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

Open access

Abstract

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.

If the inline PDF is not rendering correctly, you can download the PDF file here.

  • 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.

Search
Journal information
Metrics
All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 194 103 2
PDF Downloads 137 77 1