Effect of molecular chirality and side chain bulkiness on angiogenesis of haloacetylcarbamoyl-2-nitroimidazole compounds

Anticancer Research

Volumn 27, Issue 6 A, 2007, Pages 3693-3700

  Ohkura, Kazuto ^a   Uto, Yoshihiro ^b   Nagasawa, Hideko ^c   Hori, Hitoshi ^b  

^a CHIBA INSTITUTE OF SCIENCE   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

^c GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Angiogenesis; Chirality; Molecular dynamics; Radiosensitization

Indexed keywords

ANGIOGENESIS INHIBITOR; ANTINEOPLASTIC AGENT; HALOACETYLCARBAMOYL 2 NITROIMIDAZOLE DERIVATIVE; TX 1863; TX 1866; TX 1878; TX 1879; TX 1880; TX 1881; TX 1882; TX 1883; TX 1897; TX 1898; TX 1899; TX 1900; UNCLASSIFIED DRUG;

ANGIOGENESIS; ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; CELL PROLIFERATION; CHIRALITY; CONFERENCE PAPER; CONFORMATION; DRUG DESIGN; DRUG INHIBITION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENERGY; LUNG ENDOTHELIUM; MOLECULAR DYNAMICS; NONHUMAN; PRIORITY JOURNAL; SOLVATION;

ANGIOGENESIS INHIBITORS; ANIMALS; CELL PROLIFERATION; CHICK EMBRYO; COMPUTER SIMULATION; CYCLOHEXANES; ENDOTHELIUM, VASCULAR; NITROIMIDAZOLES; PROTEIN CONFORMATION; RATS; SESQUITERPENES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 35349021994     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (29)

1. Carmeliet P and Jain R: Angiogenesis in cancer and other diseases. Nature 407: 249-257, 2000.
2. Drevs J, Laus C, Medinger M, Schmidt-Gersbach C and Unger C: Antiangiogenesis: current clinical data and future perspectives. Onkologie 25: 520-527, 2002.
3. Madhusudan S and Harris AL: Drug inhibition of angiogenesis. Curr Opin Pharmacol 2: 403-414, 2002.
4. Stopeck A, Sheldon M, Vahedian M, Cropp G, Gosalia R and Hannah A: Results of a Phase I dose-escalating study of the antiangiogenic agent, SU5416, in patients with advanced malignancies. Clin Cancer Res 8: 2798-2805, 2002.
5. Wedge SR, Ogilvie DJ, Dukes M, Kendrew J, Chester R, Jackson JA, Boffey S J, Valentine PJ, Curwen JO, Musgrove HL, Graham GA, Hughes GD, Thomas AP, Stokes ES, Curry B, Richmond GH, Wadsworth PF, Bigley AL and Hennequin LF: ZD6474 inhibits vascular endothelial growth factor signaling, angiogenesis, and tumor growth following oral administration. Cancer Res 62: 4645-4655, 2002.
6. Laird AD, Christensen JG, Li G, Carver J, Smith K, Xin X, Moss KG, Louie SG, Mendel DB and Cherrington JM: SU6668 inhibits Flk-1/KDR and PDGFRbeta in vivo, resulting in rapid apoptosis of tumor vasculature and tumor regression in mice. FASEB J 16: 681-690, 2002.
7. Ingber D, Fujita T, Kishimoto S, Sudo K, Kanamura T, Brem H and Folkman J: Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth. Nature 348: 555-557, 1990.
8. Kudelka AP, Levy T, Verschraegen CF, Edwards CL, Piamsomboon S, Termrungruanglert W, Freedman RS, Kaplan AL, Kieback DG, Meyers CA, Jaeckle KA, Loyer E, Steger M, Mante R, Mavligit G, Killian A, Tang RA, Gutterman JU and Kavanagh JJ: A phase I study of TNP-470 administered to patients with advanced squamous cell cancer of the cervix. Clin Cancer Res 3: 1501-1505, 1997.
9. Hotz HG, Reber HA, Hotz B, Sanghavi PC, Yu T, Foitzik T, Buhr HJ and Hines OJ: Angiogenesis inhibitor TNP-470 reduces human pancreatic cancer growth. J Gastrointest Surg 5: 131-138, 2001.
10. Bhargava P, Marshall JL, Rizvi N, Dahut W, Yoe J, Figuera M, Phipps K, Ong VS, Kato A and Hawkins MJ: A Phase I and pharmacokinetic study of TNP-470 administered weekly to patients with advanced cancer. Clin Cancer Res 5: 1989-1995, 1999.
11. Shimamura M, Nagasawa H, Ashino H, Yamamoto Y, Hazato T, Uto Y, Hori H and Inayama S: A novel hypoxia-dependent 2-nitroimidazole KIN-841 inhibits tumour-specific angiogenesis by blocking production of angiogenic factors. Br J Cancer 88: 307-313, 2003.
12. Inomata T, Ogawa Y, Itoh S, Kariya S, Hamada N, Nishioka A, Yoshida S, Nagasawa H, Hori H and Inayama S: Lung metastasis suppression of the bifunctional new radiosensitizer KIN-806. Int J Mol Med 4: 257-260, 1999.
13. Abu-Zeid M, Hori H, Nagasawa H, Uto Y and Inayama S: Studies of methyl 2-nitroimidazole-1-acetohydroxamate (KIN-804) 1: effect on free radical scavenging system in mice bearing Ehrlich ascites carcinoma. Biol Pharm Bull 23: 190-194, 2000.
14. Abu-Zeid M, Hori H, Nagasawa H, Uto Y and Inayama S: Studies of methyl 2-nitroimidazole-1-acetohydroxamate (KIN-804) 2: effect on certain antioxidant enzyme systems in mice bearing Ehrlich ascites carcinoma. Biol Pharm Bull 23: 195-198, 2000.
15. Abou-Bedair FA, Hori H, Nagasawa H, Uto Y, Abu-Zeid M and Inayama S: Comparison of hypoxic cell radiosensitizers, KIN-804, KIN-844, KIN-806 and TX-1877, on brain and liver metabolizing capacities in mice bearing Ehrlich ascites carcinoma. Biol Pharm Bull 25: 591-596, 2002.
16. Kasai S, Nagasawa H, Yamashita M, Masui M, Kuwasaka H, Oshodani T, Uto Y, Inomata T, Oka S, Inayama S and Hori H: New antimetastatic hypoxic cell radiosensitizers: design, synthesis, and biological activities of 2-nitroimidazoleacetamide, TX-1877, and its analogues. Bioorg Med Chem 9: 453-464, 2001.
17. Nagasawa H, Yamashita M, Mikamo N, Shimamura M, Oka S, Uto Y and Hori H: Design, synthesis and biological activities of antiangiogenic hypoxic cytotoxin, triazine-N-oxide derivatives. Comp Biochem Physiol A Mol Integr Physiol 132: 33-40, 2002.
18. Hori H, Nagasawa H, Ishibashi M, Uto Y, Hirata A, Saijo K, Ohkura K, Kirk K L and Uehara Y: TX-1123: an antitumor 2-hydroxyarylidene-4-cyclopentene-1,3- dione as a protein tyrosine kinase inhibitor having low mitochondrial toxicity. Bioorg Med Chem 10: 3257-3265, 2002.
19. Kasai S, Nagasawa H, Shimamura M, Uto Y and Hori H: Design and synthesis of antiangiogenic/heparin-binding arginine dendrimer mimicking the surface of endostatin. Bioorg Med Chem Lett 12: 951-954, 2002.
20. Hori H, Jin CZ, Kiyono M, Kasai S, Shimamura M and Inayama S: Design, synthesis, and biological activity of antiangiogenic hypoxic cell radiosensitizer haloacetylcarbamoyl-2-nitroimidazoles. Bioorg Med Chem 5: 591-599, 1997.
21. Mah-Becherel MC, Ceraline J, Deplanque G, Chenard MP, Bergerat JP, Cazenave JP and Klein-Soyer C: Anti-angiogenic effects of the thienopyridine SR 25989 in vitro and in vivo in a murine pulmonary metastasis model. Br J Cancer 86: 803-810, 2002.
22. Aper S, Paper D, Burgermeister J, Baronikova S, Van Dyck S, Lemiere G, Vlietinck A and Pieters L: Antiangiogenic activity of synthetic dihydrobenzofuran lignans. J Nat Prod 65: 718-720, 2002.
23. Oikawa T, Shimamura M, Ashino H, Nakamura O, Kanayasu T, Morita I and Murota S: Inhibition of angiogenesis by staurosporine, a potent protein kinase inhibitor. J Antibiotics 45: 1155-1160, 1992.
24. Ohkura K and Hori H: Analysis of structure-permeability correlation of nitrophenol analogues in newborn rat abdominal skin using semiempirical molecular orbital calculation. Bioorg Med Chem 7: 309-314, 1999.
25. Zhu JW, Nagasawa H, Nagura F, Mohamad SB, Uto Y, Ohkura K and Hori H: Elucidation of strict structural requirements of brefeldin A as an inducer of differentiation and apoptosis. Bioorg Med Chem 8: 455-463, 2000.
26. Ohkura K, Sukeno A, Yamamoto K, Nagamune H, Maeda T and Kourai H: Analysis of structural features of bis-quaternary ammonium antimicrobial agents 4,4′-(alpha,omega-polymethylenedithio)bis (1-alkylpyridinium iodide)s using computational simulation. Bioorg Med Chem 11: 5035-5043, 2003.
27. Ohkura K and Hori H: Analyses of insulin-potentiating fragments of human growth hormone by computative simulation; essential unit for insulin-involved biological responses. Bioorg Med Chem 8: 1733-1740, 2000.
28. Ohkura K, Hori H and Nagamune H: Molecular dynamics of human-specific cytolysin: analysis of membrane binding motif for therapeutic application. Anticancer Res 26: 4055-4062, 2006.
29. Jin CZ, Nagasawa H, Shimamura M, Uto Y, Inayama S, Takeuchi Y, Kirk K L and Hori H: Angiogenesis inhibitor TX-1898: syntheses of the enantiomers of sterically diverse haloacetylcarbamoyl-2-nitroimidazole hypoxic cell radiosensitizers. Bioorg Med Chem 12: 4917-4927, 2004.