Stabilisation of non-canonical structures of nucleic acids by metal ions and small molecules

Coordination Chemistry Reviews

Volumn 257, Issue 19-20, 2013, Pages 2765-2783

  Biver, Tarita ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

A DNA; G quadruplex; Groove binder; I Motif; Intercalator; Metal complex; Triplex; Z DNA

Indexed keywords

EID: 84882886179     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2013.04.016     Document Type: Review

References (325)

1. Watson J.D., Crick F.H.C. Nature 1953, 171:737.
2. Choi J., Majima T. Chem. Soc. Rev. 2011, 40:5893.
3. Bochman M.L., Paeschke K., Zakian V.A. Nat. Rev. Genet. 2012, 13:770.
4. Di Antonio M., Rodriguez R., Balasubramanian S. Methods (Amsterdam, Netherlands) 2012, 57:84.
5. Vasudevaraju P., Bharathi, Garruto R.M.B., Sambamurti K., Rao K.S.J. Brain Res. Rev. 2008, 58:136.
6. Buchini S., Leumann C.J. Curr. Opin. Chem. Biol. 2003, 7:717.
7. Praseuth D., Guieysse A.L., Helene C. Biochim. Biophys. Acta Gene Struct. Expr. 1999, 1489:181.
8. Huppert J.L., Balasubramanian S. Nucleic Acids Res. 2007, 35:406.
9. Cech T.R. Cell 2004, 116:273.
10. Johannsen S., Korth M.M.T., Schnabl J., Sigel R.K.O. Chimia 2009, 63:146.
11. Lippert B. J. Chem. Soc. Dalton Trans. 1997, 21:3971.
12. Mocci F., Laaksonen A. Soft Matter 2012, 8:9268.
13. Muller J. Metallomics 2010, 2:318.
14. Hud N.V., Engelhart A.E. Sequence-specific DNA-Metal Ion Interactions 2009, 75. RSC Publishing, Cambridge. N.V. Hud (Ed.).
15. Saenger W. Principles of Nucleic Acid Structure 1984, Springer-Verlag, New York.
16. Yang H., McLaughlin C.K., Aldaye F.A., Hamblin G.D., Rys A.Z., Rouiller I., Sleiman H.F. Nat. Chem. 2009, 1:390. S390/391-S390/318.
17. Yang H., Metera K.L., Sleiman H.F. Coord. Chem. Rev. 2010, 254:2403.
18. Alam T.M., Drobny G.P. Chem. Rev. 1991, 91:1545.
19. Lee J., Kim Y.G., Kim K.K., Seok C. J. Phys. Chem. B 2010, 114:9872.
20. Pohl F.M., Jovin T.M. J. Mol. Biol. 1972, 67:375.
21. Hernandez B., Baumruk V., Gouyette C., Ghomi M. Biopolymers 2005, 78:21.
22. Kimura T., Kawai K., Tojo S., Majima T. J. Org. Chem. 2004, 69:1169.
23. Sugiyama H., Kawai K., Matsunaga A., Fujimoto K., Saito I., Robinson H., Wang A.H.J. Nucleic Acids Res. 1996, 24:1272.
24. Sagi J., Szemzo A., Otvos L., Vorlickova M., Kypr J. Int. J. Biol. Macromol. 1991, 13:329.
25. Preisler R.S., Chen H.H., Colombo M.F., Choe Y., Short B.J., Rau D.C. Biochemistry 1995, 34:14400.
26. Trumbore C.N., Myers Y.N., Hyde C.K., Hudson R.D., Rhodes C.N., Masselink J.K. Int. J. Radiat. Biol. 1994, 66:479.
27. Nordheim A., Pardue M.L., Lafer E.M., Moller A., Stollar B.D., Rich A. Nature 1981, 294:417.
28. Briane D., Delain D., Senechal H., Taillandier E., Wahrmann J.P., Herve B. Exp. Cell Res. 1987, 170:453.
29. Mazur A.K. ChemPhysChem 2008, 9:2691.
30. Jayaram B., Jain T. Annu. Rev. Biophys. Biomol. Struct. 2004, 33:343. (342 plate).
31. Falk M., Hartman K.A., Lord R.C. J. Am. Chem. Soc. 1963, 85:391.
32. Rhodes N.J., Mahendrasingam A., Pigram W.J., Fuller W., Brahms J., Vergne J., Warren R.A.J. Nature 1982, 296:267.
33. Skuratovskii I.Y., Bartenev V.N. Mol. Biol. 1978, 12:1052.
34. Brovchenko I., Krukau A., Oleinikova A., Mazur A.K. J. Am. Chem. Soc. 2008, 130:121.
35. Portugal J., Subirana J.A. EMBO J. 1985, 4:2403.
36. Brahms J., Pilet J., Phuong L.T.T., Hill L.R. Proc. Natl. Acad. Sci. U.S.A. 1973, 70:3352.
37. van Dam L., Levitt M.H. J. Mol. Biol. 2000, 304:541.
38. Schneider B., Neidle S., Berman H.M. Biopolymers 1997, 42:113.
39. Chakraborty S., Sharma S., Maiti P.K., Krishnan Y. Nucleic Acids Res. 2009, 37:2810.
40. Cetinkol O.P., Hud N.V. Nucleic Acids Res. 2009, 37:611.
41. Giri P., Kumar G.S. Mol. Biosyst. 2010, 6:81.
42. Rich A., Davies D.R., Crick F.H., Watson J.D. J. Mol. Biol. 1961, 3:71.
43. Zarudnaya M.I. Mol. Biol. 1998, 32:417.
44. Maggini R., Secco, Venturini M., Diebler H. J. Chem. Soc. Faraday Trans. 1994, 90:2359.
45. Buske F.A., Mattick J.S., Bailey T.L. RNA Biol. 2011, 8:427.
46. Vasquez K.M., Narayanan L., Glazer P.M. Science 2000, 290:530.
47. Duca M., Vekhoff P., Oussedik K., Halby L., Arimondo P.B. Nucleic Acids Res. 2008, 36:5123.
48. Jain A., Wang G., Vasquez K.M. Biochimie 2008, 90:1117.
49. Sugimoto N., Wu P., Hara H., Kawamoto Y. Biochemistry 2001, 40:9396.
50. Volker J., Klump H.H. Biochemistry 1994, 33:13502.
51. Beal P.A., Dervan P.B. Science 1991, 251:1360.
52. Vlieghe D., VanMeervelt L., Dautant A., Gallois B., Precigoux G., Kennard O. Science 1996, 273:1702.
53. Sun J.S., Debizemont T., Duvalvalentin G., Montenaygarestier T., Helene C. C. R. Acad. Sci. 1991, 313:585.
54. Khomyakova E.B., Gousset H., Liquier J., Huynh-Dinh T., Gouyette C., Takahashi M., Florentiev V.L., Taillandier E. Nucleic Acids Res. 2000, 28:3511.
55. Gellert M., Lipsett M.N., Davies D.R. Proc. Natl. Acad. Sci. U.S.A. 1962, 48:2013.
56. Paeschke K., Simonsson T., Postberg J., Rhodes D., Lipps H.J. Nat. Struct. Mol. Biol. 2005, 12:847.
57. Corey D.R. Chem. Biol. 2009, 16:1219.
58. Cech T.R. Angew. Chem. Int. Ed. 2000, 39:34.
59. Balasubramanian S., Neidle S. Curr. Opin. Chem. Biol. 2009, 13:345.
60. Fry M., Loeb L.A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91:4950.
61. Phan A.T., Kuryavyi V., Ma J.B., Faure A., Andreola M.L., Patel D.J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102:634.
62. Sidorov V., Kotch F.W., El-Khouedi M., Davis J.T. Chem. Commun. 2000, 23:2369.
63. Azzalin C.M., Reichenbach P., Khoriauli L., Giulotto E., Lingner J. Science 2007, 318:798.
64. Schoeftner S., Blasco M.A. Nat. Cell Biol. 2008, 10:228.
65. Lopez d.S.I., Stagno d.A.M., Blasco M.A. Nat. Commun. 2010, 1:33.
66. Phan A.T., Mergny J.L. Nucleic Acids Res. 2002, 30:4618.
67. Liu H.J., Xu Y., Li F.Y., Yang Y., Wang W.X., Song Y.L., Liu D.S. Angew. Chem. Int. Ed. 2007, 46:2515.
68. Brooks T.A., Kendrick S., Hurley L. FEBS J. 2010, 277:3459.
69. Sigel R.K.O., Sigel H. Acc. Chem. Res. 2010, 43:974.
70. Cooper P.J., Hamilton L.D. J. Mol. Biol. 1966, 16:562.
71. Rupprecht A., Piskur J., Schultz J., Nordenskiold L., Song Z.Y., Lahajnar G. Biopolymers 1994, 34:897.
72. Sundaresan N., Thomas T., Thomas T.J., Pillai C.K.S. Macromol. Biosci. 2006, 6:27.
73. Sundaresan N., Suresh C.H. J. Chem. Theory Comput. 2007, 3:1172.
74. Lyubartsev A.P., Laaksonen A. J. Biomol. Struct. Dyn. 1998, 16:579.
75. Brown I.D. Acta Crystallogr. B 1988, 44:545.
76. Rashin A.A., Honig B. J. Phys. Chem. 1985, 89:5588.
77. Pohl F.M. Nature 1976, 260:365.
78. Sutherland J.C., Griffin K.P., Keck P.C., Takacs P.Z. Proc. Natl. Acad. Sci. U.S.A. 1981, 78:4801.
79. Behe M., Felsenfeld G. Proc. Natl. Acad. Sci. U.S.A. 1981, 78:1619.
80. Vandesande J.H., Mcintosh L.P., Jovin T.M. EMBO J. 1982, 1:777.
81. Zacharias W., Larson J.E., Klysik J., Stirdivant S.M., Wells R.D. J. Biol. Chem. 1982, 257:2775.
82. Fazakerley G.V. Nucleic Acids Res. 1984, 12:3643.
83. Vandesande J.H., Jovin T.M. EMBO J. 1982, 1:115.
84. Gueron M., Demaret J.P., Filoche M. Biophys. J. 2000, 78:1070.
85. Zimmer C., Tymen S., Marck C., Guschlbauer W. Nucleic Acids Res. 1982, 10:1081.
86. Chen F.M. Biochemistry 1984, 23:6159.
87. Spingler B. Inorg. Chem. 2005, 44:831.
88. Spingler B., Da Pieve C. Dalton Trans. 2005, 5:1637.
89. Thiyagarajan S., Rajan S.S., Gautham N. Nucleic Acids Res. 2004, 32:5945.
90. Bharanidharan D., Thiyagarajan S., Gautham N. Acta Crystallogr. F 2007, 63:1008.
91. Taillandier E., Taboury J.A., Adam S., Liquier J. Biochemistry 1984, 23:5703.
92. Liquier J., Bourtayre P., Pizzorni L., Sournies F., Labarre J.F., Taillandier E. Anticancer Res. 1984, 4:41.
93. Sunderman F.W. Scand. J. Work. Environ. Health 1989, 15:1.
94. Taboury J.A., Taillandier E. Nucleic Acids Res. 1985, 13:4469.
95. Middendorf S.M., Diebler H. Ber. Bunsen.-Ges. 1996, 100:641.
96. Adam S., Bourtayre P., Liquier J., Taillandier E. Nucleic Acids Res. 1986, 14:3501.
97. Guerrier-Takada C., Gardiner K., Marsh T., Pace N., Altman S. Cell 1983, 35:849.
98. Breaker R.R., Joyce G.F. Chem. Biol. 1994, 1:223.
99. Brown A.K., Li J., Pavot C.M.B., Lu Y. Biochemistry 2003, 42:7152.
100. Mazumdar D., Nagraj N., Kim H.K., Meng X.L., Brown A.K., Sun Q., Li W., Lu Y. J. Am. Chem. Soc. 2009, 131:5506.
101. Ivanov V.I., Minchenkova L.E., Burckhardt G., BirchHirschfeld E., Fritzsche H., Zimmer C. Biophys. J. 1996, 71:3344.
102. Fritzsche H. Nucleic Acids Res. 1994, 22:787.
103. Wang J., Yang X.R. Spectrochim. Acta A 2009, 74:421.
104. Yamada M., Nomizu M., Satoh S., Ohkawa K., Yamamoto H., Nishi N. ChemBioChem 2003, 4:232.
105. Tabor C.W., Tabor H. Annu. Rev. Biochem. 1984, 53:749.
106. Gerner E.W., Meyskens F.L. Nat. Rev. Cancer 2004, 4:781.
107. Pakala R. Thromb. Res. 2003, 110:47.
108. Ohishi H., Odoko M., Grzeskowiak K., Hiyama Y., Tsukamoto K., Maezaki N., Ishida T., Tanaka T., Okabe N., Fukuyama K., Zhou D.-Y., Nakatani K. Biochem. Biophys. Res. Commun. 2008, 366:275.
109. Ohishi H., Ishida T., Suzuki K., Grzeskowiak K., Odoko M., Okabe N. Nucleic Acids Symp. Ser. 2004, 48:255-256.
110. Doi I., Tsuji G., Kawakami K., Nakagawa O., Taniguchi Y., Sasaki S. Chem. Eur. J. 2010, 16:11993.
111. Shimada N., Kano A., Maruyama A. Adv. Funct. Mater. 2009, 19:3590.
112. Shimada N., Yamamoto M., Kano A., Maruyama A. Biomacromolecules 2010, 11:3043.
113. Biver T., Cavazza C., Secco F., Venturini M. J. Inorg. Biochem. 2007, 101:461.
114. Bazzicalupi C., Biagini S., Bianchi A., Biver T., Boggioni A., Giorgi C., Gratteri P., Malavolti M., Secco F., Valtancoli B., Venturini M. Dalton Trans. 2010, 39:9838.
115. Song H., Kaiser J.T., Barton J.K. Nat. Chem. 2012, 4:615.
116. Lim M.H., Song H., Olmon E.D., Dervan E.E., Barton J.K. Inorg. Chem. 2009, 48:5392.
117. Barton J.K., Olmon E.D., Sontz P.A. Coord. Chem. Rev. 2011, 255:619.
118. Boon E.M., Barton J.K. Bioconjug. Chem. 2003, 14:1140.
119. Friedman A.E., Kumar C.V., Turro N.J., Barton J.K. Nucleic Acids Res. 1991, 19:2595.
120. Biver T., Boggioni A., Secco F., Turriani E., Venturini M., Yarnaoluk S. Arch. Biochem. Biophys. 2007, 465:90.
121. Biver T., Garcia B., Leal J.M., Secco F., Turriani E. Phys. Chem. Chem. Phys. 2010, 12:13309.
122. Chaires J.B., Norcum M.T. J. Biomol. Struct. Dyn. 1988, 5:1187.
123. Qu X.G., Trent J.O., Fokt I., Priebe W., Chaires J.B. Proc. Natl. Acad. Sci. U.S.A. 2000, 97:12032.
124. Xu Y., Zhang Y.X., Sugiyama H., Umano T., Osuga H., Tanaka K. J. Am. Chem. Soc. 2004, 126:6566.
125. Xing F.F., Song G.T., Ren J.S., Chaires J.B., Qu X.G. FEBS Lett. 2005, 579:5035.
126. Persil O., Santai C.T., Jain S.S., Hud N.V. J. Am. Chem. Soc. 2004, 126:8644.
127. Joung I.S., Cetinkol O.P., Hud N.V., Thomas E. Nucleic Acids Res. 2009, 37:7715.
128. Giri P., Kumar G.S. Mini-Rev. Med. Chem. 2010, 10:568.
129. Biver T., Ciatto C., Secco F., Venturini M. Arch. Biochem. Biophys. 2006, 452:93.
130. Schoenknecht T., Diebler H. J. Inorg. Biochem. 1993, 50:283.
131. Tereshko V., Wilds C.J., Minasov G., Prakash T.P., Maier M.A., Howard A., Wawrzak Z., Manoharan M., Egli M. Nucleic Acids Res. 2001, 29:1208.
132. Yang L., Wang S., Tian T., Zhou X. Curr. Med. Chem. 2012, 19:557.
133. Gilbert P.L., Graves D.E., Britt M., Chaires J.B. Biochemistry 1991, 30:10931.
134. Takezawa Y., Shionoya M. Acc. Chem. Res. 2012, 45:2066.
135. Johannsen S., Megger N., Bohme D., Sigel R.K.O., Muller J. Nat. Chem. 2010, 2:229.
136. Muller J. Eur. J. Inorg. Chem. 2008, 24:3749.
137. Liu S., Clever G.H., Takezawa Y., Kaneko M., Tanaka K., Guo X.F., Shionoya M. Angew. Chem. Int. Ed. 2011, 50:8886.
138. Clever G.H., Shionoya M. Coord. Chem. Rev. 2010, 254:2391.
139. Clever G.H., Carell T. Angew. Chem. Int. Ed. 2007, 46:250.
140. Yang H., Rys A.Z., McLaughlin C.K., Sleiman H.F. Angew. Chem. Int. Ed. 2009, 48:9919.
141. Tanaka K., Tengeiji A., Kato T., Toyama N., Shiro M., Shionoya M. J. Am. Chem. Soc. 2002, 124:12494.
142. Clever G.H., Polborn K., Carell T. Angew. Chem. Int. Ed. 2005, 44:7204.
143. Hatano A., Tanaka K., Shiro M., Shionoya M. Tetrahedron 2002, 58:2965.
144. McLaughlin C.K., Hamblin G.D., Aldaye F.A., Yang H., Sleiman H.F. Chem. Commun. 2011, 47:8925.
145. Yang H., Sleiman H.F. Angew. Chem. Int. Ed. 2008, 47:2443.
146. Yang H., Altvater F., Dowine d.B.A., McLaughlin C.K., Lo P.K., Sleiman H.F. Angew. Chem. Int. Ed. 2011, 50:4620. S4620/4621-S4620/4622.
147. Muller J., Lippert B. Angew. Chem. Int. Ed. 2006, 45:2503.
148. Ducani C., Leczkowska A., Hodges N.J., Hannon M.J. Angew. Chem. Int. Ed. 2010, 49:8942.
149. Stevens C.L., Felsenfeld G. Biopolymers 1964, 2:293.
150. Antony T., Subramaniam V. Antisense Nucleic Acid Drug Dev. 2002, 12:145.
151. Coman D., Russu I.M. Nucleic Acids Res. 2004, 32:878.
152. Felsenfeld G., Rich A. Biochim. Biophys. Acta 1957, 26:457.
153. Felsenfeld G., Davies D.R., Rich A. J. Am. Chem. Soc. 1957, 79:2023.
154. Garcia B., Leal J.M., Paiotta V., Ibeas S., Ruiz R., Secco F., Venturini M. J. Phys. Chem. B 2006, 110:16131.
155. Garcia B., Leal J.A., Paiotta V., Ruiz R., Secco F., Venturini M. J. Phys. Chem. B 2008, 112:7132.
156. Zozulya V.N., Nesterov A.B., Ryazanova O.A., Blagoi Y.P. Int. J. Biol. Macromol. 2003, 33:183.
157. Choi B.H., Yeo G.Y., Jung J., Lee B.W., Han S.W., Cho T.S. Bull. Korean Chem. Soc. 2009, 30:2691.
158. Wu P., Kawamoto Y., Hara H., Sugimoto N. J. Inorg. Biochem. 2002, 91:277.
159. Ellouze C., Piot F., Takahashi M. J. Biochem. 1997, 121:521.
160. Zozulya V.N., Ryazanova O.A., Zhigalova N.N., Blagoi Y.P. Biometals 2010, 23:1191.
161. Paris C., Geinguenaud F., Gouyette C., Liquier J., Lacoste J. Biophys. J. 2007, 92:2498.
162. Tanaka K., Yamada Y., Shionoya M. J. Am. Chem. Soc. 2002, 124:8802.
163. Sueda S., Ihara T., Takagi M. Chem. Lett. 1997, 26:1085-1086.
164. Ihara T., Ishii T., Araki N., Wilson A.W., Jyo A. J. Am. Chem. Soc. 2009, 131:3826.
165. Korolev N., Lyubartsev A.P., Nordenskiold L. J. Biomol. Struct. Dyn. 2002, 20:275.
166. Blagoi Y., Zozulya V., Egupov S., Onishchenko V., Gladchenko G. Biopolymers 2007, 86:32.
167. Sorokin V.A., Valeev V.A., Gladchenko G.O., Degtyar M.V., Andrus E.A., Karachevtsev V.A., Blagoi Y.P. Int. J. Biol. Macromol. 2005, 35:201.
168. Blagoi Y., Gladchenko G., Nafie L.A., Freedman T.B., Sorokin V., Valeev V., He Y.N. Biopolymers 2005, 78:275.
169. Gukovskaya A.S., Gukovsky I.Y., Chikh V.P., Sukhorukov B.I. Biopolymers 1980, 19:453.
170. Wan C.H., Cui M., Song F.R., Liu Z.Q., Liu S.Y. J. Am. Soc. Mass Spectrom. 2009, 20:1281.
171. Malkov V.A., Voloshin O.N., Soyfer V.N., Frankkamenetskii M.D. Nucleic Acids Res. 1993, 21:585.
172. Malkov V.A., Voloshin O.N., Veselkov A.G., Rostapshov V.M., Jansen I., Soyfer V.N., Frankkamenetskii M.D. Nucleic Acids Res. 1993, 21:105.
173. Sasaki S., Taniguchi Y., Takahashi R., Senko Y., Kodama K., Nagatsugi F., Maeda M. J. Am. Chem. Soc. 2004, 126:516.
174. Ihara T., Takeda Y., Jyo A. J. Am. Chem. Soc. 2001, 123:1772.
175. Jenkins T.C. Curr. Med. Chem. 2000, 7:99.
176. Fox K.R. Curr. Med. Chem. 2000, 7:17.
177. Capobianco M.L., De Champdore M., Francini L., Lena S., Garbesi A., Arcamone F. Bioconjug. Chem. 2001, 12:523.
178. Haq I., Ladbury J.E., Chowdhry B.Z., Jenkins T.C. J. Am. Chem. Soc. 1996, 118:10693.
179. Eick A., Riechert-Krause F., Weisz K. Bioconjug. Chem. 2010, 21:1105.
180. Sehlstedt U., Aich P., Bergman J., Vallberg H., Norden B., Graslund A. J. Mol. Biol. 1998, 278:31.
181. Arya D.P. Acc. Chem. Res. 2011, 44:134.
182. Xi H., Arya D.P. Curr. Med. Chem. 2005, 5:327.
183. Arya D.P., Coffee R.L., Willis B., Abramovitch A.I. J. Am. Chem. Soc. 2001, 123:5385.
184. Arya D.P., Micovic L., Charles I., Coffee R.L., Willis B., Xue L. J. Am. Chem. Soc. 2003, 125:3733.
185. Roulon T., Helene C., Escude C. Angew. Chem. Int. Ed. 2001, 40:1523.
186. Xue L.A., Xi H.J., Kumar S., Gray D., Davis E., Hamilton P., Skriba M., Arya D.P. Biochemistry 2010, 49:5540.
187. Park Y.W., Breslauer K.J. Proc. Natl. Acad. Sci. U.S.A. 1992, 89:6653.
188. Umemoto K., Sarma M.H., Gupta G., Luo J., Sarma R.H. J. Am. Chem. Soc. 1990, 112:4539.
189. Pilch D.S., Breslauer K.J. Proc. Natl. Acad. Sci. U.S.A. 1994, 91:9332.
190. Jain A.K., Bhattacharya S. Bioconjug. Chem. 2010, 21:1389.
191. Hampel K.J., Crosson P., Lee J.S. Biochemistry 1991, 30:4455.
192. Thomas T., Thomas T.J. Biochemistry 1993, 32:14068.
193. Beccia M.R., Biver T., Pardini A., Spinelli J., Secco F., Venturini M., Vazquez N.B., Cornejo M.P.L., Herrera V.I.M., Gotor R.P. Chem. Asian J. 2012, 7:1803.
194. Fortsch I., Baguley B., Zimmer C. Anti-Cancer Drug Des. 1998, 13:417.
195. Fortsch I., BirchHirschfeld E., Schutz H., Zimmer C. J. Biomol. Struct. Dyn. 1996, 14:317.
196. Mergny J.L., Collier D., Rougee M., Montenaygarestier T., Helene C. Nucleic Acids Res. 1991, 19:1521.
197. Tuite E., Norden B. Bioorg. Med. Chem. 1995, 3:701.
198. Kukreti S., Sun J.S., Garestier T., Helene C. Nucleic Acids Res. 1997, 25:4264.
199. Sinha R., Kumar G.S. J. Phys. Chem. B 2009, 113:13410.
200. Bhowmik D., Hossain M., Buzzetti F., D'Auria R., Lombardi P., Kumar G.S. J. Phys. Chem. B 2012, 116:2314.
201. Bhowmik D., Das S., Hossain M., Haq L., Kumar G.S. PLoS ONE 2012, 7:e37939.
202. Ihmels H., Otto D., Dall'Acqua F., Faccio A., Moro S., Viola G. J. Org. Chem. 2006, 71:8401.
203. Jain S.S., Polak M., Hud N.V. Nucleic Acids Res. 2003, 31:4608.
204. MoraruAllen A.A., Cassidy S., Alvarez J.L.A., Fox K.R., Brown T., Lane A.N. Nucleic Acids Res. 1997, 25:1890.
205. Biver T., Boggioni A., Garcia B., Leal J.M., Ruiz R., Secco F., Venturini M. Nucleic Acids Res. 2010, 38:1697.
206. Ray A., Kumar G.S., Das S., Maiti M. Biochemistry 1999, 38:6239.
207. Keppler M.D., Read M.A., Perry P.J., Trent J.O., Jenkins T.C., Reszka A.P., Neidle S., Fox K.R. Eur. J. Biochem. 1999, 263:817.
208. Mergny J.L., Duvalvalentin G., Nguyen C.H., Perrouault L., Faucon B., Rougee M., Montenaygarestier T., Bisagni E., Helene C. Science 1992, 256:1681.
209. Keppler M.D., Neidle S., Fox K.R. Nucleic Acids Res. 2001, 29:1935.
210. Escude C., Sun J.S., Nguyen C.H., Bisagni E., Garestier T., Helene C. Biochemistry 1996, 35:5735.
211. Pilch D.S., Martin M.T., Nguyen C.H., Sun J.S., Bisagni E., Garestier T., Helene C. J. Am. Chem. Soc. 1993, 115:9942.
212. Vinogradov S., Roig V., Sergueeva Z., Nguyen C.H., Arimondo P., Thuong N.T., Bisagni E., Sun J.S., Helene C., Asseline U. Bioconjug. Chem. 2003, 14:120.
213. Wilson W.D., Tanious F.A., Mizan S., Yao S.J., Kiselyov A.S., Zon G., Strekowski L. Biochemistry 1993, 32:10614.
214. Keppler M., Zegrocka O., Strekowski L., Fox K.R. FEBS Lett. 1999, 447:223.
215. Muller J., Drumm M., Boudvillain M., Leng M., Sletten E., Lippert B. J. Biol. Inorg. Chem. 2000, 5:603.
216. Tan L.F., Liu J., Shen J.L., Liu X.H., Zeng L.L., Jin L.H. Inorg. Chem. 2012, 51:4417.
217. Munoz J., Gelpi J.L., Soler-Lopez M., Subirana J.A., Orozco M., Luque F.J. J. Phys. Chem. B 2002, 106:8849.
218. Misra V.K., Draper D.E. Proc. Natl. Acad. Sci. U.S.A. 2001, 98:12456.
219. Li W., Nordenskiold L., Mu Y. J. Phys. Chem. B 2011, 115:14713.
220. Robinson H., Gao Y.-G., Sanishvili R., Joachimiak A., Wang A.H.-J. Nucleic Acids Res. 2000, 28:1760.
221. Floris R., Scaggiante B., Manzini G., Quadrifoglio F., Xodo L.E. Eur. J. Biochem. 1999, 260:801.
222. Olivas W.M., Maher L.J. Nucleic Acids Res. 1995, 23:1936.
223. Potaman V.N., Soyfer V.N. J. Biomol. Struct. Dyn. 1994, 11:1035.
224. Sponer J., Sabat M., Burda J.V., Doody A.M., Leszczynski J., Hobza P. J. Biomol. Struct. Dyn. 1998, 16:139.
225. Lyamichev V.I., Voloshin O.N., Frankkamenetskii M.D., Soyfer V.N. Nucleic Acids Res. 1991, 19:1633.
226. Cassidy S.A., Strekowski L., Wilson W.D., Fox K.R. Biochemistry 1994, 33:15338.
227. Choi S.D., Kim M.S., Kim S.K., Lincoln P., Tuite E., Norden B. Biochemistry 1997, 36:214.
228. Escude C., Nguyen C.H., Mergny J.L., Sun J.S., Bisagni E., Garestier T., Helene C. J. Am. Chem. Soc. 1995, 117:10212.
229. Wei D.G., Parkinson G.N., Reszka A.P., Neidle S. Nucleic Acids Res. 2012, 40:4691.
230. Kwan I.C.M., Delley R.J., Hodgson D.R.W., Wu G. Chem. Commun. 2011, 47:3882.
231. Gray R.D., Li J., Chaires J.B. J. Phys. Chem. B 2009, 113:2676.
232. Burge S., Parkinson G.N., Hazel P., Todd A.K., Neidle S. Nucleic Acids Res. 2006, 34:5402.
233. Gaynutdinov T.I., Brown P., Neumann R.D., Panyutin I.G. Biochemistry 2009, 48:11169.
234. Chen F.M. Biochemistry 1992, 31:3769.
235. Dailey M.M., Miller M.C., Bates P.J., Lane A.N., Trent J.O. Nucleic Acids Res. 2010, 38:4877.
236. Lane A.N., Chaires J.B., Gray R.D., Trent J.O. Nucleic Acids Res. 2008, 36:5482.
237. Ida R., Wu G. J. Am. Chem. Soc. 2008, 130:3590.
238. Hud N.V., Plavec J. The Role of Cations in Determining Quadruplex Structure and Stability 2006, Royal Society of Chemistry, Cambridge.
239. Plavec J. Metal Ion Coordination in g-Quadruplexes 2009, John Wiley & Sons Ltd., Chichester.
240. Podbevsek P., Hud N.V., Plavec J. Nucleic Acids Res. 2007, 35:2554.
241. Sket P., Plavec J. J. Am. Chem. Soc. 2007, 129:8794.
242. Wong A., Wu G. J. Am. Chem. Soc. 2003, 125:13895.
243. Li T., Wang E.K., Dong S.J. J. Am. Chem. Soc. 2009, 131:15082.
244. Liu W., Zhu H., Zheng B., Cheng S., Fu Y., Li W., Lau T.C., Liang H.J. Nucleic Acids Res. 2012, 40:4229.
245. Akhshi P., Acton G., Wu G. J. Phys. Chem. B 2012, 116:9363.
246. Ma L., Iezzi M., Kaucher M.S., Lam Y.-F., Davis J.T. J. Am. Chem. Soc. 2006, 128:15269.
247. Hud N.V., Schultze P., Sklenar V., Feigon J. J. Mol. Biol. 1999, 285:233.
248. Cesare M., Flaminia A., Virno A., Randazzo F., Mocci G., Saba A., Lai Magn. Reson. Chem. 2009, 47:1036.
249. Williamson J.R., Raghuraman M.K., Cech T.R. Cell 1989, 59:871.
250. Smargiasso N., Rosu F., Hsia W., Colson P., Baker E.S., Bowers M.T., De Pauw E., Gabelica V. J. Am. Chem. Soc. 2008, 130:10208.
251. Lin C.T., Tseng T.Y., Wang Z.F., Chang T.C. J. Phys. Chem. B 2011, 115:2360.
252. Hu D., Ren J., Qu X. Chem. Sci. 2011, 2:1356.
253. Hightower J.B., Olmos D.R., Walmsley J.A. J. Phys. Chem. B 2009, 113:12214.
254. Li T., Ackermann D., Hall A.M., Famulok M. J. Am. Chem. Soc. 2012, 134:3508.
255. Li W., Wu P., Ohmichi T., Sugimoto N. FEBS Lett. 2002, 526:77.
256. Zhao Y., Cao L., Ouyang J., Wang M., Wang K., Xia X.-H. Anal. Chem. (Washington, DC, US) 2013, 85:1053.
257. Sengupta B., Springer K., Buckman J.G., Story S.P., Abe O.H., Hasan Z.W., Prudowsky Z.D., Rudisill S.E., Degtyareva N.N., Petty J.T. J. Phys. Chem. C 2009, 113:19518.
258. Halder K., Hartig J.S. Met. Ions Life Sci. 2011, 9:125.
259. Xu Y., Kaminaga K., Komiyama M. J. Am. Chem. Soc. 2008, 130:11179.
260. Han H.Y., Hurley L.H. Trends Pharmacol. Sci. 2000, 21:136.
261. Campbell N.H., Abd Karim N.H., Parkinson G.N., Gunaratnam M., Petrucci V., Todd A.K., Vilar R., Neidle S. J. Med. Chem. 2012, 55:209.
262. Georgiades S.N., Abd Karim N.H., Suntharalingam K., Vilar R. Angew. Chem. Int. Ed. 2010, 49:4020.
263. Jain A.K., Bhattacharya S. Bioconjug. Chem. 2011, 22:2355.
264. Monchaud D., Teulade-Fichou M.P. Org. Biomol. Chem. 2008, 6:627.
265. Kerwin S.M. Curr. Pharm. Des. 2000, 6:441.
266. Fedoroff O.Y., Rangan A., Chemeris V.V., Hurley L.H. Biochemistry 2000, 39:15083.
267. Li X., Peng Y.H., Ren J.S., Qu X.G. Proc. Natl. Acad. Sci. U.S.A. 2006, 103:19658.
268. Chen X., Zhou X., Han T., Wu J., Zhang J., Guo S. ACS Nano 2013, 7:531.
269. Jain A.K., Bhattacharya S. Curr. Pharm. Des. 2012, 18:1917.
270. Li G.R., Huang J., Zhang M., Zhou Y.Y., Zhang D., Wu Z.G., Wang S.R., Weng X.C., Zhou X., Yang G.F. Chem. Commun. 2008, 38:4564.
271. Huang J., Li G.R., Wu Z.G., Song Z.B., Zhou Y.Y., Shuai L., Weng X.C., Zhou X., Yang G.F. Chem. Commun. 2009, 8:902.
272. Phan A.T., Kuryavyi V., Gaw H.Y., Patel D.J. Nat. Chem. Biol. 2005, 1:167.
273. Chen Z., Zheng K.W., Hao Y.H., Tan Z. J. Am. Chem. Soc. 2009, 131:10430.
274. Jain A.K., Paul A., Maji B., Muniyappa K., Bhattacharya S. J. Med. Chem. 2012, 55:2981.
275. Jain A.K., Reddy V.V., Paul A., Muniyappa K., Bhattacharya S. Biochemistry 2009, 48:10693.
276. Dash J., Das R.N., Hegde N., Pantos G.D., Shirude P.S., Balasubramanian S. Chem. Eur. J. 2012, 18:554.
277. Paul A., Jain A.K., Misra S.K., Maji B., Muniyappa K., Bhattacharya S. PLoS ONE 2012, 7:e39467.
278. Paul A., Maji B., Misra S.K., Jain A.K., Muniyappa K., Bhattacharya S. J. Med. Chem. 2012, 55:7460.
279. Martino L., Virno A., Pagano B., Virgilio A., Di Micco S., Galeone A., Giancola C., Bifulco G., Mayol L., Randazzo A. J. Am. Chem. Soc. 2007, 129:16048.
280. Cocco M.J., Hanakahi L.A., Huber M.D., Maizels N. Nucleic Acids Res. 2003, 31:2944.
281. Pagano B., Virno A., Mattia C.A., Mayol L., Randazzo A., Giancola C. Biochimie 2008, 90:1224.
282. Pagano B., Mattia C.A., Virno A., Randazzo A., Mayol L., Giancola C. Nucleosides Nucleotides Nucleic Acids 2007, 26:761.
283. Moore M.J.B., Cuenca F., Searcey M., Neidle S. Org. Biomol. Chem. 2006, 4:3479.
284. Zaffaroni N., Lualdi S., Villa R., Bellarosa D., Cermele C., Felicetti P., Rossi C., Orlandi L., Daidone M.G. Eur. J. Cancer 2002, 38:1792.
285. Chen Q., Kuntz I.D., Shafer R.H. Proc. Natl. Acad. Sci. U.S.A. 1996, 93:2635.
286. David W.M., Brodbelt J., Kerwin S.M., Thomas P.W. Anal. Chim. 2002, 74:2029.
287. White E.W., Tanious F., Ismail M.A., Reszka A.P., Neidle S., Boykin D.W., Wilson W.D. Biophys. Chem. 2007, 126:140.
288. Kerwin S.M., Sun D., Kern J.T., Rangan A., Thomas P.W. Bioorg. Med. Chem. Lett. 2001, 11:2411.
289. Zhang Y., Cao E.H., Liang X.Q., Qin J.F. Eur. J. Pharmacol. 2003, 474:141.
290. Rosu F., De Pauw E., Guittat L., Alberti P., Lacroix L., Mailliet P., Riou J.F., Mergny J.L. Biochemistry 2003, 42:10361.
291. Koeppel F., Riou J.F., Laoui A., Mailliet P., Arimondo P.B., Labit D., Petitgenet O., Helene C., Mergny J.L. Nucleic Acids Res. 2001, 29:1087.
292. Alberti P., Ren J.S., Teulade-Fichou M.P., Guittat L., Riou J.F., Chaires J.B., Helene C., Vigneron J.P., Lehn J.M., Mergny J.L. J. Biomol. Struct. Dyn. 2001, 19:505.
293. Wang L., Wu Y., Chen T., Wei C. Int. J. Biol. Macromol. 2013, 52:1.
294. Perry P.J., Reszka A.P., Wood A.A., Read M.A., Gowan S.M., Dosanjh H.S., Trent J.O., Jenkins T.C., Kelland L.R., Neidle S. J. Med. Chem. 1998, 41:4873.
295. Neidle S. Curr. Opin. Struct. Biol. 2009, 19:239.
296. Han F.X.G., Wheelhouse R.T., Hurley L.H. J. Am. Chem. Soc. 1999, 121:3561.
297. Romera C., Bombarde O., Bonnet R., Gomez D., Dumy P., Calsou P., Gwan J.F., Lin J.H., Defrancq E., Pratviel G. Biochimie 2011, 93:1310.
298. Izbicka E., Wheelhouse R.T., Raymond E., Davidson K.K., Lawrence R.A., Sun D.Y., Windle B.E., Hurley L.H., Von Hoff D.D. Cancer Res. 1999, 59:639.
299. Fedoroff O.Y., Salazar M., Han H.Y., Chemeris V.V., Kerwin S.M., Hurley L.H. Biochemistry 1998, 37:12367.
300. Han H.Y., Cliff C.L., Hurley L.H. Biochemistry 1999, 38:6981.
301. Marco-Haviv Y., Baran N., Manor H. J. Mol. Biol. 1999, 286:45.
302. El-Sayed A.A., Pedersen E.B., Khaireldin N.A. Nucleosides Nucleotides Nucleic Acids 2012, 31:872.
303. Zhang J., Zhang F., Li H., Liu C., Xia J., Ma L., Chu W., Zhang Z., Chen C., Li S., Wang S. Curr. Med. Chem. 2012, 19:2957.
304. Reed J.E., Neidle S., Vilar R. Chem. Commun. 2007, 42:4366.
305. Reed J.E., White A.J.P., Neidle S., Vilar R. Dalton Trans. 2009, 14:2558.
306. Larsen A.F., Nielsen M.C., Ulven T. Chem. Eur. J. 2012, 18:10892.
307. Shi S., Zhao J., Geng X., Yao T., Huang H., Liu T., Zheng L., Li Z., Yang D., Ji L. Dalton Trans. 2010, 39:2490.
308. Bianco S., Musetti C., Waldeck A., Sparapani S., Seitz J.D., Krapcho A.P., Palumbo M., Sissi C. Dalton Trans. 2010, 39:5833.
309. Bhattacharjee A.J., Ahluwalia K., Taylor S., Jin O., Nicoludis J.M., Buscaglia R., Chaires J.B., Kornfilt D.J.P., Marquardt D.G.S., Yatsunyk L.A. Biochimie 2011, 93:1297.
310. Reed J.E., Arnal A.A., Neidle S., Vilar R. J. Am. Chem. Soc. 2006, 128:5992.
311. Suntharalingam K., White A.J.P., Vilar R. Inorg. Chem. 2010, 49:8371.
312. Chaput J.C., Switzer C. Proc. Natl. Acad. Sci. U.S.A. 1999, 96:10614.
313. Nikan M., Sherman J.C. J. Org. Chem. 2009, 74:5211.
314. Briem H., Kuntz I.D. J. Med. Chem. 1996, 39:3401.
315. Collie G.W., Promontorio R., Hampel S.M., Micco M., Neidle S., Parkinson G.N. J. Am. Chem. Soc. 2012, 134:2723.
316. Wu W.B., Chen S.H., Hou J.Q., Tan J.H., Ou T.M., Huang S.L., Li D., Gu L.Q., Huang Z.S. Org. Biomol. Chem. 2011, 9:2975.
317. Tan J.H., Ou T.M., Hou J.Q., Lu Y.J., Huang S.L., Luo H.B., Wu J.T., Huang Z.S., Wong K.Y., Gu L.Q. J. Med. Chem. 2009, 52:2825.
318. Siddiqui-Jain A., Grand C.L., Bearss D.J., Hurley L.H. Proc. Natl. Acad. Sci. U.S.A. 2002, 99:11593.
319. Waller Z.A.E., Sewitz S.A., Hsu S.T.D., Balasubramanian S. J. Am. Chem. Soc. 2009, 131:12628.
320. Li H.H., Liu Y.Q., Lin S., Yuan G. Chem. Eur. J. 2009, 15:2445.
321. Ou T.M., Lu Y.J., Zhang C., Huang Z.S., Wang X.D., Tan J.H., Chen Y., Ma D.L., Wong K.Y., Tang J.C.O., Chan A.S.C., Gu L.Q. J. Med. Chem. 2007, 50:1465.
322. De Cian A., DeLemos E., Mergny J.L., Teulade-Fichou M.P., Monchaud D. J. Am. Chem. Soc. 2007, 129:1856.
323. Haq I., Trent J.O., Chowdhry B.Z., Jenkins T.C. J. Am. Chem. Soc. 1999, 121:1768.
324. Zheng X.H., Zhong Y.F., Tan C.P., Ji L.N., Mao Z.W. Dalton Trans. 2012, 41:11807.
325. Dixon I.M., Lopez F., Tejera A.M., Esteve J.P., Blasco M.A., Pratviel G., Meunier B. J. Am. Chem. Soc. 2007, 129:1502.