QSAR, docking and ADMET studies of artemisinin derivatives for antimalarial activity targeting Plasmepsin II, a hemoglobin-degrading enzyme from P. falciparum

Current Pharmaceutical Design

Volumn 18, Issue 37, 2012, Pages 6133-6154

  Qidwai, Tabish ^a   Yadav, Dharmendra K ^a   Khan, Feroz ^a   Dhawan, Sangeeta ^a   Bhakuni, R S ^a  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

Author keywords

Antimalarial activity; Artemisinin; Docking; Drug likeness; eADMET; Plasmodium falciparum; QSAR; Toxicity risk assessment

Indexed keywords

ARTEMISININ DERIVATIVE; PLASMEPSIN II;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; ATOM; BINDING AFFINITY; BINDING SITE; CONTROLLED STUDY; DRUG ADSORPTION; DRUG BIOAVAILABILITY; DRUG ISOLATION; DRUG PROTEIN BINDING; DRUG SYNTHESIS; IN VIVO STUDY; LEUKOCYTOSIS; LIVER TOXICITY; MOLECULAR DOCKING; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLASMODIUM YOELII INFECTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RISK ASSESSMENT;

ADMINISTRATION, ORAL; ANIMALS; ANTIMALARIALS; ARTEMISININS; ASPARTIC ACID ENDOPEPTIDASES; BINDING SITES; BIOLOGICAL AVAILABILITY; COMPUTER-AIDED DESIGN; DISEASE MODELS, ANIMAL; DRUG DESIGN; ENZYME INHIBITORS; LACTONES; LINEAR MODELS; MAGNETIC RESONANCE SPECTROSCOPY; MALARIA; MICE; MODELS, BIOLOGICAL; MODELS, MOLECULAR; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; PLASMODIUM FALCIPARUM; PLASMODIUM YOELII; PROTEIN CONFORMATION; PROTOZOAN PROTEINS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REPRODUCIBILITY OF RESULTS;

EID: 84873956859     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/138161212803582397     Document Type: Article

References (48)

1. World Health Organization. Global Report on Antimalarial Efficacy and Drug Resistance: 2000-2010; WHO Report 2010; WHO Geneva.
2. Greenwood BM, Bojang K, Whitty CJ, Targett GA. Malaria. Lancet 2005; 365: 1487-98.
3. Maiteki-Sebuguzi C, Jagannathan P, Yau VM, Clark TD, Meya DN. Safety and tolerability of combination antimalarial therapies for uncomplicated falciparum malaria in Ugandan children. Malaria J 2008; 7: 106-9.
4. Olliaro PL, Taylor WR. Developing artemisinin-based drug combinations for the treatment of drug-resistant falciparum malaria: A review. J Postgrad Med 2004; 50: 40-4.
5. Adjuik M, Babiker A, Garner P, Olliaro P, Taylor W, White N. Artesunate combinations for treatment of malaria: Meta-analysis. Lancet 2004; 363: 9-17.
6. Nosten F, White NJ. Artemisinin-based combination treatment of falciparum malaria. Am J Trop Med Hyg 2007; 77: 181-92.
7. World Health Organization. The Role of Artemisinin and its Derivatives in the Current Treatment of Malaria. World Health Organization Report 1995; WHO Geneva.
8. Nontprasert A, Pukrittayakamee S, Dondorp AM, Clemens R, Looareesuvan S, White NJ. Neuropathologic toxicity of artemisinin derivatives in a mouse model. Am J Trop Med Hyg 2002; 67: 423-9.
9. World Health Organization. Assessment of the Safety of Artemisinin Compounds in Pregnancy. World Health Organization Report 2003; WHO Geneva.
10. Raji Y, Osonuga TO, Akinsomisoye OS, Osonuga OA, Mewoyeka OO. Gonadotoxicity evaluation of oral artemisinin derivatives in male rats. J Med Sci 2005; 5: 303-6
11. Nwanjo HU, Iroagba II, Natuanya IN, Eze NA. Antifertility activity of dihydroartemisinin in male albino rats. Internet J Endocrin 2007; 4: 1-5.
12. Obianime AW, Aprioku JS. Comparative testicular histopathological effects of artemisinin derivatives and some ACTS in the guineapig. J Exp Clin Anatomy 2009; 8: 31-40.
13. Fidock DA, Rosenthal PJ, Croft SL, Brun R, Nwaka S. Antimalarial drug discovery: efficacy models for compound screening. Nat Rev Drug Discov 2004; 3: 509-20.
14. Khan MA, RA Jr. Smego, ST Razi, ST Beg. Emerging drug resistance and guidelines for treatment of malaria. Med Today 2006; 4: 81-7.
15. White NJ. Antimalarial drug resistance. J Clin Invest 2004; 113: 1084-92.
16. Silva AM, Lee AY, Gulnik SV, et al. Structure and inhibition of plasmepsin II, a hemoglobin-degrading enzyme from Plasmodium falciparum. Proc Natl Acad Sci USA 1996; 93(19): 10034-9.
17. Muegge I. A knowledge-based scoring function for protein-ligand interactions: probing the reference state. Perspec Drug Dis Des 2000; 20: 99-114.
18. Martin C. A general and fast scoring function for protein ligand interactions: a simplified potential approach. J Med Chem 1999; 42: 791-804.
19. Yadav DK, Meena A, Srivastava A, Chanda D, Khan F, Chattopadhyay SK. Development of QSAR model for immunomodulatory activity of natural coumarinolignoids. Drug Des Dev Ther 2010; 4: 173-86
20. Meena A, Yadav DK, Srivastava A, Khan F, Chanda D, Chattopadhyay SK. In Silico Exploration of Anti-Inflammatory Activity of Natural Coumarinolignoids. Chem Biol Drug Des 2011; 78: 567-79.
21. Yadav DK, Khan F, Negi AS. Pharmacophore modeling, molecular docking, QSAR, and in silico ADMET studies of gallic acid derivatives for immunomodulatory activity. J Mol Model 2011, DOI 10.1007/s00894-011-1265-3.
22. O'Neill PM, Searle NL, Kan KW, et al. Novel, Potent, Semisynthetic Antimalarial Carba Analogues of the First-Generation 1,2,4-Trioxane Artemether. J Med Chem 1999; 42: 5487-93.
23. Posner GH, Parker MH, Northrop J, et al. Orally Active, Hydrolytically Stable, Semisynthetic, Antimalarial Trioxanes in the Artemisinin Family. J Med Chem 1999; 42: 300-4.
24. O'Neill PM, Miller A, Bishop LPD, H et al. Synthesis, Antimalarial Activity, Biomimetic Iron(II) Chemistry, and In Vivo Metabolism of Novel, Potent C-10-Phenoxy Derivatives of Dihydroartemisinin. J Med Chem 2001; 44: 58-68.
25. Avery MA, Muraleedharan KM, Desai PV, Bandyopadhyaya AK, Furtado MM, Tekwani BL. Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 8. Design, Synthesis, and CoMFA Studies toward the Development of Artemisinin-Based Drugs against Leishmaniasis and Malaria. J Med Chem 2003; 46: 4244-58.
26. Hodgson J. ADMET-turning chemicals into drugs. Nat Biotechnol 2001; 19: 722-6.
27. Sean E, Sergey A, Andy R, et al. A combined approach to drug metabolism and toxicity assessment. Drug Metab Dispos 2006; 34: 495-503.
28. Norinder U, Bergström CAS. Prediction of ADMET properties. Chem Med Chem 2006; 1: 920-37.
29. Reichel A, Begley DJ. Potential of immobilized artificial membranes for predicting drug penetration across the blood-brain barrier. Pharm Res 1998; 15: 1270-4.
30. Lombardo F, Gifford E, Shalaeva MY. In silico ADME prediction: data, models, facts and myths. Mini-Rev Med Chem 2003; 3: 861-75.
31. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 2001; 46: 3-26.
32. Ertl P, Rohde B, Selzer P. Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties. J Med Chem 2000; 43: 3714-7.
33. Veber DF, Stephen R, Johnson, Cheng HY, et al. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2002; 45: 2615-23.
34. Clark DE. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 1. Prediction of intestinal absorption. J Pharm Sci 1999; 88: 807-14.
35. Khanuja SPS, Paul S, Shasany AK, et al. High artemisinin yielding plant named "CIM-arogya" US Patent-7375260; 2008.
36. Brossi A, Venugopalan B, Gerpe LD, et al. Arteether, a new antimalarial drug: synthesis and antimalarial properties. J Med Chem 1988; 31: 645-50.
37. Bhakuni RS, Jain DC, Sharma RP. An improved procedure for the synthesis of ethers of di-hydroartemisinin. Indian J Chem B Org 1995; 34b: 529-30.
38. Agarwal J, Singh SP, Chanda D, Bawankule DU, Bhakuni RS, Pal A. Antiplasmodial activity of artecyclopentyl mether a new artemisinin derivative and its effect on pathogenesis in Plasmodium yoelii nigeriensis infected mice. Parasitol Res 2011; 109: 1003-8.
39. Aprioku JS, Obianime AW. Structure-Activity-Relationship (SAR) of Artemisinins on some Biological Systems in Male Guinea Pigs. Insight Pharmaceutical Sciences 2011; 1(1): 1-10.
40. Avery MA, Gaston MA, Rodrigues CR, et al. Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 6. The Development of Predictive In vitro Potency Models Using CoMFA and HQSAR Methodologies. J Med Chem 2002; 45: 292-303.
41. Guha R, Jurs PC. Development of QSAR Models To Predict and Interpret the Biological Activity of Artemisinin Analogues. J Chem Inf Comput Sci 2004; 44: 1440-9.
42. Capela R, Oliveira R, Gonçalves LM, et al. Artemisinin-dipeptidyl vinyl sulfone hybrid molecules: Design, synthesis and preliminary SAR for antiplasmodial activity and falcipain-2 inhibition. Bioorg Med Chem Lett 2009; 19: 3229-32.
43. Nwanjo HU, Oze G. Acute hepatotocixity following administration of artesunate in guinea pigs. Internet J Toxicol 2007; 4(1).
44. Gasasira AF, Kamya MR, Achan J, Mebrahtu T, Kalyango JN. High risk of neutropenia in HIV-infected children following treatment with artesunate plus amodiaquine for uncomplicated malaria in Uganda. Clin Infect Dis 2008; 46: 985-91.
45. Li QG, Peggins JO, Fleckenstein LL, Masonic K, Heiffer MH, Brewer TG. The pharmacokinetics and bioavailability of dihydroartemisinin, arteether, artemether, artesunic acid and artelinic acid in rats. J Pharmacy Pharmacol 1998; 50: 173-82.
46. Looareesuwan S, Wilairatana P, Vanijanonta S, Pitisuttithum P, Viravan C, Kraisintu K. Treatment of acute, uncomplicated, falciparium malaria with oral dihydroartemisinin. Ann Trop Med Parasitol 1996; 90: 21-8.
47. Svensson US, Maki-Jouppila M, Hoffmann KJ, Ashton M. Characterisation of the human liver in vitro metabolic pattern of artemisinin and auto-induction in the rat by use of nonlinear mixed effects modelling. Biopharm Drug Dispos 2003; 24: 71-85.
48. Simonsson US, Jansson B, Hai TN, Huong DX, Tybring G, Ashton M. Artemisinin autoinduction is caused by involvement of cytochrome P450 2B6 but not 2C9. Clin Pharmacol Ther 2003; 74: 32-43.