Effects of N7-methylation, N7-platination, and C8-hydroxylation of guanine on H-bond formation with cytosine: Platinum coordination strengthens the Watson-Crick pair

Journal of Biological Inorganic Chemistry

Volumn 5, Issue 3, 2000, Pages 287-299

  Sigel, Roland K O ^a   Freisinger, Eva ^a   Lippert, Bernhard ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Guanine cytosine; Hydrogen bonding; Platinum complex; Stability; Watson Crick

Indexed keywords

CYTOSINE; CYTOSINE DERIVATIVE; GUANINE DERIVATIVE; PLATINUM;

ACIDIFICATION; ARTICLE; BASE PAIRING; CHEMICAL MODIFICATION; COMPLEX FORMATION; HYDROGEN BOND; HYDROXYLATION; METHYLATION; MOLECULAR STABILITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0034126663     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/PL00010657     Document Type: Article

References (69)

1. Blackburn GM, Gait MJ (1990) Nucleic acids in chemistry and biology. IRL Press, Oxford
2. Reedijk J (1996) J Chem Soc Chem Commun 801-806
3. Takahara PM, Frederick A, Lippard SJ (1996) J Am Chem Soc 118:12309-12321
4. Kozelka J, Fouchet M-H, Chottard JC (1992) Eur J Biochem 205:895-906
5. Huang H, Zhu L, Reid BR, Drobny GP, Hopkins PB (1995) Science 270:1842-1845
6. Ano SO, Intini FP, Natile G, Marzilli LG (1998) J Am Chem Soc 120:12017-12022
7. Oivanen M, Lönnberg H, Zhou X, Chattopadhyaya J (1987) Tetrahedron 43:1133-1140
8. McCloskey JA, Nishimura S (1977) Ace Chem Res 10:403-410
9. Stryer L (1988) Biochemistry. Freeman, New York, p 720
10. Sussman JL, Holbrook SR, Wade Warrant R, Church GM, Kim S-H (1978) J Mol Biol 123:607-630
11. Pfleiderer W (1961) Liebigs Ann Chem 647:167-173
12. Yamagata Y, Fukumoto S, Hamada K, Fujiwara T, Tomita K (1983) Nucleic Acids Res 11:6475-6486
13. Metzger S, Lippert B (1996) Angew Chem Int Ed Engl 35:1228-1229
14. Lawley PD, Brookes P (1961) Nature 192:1081-1082
15. Newbold RF, Warren W, Medclaf ASC, Amos J (1980) Nature 283:596-599
16. Song B, Zhao J, Griesser R, Meiser C, Sigel H, Lippert B (1999) Chem Eur J 5:2374-2387
17. Faggiani R, Lock CJL, Lippert B (1980) J Am Chem Soc 102:5418-5419
18. Faggiani R, Lippert B, Lock CJL, Speranzini RA (1982) Inorg Chem 21:3216-3225
19. Lippert B (1981) J Am Chem Soc 103:5691-5697
20. Schröder G, Lippert B, Sabat M, Lock CJL, Faggiani R, Song B, Sigel H (1995) J Chem Soc Dalton Trans 3767-3775
21. Villani G, Tanguy Le Gac N, Hoffmann J-S (1999) In: Lippert B (ed) Cisplatin: chemistry and biochemistry of a leading anticancer drug. VHCA/Wiley-VCH, Zürich/Weinheim, pp 135-157
22. Arpalahti J, Jokilammi A, Hakala H, Lönnberg H (1991) J Phys Org Chem 4:301-309
23. Choi H-K, Huang SK-S, Bau R (1988) Biochem Biophys Res Commun 156:1125-1129
24. Dieter-Wurm I, Sabat M, Lippert B (1992) J Am Chem Soc 114:357-359
25. Sigel RKO, Lippert B (1999) J Chem Soc Chem Commun 2167-2168
26. Sponer J, Burda JV, Sabat M, Leszczynski J, Hobza P (1998) J Phys Chem A 102:5951-5957
27. Burda JV, Sponer J, Leszczynski J, Hobza P (1997) J Phys Chem B 101:9670-9677
28. Anwander EHS, Probst MM, Rode BM (1990) Biopolymers 29:757-769
29. Lippert B (1997) J Chem Soc Dalton Trans 3971-3976
30. Steenken S (1989) Chem Rev 89:503-520
31. Lindahl T (1993) Nature 362:709-715
32. Kauffman GB, Cowan DO (1963) Inorg Synth 7:239-245
33. Arpalahti J, Schöllhorn H, Thewalt U, Lippert B (1988) Inorg Chim Acta 153:51-55
34. Chow YM, Britton B (1975) Acta Crystallogr B31:1934-1937
35. Krüger G (1894) Hoppe Seyler's Z Physiol Chem 18:434-458
36. Kistenmacher TJ, Rossi M, Caradonna JP, Marzilli LG (1979) Adv Mol Relax Interact Processes 15:119-133
37. Frommer G, Schöllhorn H, Thewalt U, Lippert B (1990) Inorg Chem 29:1417-1422
38. Sigel RKO, Sabat M, Freisinger E, Mower A, Lippert B (1999) Inorg Chem 38:1481-1490
39. Sigel RKO, Thompson SM, Freisinger E, Lippert B (1999) J Chem Soc Chem Commun 19-20
40. Lumry R, Smitz EL, Glantz RR (1951) J Am Chem Soc 73:4335-4340
41. Glasoe PK, Long FA (1960) J Phys Chem 64:188-190
42. Tribolet R, Sigel H (1987) Eur J Biochem 163:353-363
43. Martin RB (1963) Science 139:1198-1203
44. Otwinowsky Z, Minor W (1996) Methods Enzymol 276:307-326
45. Sheldrick GM (1990) Acta Crystallogr A46:467-473
46. Sheldrick GM (1990) SHELXTL-PLUS (VMS). Siemens Analytical X-Ray Instruments, Madison, Wis
47. Sheldrick GM (1993) SHELXL-93; program for crystal structure refinement. University of Göttingen, Germany
48. Sheldrick GM (1997) SHELXL97; program for the refinement of crystal structures. University of Göttingen, Germany
49. Mitchell PR, Sigel H (1978) Eur J Biochem 88:149-154
50. Scheller HK, Hofstetter F, Mitchell PR, Prijs B, Sigel H (1981) J Am Chem Soc 103:247-260
51. Sigel H, Corfù NA (1996) Eur J Biochem 240:508-517
52. Mitchell PR (1979) J Chem Soc Dalton Trans 771-776
53. Strazewski P (1995) Helv Chim Acta 78:1112-1143
54. Sigel RKO, Freisinger E, Lippert B (1998) J Chem Soc Chem Commun 219-220
55. Newmark R, Cantor CR (1968) J Am Chem Soc 90:5010-5017
56. Peterson SB, Led JJ (1981) J Am Chem Soc 103:5308-5313
57. Schröder G, Sabat M, Baxter I, Kozelka J, Lippert B (1997) Inorg Chem 36:490-493
58. Sigel RKO, Freisinger E, Metzger S, Lippert B (1998) J Am Chem Soc 120:12000-12007
59. Schreiber A, Lüth MS, Erxleben A, Fusch EC, Lippert B (1996) J Am Chem Soc 118:4124-4132
60. Harris MG, Stewart R (1977) Can J Chem 55:3807-3814
61. Schöllhorn H, Raudaschl-Sieber G, Müller G, Thewalt U, Lippert B (1985) J Am Chem Soc 107:5932-5937
62. Lippert B, Raudaschl G, Lock CJL, Pilon P (1984) Inorg Chim Acta 93:43-50
63. Sherman SE, Gibson D, Wang AH-J, Lippard SJ (1985) Science 230:412-417
64. Lippert B (ed) (1999) Cisplatin: chemistry and biochemistry of a leading anticancer drug. VHCA/Wiley-VCH, Zürich/ Weinheim
65. Huang H, Zhu L, Reid BR, Drobny GP, Hopkins PB (1995) Science 270:1842-1845
66. Paquet F, Pérez C, Leng M, Lancelot G, Malinge J-M (1996) J Biomol Struct Dyn 14:67-77
67. Herman F, Kozelka J, Stoven V, Guittet E, Girault J-P, Huynh-Dinh T, Igolen J, Lallemand J-Y, Chottard J-C (1990) Eur J Biochem 194:119-133
68. Fouchet M-H, Guittet E, Cognet JAH, Kozelka J, Gauthier C, Le Bret M, Zimmermann K, Chottard J-C (1997) JBIC 2:83-92
69. Zaludová R, Kleinwächter V, Brabec V (1996) Biophys Chem 60:135-142