632
Views
10
CrossRef citations to date
0
Altmetric
Research Article

Particular interaction between pyrimethamine derivatives and quadruple mutant type dihydrofolate reductase of Plasmodium falciparum: CoMFA and quantum chemical calculations studies

, , , , &
Pages 471-479 | Received 26 Oct 2007, Accepted 25 Feb 2008, Published online: 20 Oct 2008

References

  • RW Snow, CA Guerra, AM Noor, HY Myint, and SI Hay. (2005). Estimating clinical episodes of malaria. Nature 434:214–217.
  • P Prapunwattana, W Sirawaraporn, Y Yuthavong, and DV Santi. (1996). Chemical synthesis of the Plasmodium falciparum dihydrofolate reductase-thymidylate synthase gene. Mol Biochem Parasitol 83:93–106.
  • J Yuvaniyama, P Chitnumsub, S Kamchonwongpaisan, J Vanichtanankul, W Sirawaraporn, P Taylor, MD Walkinshaw, and Y Yuthavong. (2003). Insights into antifolate resistance from malarial DHFR-TS structures. Nat Struct Biol 10:357–365.
  • T Dasgupta, and KS Anderson. (2008). Probing the role of parasite-specific, distant structural regions on communication and catalysis in the bifunctional thymidylate synthase- dihydrofolate reductase from Plasmodium falciparum. Biochemistry 47 (5):1336–1345.
  • RT Delfino, OA Santos-Filho, and JD Figueroa-Villar. (2002). Type2 antifolates in the chemotherapy of falciparum malaria. J Braz Chem Soc 13:727–741.
  • NT Marbiah, E Petersen, K David, E Magbity, J Lines, and DJ Bradley. (1998). A controlled trial of lambda-cyhalothrin-impregnated bed nets and/or dapsone/pyrimethamine for malaria control in Sierra Leone. Am J Trop Med Hyg 58 (1):1–6.
  • A Sowunmi, BA Fateye, AA Adedeji, GO Gbotosho, TC Happi, AE Bamgboye, OM Bolaji, and AMJ Oduola. (2006). Predictors of the failure of treatment with pyrimethamine-sulfadoxine in children with uncomplicated falciparum malaria. Acta Trop 98:6–14.
  • AP Alker, V Mwapasa, and R Meshnick. (2004). Rapid real-time PCR genotyping of mutations associated with sulfadoxine-pyrimethamine resistance in Plasmodium falciparum. Antimicrob Agents Chemother 48 (8):2924–2929.
  • DC Warhurst. (2002). Resistance to antifolate in Plasmodium falciparum, the causative agent of tropical malaria. Sci Prog 85:89–111.
  • W Sirawaraporn. (1998). Dihydrofolate reductase and antifolate resistance in malaria. Drug Resist Updat 1:397–406.
  • RT Delfino, OA Santos-Filho, and JD Figueroa-Villar. (2002). Molecular modeling of wild-type and antifolate resistant mutant Plasmodium falciparum DHFR. Biophys Chem 98:287–300.
  • DS Peterson, WK Milhous, and TE Wellems. (1990). Molecular basis of differential resistance to cycloguanil and pyrimethamine in Plasmodium falciparum malaria. Proc Natl Acad Sci USA 87:3018–3022.
  • W Sirawaraporn, T Sathitkul, R Sirawaraporn, Y Yuthavong, and DV Santi. (1997). Antifolate-resistant mutants of Plasmodium falciparum dihydrofolate reductase. Proc Natl Acad Sci USA 94:1124–1129.
  • IM Hastings, and MJ Donnelly. (2005). The impact of antimalarial drug resistance mutations on parasite fitness, and its implications for the evolution of resistance. Drug Resist Updat 8:43–50.
  • D Walliker, P Hunt, and H Babiker. (2005). Fitness of drug-resistant malaria parasites. Acta Trop 94:251–259.
  • S Kamchonwongpaisan, R Quarrell, N Charoensetakul, R Ponsinet, T Vilaivan, J Vanichtanankul, B Tarnchompoo, W Sirawaraporn, G Lowe, and Y Yuthavong. (2004). Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities. J Med Chem 47:673–680.
  • H Kubinyi, H Kubinyi. QSAR: Hansch Analysis and Related Approaches VCH: Weinheim. 1993.
  • C Hansch, and A Leo. Exploring QSAR. Fundamentals and Applications in Chemistry and Biology. American Chemical Society, Washington, DC, (1995) .
  • RD CramerIII, DE Patterson, and JD Bunce. (1988). Comparative molecular field analysis CoMFA: 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959–5967.
  • H Kubinyi, G Flokers, and YC Martin. (1998). 3D QSAR in drug design: Ligand-protein interactions and molecular similarlity. Perspect Drug Discovery Des 3–398.
  • SS Sao, and M Karplus. (2001). Evaluation of designed ligands by a multiple screening method: Application to glycogen phosphorylase inhibitors constructed with a variety of approaches. J Comput Aided Mol. Des 15:613–647.
  • S Saen-oon, M Kuno, and S Hannongbua. (2005). Binding energy analysis for wild-type and Y181C Mutant HIV-1 RT/8-Cl TIBO complex structures: Quantum chemical calculations based on the ONIOM method. PROTEINS: Structure, Function, and Bioinformatics 61:859–869.
  • M Kuno, R Hongkrengkai, and S Hannongbua. (2006). ONIOM-BSSE scheme for H–¶ system and applications on HIV-1 reverse transcriptase. Chem Phys Lett 424:172–177.
  • SYBYL 7.0., Tripos Associates Inc., 1699 South Hanley Road, Suite 303, St. Louis, Missouri 63144, USA.
  • A Streitwieser. Molecular Orbital Theory for Organic Chemists. New York, Wiley, (1961) .
  • M Clark, and RD CramerIII. (1993). The probability of chance correlation using partial least squares (PLS). Quant Struct-Act Relat 12 (2):137–145.
  • BL Bush, and RB NachbarJr. (1993). Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA. J Comput Aided Mol Des 7:587–619.
  • SJ Cho, and A Tropsha. (1995). Cross-validated R2-guided region selection for comparative molecular field analysis: A simple method to achieve consistent results. J Med Chem 38:1060–1066.
  • A Golbraikh, and A Tropsha. (2002). Beware of q2!. J Mol Graph Mod 20:269–276.
  • S Hannongbua, K Nivesanond, L Lawtrakul, P Pungpo, and P Wolschann. (2001). 3D-quantitative structure-activity relationships of HEPT derivatives as HIV-1 reverse transcriptase inhibitors, based on ab initio calculations. J Chem Inf Comput Sci 41:848–855.
  • MJ Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA Robb, JR Cheeseman, JA MontgomeryJr., T Vreven, KN Kudin, JC Burant, JM Millam, SS Iyengar, J Tomasi, V Barone, B Mennucci, M Cossi, G Scalmani, N Rega, GA Petersson, H Nakatsuji, M Hada, M Ehara, K Toyota, R Fukuda, J Hasegawa, M Ishida, T Nakajima, Y Honda, O Kitao, H Nakai, M Klene, X Li, JE Knox, HP Hratchian, JB Cross, C Adamo, J Jaramillo, R Gomperts, RE Stratmann, O Yazyev, AJ Austin, R Cammi, C Pomelli, JW Ochterski, PY Ayala, K Morokuma, GA Voth, P Salvador, JJ Dannenberg, VG Zakrzewski, S Dapprich, AD Daniels, MC Strain, O Farkas, DK Malick, AD Rabuck, K Raghavachari, JB Foresman, JV Ortiz, Q Cui, AG Baboul, S Clifford, J Cioslowski, BB Stefanov, G Liu, A Liashenko, P Piskorz, I Komaromi, RL Martin, DJ Fox, T Keith, MA Al-Laham, CY Peng, A Nanayakkara, M Challacombe, PMW Gill, B Johnson, W Chen, MW Wong, C Gonzalez, and JA Pople. . Gaussian, Inc, Pittsburgh, (2003) Gaussian 03, revision B.05.
  • SF Boys, and F Bernardi. (1970). The calculations of small molecular interaction by the difference of separate total energies some procedures with reduced error. Mol Phys 19:553–566.
  • Y Yuthavong. (2002). Basis for antifolate action and resistance in malaria. Microb Inf 4:175–182.
  • G Rastelli, W Sirawaraporn, P Sompornpisut, T Vilaivan, S Kamchonwongpaisan, R Quarrell, G Lowe, Y Thebtaranonth, and Y Yuthavong. (2000). Interaction of pyrimethamine, cycloguanil, WR99210 and their Analogues with Plasmodium falciparum Dihydrofolate reductase: Structural basis of antifolate resistance. Bioorg Med Chem 8:1117–1128.
  • Y Yuthavong, J Yuvaniyama, P Chitnumsub, J Vanichtanankul, S Chusacultanachai, B Tarnchompoo, T Vilaivan, and S Kamchonwongpaisan. (2005). Malarial (Plasmodium falciparum) dihydrofolate reductase-thymidylate synthase: Structural basis for antifolate resistance and development of effective inhibitors. Parasitology 130:249–259.

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.