAPY;

EID: 69849084727     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1521     Document Type: Article

References (56)

1. M. G.H. Vicente, Curr. Med. Chem. - Anti-Cancer Agents 2001, 1, 175.
2. D. E. J. G. J. Dolmans, D. Fukumura, R. K. Jain, Nature Rev. Cancer 2003, 3, 380.
3. Z. Huang, Technol. Cancer Res. Treat. 2005, 4, 283.
4. B. Kavar, A. H. Kaye, in Current Clinical Oncology: High-Grade Gliomas: Diagnosis andTreatment (Ed.:G. H. Barnett), Humana Press: Totawa, NJ, 2007, p. 461.
5. F. Figge, G. S.Weiland, L. O. J.Manganiello, Proc. Soc. Exp. Biol. Med. 1948, 68, 640.
6. R. R. Allison, G. H. Downie, R. Cuenca, X.-H. Hu, C. J. H. Childs, C. H. Sibata, Photodiagnosis Photodynamic Ther. 2004, 1, 27.
7. M. R. Detty, S. L. Gibson, S. J. Wagner, J. Med. Chem. 2004, 47, 3897.
8. V. A. Privalov, A. V. Lappa, E. V. Kochneva, Proceedings SPIE Therapeutic Laser Applications and Laser-Tissue Interactions II (Eds.: H. van der Bergh, A. Vogel), Vol.5863, SPIE: New York, 2005, p. 186.
9. S. Bonneau, C. Vever-Bizet, P. Morliere, J.-C. Maziere, D. Brault, Biophys. J. 2002, 83, 3470.
10. S. Bonneau, C. Vever-Bizet, H. Mojzisova, D. Brault, Int. J. Pharmaceutics 2007, 344, 78.
11. H. Mojzisova, S. Bonneau, C. Vever-Bizet, D. Brault, Biochim. Biophys. Acta 2007, 1768, 2748.
12. M. F. Hawthorne, Angew. Chem., Int. Ed. Engl. 1993, 32, 950.
13. A. H. Soloway, W. Tjarks, B. A. Barnum, F.-G. Rong, R. F. Barth, I. M. Codogni, J. G.Wilson, Chem. Rev. 1998, 98, 1515.
14. R. F. Barth, J. A. Coderre, M.G. H. Vicente, T. E. Blue, Clin. Cancer Res. 2005, 11, 3987.
15. G. Rana, K. Vyakaranam, J. A. Maguire, N. S. Hosmane, MetallotherapeuticDrugsandMetal-BasedDiagnostic Agents: The Use ofMetals inMedicine (Eds.:M.Gielen, E. R. T. Tiekink), Wiley-VCH: New York, 2005, 19.
16. A. A. Vitale, G. Hoffmann, A. B. Pomilio, Mol.Med.Chem.2005, 8, 1.
17. V. I. Bregadze, I. B. Sivaev, S. A. Glazun, Anti-Cancer Agents Med. Chem. 2006, 6, 75.
18. G. Wu, R. F. Barth, W. Yang, R. Lee, W. Tjarks, M. V. Backer, J. M. Backer, Nanotechnologies for the Life Sciences. Vol.6, Nanomaterials for Cancer Therapy (Ed.: C. S. S. R. Kumar), Wiley-VCH: New York, 2006, 122.
19. Z. Yinghuai, K. C. Yan, J. A. Maguire, N. S. Hosmane, Curr. Chem. Biol. 2007, 1, 141.
20. I. B. Sivaev, V. I. Bregadze, Eur. J. Inorg. Chem. 2009, 1433.
21. V. I. Bregadze, I. B. Sivaev, D. Gabel, D. Wöhrle, J. Porphyrins Phthalocyanines 2001, 5, 767.
22. R. P. Evstigneeva, A. V. Zaitsev, V. N. Luzgina, V. A. Ol'shevskaya, A. A. Shtil, Curr. Med. Chem. Anti- Cancer Agents. 2003, 3, 383.
23. M. W. Renner, M. Miura, M. W. Easson, M. G. H. Vicente, Anti-Cancer Agents Med. Chem. 2006, 6, 145;.
24. V. A.Ol'shevskaya, A. V. Zaytsev, A. N. Savchenko, A. A. Shtil, C. S. Cheong, V. N. Kalinin, Bull. Korean Chem. Soc. 2007, 28, 1910.
25. M. A. Rosenthal, B. Kavar, J. S. Hill, D. J. Morgan, R. L. Nation, S. S. Stylli, R. L. Basser, S. Uren, H. Geldard, M. D. Green, S. B. Kahl, A. H. Kaye, J. Clin. Oncol. 2001, 19, 519.
26. P. G. Spizzirri, J. S. Hill, S. B. Kahl, K. P. Ghiggino, Photochem. Photobiol. 2007, 64, 975.
27. S.Mathai, T. A. Smith, K. P.Ghiggino, Photochem. Photobiol. Sci. 2007, 6, 995.
28. A. S. Brandis, Y. Salomon, A. Scherz, Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Eds.: B. Grimm, R. J. Porra, W. Rüdiger, H. Scheer), Springer: Berlin, 2006, 461.
29. A. F. Mironov, M. A. Grin, J. Porphyrins Phthalocyanines 2008, 12, 1163.
30. A. V. Kuchin, V. A. Ol'shevskaya, M. V. Mal'shakova, D. V. Belykh, P. V. Petrovskii, O. G. Ivanov, A. A. Shtil, V. N. Kalinin, Dokl. Chem. 2006, 409, 135.
31. V. A. Ol'shevskaya, A. N. Savchenko, A. V. Zaitsev, E. G. Kononova, P. V. Petrovskii, A. A. Ramonova, V. V. Tatarskiy, O. V.Uvarov, M.M. Moisenovich, V.N. Kalinin, A. A. Shtil, J. Organomet. Chem. 2009, 694, 1632.
32. V. A. Ol'shevskaya, R.G.Nikitina, A. N. Savchenko, M. V. Maslakova, A. M. Vinogradov, G. V. Golovina, D. V. Belykh, A. V. Kutchin, M. A. Kaplan, V. N. Kalinin, V. A. Kuzmin, A. A. Shtil, Bioorg. Med. Chem. 2009, 17, 1297.
33. I. B. Sivaev, V. I. Bregadze, S. Sjöberg, Collect. Czech. Chem. Commun. 2002, 67, 679.
34. I. B. Sivaev, V. I. Bregadze, N. T. Kuznetsov, Russ. Chem. Bull. 2002, 51, 1362.
35. I. B. Sivaev, V. I. Bregadze, Collect. Czech. Chem. Commun. 1999, 64, 783.
36. I. B. Sivaev, Z. A. Starikova, S. Sjöberg, V. I. Bregadze, J. Organomet. Chem. 2002, 649, 1.
37. E. Hao, T. J. Jensen, B. H. Courtney, M. G. H. Vicente, Biooconjugate Chem. 2005, 16, 1495.
38. M. Sibrian-Vazquez, E. Hao, T. J. Jensen, M. G. H. Vicente, Biooconjugate Chem. 2006, 17, 928.
39. E. Hao, M. Sibrian-Vazquez, W. Serem, J. C. Garno, F. R. Fronczek, M. G. H. Vicente, Chem. Eur. J. 2007, 13, 9035.
40. E. Hao, M. Zhang, W. E, K. M. Kadish, F. R. Fronczek, B. H. Courtney, M. G. H. Vicente, Bioconjugate Chem. 2008, 19, 2171.
41. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128.
42. J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249.
43. A. Olejniczak, B. Wojtczak, Z. J. Lesnikowski, Nucleosides, Nucleotides, Nucl. Acids, 2007, 26, 1611.
44. B. A. Wojtszak, A. Andrysiak, B. Grüner, Z. J. Lesnikowski, Chem. Eur. J. 2008, 14, 10675.
45. A. Semioshkin, J. Laskova, B.Wojtczak, A. Andrysiak, I. Godovikov, V. Bregadze, Z. J. Lesnikowski, J. Organomet. Chem. 2009, 694, 1375.
46. N. N. Kondakov, O. G. Ovchinnikova, A. V. Orlova, P. I. Abronina, L. O. Kononov, I. B. Sivaev, V. I. Bregadze, Abstracts of the 4th European Meeting on Boron Chemistry, Bremen, 2007, 90.
47. C. Di Meo, L. Panza, F. Campo, D. Capitani, L. Mannina, A. Banzato, M. Rondina, A. Rosato, V. Crescenzi, Macromol. Biosci. 2008, 8, 670.
48. M. A.Grin, I. S. Lonin, A. I.Makarov, F. V. Toukach, V. V. Kachala, A. V.Orlova, A. F.Mironov, Mendeleev Commun. 2008, 18, 135.
49. A. V. Orlova, N. N. Kondakov, B. G. Kimel, L. O. Kononov, E. G. Kononova, I. B. Sivaev, V. I. Bregadze, Appl. Organomet. Chem. 2007, 21, 98.
50. A. A. Semioshkin, S. N. Osipov, J. N. Grebenyuk, E. A. Nizhnik, I. A. Godovikov, G. T. Shchetnikov, V. I. Bregadze, Collect. Czech. Chem. Commun. 2007, 72, 1717.
51. A. A. Semioshkin, I. B. Sivaev, V. I. Bregadze, DaltonTrans. 2008, 977.
52. A. Feofanov, A. Grichine, T. Karmakova, A. Pljutinskaya, V. Lebedeva, A. Filyasova, R. Yakubovskaya, A. Mironov, M. Egret- Charlier, P. Vigny, Photochem. Photobiol. 2002, 74, 633.
53. A. V. Feofanov, A. I. Nazarova, T. A. Karmakova, A. D. Plyutinskaya, A. I. Grishin, R. I. Yakubovskaya, V. S. Lebedeva, R. D. Ruziev, A. F. Mironov, J.-C. Maurizot, P. Vigny, Russ. J. Bioorg. Chem. 2004, 30, 374.
54. A. I. Nazarova, A. V. Feofanov, T. A. Karmakova, G. V. Sharonov, A. D. Plyutinskaya, R. I. Yakubovskaya, V. S. Lebedeva, A. F. Mironov, J.-C. Maurizot, P. Vigny, Russ. J. Bioorg. Chem. 2005, 31, 482.
55. G. V. Sharonov, T. A. Karmakova, R. Kassies, A.D. Pljutinskaya, M. A. Grin, M. Refregiers, R. I. Yakubovskaya, A. F.Mironov, J.-C. Maurizot, P. Vigny, C.Otto, A. V. Feofanov, Free Radic. Biol.Med. 2006, 40, 407.
56. F. Teixidor, J. Pedrajas, I. Rojo, C. Vin∼as, R. Kivekäs, R. Sillanpää, I. Sivaev, V. Bregadze, S. Sjöberg, Organometallics 2003, 22, 3414.