Design, synthesis, and radiosensitizing activities of sugar-hybrid hypoxic cell radiosensitizers

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 2, 2008, Pages 675-682

  Nakae, Takashi ^a   Uto, Yoshihiro ^a   Tanaka, Motoko ^a   Shibata, Haruna ^a   Nakata, Eiji ^a   Tominaga, Masahide ^b   Maezawa, Hiroshi ^b   Hashimoto, Toshihiro ^c   Kirk, Kenneth L ^d   Nagasawa, Hideko ^e   Hori, Hitoshi ^a  

^a Graduate School   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

^c TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^d NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^e GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Electronic states; Hydrophobicity; Hypoxic cell radiosensitizers; Sugar hybrids

Indexed keywords

[2 (2 NITRO 1H IMIDAZOL 1 YL) N METHYLACETAMIDO]ETHYL 2 ACETAMIDO 2 DEOXY 3,4,6 TRI O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; [2 (2 NITRO 1H IMIDAZOL 1 YL) N METHYLACETAMIDO]ETHYL 2 ACETAMIDO 2 DEOXY BETA DEXTRO GALACTOPYRANOSIDE; [2 (2 NITRO 1H IMIDAZOL 1 YL) N METHYLACETAMIDO]ETHYL 2,3,4,6 TETRA O ACETYL ALPHA DEXTRO MANNOPYRANOSIDE; [2 (2 NITRO 1H IMIDAZOL 1 YL) N METHYLACETAMIDO]ETHYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; [2 (2 NITRO 1H IMIDAZOL 1 YL) N METHYLACETAMIDO]ETHYL 2,3,4,6 TETRA O ACETYL BETA N GLUCOPYRANOSIDE; [2 (2 NITRO 1H IMIDAZOL 1 YL) N METHYLACETAMIDO]ETHYL ALPHA DEXTRO MANNOPYRANOSIDE; [2 (2 NITRO 1H IMIDAZOL 1 YL) N METHYLACETAMIDO]ETHYL BETA DEXTRO GALACTOPYRANOSIDE; [2 (2 NITRO 1H IMIDAZOL 1 YL) N METHYLACETAMIDO]ETHYL BETA DEXTRO GLUCOPYRANOSIDE; CARBOHYDRATE DERIVATIVE; GALACTOSAMINE; GALACTOSE; GLUCOSE DERIVATIVE; HYDROXYL GROUP; MANNOSE; OCTANOL; PERACETIC ACID; RADIOSENSITIZING AGENT; TX 1877; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ARTICLE; CELL HYPOXIA; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DESIGN; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; HYBRID; HYDROPHOBICITY; IN VITRO STUDY; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PHYSICAL CHEMISTRY; RADIOSENSITIZATION;

ALGORITHMS; CARBOHYDRATES; CELL HYPOXIA; DRUG DESIGN; HUMANS; MALE; MOLECULAR STRUCTURE; NITROIMIDAZOLES; RADIATION-SENSITIZING AGENTS;

EID: 38549114110     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.10.035     Document Type: Article

References (27)

1. Ewing D., and Jones S.R. Arch. Biochem. Biophys. 254 (1987) 53
2. Nordsmark M., Bentzen S.M., Rudat V., Brizel D., Lartigau E., Stadler P., Becker A., Adam M., Molls M., Dunst J., Terris D.J., and Overgaard J. Radiother. Oncol. 77 (2005) 18
3. Adams G.E., Hasan N.M., and Joiner M.C. Radiother. Oncol. 44 (1997) 101
4. Hall E.J., and Giaccia A.J. Radiobiology for the Radiologist. 6th ed. (2006), Lippincott Williams & Wilkins, Philadelphia 85-105
5. Nagasawa H., Uto Y., Kirk K.L., and Hori H. Biol. Pharm. Bull. 29 (2006) 2335
6. Paulson O.B., Melggard B., Hansen H.S., Kamieniecka Z., Køhler O., Hansen J.M., Pedersen A.G., Tang X., and Trojaborg W. Acta Neurol. Scand. Suppl. 100 (1984) 133
7. Overgaard J., Eriksen J.G., Nordsmark M., Alsner J., and Horsman M.R. Lancet. Oncol. 6 (2005) 757
8. Pandey S.K., Zheng X., Morgan J., Missert J.R., Liu T.H., Shibata M., Bellnier D.A., Oseroff A.R., Henderson B.W., Dougherty T.J., and Pandey R.K. Mol. Pharm. 4 (2007) 448
9. Sylvain I., Zerrouki R., Granet R., Huang Y.M., Lagorce J.F., Guilloton M., Blais J.C., and Krausz P. Bioorg. Med. Chem. 10 (2002) 57
10. Mikata Y., Shinohara Y., Yoneda K., Nakamura Y., Esaki K., Tanahashi M., Brudziñska I., Hirohara S., Yokoyama M., Mogami K., Tanase T., Kitayama T., Takashiba K., Nabeshima K., Takagi R., Takatani M., Okamoto T., Kinoshita I., Doe M., Hamazawa A., Morita M., Nishida F., Sakakibara T., Orvig C., and Yano S. J. Org. Chem. 66 (2001) 3783
11. Idutsu Y., Sasaki A., Matsumura S., and Toshima K. Bioorg. Med. Chem. Lett. 15 (2005) 4332
12. Toshima K., Ozawa T., Kimura T., and Matsumura S. Bioorg. Med. Chem. Lett. 14 (2004) 2777
13. Toshima K., Okuno Y., and Matsumura S. Bioorg. Med. Chem. Lett. 13 (2003) 3281
14. Toshima K., Okuno Y., Nakajima Y., and Matsumura S. Bioorg. Med. Chem. Lett. 12 (2002) 671
15. Kasai S., Nagasawa H., Yamashita M., Masui M., Kuwasaka H., Oshodani T., Uto Y., Inomata T., Oka S., Inayama S., and Hori H. Bioorg. Med. Chem. 9 (2001) 453
16. Kasai S., Nagasawa H., Kuwasaka H., Oshodani T., Nishioka A., Ogawa Y., Yoshida S., Inayama S., Inomata T., and Hori H. Int. J. Radiat. Oncol. Biol. Phys. 42 (1998) 799
17. Abou-Bedair F.A., Hori H., Nagasawa H., Uto Y., Abu-Zeid M., and Inayama S. Biol. Pharm. Bull. 25 (2002) 591
18. Oshikawa T., Okamoto M., Ahmed S.U., Furuichi S., Tano T., Sasai A., Kan S., Kasai S., Uto Y., Nagasawa H., Hori H., and Sato M. Int. J. Cancer 116 (2005) 571
19. Murakami T., Hirono R., Sato Y., and Furusawa K. Carbohydr. Res. 342 (2007) 1009
20. Kong F. Carbohydr. Res. 342 (2007) 345
21. Aich U., and Loganathan D. Carbohydr. Res. 341 (2006) 19
22. Gouin S.G., Pilgrim W., Porter R.K., and Murphy P.V. Carbohydr. Res. 340 (2005) 1547
23. Adams G.E., Flockhart I.R., Smithen C.E., Stratfold I.J., Wardman P., and Watts M.E. Radiat. Res. 67 (1976) 9
24. Kim J.W., and Dang C.V. Cancer Res. 66 (2006) 8927
25. Pavlovic M., Wroblewski K., Manevich Y., Kim S., and Biaglow J.E. Br. J. Cancer Suppl. 74 (1996) S222
26. Brown J.M., and Workman P. Radiat. Res. 82 (1980) 171
27. Nagasawa H., Bando M., Hori H., Satoh T., Tada T., Onoyama Y., and Inayama S. Int. J. Radiat. Oncol. Biol. Phys. 22 (1992) 561