Pentamidine binds to tRNA through non-specific hydrophobic interactions and inhibits aminoacylation and translation

Nucleic Acids Research

Volumn 36, Issue 5, 2008, Pages 1654-1664

  Sun, Tao ^a   Zhang, Yi ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; HYDROXYL RADICAL; PENTAMIDINE; RIBONUCLEASE; TRANSFER RNA;

AMINOACYLATION; ANTICODON; ANTIMICROBIAL ACTIVITY; ARTICLE; BASE PAIRING; BINDING KINETICS; CONTROLLED STUDY; DRUG BINDING SITE; DRUG STRUCTURE; ENTROPY; ESCHERICHIA COLI; GEL MOBILITY SHIFT ASSAY; HOST CELL; HYDROPHOBICITY; IN VITRO STUDY; IN VIVO STUDY; INHIBITION KINETICS; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN FOOTPRINTING; RNA BINDING; RNA STRUCTURE; TRANSLATION REGULATION;

AMINOACYLATION; ANTI-INFECTIVE AGENTS; ANTICODON; BASE SEQUENCE; HYDROPHOBICITY; MOLECULAR SEQUENCE DATA; NUCLEIC ACID CONFORMATION; PENTAMIDINE; PROTEIN BIOSYNTHESIS; PROTEIN SYNTHESIS INHIBITORS; RNA, TRANSFER; RNA, TRANSFER, LEU;

SACCHAROMYCES CEREVISIAE;

EID: 41149117564     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkm1180     Document Type: Article

References (57)

1. Sands,M., Kron,M.A. and Brown,R.B. (1985) Pentamidine: A review. Rev. Infect. Dis., 7, 625-634.
2. Goa,K.L. and Campoli-Richards,D.M. (1987) Pentamidine isethionate. A review of its antiprotozoal activity, pharmacokinetic properties and therapeutic use in Pneumocystis carinii pneumonia. Drugs, 33 242 258.
3. Apted,F.I. (1980) Present status of chemotherapy and chemopropylaxis of human trypanosomiasis in the Eastern Hemisphere. Pharmacol. Therap. 11, 391-413.
4. Bryceson,A.D., Chulay,J.D., Mugambi,M., Were,J.B., Gachihi,G., Chunge,C.N., Muigai,R., Bhatt,S.M., Ho,M., Spencer,H.C. et al. (1985) Visceral leishmaniasis unresponsive to antimonial drugs. II. Response to high dosage sodium stibogluconate or prolonged treatment with pentamidine. Trans. Roy. Soc. Trop. Med. Hyg., 79, 705-714.
5. Su,T.H. and Martin,W.J.2nd. (1994) Pathogenesis and host response in Pneumocystis carinii pneumonia. Anna. Rev. Med., 45, 261-272.
6. Bray,P.G., Barrett,M.P., Ward,S.A. and de Koning,H.P. (2003) Pentamidine uptake and resistance in pathogenic protozoa: Past, present and future. Trends Parasitol., 19, 232-239.
7. Werbovetz,K. (2006) Diamidines as antitrypanosomal, antileishmanial and antimalarial agents. Curr. Opin. Investig. Drugs, 7, 147-157.
8. Fairlamb,A.H. (2003) Chemotherapy of human African trypanosomiasis: current and future prospects. Trends Parasitol., 19, 488-494.
9. Briceland,L.L. and Bailie,G.R. (1991) Pentamidine-associated nephrotoxicity and hyperkalemia in patients with AIDS. Dicp, 25 1171-1174.
10. Lachaal,M. and Venuto,R.C. (1989) Nephrotoxicity and hyperkalemia in patients with acquired immunodeficiency syndrome treated with pentamidine. Am. J. Med., 87, 260-263.
11. Dykstra,C.C. and Tidwell,R.R. (1991) Inhibition of topoisomerases from Pneumocystis carinii by aromatic dicationic molecules. J. Protozool. 38, 78S-81S.
12. Grady,R.W., Blobstein,S.H., Meshnick,S.R., Ulrich,P.C., Cerami,A., Amirmoazzami,J. and Hodnett,E.M. (1984) The in vitro trypanocidal activity of N-substituted p-benzoquinone imines: Assessment of biochemical structure-activity relationshtps using the Hansch approach. J. Cell. Biochem., 25, 15-29.
13. Shapiro,T.A. (1993) Inhibition of topoisomerases in African trypanosomes. Acta Trop., 54, 251-260.
14. Shimizu,Y.K., Weiner,A.J., Rosenblatt,J., Wong,D.C., Shapiro,M., Popkin,T., Houghton,M., Alter,H.J. and Purcell,R.H. (1990) Early events in hepatitis C virus infection of chimpanzees. Proc. Nall Acad. Sci. USA, 87, 6441-6444.
15. Shapiro,T.A. and Englund,P.T. (1990) Selective cleavage of kinetoplast DNA minicircles promoted by antitrypanosomal drugs. Proc. Natl Acad. Sci. USA, 87, 950-954.
16. Bornstein,R.S. and Yarbro,J.W. (1970) An evaluation of the mechanism of action of pentamidine isethionate. J. Surg. Oncol., 2, 393-398.
17. Makulu,D.R. and Waalkes,T.P. (1975) Interaction between aromatic diamidines and nucleic acids: Possible implications for chemotherapy. J. Natl Cancer Inst., 54, 305-309.
18. Reddy,B.S., Sondhi,S.M. and Lown,J.W. (1999) Synthetic DNA minor groove-binding drugs. Pharmacol. Therap., 84, 1-111.
19. Baraldi,P.G., Bovero,A., Fruttarolo,F., Preti,D., Tabrizi,M.A., Pavani,M.G. and Romagnoli,R. (2004) DNA minor groove binders as potential antitumor and antimicrobial agents. Med. Res. Rev., 24, 475-528.
20. Edwards,K.J., Jenkins,T.C. and Neidle,S. (1992) Crystal structure of a pentamidine-oligonucleotide complex: Implications for DNA-binding properties. Biochemistry, 31, 7104-7109.
21. Jenkins,T.C. and Lane,A.N. (1997) AT selectivity and DNA minor groove binding: Modelling, NMR and structural studies of the interactions of propamidine and pentamidine with d(CGCGAATTCGCG)2. Biochim. Biophys Acta, 1350, 189-204.
22. Nunn,C.M., Jenkins,T.C. and Neidle, S., (1993) Crystal structure of d(CGCGAATTCGCG) complexed with propamidine, a shortchain homologue of the drug pentamidine. Biochemistry, 32, 13838-13843.
23. Tidwell,R.R., Jones,S.K., Geratz,J.D., Ohemeng,K.A., Cory,M. and Hall,J.E. (1990) Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia. J. Med. Chem., 33, 1252-1257.
24. Pathak,M.K., Dhawan,D., Lindner,D.J., Borden,E.C., Farver,C. and Yi,T. (2002) Pentamidine is an inhibitor of PRL phosphatases with anticancer activity. Mol. Cancer Therap., 1, 1255-1264.
25. Cuevas,I.C., Rohloff,P., Sanchez,D.O. and Docampo,R. (2005) Characterization of farnesylated protein tyrosine phosphatase TcPRL-1 from Trypanosoma cruzi. Eukaryot. Cell, 4, 1550-1561.
26. Nguewa,P.A., Fuertes,M.A., Cepeda, V., Iborra,S., Carrion,J., Valladares,B., Alonso,C. and Perez,J.M. (2005) Pentamidine is an antiparasitic and apoptotic drug that selectively modifies ubiquitin. Chem. Biodivers., 2, 1387-1400.
27. Liu,Y. and Leibowitz,M.J. (1993) Variation and in vitro splicing of group I introns in rRNA genes of Pneumocystis carinii. Nucleic Acids Res., 21, 2415-2421.
28. Liu,Y., Tidwell,R.R. and Leibowitz,M.J. (1994) Inhibition of in vitro splicing of a group I intron of Pneumocystis carinii. J. Eukaryot. Microbiol., 41, 31-38.
29. Miletti,K.E. and Leibowitz,M.J. (2000) Pentamidine inhibition of group I intron splicing in Candida albicans correlates with growth inhibition. Antimicrob. Agents Chemother., 44, 958-966.
30. Zhang,Y., Bell,A., Perlman,P.S. and Leibowitz,M.J. (2000) Pentamidine inhibits mitochondrial intron splicing and translation in Saccharomyces cerevisiae. RNA, 6, 937-951.
31. Zhang,Y., Li,Z., Pilch,D.S. and Leibowitz,M.J. (2002) Pentamidine inhibits catalytic activity of group I intron Ca.LSU by altering RNA folding. Nucleic Acids Res., 30, 2961-2971.
32. Sutcliffe,J.A. (2005) Improving on nature: Antibiotics that target the ribosome. Curr. Opin. Microbiol., 8, 534-542.
33. Carter,A.P., Clemons,W.M., Brodersen,D.E., Morgan-Warren,R.J., Wimberly,B.T. and Ramakrishnan,V. (2000) Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics. Nature, 407, 340-348.
34. Yonath,A. and Bashan,A. (2004) Ribosomal crystallography: Initiation, peptide bond formation, and amino acid polymerization are hampered by antibiotics. Annu. Rev. Microbiol., 58, 233-251.
35. Walter,F., Vicens,Q. and Westhof,E. (1999) Aminoglycoside-RNA interactions. Curr. Opin. Chem. Biol., 3, 694-704.
36. Fourmy,D., Yoshizawa,S. and Puglisi,J.D. (1998) Paromomycin binding induces a local conformational change in the A-site of 16 S rRNA. J. Mol. Biol., 277, 333-345.
37. Fourmy,D., Recht,M.I. and Puglisi,J.D. (1998) Binding of neomycin-class aminoglycoside antibiotics to the A-site of 16 S rRNA. J. Mol. Biol. 277, 347-362.
38. Fourmy,D., Recht,M.I., Blanchard,S.C. and Puglisi,J.D. (1996) Structure of the A site of Escherichia coli 16S ribosomal RNA complexed with an aminoglycoside antibiotic. Science, 274, 1367-1371.
39. Walter,F., Putz,J., Giege,R. and Westhof,E. (2002) Binding of tobramycin leads to conformational changes in yeast tRNA(Asp) and inhibition of aminoacylation. EMBO J, 21, 760-768.
40. Mikkelsen,N.E., Johansson,K., Virtanen,A. and Kirsebom,L.A. (2001) Aminoglycoside binding displaces a divalent metal ion in a tRNA-neomycin B complex. Nat. Struct. Biol., 8, 510-514.
41. Kirillov,S., Vitali,L.A., Goldstein,B.P., Monti,F., Semenkov,Y., Makhno,V., Ripa,S., Pon,C.L. and Gualerzi,C.O. (1997) Purpuromycin: An antibiotic inhibiting tRNA aminoacylation. RNA, 3, 905 913.
42. Rambelli,F., Brigotti,M., Zamboni,M., Denaro,M., Montanaro,L. and Sperti,S. (1989) Effect of the antibiotic purpuromycin on cell-free protein-synthesizing systems. Biochem. J., 259, 307-310.
43. Landini,P., Corti,E., Goldstein,B.P. and Denaro,M. (1992) Mechanism of action of purpuromycin. Biochem. J., 284(Pt 1), 47-52.
44. Leu. Sci. China (Ser. C), 41, 225-231.
45. Xiao,M., Leibowitz,M.J. and Zhang,Y. (2003) Concerted folding of a Candida ribozyme into the catalytically active structure posterior to a rapid RNA compaction. Nucleic Acids Res., 31, 3901-3908.
46. Du,X., and Wang,E.D. (2003) Tertiary structure base pairs between D- and TpsiC-loops of Escherichia coli tRNA(Leu) play important roles in both aminoacylation and editing. Nucleic Acids Res., 31, 2865-2872.
47. Chen,J.F., Guo,N.N., Li,T., Wang,E.D. and Wang,Y.L. (2000) CP1 domain in Escherichia coli leucyl-tRNA synthetase is crucial for its editing function. Biochemistry, 39, 6726-6731.
48. Perez-Salas,U.A., Rangan,P., Krueger,S., Briber,R.M., Thirumalai,D. and Woodson,S.A. (2004) Compaction of a bacterial group I ribozyme coincides with the assembly of core helices. Biochemistry, 43, 1746-1753.
49. Xiao,M., Li,T., Yuan,X., Shang,Y., Wang,F., Chen,S. and Zhang,Y. (2005) A peripheral element assembles the compact core structure essential for group I intron self-splicing. Nucleic Acids Res., 33, 4602-4611.
50. Fox,K.R., Sansom,C.E. and Stevens,M.F. (1990) Footprinting studies on the sequence-selective binding of pentamidine to DNA. FEBS Lett., 266, 150-154.
51. Doyle,M.L. (1997) Characterization of binding interactions by isothermal titration calorimetry. Curr. Opin. Biotechnol., 8, 31-35.
52. Sprinzl,M., Horn,C., Brown,M., Ioudovitch,A. and Steinberg,S. (1998) Compilation of tRNA sequences and sequences of tRNA genes. Nucleic Acids Res., 26, 148-153.
53. Tukalo,M., Yaremchuk,A., Fukunaga,R., Yokoyama,S. and Cusack,S. (2005) The crystal structure of leucyl-RNA synthetase complexed with tRNALeu in the post-transfer-editing conformation. Nat. Struct. Mol. Biol., 12, 923-930.
54. Carter,N.S., Berger,B.J. and., Fairlamb,A.H. (1995) Uptake of diamidine drugs by the P2 nucleoside transporter in melarsen-sensitive and -resistant Trypanosoma brucei brucei. J. Biol. Chem., 270, 28153-28157.
55. Croft,S.L. and Brazil,R.P. (1982) Effect of pentamidine isethionate on the ultrastructure and morphology of Leishmania mexicana amazonensis in vitro. Ann. Trop. Med. Parasitol., 76, 37-43.
56. Hentzer,B. and Kobayasi,T. (1977) The ultrastructural changes of Leishmania tropica after treatment with pentamidine. Ann. Trop. Med. Parasitol., 71, 157-166.
57. Basselin,M., Denise,H., Coombs,G.H. and Barrett,M.P. (2002) Resistance to pentamidine in Leishmania mexicana involves exclusion of the drug from the mitochondrion. Antimicrob. Agents Chemother., 46, 3731-3738.