470
Views
11
CrossRef citations to date
0
Altmetric
Research Article

Modeling of cyclooxygenase-2 and 5-lipooxygenase inhibitory activity of apoptosis-inducing agents potentially useful in prostate cancer chemotherapy: Derivatives of diarylpyrazole

, &
Pages 607-615 | Received 28 Jan 2008, Accepted 21 May 2008, Published online: 01 Apr 2009

References

  • M Cuendet, and JM Pezzuto. (2000). The role of cyclooxygenase and lipoxygenase in cancer chemoprevention. Drug Metabol Drug Interact 17:109–157.
  • D Nie, and KV Honn. (2002). Cyclooxygenase, lipoxygenase and tumor angiogenesis. Cell Mol Life Sci 59:799–807.
  • G Gasparini, R Longo, R Sarmiento, and A Morabito. (2003). Inhibitors of cyclooxygenase 2: A new class of anticancer agents?. Lancet Oncol 4:605–615.
  • DG Haller. (2003). COX-2 inhibitors in oncology. Semin Oncol 30:2–8.
  • D Nie, M Che, D Grignon, K Tang, and KV Honn. (2001). Role of eicosanoids in prostate cancer progression. Cancer Metastasis Rev 20:195–206.
  • S Gupta, M Srivastava, N Ahmad, DG Bostwick, and H Mukhtar. (2000). Over-expression of cyclooxygenase-2 in human prostate adenocarcinoma. Prostate 42:73–78.
  • S Madaan, PD Abel, KS Chudhary, R Heyritt, MA Stott, GW Stamp, and EN Lalani. (2000). Cytoplasmic induction and over-expression of cyclooxygenase-2 in human prostate cancer: Implications for prevention and treatment. BJU Int 86:736–741.
  • T Hussain, S Gupta, and H Mukhtar. (2003). Cyclooxygenase-2 and prostate carcinogenesis. Cancer Lett 191:125–135.
  • AL Sabichi, and SM Lippman. (2003). COX-2 inhibitors and other NSAIDs in bladder and prostate cancer. Prog Exp Tumor Res 37:163–178.
  • FA Attiga, PM Fernandez, AT Weeraratna, MJ Manyak, and SR Patierno. (2000). Inhibitors of prostaglandin synthesis inhibit human prostate tumor cell invasiveness and reduce the release of matrix metalloproteinases. Cancer Res 60:4629–4637.
  • I Shureiqi, and SM Lippman. (2001). Lipoxygenase modulation to reverse carcinogenesis. Cancer Res 61:6307–6312.
  • GP Pidgeon, M Kandouz, A Meram, and KV Honn. (2002). Mechanisms controlling cell cycle arrest and induction of apoptosis after 12-lipoxygenase inhibition in prostate cancer cells. Cancer Res 62:2721–2727.
  • LC His, LC Wilson, and TE Eling. (2002). Opposing effects of 15-lipoxygenase-1 and -2 metabolites on MAPK signalling in prostate. Alteration in peroxisome proliferators-activated receptor gamma. J Biol Chem 277:40549–40556.
  • SB Shappell, RA Gupta, S Manning, R Whitehead, WE Boeglin, C Schneider, T Case, J Price, GS Jack, TM Wheeler, RJ Matusik, AR Brash, and RN DuBois. (2001). (15S)-hydroxyeicosatetraenoic acid activates peroxisome proliferatoractivated receptor γ and inhibits proliferation in PC 3 prostate carcinoma cells. Cancer Res 61:497–503.
  • UP Kelavkar, JB Nixon, C Cohen, D Dillehay, TE Eling, and KF Badr. (2001). Overexpression of 15-lipoxygenase-1 in PC 3 human prostate cancer cells increases tumorigenesis. Carcinogenesis 22:1765–1773.
  • KM Anderson, T Seed, M Vos, J Mulshine, J Meng, W Alrefai, D Ou, and JE Harris. (1998). 5-lipoxygenase inhibitors reduce PC 3 cell proliferation and initiate non-necrotic cell death. Prostate 37:161–173.
  • XH Liu, A Kirschenbaum, S Yao, R Lee, JF Holland, and AC Levine. (2000). Inhibition of cyclooxygenase-2 suppresses angiogenesis and the growth of prostate cancer in vivo. J Urol 164:820–825.
  • X Song, HP Lin, A Johnson, PH Tseng, YT Yang, SK Kulp, and CS Chen. (2002). Cyclooxygenase-2, player or spectator in cyclooxygenase-2 inhibitor-induced apoptosis in prostate cancer cells. J Natl Cancer Inst 94:585–591.
  • J Zhu, X Song, HP Lin, DC Young, S Yan, VE Marquez, and CS Chen. (2002). Using cyclooxygenase-2 inhibitors as molecular platforms to develop a new class of apoptosis-inducing agents. J Natl Cancer Inst 94:1745–1757.
  • J Marx. (2001). Cancer research. Anti-inflammatories inhibit cancer growths. But how?. Science 291:581–582.
  • P Srinath, PN Rao, EE Knaus, and MR Suresh. (2003). Effect of cyclooxygenase-2 (COX-2) inhibitors on prostate cancer cell proliferation. Anticancer Res 23:3923–3928.
  • A Gugliucci, L Ranzato, L Scorrano, R Colonna, V Petronilli, C Cusan, M Prato, M Mancini, F Pagano, and P Bernardi. (2002). Mitochondria are direct targets of the lipoxygenase inhibitor MK886. A strategy for cell killing by combined treatment with MK886 and cyclooxygenase inhibitors. J Biol Chem 277:31789–31795.
  • N Pommery, T Taverne, A Telliez, L Goossens, C Charlier, J Pommery, JF Goossens, R Houssin, F Durant, and JH Henichart. (2004). New COX-2/5-LOX inhibitors: Apoptosis-inducing agents potentially useful in prostate cancer chemotherapy. J Med Chem 47:6195–6206.
  • GR Desiraju, B Gopalakrishnan, RKR Jetti, D Raveendra, JARP Sarma, and HS Subramanya. (2000). Three-dimensional quantitative structural activity relationship (3D-QSAR) studies of some 1,5-darylpyrazole analog based design of selective cyclooxygenase-2 inhibitors. Molecules 5:945–955.
  • H Liu, X Huang, J Shen, X Luo, M Li, B Xiong, G Chen, J Shen, Y Yang, H Jiang, and K Chen. (2002). Inhobitory mode of 1,5-diarylpyrazole derivatives against cyclooxygenase-2 and cyclooxygenase-1: Molecular docking and 3D QSAR analysis. J Med Chem 45:4816–4827.
  • SK Singh, V Saibaba, KS Rao, PG Reddy, PR Daga, SA Rajjak, P Misra, and YK Rao. (2005). Synthesis and SAR/3D-QSAR studies on the COX-2 inhibitory activity of 1,5-diarylpyrazoles to validate the modified pharmacophore. Euro J Med Chem 40:977–990.
  • S Prasanna, E Manivannan, and SC Chaturvedi. (2005). QSAR analysis of conformationally restricted 1,5-diarylpyrazoles as selective COX-2 inhibitors: Application of connection table representations of ligands. Bioorg Med Chem Lett 15:2097–2102.
  • R Thilagavathi, and AK Chakraborti. (2005). Importance of alignment in developing 3D-QSAR models of 1,5-diarylpyrazoles for prediction of COX-2 inhibitory activity. Internet Electron J Mol Des 4:603–612.
  • S Revathi, AK Gupta, LK Soni, S Kavitha, R Wagh, and SG Kaskhedikar. (2006). Rationalization of physicochemical characters of 1,5-diarylpyrazole analogs as dual (COX-2/LOX-5) inhibitors: A QSAR approach. J Pharma Biomed Anal 42:283–289.
  • Dragon software (version 1.11-2001) by Todeschini R, Consonni V. Milano, Italy.
  • Chemdraw ultra 6.0 and Chem3D ultra, Cambridge Soft Corporation, Cambridge, USA.
  • YS Prabhakar. (2003). A combinatorial approach to the variable selection in multiple linear regression: Analysis of Selwood et al data set–A case study. QSAR Comb Sci 22:583–595.
  • MK Gupta, R Sagar, AK Shaw, and YS Prabhakar. (2005). CP-MLR directed QSAR studies on the antimycobacterial activity of functionalized alkenols-topological descriptors in modeling the activity. Bioorg Med Chem 13:343–351.
  • YS Prabhakar, RK Rawal, MK Gupta, VR Solomon, and SB Katti. (2005). Topological descriptors in modeling the HIV inhibitory activity of 2-aryl-3-pyridyl-thiazolidin-4-ones. Comb Chem High Thro Screen 8:431–437.
  • MK Gupta, and YS Prabhakar. (2006). Topological descriptors in modeling the antimalarial activity of 4-(3′,5′-disubstituted aniline)quinolines. J Chem Inf Model 46:93–102.
  • S-S So, and M Karplus. (1997). Three-dimensional quantitative structure-activity relationship from molecular similarity matrices and genetic neural networks. 1. Method and validation. J Med Chem 40:4347–4359.
  • YS Prabhakar, VR Solomon, RK Rawal, MK Gupta, and SB Katti. (2004). CP-MLR/PLS directed structure-activity modeling of the HIV-1 RT inhibitory activity of 2,3-diaryl-1,3-thiazolidin-4-ones. QSAR Comb Sci 23:234–244.
  • SYSTAT, Version 7.0; SPSS Inc., 444 North Michigan Avenue, Chicago, IL, 60611.
  • H Akaike. Information theory and an extension of the minimum likelihood principle. In: BN Petrov, and F Csaki, editors. Second international symposium on information theory. Budapest: Akademiai Kiado; (1973). p 267–281.
  • H Akaike. (1974). A new look at the statistical identification model. IEEE Trans Autom Control AC-19:716–723.
  • H Kubinyi. (1994). Variable selection in QSAR studies. I. An evolutionary algorithm. Quant Struct-Act Relat 13:285–294.
  • H Kubinyi. (1994). Variable selection in QSAR studies. II. A highly efficient combination of systematic search and evolution. Quant Struct-Act Relat 13:393–401.
  • Friedman J. In Technical Report No. 102. Laboratory for Computational Statistics, Stanford University: Stanford; 1990.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.