Ab Initio and DFT Study on Cyclophosphamide: Anticancer and Immunomodulating Agents
Giuseppe Bruno
+ Author Affiliations
- Author Affiliations
Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Viale F. Stagno d’Alcontres, 98166, Messina, Italy. Email: gbruno@unime.it
Australian Journal of Chemistry 71(7) 511-523 https://doi.org/10.1071/CH18133
Submitted: 31 March 2018 Accepted: 02 June 2018 Published: 3 July 2018
Abstract
Cyclophosphamide is presently the most frequently used drug for antineoplastic chemotherapy. It has shown a great response in the treatment of human malignancies including leukemia, lymphoma, germ cell tumours, medulloblastomas, and carcinomas of the breast, lung, and cervix. Cyclophosphamide is also one of the most important immunosuppressive agents. This study investigates the quantum-chemical electronic properties of cyclophosphamide, as well as some of its metabolites, which are computed using ab-initio and DFT calculations. The interaction energy calculations between water molecules and the cyclophosphamide show how, in the solid state, the presence of water of crystallisation will make cyclophosphamide more stable over time. Atomic charges, dipole moment, frontier molecular orbitals, electrostatic potential isosurface, geometric parameters, and proton affinity on every nitrogen site enable the characterisation of the electronic properties and clearly illustrate the reactive sites that could be associated with this biologically important class of molecules.
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