Comparison of the Extent of Macrochelate Formation in Complexes of Divalent Metal Ions with Guanosine (GMP2-), Inosine (IMP2-), and Adenosine 5ʹ-Monophosphate (AMP2-). The Crucial Role of N-7 Basicity in Metal Ion-Nucleic Base Recognition

Journal of the American Chemical Society

Volumn 116, Issue 7, 1994, Pages 2958-2971

  Sigel, Helmut ^a   Massoud, Salah S ^a   Corfú, Nicolas A ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE PHOSPHATE; GUANOSINE PHOSPHATE; INOSINE PHOSPHATE; METAL ION;

ARTICLE; COMPLEX FORMATION; MODEL; POTENTIOMETRY; STRUCTURE ACTIVITY RELATION; TITRIMETRY;

EID: 0028271201     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00086a028     Document Type: Article

References (137)

1. Westheimer, F.H. Science 1987, 235, 1173-1178.
2. Boyer, P.D. Biochemistry 1987, 26, 8503-8507.
3. Sigel, H. ACS Symp. Ser. 1989, 402, 159-204.
4. Szent-Gydrgyi, A. In Enzymes: Units of Biological Structure and Function: Gaebler, O.H., Ed.; Academic Press: New York, 1956; pp 393-397.
5. Martin, R.B.; Mariam, Y.H. Met. Ions Biol. Syst. 1979, 8, 57-124.
6. Martin, R.B. Met. Ions Biol. Syst. 1988, 23, 315-330.
7. Sigel, H. Eur. J. Biochem. 1987, 165, 65-72.
8. Sigel, H. Chimia 1987, 41, 11-26.
9. Sigel, H. Experientia 1966, 22, 497-499.
10. Sigel, H.; Erlenmeyer, H. Helv. Chim. Acta 1966, 49, 1266-1274.
11. Sigel, H.; Scheller, K.H. Eur. J. Biochem. 1984, 138, 291-299.
12. Massoud, S.S.; Liang, G.; Tribolet, R.; Sigel, H. Rec. Trav. Chim. Pays-Bas 1987, 106, 207.
13. Frey, C.M.; Stuehr, J. Met. Ions Biol. Syst. 1974, 1, 51-116.
14. Thomas, J.C.; Frey, C.M.; Stuehr, J.E. Inorg. Chem. 1980, 19, 505-510.
15. Taylor, R.S.; Diebler, H. Bio Inorg. Chem. 1976, 6, 247-264.
16. Peguy, A.; Diebler, H. J. Phys. Chem. 1977, 81, 1355-1358.
17. Nagasawa, A.; Diebler, H. J. Phys. Chem. 1981, 85, 3523-3528.
18. Diebler, H. J. Mol. Catal. 1984, 23, 209-217.
19. Mariam, Y.H.; Martin, R.B. Inorg. Chim. Acta 1979, 35, 23-28.
20. Reily, M.D.; Marzilli, L.G. J. Am. Chem. Soc. 1986, 108, 8299-8300.
21. Reily, M.D.; Hambley, T.W.; Marzilli, L.G. J. Am. Chem. Soc. 1988, 110, 2999-3007.
22. Alessio, E.; Xu, Y.; Cauci, S.; Mestroni, G.; Quadrifoglio, F.; Viglino, P.; Marzilli, L.G. J. Am. Chem. Soc. 1989, 111, 7068-7071.
23. Torres, L.M.; Marzilli, L.G. J. Am. Chem. Soc. 1991, 113, 4678-4679.
24. Green, M.; Miller, J.M. J. Chem. Soc., Chem. Commun. 1987, 1864-1865.
25. Evans, D.J.; Green, M.; van Eldik, R. Inorg. Chim. Acta 1987, 128, 27-29.
26. Orton, D.M.; Green, M. J. Chem. Soc., Chem. Commun. 1991, 1612-1614.
27. Kuo, L.Y.; Kanatzidis, M.G.; Marks, T.J. J. Am. Chem. Soc. 1987, 109, 7207-7209.
28. Sigel, H.; Massoud, S.S.; Tribolet, R. J. Am. Chem. Soc. 1988, 110, 6857-6865.
29. Martin, R.B.; Sigel, H. Comments Inorg. Chem. 1988, 6, 285-314.
30. Massoud, S.S.; Sigel, H. Inorg. Chem. 1988, 27, 1447-1453.
31. Tribolet, R.; Sigel, H. Eur. J. Biochem. 1987, 163, 353-363.
32. Smith, R.M.; Martell, A.E.; Chen, Y. Pure Appl. Chem. 1991, 63, 1015-1080.
33. Sigel, H.; Corfü, N.A.; Ji, L.-N.; Martin, R.B. Comments Inorg. Chem. 1992, 13, 35-59.
34. Corfü, N.A.; Sigel, H. Eur. J. Biochem. 1991, 199, 659-669.
35. Lepre, C.A.; Lippard, S.J. In Nucleic Acids and Molecular Biology, Eckstein, F., Lilley, D.M.J., Eds.; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 4.
36. Lippard, S.J. Pure Appl. Chem. 1987, 59, 731-742
37. Sherman, S.E.; Lippard, S.J. Chem. Rev. 1987, 87, 1153-1181.
38. Reedijk, J. Inorg. Chim. Acta 1992, 198-200, 873-881.
39. Reedijk, J.; Fichtinger-Schepman, A.M.J.; van Oosterom, A.T.; van de Putte, P. Struct. Bonding 1987, 67, 53-89.
40. Sigel, H.; Zuberbfihler, A.D.; Yamauchi, O. Anal. Chim. Acta 1991, 255, 63-72.
41. Bastian, M.; Sigel, H. J. Coord. Chem. 1991, 23, 137-154.
42. Irving, M.M.; Miles, M.G.; Pettit, L.D. Anal. Chim. Acta 1967, 38, 475-488.
43. Griesser, R.; Sigel, H. Inorg. Chem. 1970, 9, 1238-1243.
44. Sigel, H.; Griesser, R.; Prijs, B. Z. Naturforsch. B: Anorg. Chem., Org. Chem., Biochem., Biophys., Biol. 1972, 27B, 353-364.
45. Lünnberg, H.; Vihanto, P. Inorg. Chim. Acta 1981, 56, 157-161.
46. Kinjo, Y.; Tribolet, R.; Corfü, N.A.; Sigel, H. Inorg. Chem. 1989, 28, 1480-1489.
47. Sigel, H.; Chen, D.; Corfü, N.A.; Gregáñ, F.; Holy, A.; StraSák, M. Helv. Chim. Acta 1992, 75, 2634-2656.
48. Sigel, H. Biol. Trace Eiem. Res. 1989, 21, 49-59.
49. Scheller, K.H.; Hofstetter, F.; Mitchell, P.R.; Prijs, B.; Sigel, H. J. Am. Chem. Soc. 1981, 103, 247-260.
50. Neurohr, K.J.; Mantsch, M.H. Can. J. Chem. 1979, 57, 1986-1994.
51. Scheller, K.H.; Sigel, H. J. Am. Chem. Soc. 1983, 105, 5891-5900.
52. Corfü, N.A.; Tribolet, R.; Sigel, H. Eur. J. Biochem. 1990, 191, 721-735.
53. Leroy, J.L.; Guéron, M. J. Am. Chem. Soc. 1986, 108, 5753-5759.
54. Martin, R.B. Acc. Chem. Res. 1985, 18, 32-38.
55. Tauler, R.; Cid, J.F.; Casassas, E. J. Inorg. Biochem. 1990, 39, 277-285.
56. Christensen, J.J.; Rytting, J.H.; Izatt, R.M. J. Chem. Soc. B 1970, 1643-1646, 1646-1648.
57. Christensen, J.J.; Rytting, J.H.; Izatt, R.M. Biochemistry 1970, 9, 4907-4913.
58. Martin, R.B. Met. Ions Biol. Syst. 1979, 9, 1-39.
59. Massoud, S.S.; Sigel, H. Bull. Chem. Soc. Ethiop. 1988, 2, 9-14.
60. Reddy, P.R.; Adharani, T.K. Indian J. Chem. 1990, 29A, 1002-1007.
61. Sigel, H.; Tribolet, R.; Malini-Balakrishnan, R.; Martin, R.B. Inorg. Chem. 1987, 26, 2149-2157.
62. Gellert, R.W.; Bau, R. Met. Ions Biol. Syst. 1979, 8, 1-55.
63. Terrön, A. Comments Inorg. Chem. 1993, 14, 63-88.
64. Aoki, K. Crystal Structures of Metal Ion-Nucleotide Complexes. In Landolt-Bbrnstein; Band 1: Nukleinshuren; Teilband b: Kristallographische undstrukturelle Daten II; Saenger, W., Ed.; Springer Verlag: Berlin, Heidelberg, New York, London, Paris, and Tokyo, 1989; pp 171-246.
65. Aoki, K. Nucleosides, Nucleotides and Metal Ions. In Bioactive Molecules; Volume 8; Metalloproteins; Otsuka, S., Yamanaka, T., Eds.; Elsevier: Amsterdam, Oxford, New York, and Tokyo, 1988; pp 457-490.
66. Sletten, E. In The Purines—Theory and Experiment; The Jerusalem Symposia on Quantum Chemistry and Biochemistry, IV; The Israel Academy of Sciences and Humanities: Jerusalem, 1972; pp 160-169.
67. Frommer, G.; Preut, H.; Lippert, B. Inorg. Chim. Acta 1992, 193, 111-117.
68. Sletten, E. In Metal-Ligand Interactions in Organic Chemistry and Biochemistry, Part 1; Pullman, B., Goldblum, N., Eds.; D. Reidel Publ. Comp.: Dordrecht-Holland, 1977; pp 53-64.
69. Sternglanz, H.; Subramanian, E.; Lacey, J.C., Jr.; Bugg, C.E. Biochemistry 1976, 15, 4797-4802.
70. Aoki, K.; Clark, G.R.; Orbell, J.D. Biochim. Biophys. Acta 1976, 425, 369-371.
71. Sletten, E.; Lie, B. Acta Crystailogr. 1976, B32, 3301-3304.
72. Clark, G.R.; Orbell, J.D.; Aoki, K. Acta Crystailogr. 1978, B34, 2119-2128.
73. De Meester, P.; Goodgame, D.M.L.; Jones, T.J.; Skapski, A.C. Biochim. Biophys. Acta 1974, 353, 392-394.
74. Clark, G.R.; Orbell, J.D.; Waters, J.M. Biochim. Biophys. Acta 1979, 562, 361-364.
75. De Meester, P.; Goodgame, D.M.L.; Jones, T.J.; Skapski, A.C. Biochem. J. 1974, 139, 791-792.
76. Sigel, H.; McCormick, D.B. Acc. Chem. Res. 1970, 3, 201-208.
77. Perno, J.R.; Cwikel, D.; Spiro, T.G. Inorg. Chem. 1987, 26, 400-405.
78. De Meester, P.; Goodgame, D.M.L.; Jones, T.J.; Skapski, A.C.C.R. Acad. Sci. Ser. C 1974, C279, 667-669.
79. Poojary, M.D.; Manohar, H. J. Chem. Soc., Dalton Trans. 1986, 309-312.
80. Aoki, K. Bull. Chem. Soc. Jpn. 1975, 48, 1260-1271.
81. Gellert, R.W.; Shiba, J.K.; Bau, R. Biochem. Biophys. Res. Commun. 1979, 88, 1449-1453.
82. De Meester, P.; Goodgame, D.M.L.; Skapski, A.C.; Smith, B.T. Biochim. Biophys. Acta 1974, 340, 113-115.
83. Clark, G.R.; Orbell, J.D. J. Chem. Soc., Chem. Commun. 1974, 139-140.
84. Aoki, K. Acta Crystailogr. 1976, B32, 1454-1459.
85. Kistenmacher, T.J.; Marzilii, L.G.; Szalda, D.J. Acta Crystailogr. 1976, B32, 186-193.
86. Sletten, E.; Ruud, M. Acta Crystailogr. 1975, B31, 982-985.
87. Szalda, D.J.; Kistenmacher, T.J.; Marzilii, L.G. Inorg. Chem. 1975, 14, 2623-2629.
88. Sorrell, T.; Epps, L.A.; Kistenmacher, T.J.; Marzilii, L.G. J. Am. Chem. Soc. 1977, 99, 2173-2179.
89. Sorrell, T.; Epps, L.A.; Kistenmacher, T.J.; Marzilii, L.G. J. Am. Chem. Soc. 1978, 100, 5756-5763.
90. Brown, E.A.; Bugg, C.E. J. Cryst. Mol. Struct. 1980, 10, 19-30.
91. Brown, E.A.; Bugg, C.E. Acta Crystallogr. 1980, B36, 2597-2604.
92. Einspahr, H.; Bugg, C.E. Met. Ions Biol. Syst. 1984, 17, 51-97.
93. Wang, A.H.-J.; Quigley, G.J.; Kolpak, F.J.; van der Marel, G.; van der Boom, J.H.; Rich, A. Science 1981, 211, 171-176.
94. Gessner, R.V.; Quigley, G.J.; Wang, A.H.-J.; van der Marel, G.A.; van der Boom, J.H.; Rich, A. Biochemistry 1985, 24, 237-240.
95. Tajmir-Riahi, H.-A. Biochim. Biophys. Acta 1990, 1087, 49-54.
96. Theophanides, T.; Polissiou, M. Magnesium 1986, 5, 221-233.
97. Tajmir-Riahi, H.-A. Bio Polymers 1991, 31, 101-108.
98. Sigel, H. Chem. Soc. Rev. 1993, 22, 255-267.
99. Alexander, R.S.; Kanyo, Z.F.; Chirlian, L.E.; Christianson, D.W. J. Am. Chem. Soc. 1990, 112, 933-937.
100. Brintzinger, H. Helv. Chim. Acta 1965, 48, 47-54.
101. Brintzinger, H.; Hammes, G.G. Inorg. Chem. 1966, 5, 1286-1287.
102. Poojary, M.D.; Begum, N.S.; Manchar, H.; Bau, R. J. Chem. Soc., Chem. Commun. 1985, 821-822.
103. Begum, N.S.; Poojary, M.D.; Manchar, H. J. Chem. Soc., Dalton Trans. 1989, 1507-1512.
104. Farmer, P.J.; Cave, J.R.; Fletcher, T.M.; Rhubottom, J.A., Jr.; Walmsley, J.A. Inorg. Chem. 1991, 30, 3414-3420.
105. Marzilli, L.G.; de Castro, B.; Solorzano, C. J. Am. Chem. Soc. 1982, 104, 461-466.
106. Quirös, M.; Salas, J.M.; Sánchez, M.P.; Alabart, J.R.; Faure, R. Inorg. Chem. 1991, 30, 2916-2921.
107. Kohzuma, T.; Masuda, H.; Yamauchi, O. J. Am. Chem. Soc. 1989, 111, 3431-3433.
108. Burgmayer, S.J.N.; Stiefel, E.I. Inorg. Chem. 1988, 27, 4059-4065.
109. Fischer, B.; Stráhle, J.; Viscontini, M. Helv. Chlm. Acta 1991, 74, 1544-1554.
110. Yamanouchi, K.; Huneke, J.T.; Enemark, J.H.; Taylor, R.D.; Spence, J.T. Acta Crystallogr. 1979, B35, 2326-2330.
111. Lorberth, J.; El-Essawi, M.; Massa, W.; Labib, L. Angew. Chem. 1988, 100, 1194-1195
112. Lorberth, J.; El-Essawi, M.; Massa, W.; Labib, L. Angew. Chem., Int. Ed. Engl. 1988, 27, 1160-1161.
113. Cozak, D.; Mardhy, A.; Olivier, M.J.; Beauchamp, A.L. Inorg. Chem. 1986, 25, 2600-2606.
114. Szalda, D.J.; Kistenmacher, T.J.; Marzilli, L.G. J. Am. Chem. Soc. 1976, 98, 8371-8377.
115. Colado, E.; Surez-Varela, J.; Dominguez-Vera, J.M.; Avila-Rosön, J.C.; Hidalgo, M.A.; Martm-Ramos, D. Inorg. Chim. Acta 1992, 202, 219-224.
116. Nonella, M.; HSnggi, G.; Dubler, E. J. Mol. Struct. (Theochem.) 1993, 279, 173-190.
117. Dubler, E.; Gyr, E. Inorg. Chem. 1988, 27, 1466-1473.
118. Sletten, E.; Apeland, A. Acta Crystallogr. 1975, B31, 2019-2022.
119. Diebler, H.; Secco, F.; Venturini, M. Biophys. Chem. 1987, 26, 193-205.
120. Dhathathreyan, K.S.; Diebler, H. Ber. Bunsenges. Phys. Chem. 1991, 95, 880-886.
121. Eastman, A. Pharmacol. Ther. 1987, 34, 155-166.
122. Laoui, A.; Kozelka, J.; Chottard, J.-C. Inorg. Chem. 1988, 27, 2751-2753.
123. Hohmann, H.; Hellquist, B.; van Eldik, R. Inorg. Chem. 1992, 31, 1090-1095.
124. Suvachittanont, S.; Hohmann, H.; van Eldik, R.; Reedijk, J. Inorg. Chem. 1993, 32, 4544-4548.
125. Yohannes, P.G.; Zon, G.; Doetsch, P.W.; Marzilli, L.G. J. Am. Chem. Soc. 1993, 115, 5105-5110.
126. Hambley, T.W. Comments Inorg. Chem. 1992, 14, 1-26.
127. Pullman, A.; Zakrzewska, C.; Perahia, D. Int. J. Quantum Chem. 1979, 16, 395-403.
128. Freystein, N.A.; Davis, J.T.; Reid, B.R.; Sletten, E. Acta Chem. Scand. 1993, 47, 649-657.
129. Gao, Y.-G.; Sriram, M.; Wang, A.H.-J. Nucleic Acids Res. 1993, 21, 4093-4101.
130. Jia, X.; Zon, G.; Marzilli, L.G. Inorg. Chem. 1991, 30, 228-239.
131. Schoenknecht, T.; Diebler, H. J. Inorg. Biochem. 1993, 50, 283-298.
132. Mansy, S.; Chu, G.Y.H.; Duncan, R.E.; Tobias, R.S. J. Am. Chem. Soc. 1978, 100, 607-616.
133. Inagaki, K.; Tamaoki, N.; Kidani, Y. Inorg. Chim. Acta 1980, 46, L93-L95.
134. Ji, L.-n.; Corfü, N.A.; Sigel, H. J. Chem. Dalton Trans. 1991, 1367-1375.
135. Kinjo, Y.; Ji, L.-n.; Corfü, N.A.; Sigel, H. Inorg. Chem. 1992, 31, 5588-5596.
136. Massoud, S.S.; Sigel, H. Eur. J. Biochem. 1989, 179, 451-458.
137. Massoud, S.S.; Tribolet, R.; Sigel, H. Eur. J. Biochem. 1990, 187, 387-393.