240
Views
46
CrossRef citations to date
0
Altmetric
Original Articles

Intercalation of Daunomycin into Stacked DNA Base Pairs. DFT Study of an Anticancer Drug

, , , , , & show all
Pages 115-129 | Received 20 Mar 2008, Published online: 15 May 2012

References and Footnotes

  • Arcamone , F. 1981 . Doxorubicin-Anticancer Antibiotics. New York , NY : Academic Press .
  • Gewirtz , D. A. 1999 . Biochem Pharmacol , 57 : 727 – 741 . refs. therein
  • Hendry , L. B. , Mahesh , V. B. , Bransome , E. D. Jr. and Ewing , D. E. 2007 . Mutat Res , 623 : 53 – 71 . (a). (b) L. Strekowski and B. Wilson. Mutat Res 623, 3–13 (2007); (c) L. R. Ferguson and W. A. Denny. Mutat Res 623, 14–23 (2007)
  • Kelley , S. O. , Jackson , N. M. , Hill , M. G. and Barton , J. K. 1999 . Angew Chem Int Ed , 38 : 941 – 945 .
  • Rabbani , A. , Abdosamadi , S. , Sari-Saraf , N. and See, for example . 2007 . Acta Pharmacol Sin , 28 : 731 – 737 . (a). (b) S. J. Zargar and A. Rabbani. Int J Biol Macromol 28, 75–79 (2000)
  • Capobianco , M. L. , De Champdore , M. , Arcamone , F. , Garbesi , A. , Guianvarc'h , D. , Arimondo , P. B. and See, for example . 2005 . Bioorg Med Chem , 13 : 3209 – 3218 . (a). (b) Y. S. Rho, W.-J. Kim, and J. Y. Dong. Bull Korean Chem Soc 27, 1359–1363 (2006); (c) G. M. Carbone, E. Mc Guffie, S. Napoli, C. E. Flanagan, C. Dembech, U. Negri, F. Arcamone, M. L. Capobianco, and C. V. Catapano. Nucleic Acids Res 32, 2396–2410 (2004); (d) D. A. Veselkov, L. Karawajew, A. N. Veselkov, and D. B. Davies. Mol Phys 102, 1933–1942 (2004)
  • Davies , D. B. , Eaton , R. J. , Baranovsky , S. F. and Veselkov , A. N. 2000 . J Biomol Struct Dyn , 17 : 887 – 901 . refs. therein
  • Saenger , W. 1984 . Principles of Nucleic Acid Structure 350 – 367 . New York : Springer Verlag . (a). (b) V. A. Bloomfield, D. M. Crothers, and I. Tinoco Jr. Nucleic Acids, structures, properties and functions, p 535–596. University Science Books, Sausalito (CA) (2000)
  • Suh , D. , Oh , Y.-K. , Hur , M.-W. , Ahn , B. and Chaires , J. B. 2002 . Nucleosides, Nucleotides Nucleic Acids , 21 : 637 – 649 . (a). (b) C. Medhi, J. B. O. Mitchell, S. L. Price, and A. B. Tabor. Biopolymers 52, 84–93 (1999); (c) X. Shi and R. B. Macgregor, Jr. Biophys Chem 125, 471–482 (2007); (c) D. Tsankov, V. Maharaj, J. H. van de Sande, and H. Wieser. Vib Spectrosc 43, 152–164 (2007); (d) J. B. Chaires. Biophys Chem 35, 191–202 (1990); (e) H. Bao, X. Wang, H. Yu, M. Fu, X. Qu, Y. Zheng, and J. Ren. Chem Phys Lett 436, 252–257 (2007); (f) G.-F. Cheng, J. Zhao, Y.-H. Tu, P.-G. He, and Y.-Z. Fang. Chin J Chem 23, 576–580 (2005)
  • Nunn , C. M. , Van Meervelt , L. , Zhang , S. , Moore , M. H. and Kennard , O. 1991 . J Mol Biol , 222 : 167 – 177 . (a). (b) C. A. Frederick, L. D. Williams, G. Ughetto, G. A. van der Marel, J. H. van Boom, A. Rich, and A. H.-J. Wang. Biochemistry 29, 2538–2549 (1990)
  • Xodo , L. E. , Manzini , G. , Ruggiero , J. and Quadrifoglio , F. 1988 . Biopolymers , 27 : 1839 – 1857 . (a). (b) A. Skorobogaty, R. J. White, D. R. Phillips, and J. A. Reiss. Drug Des Deliv 3, 125–151 (1988)
  • Chen , K.-X. , Gresh , N. and Pullman , B. 1985 . J Biomol Struct Dyn , 3 : 445 – 466 .
  • Robinson , H. , Priebe , W. , Chaires , J. B. and Wang , A. H.-J. 1997 . Biochemistry , 36 : 8663 – 8670 . (a). (b) I. Berger, L. Su, J. R. Spitzner, C.-H. Kang, T. G. Burke, and A. Rich. Nucleic Acids Res 23, 4488–4494 (1995); (c) G. A. Leonard, T. Brown, and W. N. Hunter. Eur J Biochem 204, 69–74 (1992); (d) B. Langlois d'Estaintot, B. Gallois, T. Brown, and W. N. Hunter. Nucleic Acids Res 20, 3561–3566 (1992)
  • Parajuli , R. and Medhi , C. 2006 . Ind J Chem , 45A : 146 – 158 . (a). (b) D. Reha, M. Kabelac, F. Ryjacek, J. Sponer, J. E. Sponer, M. Elstner, S. Suhai, and P. Hobza. J Am Chem Soc 124, 3366–3376 (2002); (c) T. Kubar, M. Hanus, F. Ryjacek, and P. Hobza. Chem Eur J 12, 280–290 (2006); P. Hobza, J. Sponer, and M. Polasek. J Am Chem Soc 117, 792–798 (1995);(d) J. Sponer, J. Leszczynski, and P. Hobza. J Phys Chem 100, 5590–5596 (1996); (e) P. Jurecka, J. Sponer, and P. Hobza. J Phys Chem B 108, 5466–5471 (2004); (f) P. Hobza, M. Kabelac, J. Sponer, P. Mejzlik, and J. Vondrasek. J Comput Chem 18, 1136–1150 (1997)
  • Cashman , D. J. and Kellogg , G. E. 2004 . J Med Chem , 47 : 1360 – 1374 . (a). (b) J. Gallego, A. R. Ortiz, B. de Pascual-Teresa, and F. Gago. J Comput-Aided Mol Des 11, 114–128 (1997); (c) J. Gallego, F. J. Luque, M. Orozco, C. Burgos, J. Alvarez-Builla, M. M. Rodrigo, and F. Gago. J Med Chem 37, 1602–1609 (1994); (d) D. Han, H. Wang, and N. Ren. J Mol Struct (Theochem) 711, 185–192 (2004); (e) D. A. Bondarev, W. J. Skawinski, and C. A. Venanzi. J Phys Chem B 104, 815–822 (2000)
  • Zhao , Y. , Truhlar , D. G. and See, for example . 2006 . J Phys Chem A , 110 : 5121 – 5129 . (a). (b) Y. Zhao, N. E. Schultz, and D. G. Truhlar. J Chem Theory Comput 2, 364–382 (2006)
  • Swart , M. , van der Wijst , T. , Fonseca Guerra , C. and Bickelhaupt , F. M. 2007 . J Mol Model , 12 : 1245 – 1257 . references therein
  • Slater , J. C. 1974 . Quantum Theory of Molecules and Solids, Vol. 4. New York : McGraw-Hill . (a). (b) S. H. Vosko, L. Wilk, and M. Nusair. Can J Phys 58, 1200–1211 (1980)
  • Keal , T. W. and Tozer , D. J. 2004 . J Chem Phys , 121 : 5654 – 5660 .
  • Fonseca Guerra , C. , Bickelhaupt , F. M. , Snijders , J. G. and Baerends , E. J. 1999 . Chem Eur J , 5 : 3581 – 3594 . (a). (b) C. Fonseca Guerra, F. M. Bickelhaupt, J. G. Snijders, and E. J. Baerends. J Am Chem Soc 122, 4117–4128 (2000); (c) T. van der Wijst, C. Fonseca Guerra, M. Swart, and F. M. Bickelhaupt. Chem Phys Lett 426, 415–421 (2006)
  • Bickelhaupt , F. M. and Baerends , E. J. 2000 . Rev Comput Chem, Vol. Edited by: Lipkowitz , K. B. and Boyd , D. B. Vol. 15 , New York : Wiley-VCH . pp 1–86
  • te Velde , G. , Bickelhaupt , F. M. , Baerends , E. J. , Fonseca Guerra , C. , van Gisbergen , S. J.A. , Snijders , J. G. and Ziegler , T. 2001 . J Comput Chem , 22 : 931 – 967 . (a). (b) C. Fonseca Guerra, O. Visser, J. G. Snijders, G. te Velde, and E. J. Baerends. In Methods and Techniques for Computational Chemistry, pp 305–395. Eds., E. Clementi and G. Corongiu. STEF, Cagliari (1995); (c) E. J. Baerends, D. E. Ellis, and P. Ros. Chem Phys 2, 41–51 (1973); (d) E. J. Baerends and P. Ros. Chem Phys 8, 412–418 (1975); (e) E. J. Baerends and P. Ros. Int J Quantum Chem Symp 12, 169–190 (1978); (f) C. Fonseca Guerra, J. G. Snijders, G. te Velde, and E. J. Baerends. Theor Chem Acc 99, 391–403 (1998); (g) P. M. Boerrigter, G. te Velde, and E. J. Baerends. Int J Quantum Chem 33, 87–113 (1988); (h) G. te Velde and E. J. Baerends. J Comp Phys 99, 84–98 (1992); (i) J. G. Snijders, E. J. Baerends, and P. Vernooijs. At Nucl Data Tables 26, 483–509 (1982); (j) J. Krijn and E. J. Baerends. Fit-Functions in the HFS-Method, Internal Report (in Dutch). Vrije Universiteit, Amsterdam (1984); (k) L. Versluis and T. Ziegler. J Chem Phys 88, 322–328 (1988); (l) A. D. Becke. J Chem Phys 84, 4524–4529 (1986); (m) A. Becke. Phys Rev A 38, 3098–3100 (1988); (n) J. P. Perdew. Phys Rev B 33, 8822–8824 (1986) [Erratum: Phys Rev B 34, 7406–7406 (1986)); (o) L. Fan and T. Ziegler. J Chem Phys 94, 6057–6063 (1991)]
  • Baerends , E. J. , Autschbach , J. , Bérces , A. , Bickelhaupt , F. M. , Bo , C. , de Boeij , P. L. , Boerrigter , P. M. , Cavallo , L. , Chong , D. P. , Deng , L. , Dickson , R. M. , Ellis , D. E. , Fan , L. , Fischer , T. H. , Fonseca Guerra , C. , Van Gisbergen , S. J. A. , Groeneveld , J. A. , Gritsenko , O. V. , Grüning , M. , Harris , F. E. , van den Hoek , P. , Jacob , C. R. , Jacobsen , H. , Jensen , L. , van Kessel , G. , Kootstra , F. , van Lenthe , E. , Mc Cormack , D. A. , Michalak , A. , Neugebauer , J. , Osinga , V. P. , Patchkovskii , S. , Philipsen , P. H. T. , Post , D. , Pye , C. C. , Ravenek , W. , Ros , P. , Schipper , P. R. T. , Schreckenbach , G. , Snijders , J. G. , Solà , M. , Swart , M. , Swerhone , D. , te Velde , G. , Vernooijs , P. , Versluis , L. , Visscher , L. , Visser , O. , Wang , F. , Wesolowski , T. A. , van Wezenbeek , E. M. , Wiesenekker , G. , Wolff , S. K. , Woo , T. K. , Yakovlev , A. L. , Ziegler , T. and ADF . 2006 . Scientific Computing and Modeling Amsterdam , , The Netherlands (http://www.scm.com)
  • van Zeist , W.-J. , Fonseca Guerra , C. and Bickelhaupt , F. M. PyFrag 2007.01 (a), Department of Theoretical Chemistry, Vrije Universiteit, Amsterdam; (b) W.-J. van Zeist, C. Fonseca Guerra, and F. M. Bickelhaupt. J Comput Chem 29, 312–315 (2008)
  • Morokuma , K. 1971 . J Chem Phys , 55 : 1236 – 1244 . (a). (b) K. Kitaura and K. Morokuma. Int J Quantum Chem 10, 325–340 (1976)
  • Ziegler , T. and Rauk , A. 1979 . Inorg Chem , 18 : 1755 – 1759 . (a). (b) T. Ziegler and A. Rauk. Inorg Chem 18, 1558–1565 (1979); (c) T. Ziegler and A. Rauk. Theor Chim Acta 46, 110 (1977)
  • Stone , A. J. 1996 . The Theory of Intermolecular Forces. Oxford : Clarendon Press . (a). (b) A. J. Stone. Chem Phys Lett 211, 101–109 (1993); (c) A. Hesselmann, G. Jansen, and M. Schütz. J Chem Phys 122, 014103 (2005); (d) B. Jeziorski, R. Moszynski, and K. Szalewicz. Chem Rev 94, 1887–1930 (1994); (e) A. Fiethen, G. Jansen, A. Hesselmann, and M. Schütz. J Am Chem Soc 130, 1802–1803 (2008); (f) A. Hesselmann, G. Jansen, and M. Schütz. J Am Chem Soc 128, 11730–1173 (2006)
  • Fonseca Guerra , C. , Handgraaf , J.-W. , Baerends , E. J. and Bickelhaupt , F. M. 2004 . J Comput Chem , 25 : 189 – 210 . (b) F. M. Bickelhaupt, N. J. R. van Eikema Hommes, C. Fonseca Guerra, and E. J. Baerends. Organometallics 15, 2923–2931 (1996)
  • Voronoi , G. F. 1908 . J Reine Angew Math , 134 : 198 – 287 . (a). (b) C. Kittel. Introduction to Solid State Physics. Wiley, New York (1986)
  • Swart , M. , Rösler , E. and Bickelhaupt , F. M. 2007 . Eur J Inorg Chem , : 3646 – 3654 .
  • Klamt , A. and Schüürmann , G. 1993 . J Chem Soc Perkin Trans , 2 : 799 – 805 . (a) (b) C. C. Pye and T. Ziegler. Theor Chem Acc 101, 396–408 (1999)
  • Atkins , P. W. 1994 . Physical Chemistry. Oxford : Oxford University Press .
  • Swart , M. , van Duijnen , P. T. and Snijders , J. G. 2000 . J Comput Chem , 22 : 79 – 88 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.