Aminoalkyl derivatives of guanidine diaromatic minor groove binders with antiprotozoal activity

Journal of Medicinal Chemistry

Volumn 56, Issue 3, 2013, Pages 700-711

  McKeever, Caitriona ^a   Kaiser, Marcel ^b,c   Rozas, Isabel ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; GUANIDINE DERIVATIVE;

ANTIPROTOZOAL ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DENATURATION; DRUG STRUCTURE; IN VITRO STUDY; NONHUMAN; PLASMODIUM FALCIPARUM; TRYPANOSOMA RHODESIENSE;

EID: 84962407449     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301614w     Document Type: Article

References (53)

1. Bell, A.; Kittler, L.; Lober, G.; Zimmer, C. DNA binding properties of minor groove binders and their influence on the topoisomerase II cleavage reaction J. Mol. Recog. 1997, 10, 245-255
2. Baraldi, P. G.; Bovero, A.; Fruttarolo, F.; Preti, D.; Tabrizi, M. A.; Pavani, M. G.; Romagnoli, R. DNA minor groove binders as potential antitumor and antimicrobial agents Med. Res. Rev. 2004, 24, 475-528
3. Lanteri, C. A.; Trumpower, B. L.; Tidwell, R. R.; Meshnick, S. R. DB75, a novel trypanocidal agent, disrupts mitochondrial function in Saccharomyces cerevisiae Antimicrob. Agents Chemother. 2004, 48, 3968-3974
4. Rodriguez, F.; Rozas, I.; Kaiser, M.; Brun, R.; Nguyen, B.; Wilson, W. D.; Nelson, G.; Dardonville, C. New bis(2-aminoimidazoline) and bisguanidine DNA minor groove binders with potent in vivo antitrypanosomal and antiplasmodial activity J. Med. Chem. 2008, 51, 909-923
5. Laugthton, C. A.; Tanious, F.; Nunn, C. M.; Boykin, D. W.; Wilson, W. D.; Neidle, S. A Crystallographic and spectroscopic study of the complex between d(CGCGAATTCGCG)2 and 2,5-bis(4-guanylphenyl)furan, an analogue of berenil. Structural origins of enhanced DNA-binding affinity Biochemistry 1996, 35, 5655-5661
6. Boykin, D. W.; Kumar, A.; Xiao, G.; Wilson, W. D.; Bender, B. C.; McCurdy, D. R.; Hall, J. E.; Tidwell, R. R. 2,5-Bis[4-(N -alkylamidino)phenyl] furans as anti-Pneumocystis carinii agents J. Med. Chem. 1998, 41, 124-129
7. Boykin, D. W.; Kumar, A.; Spcychala, J.; Zhou, M.; Lombardy, R. J.; Wilson, W. D.; Dykstra, C. C.; Jones, S. K.; Hall, J. E. Dicationic diarylfurans as anti-Pneumocystis carinii agents J. Med. Chem. 1995, 38, 912-916
8. Glass, S. L.; Nguyen, B.; Goodwin, K. D.; Dardonville, C.; Wilson, W. D.; Long, E. C.; Georgiadis, M. M. Crystal structure of a trypanocidal 4,4 ′ -bis(2-imidazolinylamino) diphenylamine bound to DNA Biochemistry 2009, 48, 5943-5952
9. Tidwell, R.; Boykin, D. Minor groove binders as antimicrobial agents. Small molecule DNA and RNA binder: synthesis to nucleic acid complexes; Wiley-VCH: New York, 2003; pp 416-460.
10. Ismail, M. A.; Brun, R.; Easterbrook, J. D.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. Synthesis and antiprotozoal activity of aza-analogues of furamidine J. Med. Chem. 2003, 46, 4761-4769
11. Arafa, R. K.; Brun, R.; Wenzler, T.; Tanious, F. A.; Wilson, W. D.; Stephens, C. E.; Boykin, D. W. Synthesis, DNA affinity, and antiprotozoal activity of fused ring dicationic compounds and their prodrugs J. Med. Chem. 2005, 48, 5480-5488
12. Dardonville, C.; Barrett, M. P.; Brun, R.; Kaiser, M.; Tanious, F.; Wilson, W. D. DNA binding affinity of bisguanidine and bis(2-aminoimidazoline) derivatives with in vivo antitrypanosomal activity J. Med. Chem. 2006, 49, 3748-3752
13. Ismail, M. A.; Arafa, R. K.; Brun, R.; Wenzler, T.; Miao, Y.; Wilson, W. D.; Generaux, C.; Bridges, A.; Hall, J. E.; Boykin, D. W. Synthesis, DNA affinity, and antiprotozoal activity of linear dications: Terphenyl diamidines and analogues J. Med. Chem. 2006, 49, 5324-5332
14. Wilson, W. D.; Tanious, F. A.; Mathis, A.; Tevis, D.; Hall, J. E.; Boykin, D. W. Antiparasitic compounds that target DNA Biochimie 2008, 90, 999-1014
15. Arafa, R. K.; Wenzler, T.; Brun, R.; Chai, Y.; Wilson, W. D. Molecular modeling study and synthesis of novel dicationic flexible triaryl guanidines and imidamides as antiprotozoal agents Eur. J. Med. Chem. 2011, 46, 5852-5860
16. Shapiro, T. A.; Englund, P. T. Selective cleavage of kinetoplast DNA minicircles promoted by antitrypanosomal drugs Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 950-954
17. Daliry, A.; Pires, M. Q.; Silva, C. F.; Pacheco, R. S.; Munde, M.; Stephens, C. E.; Kumar, A.; Ismail, M. A.; Liu, Z.; Farahat, A. A.; Akay, S.; Som, P.; Hu, Q.; Boykin, D. W.; Wilson, W. D.; De Castro, S. L.; Soeiro, M. N. C. The trypanocidal activity of amidine compounds does not correlate with their binding affinity to Trypanosoma cruzi kinetoplast DNA Antimicrob. Agents Chemother. 2011, 55, 4765-4773
18. Nzila, A. The past, present and future of antifolates in the treatment of Plasmodium falciparum infection J. Antimicrob. Chemother. 2006, 57, 1043-1054
19. Rastelli, G.; Sirawaraporn, W.; Sompornpisut, P.; Vilaivan, T.; Kamchonwongpaisan, S.; Quarrell, R.; Lowe, G.; Thebtaranonth, Y.; Yuthavong, Y. Interaction of pyrimethamine, cycloguanil, WR99210 and their analogues with Plasmodium falciparum dihydrofolate reductase: Structural basis of antifolate resistance Bioorg. Med. Chem. 2000, 8, 1117-1128
20. Anderson, A. C. Targeting DHFR in parasitic protozoa Drug Discovery Today 2005, 10, 121-128
21. Tarnchompoo, B.; Sirichaiwat, C.; Phupong, W.; Intaraudom, C.; Sirawaraporn, W.; Kamchonwongpaisan, S.; Vanichtanankul, J.; Thebtaranonth, Y.; Yuthavong, Y. Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum J. Med. Chem. 2002, 45, 1244-1252
22. Nagle, P. S.; Rodriguez, F.; Kahvedžić, A.; Quinn, S. J.; Rozas, I. Asymmetrical diaromatic guanidinium/2-aminoimidazolinium derivatives: Synthesis and DNA affinity J. Med. Chem. 2009, 52, 7113-7121
23. Nagle, P. S.; Quinn, S. J.; Kelly, J. M.; O'Donovan, D. H.; Khan, A. R.; Rodriguez, F.; Nguyen, B.; Wilson, W. D.; Rozas, I. Understanding the DNA binding of novel non-symmetrical guanidinium/2-aminoimidazolinium derivatives Org. Biomol. Chem. 2010, 8, 5558-5567
24. Guetzoyan, L.; Ramiandrasoa, F.; Dorizon, H.; Desprez, C.; Bridoux, A.; Rogier, C.; Pradines, B.; Perrée-Fauvet, M. In vitro efficiency of new acridyl derivatives against Plasmodium falciparum Bioorg. Med. Chem. 2007, 15, 3278-3289
25. Bottari, G.; Leigh, D. A.; Pérez, E. M. Chiroptical switching in a bistable molecular shuttle J. Am. Chem. Soc. 2003, 125, 13360-13361
26. Forbes, C. C.; DiVittorio, K. M.; Smith, B. D. Bolaamphiphiles promote phospholipid translocation across vesicle membranes J. Am. Chem. Soc. 2006, 128, 9211-9218
27. 2- adrenoceptor antagonists, 1: Toward new antidepressants with heteroatomic linkers J. Med. Chem. 2007, 50, 4516-4527
28. Röhrig, C. H.; Loch, C.; Guan, J. Y.; Siegal, G.; Overhand, M. Fragment-based synthesis and SAR of modified FKBP ligands: Influence of different linking on binding affinity Chem. Med. Chem. 2007, 2, 1054-1070
29. Wang, W. J.; McMurray, J. S. A selective method for the preparation of primary amides: synthesis of Fmoc-L-4-carboxamidophenylalanine and other compounds Tetrahedron Lett. 1999, 40, 2501-2504
30. Avenoza, A.; Busto, J. H.; Peregrina, J. M.; Rodríguez, F. Incorporation of Ahc into model dipeptides as an inducer of a β-turn with a distorted amide bond. Conformational analysis J. Org. Chem. 2002, 67, 4241-4249
31. Kahvedžić, A. New families of minor groove binders: Synthesis, biophysical and biochemical evaluation and their role in apoptosis. Ph.D. thesis, Trinity College Dublin, 2011.
32. Arafa, R. K.; Wenzler, T.; Brun, R.; Chai, Y.; Wilson, W. D. Molecular modeling study and synthesis of novel dicationic flexible triaryl guanidines and imidamides as antiprotozoal agents Eur. J. Med. Chem. 2011, 46, 5852-5860
33. Cory, M.; Tidwell, R. R.; Fairley, T. A. Structure and DNA binding activity of analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) J. Med. Chem. 1992, 35, 431-438
34. Tao, B.; Huang, T. L.; Zhang, Q.; Jackson, L.; Queener, S. F.; Donkor, I. O. Synthesis and anti-Pneumocystis carinii activity of conformationally restricted analogues of pentamidine Eur. J. Med. Chem. 1999, 34, 531-538
35. Wilson, W. D.; Ratmeyer, L.; Zhao, M.; Strekowski, L.; Boykin, D. The search for structure-specific nucleic acid-interactive drugs: effects of compound structure on RNA versus DNA interaction strength? Biochemistry 1993, 32, 4098-4104
36. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
37. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37, 785-789
38. Frisch, M. J.; Pople, J. A.; Binkley, J. S. Self-consistent molecular orbital methods. 25. Supplementary functions for Gaussian basis sets J. Chem. Phys. 1984, 80, 3265-3269
39. Miertuš, S.; Scrocco, E.; Tomasi, J. Electrostatic interaction of a solute with a continuum. a direct utilization of ab initio molecular potentials for the prevision of solvent effects Chem. Phys. 1981, 55, 117-129
40. Seebacher, W.; Brun, R.; Weis, R. New 4-aminobicyclo[2.2.2]octane derivatives and their activities against Plasmodium falciparum and Trypanosoma b. rhodesiense Eur. J. Pharm. Sci. 2004, 21, 225-233
41. Caspers, P.; Gentz, R.; Matile, H.; Pink, J. R.; Sinigaglia, F. The circumsporozoite protein gene from NF54, a Plasmodium-falciparum isolate used in malaria vaccine trials Mol. Biochem. Parasitol. 1989, 35, 185-190
42. Gartner, T. K.; Podleski, T. R. Evidence that a membrane-bound lectin mediates fusion of L6 myoblasts Biochem. Biophys. Res. Commun. 1975, 67, 972-978
43. Kinsella, G.; Rodriguez, F.; Watson, G.; Rozas, I. Computational approach to the basicity of a series of α1-adrenoceptor ligands in aqueous solution Bioorg. Med. Chem. 2007, 15, 2850-2855
44. Hall, H. K., Jr. Correlation of the base strengths of amines J. Am. Chem. Soc. 1957, 79, 5441-5444
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseira, G. E.; Robb, M. A.; Cheesman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomeli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Ciolowski, J.; Fox, D. J. Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford, CT, 2009.
46. Baltz, T.; Baltz, D.; Giround, C.; Crockett, J. Cultivation in a semi-defined medium of animal infective forms of Trypanosoma brucei, T. equiperdum, T. evansi, T. rhodesiense and T. gambiense EMBO J. 1985, 4, 1273-1277
47. Räz, B.; Iten, M.; Grether-Buhler, Y.; Kaminsky, R.; Brun, R. The Alamar Blue® assay to determine drug sensitivity of African trypanosomes (T.b. rhodesiense and T.b. gambiense) in vitro Acta Trop. 1997, 68, 139-147
48. 50 in studies of drug resistance of malaria parasites Acta Trop. 1993, 55, 257-261
49. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique Antimicrob. Agents Chemother. 1979, 16, 710-718
50. Matile, H.; Pink, J. R. L. Plasmodium falciparum malaria parasite cultures and their use in immunology. In Immunological Methods; Lefkovits, I.; Pernis, B., Ed.; Academic Press: San Diego, 1990.
51. Ponnudurai, T.; Leeuwenberg, A. D.; Meuwissen, J. H. Chloroquine sensitivity of isolates of Plasmodium falciparum adapted to in vitro culture Trop. Geogr. Med. 1981, 33, 50-54
52. Page, B.; Page, M.; Noel, C. A new fluorometric assay for cytotoxicity measurements in-vitro Int. J. Oncol. 1993, 3, 473-476
53. 3H]thymidine incorporation assay J. Immunol. Methods 1994, 170, 211-213