Comparative Analysis of Different DNA-Binding Drugs for Leishmaniasis Cure: A Pharmacoinformatics Approach

Chemical Biology and Drug Design

Volumn 80, Issue 1, 2012, Pages 54-63

  Chauhan, Nutan ^a   Vidyarthi, Ambarish Sharan ^a   Poddar, Raju ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY   (India)

Author keywords

ADME T; DNA binding drug; Docking; Drug likeness; Leishmania

Indexed keywords

2, 4 BIS( 4 AMIDINOPHENYL)FURAN; 2, 5 BIS( 4 AMIDINOPHENYL)THIOPHENE; ACRIDINE; ANTILEISHMANIAL AGENT; BERBERIN CHLORIDE; BERBERINE; BERBERINE DERIVATIVE; BISINDOLYL METHANE; CANADINE; DIINDOLYL METHANE; DIMINAZENE ACETURATE; DNA; DUOCARMYCIN DERIVATIVE; LIGAND; N [ 2 (METHYLSULFANYL) 4 [ 5 [ 3 (METHYLSULFANYL) 4 (PYRIDINE 2 IMIDAMIDO)PHENYL]FURAN 2 YL]PHENYL]PYRIDINE 2 CARBOXIMIDAMIDE; N [ 3 CHLORO 4 [ 5 [ 2 CHLORO 4 (PYRIDINE 2 IMIDAMIDO)PHENYL]FURAN 2 YL]PHENYL]PYRIDINE 2 CARBOXIMIDAMIDE; N [ 5 ( 2 CHLOROETHYL) 8 HYDROXY 3 METHYLQUINOLIN 7 YL] 5,6,7 TRIMETHOXY 1H INDOLE 2 CARBOXAMIDE; N [ 6 (ACETYLAMINO) 3 ACRIDINYL]ACETAMIDE; N [ 6 (BENZOYLAMINO) 3 ACRIDINYL]BENZAMIDE; N METHYLTETRAHYDRO BERBERINIUM IODIDE; PENTAMIDINE; UNCLASSIFIED DRUG;

ARTICLE; BIOINFORMATICS; CHEMICAL COMPOSITION; COMPUTER MODEL; CONTROLLED STUDY; DNA STRUCTURE; DRUG ABSORPTION; DRUG DISTRIBUTION; DRUG DNA BINDING; DRUG EXCRETION; DRUG METABOLISM; DRUG PROTEIN BINDING; DRUG TARGETING; HUMAN; LEISHMANIASIS; MOLECULAR DOCKING; MONTE CARLO METHOD; PHARMACOINFORMATICS; PRIORITY JOURNAL;

ANTIPROTOZOAL AGENTS; BINDING SITES; COMPUTER SIMULATION; DATABASES, PROTEIN; DNA; HUMANS; LEISHMANIASIS;

EID: 84862132900     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01329.x     Document Type: Article

References (29)

1. Grimaldi R., Tesh G.R., McMahon-Pratt C. (1989) A review of the geographic distribution and epidemiology of leishmaniasis in the New World. Am J Trop Med Hyg;41:687-725.
2. Herwalt B.L. (1999) Leishmaniasis Lancet;354:1191-1199.
3. Mrozek A., Karolak-Wojciechowska J., Bsiri N., Barbe J. (2000) Quantitative analysis of structure-activity relationship in the acridine serie. Part 1. Antiparasitic 9-thioaryl-acridine derivatives. Acta Pol Pharm;57:345-351.
4. DasGupta B.M., Dikshit B.B. (1929) Berberine in treatment of oriental sore. Indian Med Gaz;64:67-70.
5. Leon W., Brun R., Krassner S.M. (1977) Effect of berenil on growth, mitochondrial DNA and respiration of Leishmania tarentolae promastigotes. J Eukaryot Microbiol;24:444-448.
6. Ghosh A.K., Rakshit M.M., Ghosh D.K. (1983) Effect of berberine chloride on Leishmania donovani. Indian J Med Res;78:407-416.
7. Ghosh A.K., Bhattacharyya F.K., Ghosh D.K. (1985) Leishmania donovani: amastigote inhibition and mode of action of berberine. Exp Parasitol;60:404-413.
8. Shapiro T.A., Englund P.T. (1990) Selective cleavage of kinetoplast DNA minicircles promoted by antitrypanosomal drugs. Proc Natl Acad Sci U S A;87:950-954.
9. Vennerstrom J.L., Lovelace J.K., Waits V.B., Hanson W.L., Klayman D.L. (1990) Berberine derivatives as antileishmanial drugs. Antimicrob Agents Chemother;34:918-921.
10. Edwards K.J., Jenkins T.C., Neidle S. (1992) Crystal structure of a pentamidine-oligonucleotide complex: implications for DNA-binding properties. Biochemistry;31:7104-7109.
11. Stephens C.E., Brun R., Salem M.M., Werbovetz K.A., Tanious F., Wilson W.D., Boykin D.W. (2003) The activity of diguanidino and 'reversed' diamidino 2, 5-diarylfurans versus Trypanosoma cruzi and Leishmania donovani. Bioorg Med Chem Lett;13:2065-2069.
12. Giorgio C.D., Shimi K., Boyer G., Delmas F., Galy J.P. (2007) Synthesis and antileishmanial activity of 6-mono-substituted and 3, 6-di-substituted acridines obtained by acylation of proflavine. Eur J Med Chem;42:1277-1284.
13. Hu L., Arafa R.K., Ismail M.A., Wenzler T., Brun R., Munde M., Wilson W.D., Nzimiro S., Samyesudhas S., Werbovetz K.A., Boykin D.W. (2008) Azaterphenyl diamidines as antileishmanial agents. Bioorg Med Chem Lett;18:247-251.
14. Chavda S., Babu B., Yanow S.K., Jardim A., Spithill T.W., Kiakos K., Kluza J., Hartley J.A., Lee M. (2010) A novel achiral seco-cyclopropylpyrido[e]indolone (CPyI) analog of CC-1065 and the duocarmycins: synthesis, DNA interactions, in vivo anticancer and anti-parasitic evaluation. Bioorg Med Chem;18:5016-5024.
15. Coletta A., Rocca B.M.D., Jaisankar P., Majumder H.K., Chillemi J., Sanna N., Desideri A. (2010) Assignment of UV-vis spectrum of (3, 3′)-diindolylmethane, a Leishmania donowani topoisomerase IB inhibitor and a candidate DNA minor groove binder. J Phys Chem A;114:7121-7126.
16. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shelley M., Perry J.K., Shaw D.E., Francis P., Shenkin P.S. (2004) Glide, A New approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem;47:1739-1749.
17. Lipinski C.A, Lombardo F., Dominy B.W., Feeney P.J. (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev;23:3-25.
18. Lipinski C.A. (2000) Drug-like properties and the causes of poor solubility and poor permeability. J Pharm Tox Meth;44:235-249.
19. Gamage S.A., Figgit D.P., Wojcik S.J., Ralph R.K., Ransijn A., Mauel J., Yardley V., Snowdon D.S., Croft L., Denny W. (1997) Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1′-substituted 9-anilino-acridines. J Med Chem;40:2634-2642.
20. Girault S., Delarue S., Grellier P., Berecibar A., Maes L., Quirijnen L., Lemiere P., Debreu-Fontaine M.A., Sergheraert C. (2001) Antimalarial in-vivo activity of bis(9-amino-6-chloro-2-methoxyacridines). J Pharm Pharmacol;53:935-938.
21. Anderson M.O., Sherrill J., Madrid P.B., Liou A.P., Weisman J.L., DeRisi J.L., Guy R.K. (2006) Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum. Bioorg Med Chem;14:334-343.
22. Putzer B. (1934) Berberine and its derivatives in the treatment of oriental sore. Med Chem Aspects;2:274-280.
23. Ferraroni M., Bazzicalupi C., Bilia A.R., Gratteri P. (2011) X-Ray diffraction analyses of the natural isoquinoline alkaloids Berberine and Sanguinarine complexed with double helix DNA d(CGTACG). Chem Commun;47:4917-4919.
24. Lane A.N., Jenkins T.C., Brown T., Stephen N. (1991) Interaction of berenil with the EcoRI dodecamer d(CGCGAATTCGCG)2 in solution studied by NMR. Biochemistry;30:1372-1385.
25. 2+transport by digitonin-permeabilized Leishmania donovani. Effect of Ca2+, pentamidine and WR-6026 on mitochondrial membrane potential in situ. Biochem J;284:463-467.
26. Cain B.F., Atwell G.J., Seelye R.N. (1969) Potential antitumour agents. X. Bisquaternary salts. J Med Chem;12:199-206.
27. Goodsell D., Dickerson R.E. (1986) Isohelical analysis of DNA groove-binding drugs. J Med Chem;29:727-733.
28. Brendle J.J., Outlaw A., Kumar A., Boykin D.W., Patrick D.A., Tidwell R.R., Werbovetz K.A. (2002) Antileishmanial activities of several classes of aromatic dications. Antimicrob Agents Chemother;46:797-807.
29. Boger D. L., Johnson D.S. (1995) CC-1065 and the duocarmycins: unraveling the keys to a new class of naturally derived DNA alkylating agents. Proc Natl Acad Sci U S A;92:3642-3649.