Boron-fullerene nanoparticle as a carrier for delivery ofcyclophosphamide and its tow derivatives

The structures of boron-doped fullerene B-C59 (1) as a drug delivery system, phosphoramide (2) and two phosphoramides (3 and 4) which are derivatives of cyclophosphamide anticancer prodrug as well as their covalently bonded structures to B-C59 (5, 6 and 7) were optimized by DFT computations at B3LYP level of theory using 6-31G(d) basis set. Comparing compounds 5, 6 and 7 reveals that the fluoroderivative (-22.8318 kcal/mol) is more stable than bromo derivative (-22.5569 kcal/mol) and cyclophosphamide (-22.0483 kcal/mol). The dipole moments of drugs (~ 5.2, 5.1 D) have almost half values compared with those of their related compounds covalently bonded to the Boron-fullerene nanoparticle (~ 9.7, 9.8 D) reflecting attachment of drugs on the B-C59 significantly enhances the polarity of the whole systems which is a desired property for drug delivery in biological media. The HOMO-LUMO band gap of B-C59 (1) is near 2.3 eV and for drugs 2, 3, 4 are near 2.7 eV while those of compounds 4, 5 are smaller (2.1 eV) indicating decrease in electrical conductivities of the isolated drugs/B-C59 upon interactions.

Keywords:

DFT , Drug delivery , Cyclophosphamide , Boron-fullerene nanoparticle , Band gap