Abstract
Interaction of cisplatin in activated diaqua-form with His-Met dipeptide is explored using DFT approach with PCM model. First the conformation space of the dipeptide is explored to find the most stable structure (labeled 0683). Several functionals with double-zeta basis set are used for optimization and obtained order of conformers is confirmed by the CCSD(T) single-point calculations. Supermolecular model is used to determine reaction coordinate for the replacement of aqua ligands consequently by N-site of histidine and S-site of methionine and reversely. Despite the monoadduct of Pt–S(Met) is thermodynamically less stable this reaction passes substantially faster (by several orders of magnitude) than coordination of cisplatin to histidine. The consequent chelate formation occurs relatively fast with energy release up to 12 kcal mol−1.
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References
Eastman A (1999) In: Lippert B (ed) Cisplatin. Wiley-VCH, Weinheim, pp 111–134
Hindmarsh K, House DA, Turnbull MM (1997) Inorg Chim Acta 257:11–18
Miller SE, House DA (1991) Inorg Chim Acta 187:125–132
Miller SE, Gerard KJ, House DA (1991) Inorg Chim Acta 190:135–144
Zimmermann T, Leszczynski J, Burda JV (2011) J Mol Model 17:2385–2393
Burda JV, Zeizinger M, Leszczynski J (2005) J Comput Chem 26:907–914
Pascoe JM, Roberts JJ (1974) Biochem Pharmacol 23:1345–1357
Peleg-Shulman T, Najajreh Y, Gibson D (2002) J Inorg Biochem 91:306–311
Kartalou M, Essigmann JM (2001) Mutat Res Fundam Mol Mech Mutagen 478:1–21
Fojta M, Pivonkova H, Brazdova M, Kovarova L, Palecek E, Pospisilova S, Vojtesek B, Kasparkova J, Brabec V (2003) Biochem Pharmacol 65:1305–1316
Pivonkova H, Pecinka P, Ceskova P, Fojta M (2006) FEBS J 273:4693–4706
Donahue BA, Augot M, Bellon SF, Treiber DK, Toney JH, Lippard SJ, Essigmann JM (1990) Biochemistry 29:5872–5880
Andrews PA, Jones JA (1991) Cancer Commun 3:1–10
Burger AM, Double JA, Newell DR (1997) Eur J Cancer 33:638–644
Zamble DB, Lippard SJ (1999) In: Lippert B (ed) Cisplatin. Wiley-VCH, Weinheim, pp 73–110
Lippert B (1999) Cisplatin: chem. and biochemistry of a leading anticancer drug. Wiley-VCH, Wienheim
Zimmermann T, Zeizinger M, Burda JV (2005) J Inorg Biochem 99:2184–2196
Zimmermann T, Chval Z, Burda JV (2009) J Phys Chem B 113:3139–3150. https://doi.org/10.1021/jp807645x
Zimmermann T, Burda JV (2010) Dalton Trans 39:1295–1301
Norman RE, Ranford JD, Sadler PJ (1992) Inorg Chem 31:877–888
Williams KM, Rowan C, Mitchell J (2004) Inorg Chem 43:1190–1196
Appleton TG, Connor JW, Hall JR (1988) Inorg Chem 27:130–137
Wei HY, Liu Q, Lin J, Jiang PJ, Guo ZJ (2004) Inorg Chem Commun 7:792–794
Riley CM, Sternson LA, Repta AJ (1983) J Pharm Sci 72:351–355
Reedijk J (1999) Chem Rev 99:2499–2510
Vrana O, Brabec V (2002) Biochemistry 41:10994–10999
Manka S, Becker F, Hohage O, Sheldrick WS (2004) J Inorg Biochem 98:1947–1956
Hohage O, Sheldrick WS (2006) J Inorg Biochem 100:1506–1513
Appleton TG, Connor JW, Hall JR, Prenzler PD (1989) Inorg Chem 28:2030–2037
Bose RN, Ghosh SK, Moghaddas S (1997) J Inorg Biochem 65:199–205
Lau JKC, Deubel DV (2005) Chem Eur J 11:2849–2855
Hagrman D, Goodisman J, Souid A-K (2004) J. Pharmacol Exp Ther 308:658–666
Dabrowiak JC, Goodisman J, Souid A-K (2002) Drug Metab Dispos 30:1378–1384
Dedon PC, Borch RF (1987) Biochem Pharmacol 36:1955–1964
Bose RN, Moghaddas S, Weaver EL, Cox EH (1995) Inorg Chem 34:5878–5883
Zou J, Yang XD, An F, Wang K (1998) J Inorg Biochem 70:227–232
Da Silva VJ, Costa LAS, Dos Santos HF (2008) Int J Quantum Chem 108:401–414
Chang GR, Zhou LX, Chen D (2006) Chin J Struct Chem 25:533–542
Robertazzi A, Platts JA (2004) J Comput Chem 25:1060–1067
Robertazzi A, Platts JA (2005) Inorg Chem 44:267–274
Robertazzi A, Platts JA (2006) Chem Eur J 12:5747–5756
Wysokinski R, Hernik K, Szostak R, Michalska D (2007) Chem Phys 333:37–48
Yuan QH, Zhou LX (2007) Chin J Struct Chem 26:962–972
Erturk H, Hofmann A, Puchta R, van Eldik R (2007) Dalton Trans 22:2295–2301
Hao L, Zhang Y, Tan HW, Chen GJ (2007) Chem J Chin Univ Chin 28:1160–1164
Pavelka M, Lucas MFA, Russo N (2007) Chem Eur J 13:10108–10116
Pavelka M, Šimánek M, Šponer J, Burda JV (2006) J Phys Chem A 110:4795–4809
Hofmann A, Jaganyi D, Munro OQ, Liehr G, van Eldik R (2003) Inorg Chem 42:1688–1700
Zhu HJ, Ziegler T (2006) J Organomet Chem 691:4486–4497
Tsipis AC, Sigalas MP (2002) J Mol Struct (Theochem) 584:235–248
Zhu C, Raber J, Eriksson LA (2005) J Phys Chem B 109:12195–12205
Song T, Hu P (2006) J Chem Phys 125:091101
Jia M, Qu W, Yang Z, Chen G (2005) Int J Mod Phys B 19:2939–2949
Zhang Y, Guo Z, You X-Z (2001) J Am Chem Soc 123:9378–9387
Lau JKC, Deubel DV (2006) J Chem Theory Comput 2:103–106
Dos Santos HF, Marcial BL, De Miranda CF, Costa LAS, De Almeida WB (2006) J Inorg Biochem 100:1594–1605
Lopes JF, Menezes VSD, Duarte HA, Rocha WR, De Almeida WB, Dos Santos HF (2006) J Phys Chem B 110:12047–12054
Costa LA, Hambley TW, Rocha WR, Almeida WB, Dos Santos HF (2006) Int J Quantum Chem 106:2129–2144
Šebesta F, Burda JV (2017) J Inorg Biochem 172:100–109
Zimmermann T, Burda JV (2009) J Chem Phys 131:135101
Zeizinger M, Burda JV, Šponer J, Kapsa V, Leszczynski J (2001) J Phys Chem A 105:8086–8092
Burda JV, Zeizinger M, Leszczynski J (2004) J Chem Phys 120:1253–1262
Parr RG, Pearson RG (1983) J Am Chem Soc 105:7512
Miertus S, Scrocco E, Tomasi J (1981) Chem Phys 55:117–129
Miertus S, Tomasi J (1982) Chem Phys 65:239–245
Glendening ED, Badenhoop K, Ree AE, Carpenter JE, Bohmann JA, Morales M, Weinhold F (2001). University of Wisconsin, Madison, Wisconsin 53706, Wisconsin
Barone V, Cossi M, Tomasi J (1997) J Chem Phys 107:3210–3221
Bader RFW (1990) Atoms in molecules: a quantum theory. Oxford University Press, Oxford
Keith TA (2014) http://aim.tkgristmill.com. Accessed 30 Sept 2014
Politzer P, Laurence PR, Jayasuriya K (1985) Environ Health Perspect 61:191–202
Murray et al (2011) WIREs Comput Mol Sci 1:153
Sjoberg P, Murray JS, Brinck T, Politzer P (1990) Can J Chem 68:1440
Murray JS, Brinck T, Grice ME, Politzer P (1992) J Mol Struct Theor Chem 256:29–45
Politzer P, Murray JS, Bulat FA (2010) J Mol Model 16:1731
Andrae D, Haussermann U, Dolg M, Stoll H, Preuss H (1990) Theor Chim Acta 77:123–141
Burda JV, Runenberg N, Pyykko P (1998) Chem Phys Lett 288:635–641
Burda JV, Zeizinger M, Sponer J, Leszczynski J (2000) J Chem Phys 113:2224–2232
Wertz DH (1980) J Am Chem Soc 102:5316–5322
Cheng M-J, Nielsen RJ, Goddard Iii WA (2014) Chem Commun 50:10994–10996. https://doi.org/10.1039/C4CC03067B
Ramachandran GN, Ramakrishnan C, Sasisekharan V (1963) J Mol Biol 7:95–99
Chojnacki H, Kuduk-Jaworska J, Jaroszewicz I, Janski JJ (2009) Pol J Chem 83:1013–1024
Melchior A, Martínez JM, Pappalardo RR, Marcos ES (2013) J Chem Theory Comput 9:4562–4573
Burda JV, Sponer J, Leszczynski J (2000) J Biol Inorg Chem 5:178–188
Kozelka J, Chottard J-C (1990) Biophys Chem 35:165–178
Burda JV, Leszczynski J (2003) Inorg Chem 42:7162–7172
Spiegel K, Carloni P (2004) Abstr Pap Am Chem Soc 227:U1547–U1547
Zeizinger M, Burda JV, Leszczynski J (2004) Phys Chem Chem Phys 6:3585–3590
Deubel DV (2005) Abstr Pap Am Chem Soc 230:U2131–U2131
Raber J, Zhu C, Eriksson LA (2005) J Phys Chem B 109:11006–11015
Pavelka M, Burda JV (2007) J Mol Model 13:367–379
Gkionis K, Mutter ST, Platts JA (2013) RSC Adv 3:4066–4073. https://doi.org/10.1039/C3RA23041D
Zhu M, Zhou L (2015) Comput Theor Chem 1051:24–34. https://doi.org/10.1016/j.comptc.2014.10.036
Ceron-Carrasco JP, Jacquemin D, Cauet E (2012) Phys Chem Chem Phys 14:12457–12464. https://doi.org/10.1039/C2CP40515F
Deubel DV (2006) J Am Chem Soc 128:1654–1663
Froeling CDW, Sheldrick WS (1997) Chem Commun 1737–1738. https://doi.org/10.1039/A702904G
Djuran MI, Dimitrijevic DP, Milinkovic SU, Bugarčic ŽD (2002) Transit Met Chem 27:151–158
Dos Santos HF, Paschoal D, Burda JV (2012) J Phys Chem A 116:11015–11024. https://doi.org/10.1021/jp307977p
Dos Santos HF, Paschoal D, Burda JV (2012) Chem Phys Lett 548:64–70. https://doi.org/10.1016/j.cplett.2012.07.080
Bradáč O, Zimmermann T, Burda JV (2008) J Mol Model 14:705–716. https://doi.org/10.1007/s00894-008-0285-0
Futera Z, Platts JA, Burda JV (2012) J Comput Chem 33:2092–2101
Bancroft DP, Lepre CA, Lippard SJ (1990) J Am Chem Soc 112:6860–6871. https://doi.org/10.1021/ja00175a020
Kleine M, Wolters D, Sheldrick WS (2003) J Inorg Biochem 97:354–363
Barnham KJ, Djuran MJ, Murdoch PDS, Sadler PJ (1994) J Chem Soc Chem Commun. https://doi.org/10.1039/C39940000721
Djuran MI, Lempers ELM, Reedijk J (1991) Inorg Chem 30:2648–2652
Acknowledgements
Authors (JVB and MM) are grateful for supporting this study to the Grant Agency of Czech Republic Project no 16-06240S. We would also like to acknowledge a generous access to computational facilities of the National Grid Infrastructure MetaCentrum, provided under the program ‘Projects of Large Infrastructure for Research, Development, and Innovations’ (LM2010005).
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Maixner, M., Dos Santos, H.F. & Burda, J.V. Formation of chelate structure between His-Met dipeptide and diaqua-cisplatin complex; DFT/PCM computational study. J Biol Inorg Chem 23, 363–376 (2018). https://doi.org/10.1007/s00775-018-1536-x
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DOI: https://doi.org/10.1007/s00775-018-1536-x