Calix[n]arene-based drug carriers: A DFT study of their electronic interactions with a chemotherapeutic agent used against leukemia

Rodrigo Galindo-Murillo, Alberto Olmedo-Romero, Eduardo Cruz-Flores, P. M. Petrar, S. Kunsági-Máté, Joaquín Barroso-Flores

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The suitability of eight differently substituted calix[n]arenes (with R=-OEt; SO3H and n=4, 5, 6, 8) as drug delivery agents for 3-phenyl-1H-[1]benzofuro[3,2-c]pyrazole (henceforth referred to as GTP), a promising new tyrosine kinase inhibitor drug, has been analyzed by means of DFT theoretical calculations at the B97D/6-31G(d,p) level of theory. Geometries and interaction energies for all inclusion complexes were calculated with NBO, as well as NBO deletion calculations in order to evaluate the energetics of the interactions between GTP and the inner walls of the calix[n]arene cavities. Second order perturbation theory analysis of the charge transfer based on the NBO population analysis was also performed to assess the energetics of the intramolecular bonding in the host guest complexes. Bond indexes suggest the formation of hydrogen-bonds as part of the stabilizing forces of the complex. Two possible insertion modes were explored for the insertion of GTP in the macrocyclic cavity yielding a total of 16 inclusion complexes studied. Interaction energies were higher for R=SO3H. Hosts (8) and (6) (n=8 and 6, respectively) are the most promising candidates for becoming GTP delivery agents within the chemical space under exploration herein.

Original languageEnglish
Pages (from-to)84-91
Number of pages8
JournalComputational and Theoretical Chemistry
Volume1035
DOIs
Publication statusPublished - May 1 2014

Fingerprint

Drug Carriers
leukemias
Guanosine Triphosphate
Discrete Fourier transforms
insertion
delivery
Leukemia
drugs
inclusions
high energy interactions
deletion
cavities
tyrosine
electronics
inhibitors
perturbation theory
Calixarenes
charge transfer
interactions
hydrogen bonds

Keywords

  • Ab initio calculations
  • Calixarenes
  • Drug carriers
  • Drug delivery
  • Host-guest systems
  • NBO calculations

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Biochemistry
  • Condensed Matter Physics

Cite this

Calix[n]arene-based drug carriers : A DFT study of their electronic interactions with a chemotherapeutic agent used against leukemia. / Galindo-Murillo, Rodrigo; Olmedo-Romero, Alberto; Cruz-Flores, Eduardo; Petrar, P. M.; Kunsági-Máté, S.; Barroso-Flores, Joaquín.

In: Computational and Theoretical Chemistry, Vol. 1035, 01.05.2014, p. 84-91.

Research output: Contribution to journalArticle

Galindo-Murillo, Rodrigo ; Olmedo-Romero, Alberto ; Cruz-Flores, Eduardo ; Petrar, P. M. ; Kunsági-Máté, S. ; Barroso-Flores, Joaquín. / Calix[n]arene-based drug carriers : A DFT study of their electronic interactions with a chemotherapeutic agent used against leukemia. In: Computational and Theoretical Chemistry. 2014 ; Vol. 1035. pp. 84-91.
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