Energetics, conformation, and recognition of DNA duplexes containing a major adduct of an anticancer azolato-bridged dinuclear PtII complex

Biochimica et Biophysica Acta - General Subjects

Volumn 1820, Issue 10, 2012, Pages 1502-1511

  Mlcouskova, Jarmila ^a,b   Malina, Jaroslav ^b   Novohradsky, Vojtech ^a,b   Kasparkova, Jana ^a,b   Komeda, Seiji ^c   Brabec, Viktor ^b  

^a PALACKÝ UNIVERSITY   (Czech Republic)

^b INSTITUTE OF BIOPHYSICS   (Czech Republic)

^c SUZUKA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

Author keywords

Anticancer; Damaged DNA binding protein; Dinuclear platinum; DNA conformation; DNA repair; Thermodynamic stability

Indexed keywords

ANTINEOPLASTIC METAL COMPLEX; AZOLATO BRIDGED DINUCLEAR PLATINUM COMPLEX; CISPLATIN; DNA POLYMERASE; DOUBLE STRANDED DNA; HIGH MOBILITY GROUP PROTEIN; PLATINUM COMPLEX; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA ADDUCT; DNA CONFORMATION; DNA CROSS LINKING; DNA DRUG COMPLEX; DNA PROBE; DRUG BINDING SITE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENERGY TRANSFER; MOLECULAR RECOGNITION; MOLECULAR STABILITY; PRIORITY JOURNAL; THERMODYNAMICS;

ANIMALS; ANTINEOPLASTIC AGENTS; BASE SEQUENCE; CALORIMETRY, DIFFERENTIAL SCANNING; CISPLATIN; DNA ADDUCTS; ENERGY METABOLISM; HUMANS; MODELS, BIOLOGICAL; MOLECULAR CONFORMATION; MOLECULAR PROBES; NUCLEIC ACID CONFORMATION; NUCLEIC ACID DENATURATION; ORGANOPLATINUM COMPOUNDS; PLATINUM; POLYMERIZATION; RATS;

EID: 84863480984     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2012.05.014     Document Type: Article

References (67)

1. J.B. Mangrum, and N.P. Farrell Excursions in polynuclear platinum DNA binding Chem. Commun. 46 2010 6640 6650
2. N. Farrell Polynuclear platinum drugs A. Sigel, H. Sigel, Metal Ions in Biological Systems vol. 42 2004 Marcel Dekker, Inc. New York, Basel 251 296
3. K.S. Lovejoy, and S.J. Lippard Non-traditional platinum compounds for improved accumulation, oral bioavailability, and tumor targeting Dalton Trans. 2009 10651 10659
4. S. Komeda, M. Lutz, A. Spek, M. Chikuma, and J. Reedijk New antitumor-active azole-bridged dinuclear platinum(II) complexes: synthesis, characterization, crystal structures, and cytotoxic studies Inorg. Chem. 39 2000 4230 4236
5. S. Teletchéa, S. Komeda, J.-M. Teuben, M.A. Elizondo-Riojas, J. Reedijk, and J. Kozelka A pyrazolato-bridged dinuclear platinum(II) complex induces only minor distortions upon DNA-binding Chem. Eur. J. 12 2006 3741 3753
6. E.R. Jamieson, and S.J. Lippard Structure, recognition, and processing of cisplatin-DNA adducts Chem. Rev. 99 1999 2467 2498
7. V. Brabec DNA modifications by antitumor platinum and ruthenium compounds: their recognition and repair Prog. Nucleic Acid Res. Mol. Biol. 71 2002 1 68
8. V. Brabec, and J. Kasparkova Modifications of DNA by platinum complexes: relation to resistance of tumors to platinum antitumor drugs Drug Resist. Updat. 8 2005 131 146
9. 3(9EtG) 9-ethylguanine) as a model compound for the 1,2-intrastrand GG cross-link J. Chem. Soc. Dalton Trans. 1999 2959 2962
10. S. Komeda, M. Lutz, A.L. Spek, Y. Yamanaka, T. Sato, M. Chikuma, and J. Reedijk A novel isomerization on interaction of antitumor-active azole-bridged dinuclear platinum(II) complexes with 9-ethylguanine. Platinum(II) atom migration from N2 to N3 on 1,2,3-triazole J. Am. Chem. Soc. 124 2002 4738 4746
11. II complex J. Inorg. Chem. 114 2012 15 23
12. D. Wang, and S.J. Lippard Cellular processing of platinum anticancer drugs Nat. Rev. Drug Discov. 4 2005 307 320
13. L. Kelland The resurgence of platinum-based cancer chemotherapy Nat. Rev. Cancer 7 2007 573 584
14. V. Brabec, and J. Kasparkova Role of DNA repair in antitumor effects of platinum drugs N. Hadjiliadis, E. Sletten, Metal Complex-DNA Interactions 2009 Wiley Chichester, UK 175 208
15. S. Komeda, S. Bombard, S. Perrier, J. Reedijk, and J.F. Kozelka Kinetic study of azole-bridged dinuclear platinum(II) complexes reacting with a hairpin-stabilized double-stranded oligonucleotide J. Inorg. Biochem. 96 2003 357 366
16. V. Brabec, and E. Palecek Interaction of nucleic acids with electrically charged surfaces. II. Conformational changes in double-helical polynucleotides Biophys. Chem. 4 1976 76 92
17. V. Brabec, and E. Palecek The influence of salts and pH on polarographic currents produced by denatured DNA Biophysik 6 1970 290 300
18. J.H. Murphy, and T.L. Trapane Concentration and extinction coefficient determination for oligonucleotides and analogs using a general phosphate analysis Anal. Biochem. 240 1996 273 282
19. N. Poklar, D.S. Pilch, S.J. Lippard, E.A. Redding, S.U. Dunham, and K.J. Breslauer Influence of cisplatin intrastrand crosslinking on the conformation, thermal stability, and energetics of a 20-mer DNA duplex Proc. Natl. Acad. Sci. U. S. A. 93 1996 7606 7611
20. C.J. Jones, and R.D. Wood Preferential binding of the xeroderma pigmentosum group A complementing protein to damaged DNA Biochemistry 32 1993 12096 12104
21. M. Missura, T. Buterin, R. Hindges, U. Hubscher, J. Kasparkova, V. Brabec, and H. Naegeli Double-check probing of DNA bending and unwinding by XPA-RPA: an architectural function in DNA repair EMBO J. 20 2001 3554 3564
22. J. Kasparkova, O. Delalande, M. Stros, M.A. Elizondo-Riojas, M. Vojtiskova, J. Kozelka, and V. Brabec Recognition of DNA interstrand cross-link of antitumor cisplatin by HMGB1 protein Biochemistry 42 2003 1234 1244
23. M. Stros DNA bending by the chromosomal protein HMG1 and its high mobility group box domains. Effect of flanking sequences J. Biol. Chem. 273 1998 10355 10361
24. M. Stros Two mutations of basic residues within the N-terminus of HMG-1 B domain with different effects on DNA supercoiling and binding to bent DNA Biochemistry 40 2001 4769 4779
25. J. Kasparkova, K.J. Mellish, Y. Qu, V. Brabec, and N. Farrell Site-specific d(GpG) intrastrand cross-links formed by dinuclear platinum complexes. Bending and NMR studies Biochemistry 35 1996 16705 16713
26. V. Brabec, M. Sip, and M. Leng DNA conformational distortion produced by site-specific interstrand cross-link of trans-diamminedichloroplatinum(II) Biochemistry 32 1993 11676 11681
27. S.A. Leharne, and B.Z. Chowdhry Thermodynamic background to differential scanning calorimetry J.E. Ladbury, B.Z. Chowdhry, Biocalorimetry: Applications of Calorimetry in the Biological Sciences 1998 J. Wiley & Sons Chichester, UK 157 182
28. C. Hofr, N. Farrell, and V. Brabec Thermodynamic properties of duplex DNA containing a site-specific d(GpG) intrastrand crosslink formed by an antitumor dinuclear platinum complex Nucleic Acids Res. 29 2001 2034 2040
29. C. Hofr, and V. Brabec Thermal and thermodynamic properties of duplex DNA containing site-specific interstrand cross-link of antitumor cisplatin or its clinically ineffective trans isomer J. Biol. Chem. 276 2001 9655 9661
30. S.F. Bellon, J.H. Coleman, and S.J. Lippard DNA unwinding produced by site-specific intrastrand cross-links of the antitumor drug cis- diamminedichloroplatinum(II) Biochemistry 30 1991 8026 8035
31. J. Kasparkova, N. Farrell, and V. Brabec Sequence specificity, conformation, and recognition by HMG1 protein of major DNA interstrand cross-links of antitumor dinuclear platinum complexes J. Biol. Chem. 275 2000 15789 15798
32. A. Rodger Linear dichroism Methods Enzymol. 226 1993 232 258
33. A. Rodger, and B. Norden Circular Dichroism and Linear Dichroism 1997 Oxford University Press Oxford, New York, Tokyo
34. J. Malina, J. Kasparkova, G. Natile, and V. Brabec Recognition of major DNA adducts of enantiomeric cisplatin analogs by HMG box proteins and nucleotide excision repair of these adducts Chem. Biol. 9 2002 629 638
35. J. Zehnulova, J. Kasparkova, N. Farrell, and V. Brabec Conformation, recognition by high mobility group domain proteins, and nucleotide excision repair of DNA intrastrand cross-links of novel antitumor trinuclear platinum complex BBR3464 J. Biol. Chem. 276 2001 22191 22199
36. J. Kasparkova, J. Zehnulova, N. Farrell, and V. Brabec DNA interstrand cross-links of the novel antitumor trinuclear platinum complex BBR3464. Conformation, recognition by high mobility group domain proteins, and nucleotide excision repair J. Biol. Chem. 277 2002 48076 48086
37. P.E. Nielsen Chemical and photochemical probing of DNA complexes J. Mol. Recognit. 3 1990 1 24
38. J. Malina, C. Hofr, L. Maresca, G. Natile, and V. Brabec DNA interactions of antitumor cisplatin analogs containing enantiomeric amine ligands Biophys. J. 78 2000 2008 2021
39. D.S. Pilch, S.U. Dunham, E.R. Jamieson, S.J. Lippard, and K.J. Breslauer DNA sequence context modulates the impact of a cisplatin 1,2-d(GpG) intrastrand cross-link and the conformational and thermodynamic properties of duplex DNA J. Mol. Biol. 296 2000 803 812
40. C. Hofr, and V. Brabec Thermal stability and energetics of 15-mer DNA duplex interstrand cross-linked by trans-diamminedichloroplatinum(II) Biopolymers 77 2005 222 229
41. J. Malina, O. Novakova, M. Vojtiskova, G. Natile, and V. Brabec Conformation of DNA GG intrastrand cross-link of antitumor oxaliplatin and its enantiomeric analog Biophys. J. 93 2007 3950 3962
42. V. Bursova, J. Kasparkova, C. Hofr, and V. Brabec Effects of monofunctional adducts of platinum(II) complexes on thermodynamic stability and energetics of DNA duplexes Biophys. J. 88 2005 1207 1214
43. D.S. Pilch, G.E. Plum, and K.J. Breslauer The thermodynamics of DNA structures that contain lesions or guanine tetrads Curr. Opin. Struct. Biol. 5 1995 334 342
44. G.E. Plum, C.A. Gelfand, and K.J. Breslauer Physicochemical approaches to structural elucidation. Effects of 3, N4-ethenodeoxycytidine on duplex stability and energetics B. Singer, H. Bartsch, Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis, Vol. Publications No. 150 1999 International Agency for Research on Cancer Lyon 169 177
45. L.A. Marky, and K.J. Breslauer Calculating thermodynamic data for transitions of any molecularity from equilibrium melting curves Biopolymers 26 1987 1601 1620
46. K.M. Comess, J.N. Burstyn, J.M. Essigmann, and S.J. Lippard Replication inhibition and translesion synthesis on templates containing site-specifically placed cis-diamminedichloroplatinum(II) DNA adducts Biochemistry 31 1992 3975 3990
47. Z. Suo, and K. Johnson DNA secondary structure effects on DNA synthesis catalyzed by HIV-1 reverse transcriptase J. Biol. Chem. 273 1998 27259 27267
48. A. Vaisman, M.W. Warren, and S.G. Chaney The effect of DNA structure on the catalytic efficiency and fidelity of human DNA polymerase beta on templates with platinum-DNA adducts J. Biol. Chem. 276 2001 18999 19005
49. E. Bassett, A. Vaisman, J.M. Havener, C. Masutani, F. Hanaoka, and S.G. Chaney Efficiency of extension of mismatched primer termini across from cisplatin and oxaliplatin adducts by human DNA polymerases beta and eta in vitro Biochemistry 42 2003 14197 14206
50. J. Kasparkova, O. Novakova, V. Marini, Y. Najajreh, D. Gibson, J.-M. Perez, and V. Brabec Activation of trans geometry in bifunctional mononuclear platinum complexes by a piperidine ligand: mechanistic studies on antitumor action J. Biol. Chem. 278 2003 47516 47525
51. B. Moriarity, O. Novakova, N. Farrell, V. Brabec, and J. Kasparkova 1,2-GG intrastrand cross-link of antitumor dinuclear bifunctional platinum compound with spermidine linker inhibits DNA polymerization more effectively than the cross-link of conventional cisplatin Arch. Biochem. Biophys. 459 2007 264 272
52. A. Alt, K. Lammens, C. Chiocchini, A. Lammens, J.C. Pieck, D. Kuch, K.P. Hopfner, and T. Carell Bypass of DNA lesions generated during anticancer treatment with cisplatin by DNA polymerase Science 318 2007 967 970
53. K. Stehlikova, H. Kostrhunova, J. Kasparkova, and V. Brabec DNA bending and unwinding due to the major 1,2-GG intrastrand cross-link formed by antitumor cis-diamminedichloroplatinum(II) are flanking-base independent Nucleic Acids Res. 30 2002 2894 2898
54. J.A. Rice, D.M. Crothers, A.L. Pinto, and S.J. Lippard The major adduct of the antitumor drug cis-diamminedichloroplatinum(II) with DNA bends the duplex by ~ 40° toward the major groove Proc. Natl. Acad. Sci. U. S. A. 85 1988 4158 4161
55. + Biophys. Chem. 35 1990 179 188
56. H.S. Koo, H.M. Wu, and D.M. Crothers DNA bending at adenine-thymine tracts Nature 320 1986 501 506
57. M. Kartalou, and J.M. Essigmann Recognition of cisplatin adducts by cellular proteins Mutat. Res. 478 2001 1 21
58. Y. Jung, and S.J. Lippard Direct cellular responses to platinum-induced DNA damage Chem. Rev. 107 2007 1387 1407
59. J. Kasparkova, O. Novakova, O. Vrana, F. Intini, G. Natile, and V. Brabec Molecular aspects of antitumor effects of a new platinum(IV) drug Mol. Pharmacol. 70 2006 1708 1719
60. V. Brabec, K. Stehlikova, J. Malina, M. Vojtiskova, and J. Kasparkova Thermodynamic properties of damaged DNA and its recognition by xeroderma pigmentosum group A protein and replication protein A Arch. Biochem. Biophys. 446 2006 1 10
61. N.E. Geacintov, S. Broyde, T. Buterin, H. Naegeli, M. Wu, S.X. Yan, and D.J. Patel Thermodynamic and structural factors in the removal of bulky DNA adducts by the nucleotide excision repair machinery Biopolymers 65 2002 202 210
62. J. SantaLucia Jr. A unified view of polymer, dumbbell, and oligonucleotide DNA nearest-neighbor thermodynamics Proc. Natl. Acad. Sci. U. S. A. 95 1998 1460 1465
63. A. Rodger, R. Marington, M.A. Geeves, M. Hicks, L. de Alwis, D.J. Halsall, and T.R. Dafforn Looking at long molecules in solution: what happens when they are subjected to Couette flow? Phys. Chem. Chem. Phys. 8 2006 3161 3171
64. D. Weaver, E. Crawford, K. Warner, F. Elkhairi, S. Khuder, and J. Willey ABCC5, ERCC2, XPA and XRCC1 transcript abundance levels correlate with cisplatin chemoresistance in non-small cell lung cancer cell lines Mol. Cancer 4 2005 18 25
65. T. Fujii, S. Toyooka, K. Ichimura, Y. Fujiwara, K. Hotta, J. Soh, H. Suehisa, N. Kobayashi, M. Aoe, T. Yoshino, K. Kiura, and H. Date ERCC1 protein expression predicts the response of cisplatin-based neoadjuvant chemotherapy in non-small-cell lung cancer Lung Cancer 59 2008 377 384
66. G.E. Plum, and K.J. Breslauer DNA lesions: a thermodynamic perspective Ann. N. Y. Acad. Sci. 726 1994 45 56
67. II complexes J. Biol. Inorg. Chem. 17 2012 187 196