Abstract
The hydrolysis reaction mechanisms of a new generation Pd(II) anticancer drugs containing coumarin derivatives have been investigated combining density functional theory with the conductor-like dielectric continuum model approach. The first and the second aquation processes have been explored for the cis and trans counterpart of title PdL2 complex. Two possibilities for the second hydrolysis process have been analyzed for both compounds. From our data emerge that cis and trans PdL2 compounds have a different behavior in water. cis-isomer readily undergo first hydrolysis process generating a mono-aqua complex while both the pathways investigated for the second aquation reaction are more energetically demanding, suggesting that the mono-aqua complex could act as active species. On the contrary, for trans-compound, both the investigated reactions for the second aquation process occur by overcoming activation barriers comparable with that found for the first hydrolysis reaction. According to our data, trans-oriented PdL2 drug could undergo degradation process generating non-active compounds with the consequent lack of pharmacological activity.
Similar content being viewed by others
References
Rosenberg B, Camp L, Krigas T (1965) Nature 205:698
Rosenberg B, Camp L, Trosko J, Mansour VH (1969) Nature 222:385
Brabec V, Leng M (1993) Proc Natl Acad Sci USA 90:5345
Zheng HH, Xu ZH, Wang K (1997) Int J Biol Macromol 20:107
Du WH, Han W, Li ZF, Wang BH (2000) Thermochim Acta 359:55
Novakova O, Kasparkova J, Malina J, Natile G, Brabec V (2003) Nucleic Acids Res 31:6450
Coluccia M, Natile G (2007) Anti-Cancer Agents Med Chem 7:111
Kalinowska-Lis U, Ochocki J, Matlawska-Wasowska K (2008) Coord Chem Rev 252:1328
Guo Z, Sadler PJ (1999) Angew Chem Int Ed 38:1512
Farrer N, Salassa L, Sadler PJ (2009) Dalton Trans 2009:10690
Blower P (2006) Dalton Trans 2006:1705
Wang X, Guo Z (2008) Dalton Trans 2008:1521
Fricker SP (2007) Dalton Trans 2007:4903
Fricker SP (2010) Metallomics 2:366
Reedijk J (2008) Macromol Symp 270:193
Martínez-Lillo J, Mastropietro TF, Lappano R, Madeo A, Alberto ME, Russo N, Maggiolini M, De Munno G (2011) Chem Commun 47:5283
Curic M, Tusek-Bozic L, Vikic-Topic D, Furlani SVA, Balzarini J, De Clercq E (1996) J Inorg Biochem 63:129
Kirschner S, Wei YK, Francis D, Bergman JS (1966) Med Chem 9:369
Higgins JD, Neely L, Fricker S (1993) J Inorg Biochem 49:149
Gonzalez ML, Tercero JM, Matilla A, Niclos-Gutierrez J, Fernandez MT, Lopez MC, Alonso C, Gonzalez S (1997) Inorg Chem 36:1806
Gill DS (1984) In: Hacker MP, Douple EB, Krakoff IH (eds) Platinum coordination complexes in cancer chemotherapy. Nijhoff, Boston, pp 267–278
Al-Allaf TA, Rashan LJ (2001) Boll Chim Farm 140:205
Al-Allaf TA, Ayoub MT, Rashan LJ (1990) J Inorg Biochem 38:47
Al-Allaf TA, Rashan LJ (1998) Eur J Med Chem 33:817
Al-Allaf TA, Rashan LJ, Khuzaie RF, Halseh WF (1997) Asian J Chem 9:239
Al-Allaf TA, Rashan LJ, Abu-Surrah AS, Fawzi R, Steimann M (1998) Trans Met Chem 23:403
Budzisz E, Keppler BK, Giester G, Wozniczka M, Kufelnicki A, Nawrot B (2004) Eur J Inorg Chem 2004:4412
Kostova I, Malonov I, Karaivanova M (2001) Arch Pharm Pharm Med Chem 334:157
Budzisz E, Małecka M, Lorenz IP, Mayer P, Kwiecien RA, Paneth P, Krajewska U, Rozalski M (2006) Inorg Chem 45:9688
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian, Inc., Wallingford
Becke AD (1993) J Chem Phys 98:5648
Lee CT, Yang WT, Parr RG (1988) Phys Rev B 37:785
Zhang Y, Guo Z, You XZ (2001) J Am Chem Soc 123:9378
Alberto ME, Lucas MF, Pavelka M, Russo N (2009) J Phys Chem B 113:14473
Alberto ME, Lucas MF, Pavelka M, Russo N (2008) J Phys Chem B 112:10765
Pavelka M, Lucas MF, Russo N (2007) Chem Eur J 13:10108
Lucas MF, Pavelka M, Alberto ME, Russo N (2009) J Phys Chem B 113:831
Alberto ME, Russo N (2011) Chem Commun 47:887
Andrae D, Haussermann U, Dolg M, Stoll H, Preuss H (1990) Theor Chim Acta 77:123
Gonzalez C, Schlegel HB (1990) J Phys Chem 94:5523–5527
Gonzalez C, Schlegel HB (1989) J Chem Phys 90:2154–2161
Cossi M, Rega N, Scalmani G, Barone V (2003) J Comput Chem 24:669
Klamt A, Jonas V, Burger T, Lohrenz JCW (1998) J Phys Chem A 102:5074
Würtz Jürgensen V, Jalkanen K (2006) Phys Biol 3:S63
Shi Z, Boyd RJ (1989) J Am Chem Soc 111:1575
Zhu C, Raber J, Eriksson L (2005) J Phys Chem B 109:12195
Melchior A, Sánchez ME, Pappalardo RR, Martínez JM (2011) Theor Chem Acc 128:627
Burda JV, Zeizinger M (2004) J Chem Phys 120:1253
Raber J, Zhu C, Eriksson L (2004) Mol Phys 102:2537
Alberto ME, Butera V, Russo N (2011) Inorg Chem 50:6965
Acknowledgment
The Università della Calabria and the MIUR PRIN 2008 (2008F5A3AF_005) are gratefully acknowledged for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Alberto, M.E., Cosentino, C. & Russo, N. Hydrolysis mechanism of anticancer Pd(II) complexes with coumarin derivatives: a theoretical investigation. Struct Chem 23, 831–839 (2012). https://doi.org/10.1007/s11224-011-9927-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-011-9927-4