Борсодержащие фталоцианины и порфиразины

И. Б. Сиваев,^a@ В. И. Брегадзе,^a А. Гюль,^b А. Ф. Миронов^c

^aИнститут элементоорганических соединений им. А.Н. Несмеянова РАН, 119991 Москва, Россия
^bTechnical University of Istanbul, Department of Chemistry, Maslak, TR34469 Istanbul, Turkey
^cМосковский государственный университет тонких химических технологий им. М.В. Ломоносова, 119571 Москва,
Россия

^@E-mail: sivaev@ineos.ac.ru

Макрогетероциклы 2012 5(4-5) 292-301

DOI: 10.6060/mhc2012.121211s

Рассмотрены дизайн и синтез борсодержащих фталоцианинов и порфиразинов, которые могут найти использование в фотодинамической и бор-нейтронозахватной терапии рака.

References

Click here to expand or collapse this section

1. Sharman W.M., Allen C.M., van Lier J.E. Drug Discovery Today 1999, 4, 507-517.
http://dx.doi.org/10.1016/S1359-6446(99)01412-9

2. Vicente M.G.H. Curr. Med. Chem. - Anti-Cancer Agents 2001, 1, 175-194.
http://dx.doi.org/10.2174/1568011013354769

3. MacDonald I.J., Dougherty T.J. J. Porphyrins Phthalocyanines 2001, 5, 105-129.
http://dx.doi.org/10.1002/jpp.328

4. Dolmans D.E.J.G.J., Fukumura D., Jain R.K. Nature Rev. Cancer 2003, 3, 380-387.
http://dx.doi.org/10.1038/nrc1071

5. Castano A.P., Demidova T.N., Hamblin M.R. Photodiagn. Photodynamic Ther. 2004, 1, 279-293.
http://dx.doi.org/10.1016/S1572-1000(05)00007-4

6. Kavar B., Kaye A.H. Photodynamic Therapy. In: Current Clinical Oncology: High-Grade Gliomas: Diagnosis and Treatment (Barnett G.H., Ed.), Totawa: Humana Press, 2007. p. 461-484.

7. Ion R.-M. The Use of Phthalocyanines and Related Complexes in Photodynamic Therapy. In: Photosensitizers in Medicine, Environment, and Security (Nyokong T., Ahsen V., Eds.), Dordrecht: Springer Science, 2012. p. 315-349.

8. Hawthorne M.F. Angew. Chem. Int. Ed. Engl. 1993, 32, 950-984.
http://dx.doi.org/10.1002/anie.199309501

9. Soloway A.H., Tjarks W., Barnum B.A., Rong F.-G., Barth R.F., Codogni I.M., Wilson J.G. Chem. Rev. 1998, 98, 1515-1562.
http://dx.doi.org/10.1021/cr941195u

10. Bregadze V.I., Sivaev I.B., Glazun S.A. Curr. Med. Chem. - Anti-Cancer Agents 2006, 6, 75-109.
http://dx.doi.org/10.2174/187152006776119180

11. Barth R.F., Goderre J.A., Vicente M.G.H., Blue T.E., Miyatake S.-I. Boron Neutron Capture Therapy of Brain Tumors (Current Status and Future Prospects). In: Current Clinical Oncology: High-Grade Gliomas: Diagnosis and Treatment (Barnett G.H., Ed.), Totawa: Humana Press, 2007. p. 431-459.

12. Calabrese G., Nesnas J.J., Barbu E., Fatouros D., Tsibouklis J. Drug Discovery Today 2012, 17, 153-159.
http://dx.doi.org/10.1016/j.drudis.2011.09.014

13. Bregadze V.I., Sivaev I.B., Gabel D., Wöhrle D. J. Porphyrins Phthalocyanines 2001, 5, 767-781.
http://dx.doi.org/10.1002/jpp.544

14. Evstigneeva R.P., Zaitseev A.V., Luzgina V.N., Ol'shevskaya V.A., Shtil A.A. Curr. Med. Chem. - Anti-Cancer Agents 2003, 3, 383-392.
http://dx.doi.org/10.2174/1568011033482260

15. Renner M.W., Miura M., Easson M.W., Vicente M.G.H. Curr. Med. Chem. - Anti-Cancer Agents 2006, 6, 145-157.
http://dx.doi.org/10.2174/187152006776119135

16. Ol'shevskaya V.A., Zaytsev A.V., Savchenko A.N., Shtil A.A., Cheong C.S., Kalinin V.N. Bull. Korean Chem. Soc. 2007, 28, 1910-1916.
http://dx.doi.org/10.5012/bkcs.2007.28.11.1910

17. Grin M.A., Brittal D.I., Tsiprovskiy A.G., Bregadze V.I., Mironov A.F. Macroheterocycles 2010, 3, 222-227.

18. Claessens C.G., Gonzalez-Rodrıguez D., Torres T. Chem. Rev. 2002, 102, 835-853.
http://dx.doi.org/10.1021/cr0101454

19. Kobayashi N., Kondo R., Nakajima S., Osa T. J. Am. Chem. Soc. 1990, 112, 9640-9641.
http://dx.doi.org/10.1021/ja00182a034

20. Musluoglu E., Gürek A., Ahsen V., Gül A., Bekaroğlu Ö. Chem. Ber. 1992, 125, 2337-2339.
http://dx.doi.org/10.1002/cber.19921251023

21. de la Torre G., Torres T. J. Porphyrins Phthalocyanines 2002, 6, 274-284.
http://dx.doi.org/10.1142/S1088424602000324

22. Morse G.E., Bender T.P. ACS Appl. Mater. Interfaces, 2012, in press, dx.doi.org/10.1021/am3015197.

23. Nemykin V.N., Lukyanets E.A. ARKIVOC 2010, (i), 136-208.

24. Dumoulin F., Durmuş M., Ahsen V., Nyokong T. Coord. Chem. Rev. 2010, 254, 2792-2847.
http://dx.doi.org/10.1016/j.ccr.2010.05.002

25. Ali H., van Lier J.E. Tetrahedron Lett. 2009, 50, 337-339.
http://dx.doi.org/10.1016/j.tetlet.2008.11.035

26. Ali H., Ait-Mohand S., Gosselin S., van Lier J.E., Guérin B. J. Org. Chem. 2011, 76, 1887-1890.
http://dx.doi.org/10.1021/jo102083g

27. Özcelik S., Keser Karaoğlan G., Gümrükcü G., Gül A. Turk. J. Chem. 2013, in press, dx.doi.org/10.3906/kim-1204-47.

28. Delman A.D., Kelly J.J., Simms B.B. J. Polym. Sci., Part A-1 1970, 8, 111-123.
http://dx.doi.org/10.1002/pol.1970.150080110

29. Barnes R.L., Block W.M., Grafstein D. US 3671489 (1972).

30. Barnes R.L., Block W.M., Grafstein D. US 3730950 (1972).

31. Wynne K.J., Davison J.B. US 4132842 (1979).

32. Alam F., Bapat B.V., Soloway A.H., Barth R.F., Mafune N., Adams D.M. Strahlenther. Onkol. 1989, 165, 121-123.

33. Alam F., Soloway A.H., Bapat B.V., Barth R.F., Adams D.M. Boron Compouns for Neutron Capture Therapy. In: Clinical Aspects of Neutron Capture Therapy (Fairchild R.G., Bond V.P., Woodhead A.D., Eds), New York: Plenum Press, 1989. p.107-111.
http://dx.doi.org/10.1007/978-1-4684-5622-6_14

34. Zakharkin L.I., Guseva V.V., Abramov I.G., Balagurova E.V. Russ. J. Gen. Chem. 2000, 70, 1296-1298

35. Tsaryova O., Semioshkin A., Wöhrle D., Bregadze V.I. J. Porphyrins Phthalocyanines 2005, 9, 268-274.
http://dx.doi.org/10.1142/S1088424605000344

36. Giuntini F., Raoul Y., Dei D., Municchi M., Chiti G., Fabris C., Colautti P., Jori G., Roncucci G. Tetrahedron Lett. 2005, 46, 2979-2982.
http://dx.doi.org/10.1016/j.tetlet.2005.03.030

37. Friso E., Roncucci G., Dei D., Soncin M., Fabris C., Chiti G., Colautti P., Esposito J., De Nardo L., Rossi C.R., Nitti D., Giuntini F., Borsetto L., Jori G. Photochem. Photobiol. Sci. 2006, 5, 39-50.
http://dx.doi.org/10.1039/b506364g

38. Kahl S.B., Li J. Inorg. Chem. 1996, 35, 3878-3880.
http://dx.doi.org/10.1021/ic9600240

39. Grimes R.N. Carboranes. London: Elsevier / Academic Press, 2011. 1139 p.

40. Pietrangeli D., Rosa A., Pepe A., Ricciardi G. Inorg. Chem. 2011, 50, 4680-4682.
http://dx.doi.org/10.1021/ic200458k

41. Sivaev I. B., Bregadze V.I., Sjöberg S. Collect. Czech. Chem. Commun. 2002, 67, 679-727.
http://dx.doi.org/10.1135/cccc20020679

42. Sivaev I. B., Bregadze V. I., Kuznetsov N.T. Russ. Chem. Bull. 2002, 51, 1362-1374.
http://dx.doi.org/10.1023/A:1020942418765

43. Zhizhin K.Yu., Malinina E.A., Goeva L.V., Chernyavsky A.S., Ivanov S.V., Lukyanets E.A., Solntsev K.A., Kuznetsov N.T. Dokl. Akad. Nauk 1997, 357, 206-208 (in Russ.).

44. Spryshkova R., Grigorieva E., Riabkova V., Spure Zh., Naidenov M., Zhizhin K., Malinina E., Chernyavsky A., Luk'yanets E., Solntsev K., Kuznetsov N., Borisov G. Biodistribution Study of Novel Dodecaborate-Phthalocyanines in the B-16 Mouse Melanoma Model. In: Frontiers in Neutron Capture Therapy, Vol.2 (Hawthorne M.F., Shelly K., Wiersema R.J., Eds), New York: Kluwer Academic / Plenum Publishers, 2001. p.1027-1032.
http://dx.doi.org/10.1007/978-1-4615-1285-1_156

45. Fabris C., Jori G., Giuntini F., Roncucci G. J. Photochem. Photobiol. B: Biol. 2001, 64, 1-7.
http://dx.doi.org/10.1016/S1011-1344(01)00184-1

46. Semioshkin A.A., Sivaev I.B., Bregadze V.I. Dalton Trans. 2008, 977-992.
http://dx.doi.org/10.1039/b715363e

47. Semioshkin A., Tsaryova O., Zhidkova O., Bregadze V., Wöhrle D. J. Porphyrins Phthalocyanines 2006, 10, 1293-1300.
http://dx.doi.org/10.1142/S1088424606000661

48. Sivaev I.B., Bregadze V.I. Collect. Czech. Chem. Commun. 1999, 64, 783-805.
http://dx.doi.org/10.1135/cccc19990783

49. Li H., Fronczek F.R., Vicente M.G.H. Tetrahedron Lett. 2008, 49, 4828-4830.
http://dx.doi.org/10.1016/j.tetlet.2008.06.021

50. Li H., Fronczek F.R., Vicente M.G.H. J. Organomet. Chem. 2009, 694, 1607-1611.
http://dx.doi.org/10.1016/j.jorganchem.2008.11.037

51. Dei D., Roncucci G., Nistri D., Raoul Y., Chiti G., Municchi M., Jori G. US 7915248 (2011).

52. Başeren S.C., Özçelik S., Gül A. J. Porphyrins Phthalocyanines 2011, 15, 742-747.
http://dx.doi.org/10.1142/S1088424611003677

53. Pietrangeli D., Riccardi G. Appl. Radiation Isotopes 2009, 67, S97-S100.
http://dx.doi.org/10.1016/j.apradiso.2009.03.023

54. Ristori S., Salvati A., Martini G., Spalla O., Pietrangeli D., Rosa A., Riccardi G. J. Am. Chem. Soc. 2007, 129, 2728-2729.
http://dx.doi.org/10.1021/ja0661459

55. Salvati A., Ristori S., Pietrangeli D., Oberdisse J., Calamai L., Martini G., Riccardi G. Biophys. Chem. 2007, 131, 43-51.
http://dx.doi.org/10.1016/j.bpc.2007.09.002

56. Altieri A., Balzi M., Bortolussi S., Bruschi P., Ciani L., Clerici A.M., Faraoni P., Ferrari C., Gadan M.A., Panza L., Pietrangeli D., Riccardi G., Ristori S. J. Med. Chem. 2009, 52, 7829-7835.
http://dx.doi.org/10.1021/jm900763b

57. Salvati A., Ristori S., Oberdisse J., Spalla O., Riccardi G., Pietrangeli D., Giustini M., Martini G. J. Phys. Chem. B 2007, 111, 10357-10364.
http://dx.doi.org/10.1021/jp0731710

58. Pietrangeli D., Rosa A., Riccardi G. J. Porphyrins Phthalocyanines 2011, 15, 1024-1032.
http://dx.doi.org/10.1142/S1088424611003963

Прикрепленный файл	Размер
mhc2012_t05n4-5_292-301.pdf	955.63 кб

Журнал "Макрогетероциклы"

Навигация

Languages

Новости

Поиск