Photoactive RuII–Polypyridyl Complexes that Display Sequence Selectivity and High-Affinity Binding to Duplex DNA through Groove Binding
Amrita Ghosh
Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorPriyadip Das
Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorMartin R. Gill
Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Search for more papers by this authorPrasenjit Kar
Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorMichael G. Walker
Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Search for more papers by this authorCorresponding Author
Dr. Jim A. Thomas
Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Jim A. Thomas, Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Amitava Das, Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorCorresponding Author
Dr. Amitava Das
Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Jim A. Thomas, Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Amitava Das, Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorAmrita Ghosh
Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorPriyadip Das
Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorMartin R. Gill
Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Search for more papers by this authorPrasenjit Kar
Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorMichael G. Walker
Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Search for more papers by this authorCorresponding Author
Dr. Jim A. Thomas
Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Jim A. Thomas, Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Amitava Das, Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorCorresponding Author
Dr. Amitava Das
Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Jim A. Thomas, Department of Chemistry, University of Sheffield, Sheffield: S3 7HF (UK), Fax: (+44) 1142229346
Amitava Das, Central Salt & Marine Chemicals Research Institute (CSIR), Bhavnagar, 364002, Gujarat (India), Fax: (+91) 2782567562
Search for more papers by this authorGraphical Abstract
Get into the groove: RuII–polypyridyl complexes with pendant catechol functionality have been prepared that show unique biphasic binding to calf-thymus DNA and to the polynucleotides poly(dA–dT)2, poly(dG–dC)2, poly(dA)–poly(dT), and poly(dG)–poly(dC) with a large preference for the alternating purine–pyrimidine sequences, particularly those containing AT.TA steps (see figure).
Abstract
The duplex-DNA binding properties of a nonintercalating polypyridyl ruthenium(II) complex that incorporates a linear extended ligand with a catechol moiety has been probed with a variety of photo- and biophysical techniques. These studies reveal that the complex groove binds to DNA sequences biphasically, and displays binding constants equivalent to those of high-affinity metallointercalators. The complex also displays preferential binding to AT-rich sequences. Changes in the structure of the coordinated catechol ligand and the incorporation of intercalating ancillary ligands into the complex were found to modulate both the optical-binding response and binding parameters of the system, which indicates that the catechol moiety plays a crucial role in the observed enhancement to binding affinities.
References
- 1
- 1aD. S. Sigman, Acc. Chem. Res. 1986, 19, 180;
- 1bD. S. Sigman, T. W. Bruice, A. Mazumder, C. L. Sutton, Acc. Chem. Res. 1993, 26, 98;
- 1cD. S. Sigman, A. Mazumder, D. M. Perrin, Chem. Rev. 1993, 93, 2295;
- 1dL. K. J. Boerner, J. M. Zaleski, Curr. Opin. Chem. Biol. 2005, 9, 135;
- 1eC. Romera, L. Sabater, A. Garofalo, I. M. Dixon, G. Pratviel, Inorg. Chem. 2010, 49, 8558;
- 1fH. T. Chifotides, K. R. Dunbar, Acc. Chem. Res. 2005, 38, 146;
- 1gW. K. Pogozelski, T. D. Tullius, Chem. Rev. 1998, 98, 1089;
- 1hC. J. Burrows, J. G. Muller, Chem. Rev. 1998, 98, 1109;
- 1iD. R. McMillin, K. M. McNett, Chem. Rev. 1998, 98, 1201;
- 1jJ. A. Cowan, Curr. Opin. Chem. Biol. 2001, 5, 634;
- 1kE. L. Hegg, J. N. Burstyn, Coord. Chem. Rev. 1998, 173, 133;
- 1lS. E. Wolkenberg, D. L. Boger, Chem. Rev. 2002, 102, 2477;
- 1mS. J. Franklin, Curr. Opin. Chem. Biol. 2001, 5, 201;
- 1nC. Liu, M. Wang, T. H. Zhang, Coord. Chem. Rev. 2004, 248, 147;
- 1oG. Pratviel, J. Bernadou, B. Meunier, Angew. Chem. 1995, 107, 819;
10.1002/ange.19951070705 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 746;
- 1pJ. Reedijk, J. Inorg. Biochem. 2001, 86, 89;
- 1qA. K. Patra, T. Bhowmick, S. Roy, S. Ramakumar, A. R. Chakravarty, Inorg. Chem. 2009, 48, 2932;
- 1rV. Rajendiran, M. Murali, E. Suresh, S. Sinha, K. Somasundaramcand, M. Palaniandavar, Dalton Trans. 2008, 148;
- 1sA. Ghosh, A. Mandoli, D. K. Kumar, N. S. Yadav, T. Ghosh, B. Jha, J. A. Thomas, A. Das, Dalton Trans. 2009, 9312.
- 2
- 2aA. Sitlani, E. C. Long, A. M. Pyle, J. K. Barton, J. Am. Chem. Soc. 1992, 114, 2303;
- 2bD. Campisi, T. Morii, J. K. Barton, Biochemistry 1994, 33, 4130;
- 2cB. P. Hudson, C. M. Dupureur, J. K. Barton, J. Am. Chem. Soc. 1995, 117, 9379.
- 3C. L. Kielkopf, K. E. Erkila, B. P. Hudson, J. K. Barton, D. C. Rees, Nat. Struct. Biol. 2000, 7, 117, and references therein.
- 4B. A. Jackson, V. Y. Alekseyev, J. K. Barton, Biochemistry 1999, 38, 4655.
- 5
- 5aB. Norden, P. Lincoln, B. Kerman, E. Tuite, Met. Ions Biol. Syst. 1996, 33, 177;
- 5bE. D. A. Stemp, J. K. Barton, Met. Ions Biol. Syst. 1996, 33, 325;
- 5cC. Moucheron, A. Kirsch-De Mesmaeker, J. M. Kelly, Struct. Bonding (Berlin) 1998, 92, 163;
- 5dK. E. Erkkila, D. T. Odom, J. K. Barton, Chem. Rev. 1999, 99, 2777;
- 5eL. N. Ji, X. H. Zou, Coord. Chem. Rev. 2001, 216–217, 513;
- 5fC. Metcalfe, J. A. Thomas, Chem. Soc. Rev. 2003, 32, 215;
- 5gM. J. Clarke, Coord. Chem. Rev. 2003, 236, 209;
- 5hH. Chao, L.-N. Li, Bioinorg. Chem. Appl. 2005, 3, 70;
- 5iJ. K. Barton, A. T. Danishefsky, J. M. Goldberg, J. Am. Chem. Soc. 1984, 106, 2172;
- 5jJ. K. Barton, J. M. Goldberg, C. V. Kumar, N. J. Turro, J. Am. Chem. Soc. 1986, 108, 2081;
- 5kJ. M. Kelly, A. B. Tossi, D. J. McConnell, C. OhUigin, Nucleic Acids Res. 1985, 13, 6017;
- 5lJ. G. Voss, J. M. Kelly, Dalton Trans. 2006, 4869;
- 5mT. Ghosh, B. G. Maiya, A. Samnta, A. D. Shukla, D. A. Jose, D. K. Kumar, A. Das, J. Biol. Inorg. Chem. 2005, 10, 496.
- 6
- 6aA. E. Friedman, J. C. Chambron, J. P. Sauvage, N. J. Turro, J. K. Barton, J. Am. Chem. Soc. 1990, 112, 4960;
- 6bR. M. Hartshorn, J. K. Barton, J. Am. Chem. Soc. 1992, 114, 5919;
- 6cF. Westerlund, F. Pierard, M. P. Eng, B. Norden, P. Lincoln, J. Phys. Chem. B 2005, 109, 17327;
- 6dE. J. C. Olson, D. Hu, A. Hoermann, A. M. Jonkman, M. R. Arkin, E. D. A. Stemp, J. K. Barton, P. F. Barbara, J. Am. Chem. Soc. 1997, 119, 11458;
- 6eR. B. Nair, B. M. Cullum, C. J. Murphy, Inorg. Chem. 1997, 36, 962;
- 6fC. Turro, S. H. Ossmann, Y. Jenkins, J. K. Barton, N. J. Turro, J. Am. Chem. Soc. 1995, 117, 9026;
- 6gB. Önfelt, J. Olofsson, P. Lincoln, B. Norden, J. Phys. Chem. A 2003, 107, 1000.
- 7
- 7aR. E. Holmlin, E. D. A. Stemp, J. K. Barton, J. Am. Chem. Soc. 1996, 118, 5236;
- 7bV. W.-W. Yam, K. K.-W. Lo, K.-K. Cheung, R. Y.-C. Kong, J. Chem. Soc. Chem. Commun. 1995, 1191;
- 7cH. D. Stoeffler, N. B. Thornton, S. L. Temkin, K. S. Schanze, J. Am. Chem. Soc. 1995, 117, 7119;
- 7dK. K.-W. Lo, C.-K. Chung, N. Zhu, Chem. Eur. J. 2006, 12, 1500.
- 8
- 8aB. Önfelt, P. Lincoln, B. Nordén, J. Am. Chem. Soc. 1999, 121, 10846;
- 8bL. M. Wilhelmsson, F. Westerlund, P. Lincoln, B. Nordén, J. Am. Chem. Soc. 2002, 124, 12092;
- 8cS. P. Foxon, T. Phillips, M. R. Gill, M. Towrie, A. W. Parker, M. Webb, J. A. Thomas, Angew. Chem. 2007, 119, 3760;
10.1002/ange.200604837 Google ScholarAngew. Chem. Intl. Ed. 2007, 46, 3686.
- 9
- 9aB. Nguyen, S. Neidle, W. D. Wilson, Acc. Chem. Res. 2009, 42, 11;
- 9bR. R. Tidwell, D. W. Boykin in DNA and RNA Binders: From Small Molecules to Drugs, Vol. 2 (Eds.: ), Wiley-VCH, Weinheim, 2003, pp. 414–460;
- 9cW. D. Wilson, B. Nguyen, F. A. Tanious, A. Mathis, J. E. Hall, C. E. Stephens, D. W. Boykin, Curr. Med. Chem. Anti-Cancer Agents 2005, 5, 389;
- 9dS. Neidle, Nat. Prod. Rep. 2001, 18, 291;
- 9eA. M. Mathis, A. S. Bridges, M. A. Ismail, A. Kumar, I. Francesconi, M. Anbazhagan, Q. Hu, F. A. Tanious, T. Wenzler, J. Saulter, W. D. Wilson, R. Brun, D. W. Boykin, R. R. Tidwell, J. E. Hall, Antimicrob. Agents Chemother. 2007, 51, 2801;
- 9fN. C. Seeman, J. M. Rosenberg, A. Rich, Proc. Natl. Acad. Sci. USA 1976, 73, 804;
- 9gR. Wing, H. Drew, T. Takano, C. Broka, S. Tanaka, K. Itakura, R. E. Dickerson, Nature 1980, 287, 755;
- 9hX. Shui, L. McFail-Isom, G. G. Hu, L. D. Williams, Biochemistry 1998, 37, 8341.
- 10
- 10aC. Zimmer, U. Wahnert, Prog. Biophys. Mol. Biol. 1986, 47, 31;
- 10bD. Patel, Proc. Natl. Acad. Sci. USA 1982, 79, 6424;
- 10cM. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, R. E. Dickerson, Proc. Natl. Acad. Sci. USA 1985, 82, 1376;
- 10dL. A. Marky, K. Breslauer, Proc. Natl. Acad. Sci. USA 1987, 84, 4359.
- 11G. I. Pascu, A. C. G. Hotze, C. Sanchez-Cano, B. M. Kariuki, M. J. Hannon, Angew. Chem. 2007, 119, 4452;
10.1002/ange.200700656 Google ScholarAngew. Chem. Intl. Ed. 2007, 46, 4374.
- 12
- 12aJ. A. Smith, J. G. Collins, B. T. Patterson, F. R. Keene, Dalton Trans. 2004, 1277;
- 12bC. B. Spillane, J. L. Morgan, N. C. Fletcher, J. G. Collins, F. R. Keene, Dalton Trans. 2006, 3122;
- 12cC. B. Spillane, J. A. Smith, J. L. Morgan, F. R. Keene, J. Biol. Inorg. Chem. 2007, 819;
- 12dJ. L. Morgan, C. B. Spillane, J. A. Smith, D. P. Buck, J. G. Collins, F. R. Keene, Dalton Trans. 2007, 4333.
- 13V. Gonzalez, T. Wilson, I. Kurihara, A. Imai, J. A. Thomas, J. Otsuki, Chem. Commun. 2008, 1868.
- 14
- 14aL. Juris, V. Balzani, R. Barigelletti, S. Campagna, P. Belser, A. V. Zelewsky, Coord. Chem. Rev. 1988, 84, 85;
- 14bV. Balzani, A. Juris, M. Venturi, S. Campagna, S. Serroni, Chem. Rev. 1996, 96, 759;
- 14cS. R. Stoyanov, J. M. Villegas, D. P. Rillema, Inorg. Chem. 2002, 41, 2941.
- 15
- 15aR. Englman, J. Jortner, Mol. Phys. 1970, 18, 145;
- 15bJ. V. Caspar, T. J. Meyer, J. Phys. Chem. 1983, 87, 952.
- 16
- 16aC. Hiort, P. Lincoln, B. Nordén, J. Am. Chem. Soc. 1993, 115, 3448;
- 16bF. M. O’Reilly, J. M. Kelly, New J. Chem. 1998, 22, 215;
- 16cC. Moucheron, A. Kirsch-DeMesmaeker, J. Phys. Org. Chem. 1998, 11, 577;
- 16dI. Ortmans, B. Elias, J. M. Kelly, C. Moucheron, A. Kirsch-DeMesmaeker, Dalton Trans. 2004, 668.
- 17A. M. Pyle, J. P. Rehman, R. Meshoyrer, C. V. Kumar, N. J. Turro, J. K. Barton, J. Am. Chem. Soc. 1989, 111, 3051.
- 18
- 18aC. Moucheron, A. Kirsch-DeMesmaeker, J. M. Kelly, J. Photochem. Photobiol. B 1997, 40, 91;
- 18bI. Ortmans, C. Moucheron, A. Kirsch-DeMesmaeker, Coord. Chem. Rev. 1998, 168, 233;
- 18cT. Phillips, I. Haq, A. J. H. Meijer, H. Adams, I. Soutar, L. Swanson, M. J. Sykes, J. A. Thomas, Biochemistry 2004, 43, 13657.
- 19
- 19aG. Ramakrishna, D. A. Jose, D. Krishna Kumar, A. Das, D. K. Palit, H. N. Ghosh, J. Phys. Chem. B 2005, 109, 15445;
- 19bS. Verma, P. Kar, A. Das, D. K. Palit, H. N. Ghosh, J. Phys. Chem. C 2008, 112, 2918.
- 20
- 20aD. A. Jose, P. Kar, D. Koley, B. Ganguly, W. Thiel, H. N. Ghosh, A. Das, Inorg. Chem. 2007, 46, 5576;
- 20bA. D. Shukla, B. Whittle, H. C. Bajaj, A. Das, M. D. Ward, Inorg. Chim. Acta 1999, 285, 89.
- 21
- 21aA. Ghosh, B. Ganguly, A. Das, Inorg. Chem. 2007, 46, 9912;
- 21bA. Ghosh, S. Verma, B. Ganguly, H. N. Ghosh, A. Das, Eur. J. Inorg. Chem. 2009, 2496.
- 22J. D. McGhee, P. H. von Hippel, J. Mol. Biol. 1974, 86, 469.
- 23E. Tuite, P. Lincoln, B. Nordén, J. Am. Chem. Soc. 1997, 119, 239.
- 24
- 24aY. Kim, J. H. Geiger, S. Hahn, P. B. Sigler, Nature 1993, 365, 512;
- 24bJ. L. Kim, D. B. Nikolov, S. K. Burley, Nature 1993, 365, 520;
- 24cM. J. Packer, M. P. Dauncey, C. A. Hunter, J. Mol. Biol. 2000, 295, 71;
- 24dM. J. Packer, M. P. Dauncey, C. A. Hunter, J. Mol. Biol. 2000, 295, 85.
- 25
- 25aH. C. M. Nelson, J. T. Finch, B. F. Luisi, A. Klug, Nature 1987, 330, 221;
- 25bM. Shatzky-Schwartz, N. D. Arbuckle, M. Eisenstein, D. Rabinovich, A. Bareket-Samish, T. E. Haran, B. F. Luisi, Z. Shakked, J. Mol. Biol. 1997, 267, 595.
- 26
- 26aM. H. Sarma, G. Gupta, R. H. Sarma, Biochemistry 1986, 25, 3659;
- 26bH. R. Drew, M. J. McCall, Annu. Rev. Cell Biol. 1988, 4, 1.
- 27See, for example:
- 27aS. R. Smith, G. A. Neyhart, W. A. Karlsbeck, H. H. Thorp, New J. Chem. 1994, 18, 397;
- 27bI. Haq, P. Lincoln, D. Suh, B. Norden, B. Z. Chowdhry, J. B. Chaires, J. Am. Chem. Soc. 1995, 117, 4788;
- 27cR. B. Nair, E. S. Teng, S. L. Kirkland, C. J. Murphy, Inorg. Chem. 1998, 37, 139.
- 28
- 28aA. M. Pyle, E. C. Long, J. K. Barton, J. Am. Chem. Soc. 1989, 111, 4520;
- 28bC. G. Coates, J. J. McGarvey, P. L. Callaghan, M. Coletti, J. G. Hamilton, J. Phys. Chem. B 2001, 105, 730;
- 28cD. A. Lutterman, A. Chouai, Y. Liu, Y. Sun, C. D. Stewart, K. R. Dunbar, C. Turro, J. Am. Chem. Soc. 2008, 130, 1163.
- 29C. Rajput, R. Rutkaite, L. Swanson, I. Haq, J. A. Thomas, Chem. Eur. J. 2006, 12, 4611.
- 30C. Metcalfe, M. Webb, J. A. Thomas, Chem. Commun. 2002, 2026.
- 31
- 31aD. L. Carlson, D. H. Huchital, E. J. Mantilla, R. D. Sheardy, W. R. Murphy, J. Am. Chem. Soc. 1993, 115, 6424;
- 31bJ.-G. Liu, Q.-L. Zhang, X.-F. Shi, L.-N. Ji, Inorg. Chem. 2001, 40, 5045;
- 31cC. Metcalfe, I. Haq, J. A. Thomas, Inorg. Chem. 2004, 43, 317.
- 32S. Satyanarayana, J. C. Dabrowiak, J. B. Chaires, Biochemistry 1992, 31, 9319.
- 33R. C. Young, T. J. Meyers, D. G. Whitten, J. Am. Chem. Soc. 1976, 98, 286.
- 34aM. E. Reichmann, S. A. Rice, C. A. Thomas, P. Doty, J. Am. Chem. Soc. 1954, 76, 3047;
- 34bP. O. Vardevanyan, A. P. Antonyan, G. A. Manukyan, A. T. Karapetyan, A. K. Shchyolkina, O. F. Borlsova, Mol. Biol. 2000, 34, 272;
- 34cJ. Ren, J. B. Chaires, Biochemistry 1999, 38, 16067–16075.
- 35
- 35aW. Paw, R. Eisenberg, Inorg. Chem. 1997, 36, 2287.
- 36
- 36aI. P. Evans, A. Spencer, G. Wilkinson, J. Chem. Soc. Dalton Trans. 1973, 204;
- 36bT. Suzuki, T. Kuchiyama, S. Kishi, S. Kaizaki, H. D. Takagi, M. Kato, Inorg. Chem. 2003, 42, 785.