Host–Guest Complexation of Cucurbit[7]Uril and Cucurbit[8]Uril with the Antineoplastic and Multiple Sclerosis Agent Mitoxantrone (Novantrone)

Abstract

The nature of interactions between the neutral/protonated mitoxantrone and the cucurbit­[n]­uril (n = 7, 8) host system was analyzed by employing density functional theory calculations. A comparison between the inclusion complexes of CB[7] and CB[8] shows various subtle differences in the complexation thermodynamics, given as changes in the Gibbs energy. Doubly and quadruply charged mitoxantrone (MX) molecules spontaneously form complexes in a water solvent, which are modeled using the polarizable continuum model approach. Both CB[7] and CB[8] complexes are stable as the geometry of the cavity allows for electrostatic interactions between the charged MX arms and the rim of the CB cavity. CB[8] also forms a stable complex with two mitoxantrone molecules with their aromatic rings stacked inside the cavity. Both CB[7] and CB[8] show properties that can be utilized in drug delivery.

N-Methyl- and N-Phenylpiperazine Functionalized Styryl Dyes Inside Cucurbiturils: Theoretical Assessment of the Factors Governing the Host–Guest Recognition

“…The calculations were performed through the utilization of the Gaussian 09 suite of programs [63]. The most appropriate combination of a method and basis set was found to be the Minnesota functional M062X [64] with the double zeta 6-31G(d,p) basis set applied, and proven to be reliable in our previous investigations of the physicochemical properties of cucurbiturils [45][46][47]49,65]. Initial geometries of the host molecules were derived from TUHGAG (CB [7]) and BATWEA (CB [8]) entries deposited in the Cambridge Crystallographic Data Centre (CCSD) [66,67].…”

Enhanced Solubility of Ibuprofen by Complexation with β-Cyclodextrin and Citric Acid

“…The geometries of the three nominal compounds as well as those of the respective inclusion complexes were optimized at the M062X/6-31G* level of theory using the Gaussian 09 package of programs [34]. Minnesota M062X functional in combination with splitvalence double-ζ basis set was employed in the calculations as it has been proven to be reliable in reproducing geometrical parameters of a number of macrocyclic compounds and their inclusion complexes [32,33,35]. Vibrational frequencies (all of them positive), thermal energies, E th , and entropies, S, at 25 • C were evaluated at the same level of theory.…”

Easy and Effective Method for α-CD:N2O Host–Guest Complex Formation

“…The geometries of all participating entities were optimized at the M062X/6-31G* level of theory using the Gaussian 09 package of programs [37]. The Minnesota M062X functional in combination with a split-valence double-ζ basis set was employed in the calculations as it has been proven to be dependable in reproducing the geometrical parameters of a number of macrocyclic cavitands and their inclusion complexes [36,[38][39][40]. Vibrational frequencies (none of them imaginary) and thermal energies, including zero-point energies, E th , at 25 • C and 1 atm pressure were evaluated at the same level of theory.…”