Quantum-chemical study of the active sites of camptothecin through their Cu(II) coordination ability

Open access


The structures of camptothecin (CPT) lactone form and its complexes with Cu(II) were optimized at B3LYP/6-311G* level of theory. Their electronic structures were evaluated via QTAIM topological analysis of electron density and Mulliken population analysis. Stability, electron density distribution and geometrical factors of the optimized systems were compared. Both CPT nitrogen atoms show lower affinity to Cu(II) compared to the oxygen ones. Both the oxygen atom in the CPT lactone ring and the one in the neighbouring carbonyl group show the highest affinity to Cu(II) and the highest stability of Cu-CPT complexes which indicates the most probable CPT reaction sites.

Alagona G, Ghio C (2009) J. Phys. Chem. A 113: 15206-15216.

Alagona G, Ghio C (2009) Phys. Chem. Chem. Phys. 11: 776-790.

Bader RFW (1990) Atoms in Molecules: A Quantum Theory, Claredon Press, Oxford.

Becke AD (1993) J. Chem. Phys. 98: 5648-5652.

Biegler-Konig F, Schonbohm J, Bayles D (2001) J.Comput. Chem. 22: 545-549. Available from: http://www.aim2000.de.

Burke TG, Mi Z (1994) J. Med. Chem. 37: 40-46.

Carbonero RG, Supko JG (2002) Clin. Cancer Res. 8: 641.

Dvoranova D, Bobeničova M, Šoralova S, Breza M (2013) Chem. Phys. Lett. 580: 141-144.

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR et al. (2003) Gaussian 03, Revision.C1, Gaussian, Inc., Pittsburgh PA.

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR et al. (2016) Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT.

Hsiang YH, Liu LF (1988) Cancer Res. 48: 1722-1726.

Kohn KW, Pommier Y (2000) Ann. N. Y. Acad. Sci. 922: 11-26.

Lee Ch, Yang W, Parr RG (1988) Phys. Rev. B 37(2): 785-789.

Lesueur-Ginot L, Demarquay D, Kiss R, Kasprzyk PG, Dassonneville L, Bailly C, Camara J, Lavergne O, Bigg DC (1999) Cancer Res. 59(12): 2939-2943.

Mammino L (2013) J. Mol. Model. 19: 2127-2142.

Mi Z, Burke TG (1994) Biochemistry 33: 10325-10336.

Mulliken RS (1955) J. Phys. Chem. 23: 1833-1840.

Mulliken RS (1955) J. Phys. Chem. 23: 1841-1846.

Puškarova I, Breza M (2016) Polym. Degrad. Stab. 128: 15-21.

Puškarova I, Breza M (2017) Chem. Phys. Let. 680: 78-82.

Redinbo MR, Stewart L, Kuhn P, Champoux JJ, Hol WGJ (1998) Science 279(5356): 1504-1513.

Sanna N, Chillemi G, Gontrani L, Grandi A, Mancini G, Castelli S, Zagotto G, Zazza C, Barone V, Desideri A (2009) J. Phys. Chem. 113(16): 5369-5375.

Ugliengo P (2006) MOLDRAW: a Program to Display and Manipulate Molecular and Crystal Structures, Torino. Available from: http://www.moldraw.unito.it.

Wall ME, Wani MC, Cook CE, Palmer KH, McPhail HT, Sim GA (1966) J. Am. Chem. Soc. 88: 3888-3890.

Acta Chimica Slovaca

The Journal of Slovak University of Technology in Bratislava

Journal Information


All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 75 75 18
PDF Downloads 47 47 10