Anticancer activity and quantitative-structure activity relationship (QSAR) studies of a series of antioxidant/anti-inflammatory aryl-acetic and hydroxamic acids

Chemical Biology and Drug Design

Volumn 74, Issue 3, 2009, Pages 266-275

  Pontiki, Eleni ^a   Hadjipavlou Litina, Dimitra ^a   Geromichalos, George ^b   Papageorgiou, Athanasios ^b  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b THEAGENIO CANCER HOSPITAL   (Greece)

Author keywords

Anticancer activity; Antioxidants; Aryl acetic acids; Aryl hydroxamic acids; Inflammation; Quantitative structure activity relationships

Indexed keywords

ARYLACETIC ACID DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; LIPOXYGENASE INHIBITOR;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CANCER CELL; CONTROLLED STUDY; CYTOTOXICITY; DIPOLE; DRUG DESIGN; ELECTRICITY; ELECTRON; HUMAN; HUMAN CELL; IC 50; LIPOPHILICITY; MOLECULAR DYNAMICS; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ACETIC ACIDS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; BENZOIC ACIDS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; HYDROXAMIC ACIDS; PHYSICOCHEMICAL PROCESSES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 68949214509     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00864.x     Document Type: Article

References (35)

1. Mates J.M., Sanchez-Jimenez F.M. (2000) Role of reactive oxygen species in apoptosis: implications for cancer therapy. Int J Biochem Cell Biol 32 : 157 170.
2. Yoshikawa T., Kokura S., Tainaka K., Naito Y., Kondo M. (1995) A novel cancer therapy based on oxygen radicals. Cancer Res 55 : 1617 1620.
3. Kong Q., Beel J.A., Lillehei K.O. (2000) A threshold concept for cancer therapy. Med Hypotheses 55 : 29 35.
4. Federico A., Morgillo F., Tuccillo C., Ciardiello F., Loguercio C. (2007) Chronic inflammation and oxidative stress in human carcinogenesis. Int J Cancer 121 : 2381 2386.
5. Cejas P., Casado E., Belda-Iniesta C., De Castro J., Espinosa E., Redondo A., Sereno M., Gárcia-Cabezas M.A., Vara J.A., Domínguez-Caceres A., Perona R., González-Baron M. (2004) Implications of oxidative stress and cell membrane lipid peroxidation in human cancer (Spain). Cancer Causes Control 15 : 707 719.
6. Garrido G., González D., Delporte C., Backhouse N., Quintero G., Núněz-Selles A.J., Morales M.A. (2001) Analgesic and anti-inflammatory effects of Mangifera indica L. extract (Vimang). Phytother Res 15 : 18 21.
7. Weber V., Rubat C., Duroux E., Lartigue C., Madesclaire M., Coudert P. (2005) New 3- and 4-hydroxyfuranones as antioxidants and anti-inflammatory agents. Bioorg Med Chem 13 : 4552 4564.
8. Cuendet M., Pezzuto J.M. (2000) The role of cyclooxygenase and lipoxygenase in cancer chemoprevention. Drug Metabol Drug Interact 17 : 109 157.
9. Klurfeld D.M., Bull A.W. (1997) Fatty acids and colon cancer in experimental models. Am J Clin Nutr 66 : 1530S 1538S.
10. Hussain S.P., Hofseth L.J., Harris C.C. (2003) Radical causes of cancer. Nat Rev Cancer 3 : 276 285.
11. Wang M.T., Honn K.V., Nie D. (2007) Cyclooxygenases, prostanoids, and tumor progression. Cancer Met Rev 26 : 525 534.
12. Liu X.H., Kisschenbaum A., Yao S., Lee R., Holland J.F., Levine A.C. (2000) Inhibition of cyclooxygenase-2 suppresses angiogenesis and the growth of prostate cancer in vivo. J Urol 164 : 820 825.
13. Zhu J., Song X., Lin H.P., Young D.C., Yan S., Marquez V.E., Chen C.S. (2002) Using cyclooxygenase inhibitors as molecular platforms to develop a new class of apoptosis-inducing agents. J Natl Cancer Inst 94 : 585 591.
14. Gunning W.T., Kramer P.M., Steele V.E., Pereira M.A. (2002) Chemoprevention by lipoxygenase and leukotriene pathway inhibitors of vinyl carbamate-induced lung tumors in mice. Cancer Res 62 : 4199 4201.
15. Orhan H., Sahin G. (2001) In vitro effects of NSAIDs and paracetamol on oxidative stress-related parameters of human erythrocytes. Exp Toxicol Pathol 53 : 133 140.
16. Pontiki E., Hadjipavlou-Litina D. (2003) Synthesis, antioxidant and antiinflammatory activity of novel aryl-acetic and aryl-hydroxamic acids. Arzneimittelforsch/Drug Res 53 : 780 785.
17. Pontiki E., Hadjipavlou-Litina D. (2006) Antioxidant and anti-inflammatory activity of aryl-acetic and hydroxamic acids as novel lipoxygenase inhibitors. Med Chem 2 : 251 264.
18. Gorman A., McCarthy J., Finucane D., Reville W., Cotter T. (1996) In : Cotter T.G., Martin S.J., editors. Trends in Endocrinology and Metabolism, vol. 8. Techniques in Apoptosis. A User's Guide. London, UK : Portland Press Ltd p. 6 7.
19. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., Boyd M.R. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Ins 82 : 1107 1112.
20. Papazisis K.T., Geromichalos G.D., Dimitriadis K.A., Kortsaris A.H. (1997) Optimization of the sulforhodamine B colorimetric assay. J Immunol Methods 208 : 151.
21. Ford M.G., Livingstone D.J. (1990) Multivariate techniques for parameter selection and data analysis exemplified by a study of pyrethroid neurotoxicity. Quant Struct Act Relat 9 : 107 114.
22. Moody T.R., Leyton J., Martinez A., Hong S., Malkinson A., Mulshine J.L. (1998) Lipoxygenase inhibitors prevent lung cancinogenesis and inhibit non-small cell lung cancer growth. Exp Lung Res 19 : 617 628.
23. Rioux N., Castonguay A. (1998) Inhibitors of lipoxygenase: a new class of cancer chemopreventive agents. Carcinogenesis (Lond.) 19 : 1393 1400.
24. Karmali R.A. (1987) Eicosanoids in breast cancer. Eur J Cancer Clin Oncol 23 : 5 7.
25. Kort W.J., Bijma A.M., Van Dam J.J., Van der Ham A.C., Hekking J.M., Van der Ingh H.F., Meijer W.S., Van Wilgenburg M.G.M., Zijlstra F.J. (1992) Eicosanoids in breast cancer patients before and after mastectomy. Prostaglamdins Leukot Essent Fatty Acids 45 : 319 327.
26. 2 in plasma samples from patients with benign and malignant tumours of the breast. Prostaglandins 29 : 513 528.
27. Bortuzzo C., Hanif R., Kashfi K., Satiano-Coico L., Shiff S.J., Rigas B. (1996) The effect of leukotrienes B and selected HETEs on the proliferation of colon cancer cells. Biochim Biophys Acta 1300 : 240 246.
28. Cramer R.D., Bruce J.D., Patterson D.E., Frank I.E. (1988) Crossvalidation, bootstrapping and partial least squares compared with multiple regression in conventional QSAR studies. Quant Struct Act Relat 7 : 18 22.
29. Yao S.-W., Lopes V.H.C., Fernández F., Garcia-Mera X., Morales M., Rodríguez-Borges J.E., Cordeiro J.E.C. (2003) Synthesis and QSAR study of the anticancer activity of some novel indane carbocyclic nucleosides. Bioorg Med Chem 11 : 4999 5006.
30. De Clercq E., Descamps J., Verhelst G., Walter R.T., Jones A.S., Torrence P.F., Shugar D. (1980) Comparative efficacy of antiherpes drugs against different strains of herpes simplex virus. J Infect Dis 141 : 563 574.
31. Estrada E., Uriarte E., Montero A., Teijeira M., Santana L., De Clercq E. (2000) A novel approach for the virtual screening and rational design of anticancer compounds. J Med Chem 43 : 1975 1985.
32. Xiao Z., Xiao Y.-D., Feng J., Golbraikh A., Tropsha A., Lee K.-H. (2002) Antitumor agents. 213. Modeling of epipodophyllotoxin derivatives using variable selection k nearest neighbor QSAR method. J Med Chem 45 : 2294 2309.
33. McKinney J.D., Darden T., Lyerly M.A., Pedersen L.G. (1985) PCB and related compound binding to the Ah receptor(s) theoretical model based on molecular parameters and molecular mechanics. Quant Struc Act Relat 4 : 166 172.
34. Waller C.L., McKinney J.D. (1992) Comparative molecular field analysis of polyhalogenated dibenzo-p-dioxins, dibenzofurans, and biphenyls. J Med Chem 35 : 3660 3666.
35. Tuppurainen K., Ruuskanen J. (2000) Electronic eigenvalue (EEVA): a new QSAR/QSPR descriptor for electronic substituent effects based on molecular orbital energies. A QSAR approach to the Ah receptor binding affinity of polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs). Chemosphere 41 : 843 848.