Novel boronated chlorin e6-based photosensitizers: Synthesis, binding to albumin and antitumour efficacy

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 3, 2009, Pages 1297-1306

  Ol'shevskaya, Valentina A ^a   Nikitina, Roza G ^b   Savchenko, Arina N ^a   Malshakova, Marina V ^c   Vinogradov, Alexander M ^d   Golovina, Galina V ^d   Belykh, Dmitry V ^c   Kutchin, Alexander V ^c   Kaplan, Mikhail A ^b   Kalinin, Valery N ^a   Kuzmin, Vladimir A ^d   Shtil, Alexander A ^e  

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

^b MEDICAL RADIOLOGICAL RESEARCH CENTER   (Russian Federation)

^c INSTITUTE OF CHEMISTRY   (Russian Federation)

^d EMANUEL INSTITUTE OF BIOCHEMICAL PHYSICS   (Russian Federation)

^e N N BLOKHIN RUSSIAN CANCER RESEARCH CENTER   (Russian Federation)

Author keywords

Boron; Cancer; Carboranylchlorins; Chlorin e6; Cytotoxicity; Drug target interactions; Photodynamic therapy; Serum albumin

Indexed keywords

ALBUMIN; CHLORIN E6 13(1) N [2 [N (2 CARBORAN 1 YL)METHYL]AMINOETHYL]AMIDE 15(2),17(3) DIMETHYL ESTER; PHOTOSENSITIZING AGENT; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG EFFICACY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SYNTHESIS; FIBROBLAST; NONHUMAN; PHOTODYNAMIC THERAPY; RAT; REACTION ANALYSIS; SARCOMA;

ALBUMINS; ANIMALS; ANTINEOPLASTIC AGENTS; BORON; CELL LINE; HUMANS; PHOTOSENSITIZING AGENTS; PORPHYRINS; RATS; TRIAZENES;

ANIMALIA; RATTUS;

EID: 58949096633     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.12.016     Document Type: Article

References (59)

1. Pandey R.K., Bellnier D.A., Smith K.M., and Dougherty T.J. Photochem. Photobiol. 53 (1991) 65
2. Nyman E.S., and Hynninen P.H. J. Photochem. Photobiol. B: Biol. 73 (2004) 1
3. Pavlov V.Yu., and Ponomarev G.V. Chem. Heterocycl. Comp. 40 (2004) 393
4. Sternberg E.D., Dolphin D., and Brückner C. Tetrahedron 54 (1998) 4151
5. Wainwright M. Anti-Cancer Agents Med. Chem. 8 (2008) 280
6. Mody T.D. J. Porphyrins Phthalocyanines 4 (2000) 362
7. Josefsen L.B., and Boyle R.W. Br. J. Pharmacol. 154 (2008) 1
8. Spikes J.D. J. Photochem. Photobiol. B: Biol. 6 (1990) 259
9. Kostron H., Obwegeser A., and Jakober R.J. Photochem. Photobiol. 36 (1996) 157
10. Soloway A.H., Tjarks W., Barnum B.A., Rong F.-G., Barth R.F., Codogni I.M., and Wilson J.G. Chem. Rev. 98 (1998) 1515
11. Evstigneeva R.P., Zaitsev A.V., Luzgina V.N., Ol'shevskaya V.A., and Shtil A.A. Curr. Med. Chem. Anti-Cancer Agents 2 (2003) 383
12. Dozzo P., Koo M.-S., Berger S., Forte T.M., and Kahl S.B. J. Med. Chem. 48 (2005) 357
13. Ratajski M., Osterloh J., and Gabel D. Anti-Cancer Agents Med. Chem. 6 (2006) 159
14. Renner M.W., Miura M.M., Easson W., and Vicente M.G.H. Anti-Cancer Agents Med. Chem. 6 (2006) 145
15. Gottumukkala V., Ongayi O., Baker D.G., Lomax L.G., and Vicente M.G.H. Bioorg. Med. Chem. 14 (2006) 1871
16. Ol'shevskaya V.A., Zaitsev A.V., Savchenko A.N., Shtil A.A., Chan S.C., and Kalinin V.N. Bull. Korean Chem. Soc. 28 (2007) 1910
17. Spiuirril P.G., Hill J.S., Kahl S.B., and Ghiggino K.P. Photochem. Photobiol. 64 (1996) 975
18. Ol'shevskaya V.A., Nikitina R.G., Zaitsev A.V., Luzgina V.N., Kononova E.G., Morozova T.G., Drozhzhina V.V., Ivanov O.G., Kaplan M.A., Kalinin V.N., and Shtil A.A. Org. Biomol. Chem. 4 (2006) 3815
19. Zheng G., Aoudia M., Lee D., Rodgers M.A., Smith K.M., Dougherty T.J., and Pandey R.K. J. Chem. Soc., Perkin Trans. 1 18 (2000) 3113
20. Belykh D.V., Karmanova L.V., Spirikhin L.V., and Kutchin A.V. Mendeleev Commun. 12 (2002) 77
21. Tamiaki H., Amakawal M., Shimonol Y., Tanikaga R., Hotzwarth A.R., and Schaffner K. Photochem. Photobiol. 63 (1996) 92
22. Szaciłowski K., Macyk W., Drzewiecka-Matuszek A., Brindell M., and Stochel G. Chem. Rev. 105 (2005) 2647
23. Morgan A.R., Garbo G.M., Keck R.W., and Selman S.H. Cancer Res. 48 (1988) 194
24. Kessel D., Morgan A., and Garbo G.M. Photochem. Photobiol. 54 (1991) 193
25. Pogue B.W., Redmond R.W., Trivedi N., and Hasan T. Photochem. Photobiol. 68 (1998) 809
26. Arnold D.P., and Blok J. Coord. Chem. Rev. 248 (2004) 299
27. Weersink R.A., Bogaards A., Gertner M., Davidson S.R.H., Zhang K., Netchev G., Trachtenberg J., and Wilson B.C. J. Photochem. Photobiol. B: Biol. 79 (2005) 211
28. Zhu T.C., and Finlay J.C. Photodiagn. Photodyn. Ther. 3 (2006) 234
29. Schreiber S., Gross S., Brandis A., Harmelin A., Rosenbach-Belkin V., Scherz A., and Salomon Y. Int. J. Cancer 99 (2002) 279
30. Woodhams J.H., MacRobert A.J., Novelli M., and Bown S.G. Int. J. Cancer 118 (2006) 477
31. Trachtenberg J., Bogaards A., Weersink R.A., Haider M.A., Evans A., McCluskey S.A., Scherz A., Gertner M.R., Yue C., Appu S., Aprikian A., Savard J., Wilson B.C., and Elhilali M. J. Urol. 178 (2007) 1974
32. Kessel D., Thompson P., Saatio K., and Nantwi K.D. Photochem. Photobiol. 45 (1987) 787
33. Mishra P., Patel S., and Datta A. J. Phys. Chem. B 110 (2006) 21238
34. Sidorova T.A., Nigmatov A.G., Kakpakova E.S., Stavrovskaya A.A., Gerassimova G.K., Shtil A.A., and Serebryakov E.P. J. Med. Chem. 45 (2002) 5330
35. Borbas K.E., Mroz P., Hamblin M.R., and Lindsey J.S. Bioconjug. Chem. 17 (2006) 638
36. Borbas K.E., Chandrashaker V., Muthiah C., Kee H.L., Holten D., and Lindsey J.S. J. Org. Chem. 73 (2008) 3145
37. Muthiah C., Taniguchi M., Kim H.J., Schmidt I., Kee H.L., Holten D., Bocian D.F., and Lindsey J.S. Photochem Photobiol. 83 (2007) 1513
38. Al-Omari S. Biomed. Mater. 2 (2007) 107
39. Thomas N., Tirand L., Chatelut E., Plénat F., Frochot C., Dodeller M., Guillemin F., and Barberi-Heyob M. Photochem. Photobiol. Sci. 7 (2008) 433
40. Zheng X., and Pandey R.K. Anti-Cancer Agents Med. Chem. 8 (2008) 241
41. Kee H.L., Kirmaier C., Tang Q., Diers J.R., Muthiah C., Taniguchi M., Laha J.K., Ptaszek M., Lindsey J.S., Bocian D.F., and Holten D. Photochem. Photobiol. 83 (2007) 1110
42. Luguya R., Jensen T.J., Smith K.M., and Vicente M.G. Bioorg. Med. Chem. 14 (2006) 5890
43. Bardos-Nagy I., Galantay R., and Fidy J. Biochim. Biophys. Acta 1512 (2001) 125
44. Chowdhary R.K., Shariff I., and Dolphin D. J. Pharm. Pharm. Sci. 6 (2003) 13
45. Mojzisova H., Bonneau S., Vever-Bizet C., and Brault D. Biochim. Biophys. Acta 1768 (2007) 366
46. Novick S., Laster B., and Quastel M.R. Int. J. Biochem. Cell Biol. 38 (2006) 1374
47. Melnikova V.O., Bezdetnaya L.N., Bour C., Festor E., Gramain M.P., Merlin J.L., Potapenko A.Ya., and Guillemin F. J. Photochem. Photobiol. B 49 (1999) 96
48. Foster T.H., Pearson B.D., Mitra S., and Bigelow C.E. Photochem. Photobiol. 81 (2005) 1544
49. Nazarova A., Ignatova A., Feofanov A., Karmakova T., Pljutinskaya A., Mass O., Grin M., Yakubovskaya R., Mironov A., and Maurizot J.C. Photochem. Photobiol. Sci. 6 (2007) 1184
50. Akhlynina T.V., Jans D.A., Statsyuk N.V., Balashova I.Y., Toth G., Pavo I., Rosenkranz A.A., Naroditsky B.S., and Sobolev A.S. Int. J. Cancer 81 (1999) 734
51. Ogura S., Yazaki K., Yamaguchi K., Kamachi T., and Okura I. J. Control Release 103 (2005) 1
52. Swamy N., Purohit A., Fernandez-Gacio A., Jones G.B., and Ray R. J. Cell Biochem. 99 (2006) 966
53. Callahan D.E., Forte T.M., Afzal S.M., Deen D.F., Kahl S.B., Bjornstad K.A., Bauer W.F., and Blakely E.A. Int. J. Radiat. Oncol. Biol. Phys. 45 (1999) 761
54. Ozawa T., Santos R.A., Lamborn K.R., Bauer W.F., Koo M.S., Kahl S.B., and Deen D.F. Mol. Pharm. 1 (2004) 368
55. Koo M.S., Ozawa T., Santos R.A., Lamborn K.R., Bollen A.W., Deen D.F., and Kahl S.B. J. Med. Chem. 50 (2007) 820
56. Wongsinkongman P., Brossi A., Wang H.K., Bastow K.F., and Lee K.H. Bioorg. Med. Chem. 10 (2002) 583
57. Ol'shevskaya V.A., Zaitsev A.V., Luzgina V.N., Kondratieva T.T., Kononova E.G., Petrovskii P.V., Mironov A.F., Kalinin V.N., Hofmann J., and Shtil A.A. Bioorg. Med. Chem. 14 (2006) 109
58. Smith K.M., Goff D.F., and Simpson D.J. J. Am. Chem. Soc. 107 (1985) 4946
59. Kalinin V.N., Rys E.G., Tyutyunov A.A., Starikova Z.A., Korlyukov A.A., Ol'shevskaya V.A., Sung D.D., Ponomaryov A.B., Petrovskii P.V., and Hey-Hawkins E. Dalton Trans. 5 (2005) 903