The binding interaction of imazapyr with cucurbit[n]uril (n = 6–8)

Combined experimental and molecular modeling study

Maali Saad Mokhtar, Fakhr Eldin O. Suliman, Abdalla A. Elbashir

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The inclusion complexes of imazapyr (IMA) with cucurbit[n]uril, CB[n] (n = 6–8), have been investigated. Fluorescence spectroscopy, MALDI-TOF, and 1HNMR were used to investigate and characterize the inclusion complexation of IMA and CB[n] in solutions. Whereas the solid state complexes have been characterized by Fourier transform infrared spectroscopy (FTIR), and powder X-ray diffraction (PXRD). IMA was found to form 1:1 complexes with CB[n] with association constants ranging from 5.80 × 102–2.65 × 103. The guest molecule IMA was found to encapsulate into the larger cavities of CB[7] and CB[8], whereas with CB[6] the molecule remains outside the cavity. Molecular dynamic (MD) simulations were used to follow the inclusion process at an atomistic level to study the mechanism and stability of inclusion. The results obtained showed that inclusion complexes of IMA with both CB[7] and CB[8] are highly stable in aqueous media, but the CB[6] smaller cavity size prohibited the formation of an inclusion complex with IMA. The results clearly show that in addition to hydrophobic effects the presence of hydrogen bonding has added greatly to the stability of these complexes.

Original languageEnglish
Pages (from-to)67-75
Number of pages9
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume194
DOIs
Publication statusPublished - Apr 5 2018

Fingerprint

Molecular modeling
inclusions
interactions
cavities
Molecules
Fluorescence spectroscopy
Complexation
X ray powder diffraction
Fourier transform infrared spectroscopy
Molecular dynamics
imazapyr
molecules
Hydrogen bonds
infrared spectroscopy
Association reactions
molecular dynamics
solid state
fluorescence
Computer simulation
hydrogen

Keywords

  • Cucurbit[n]uril
  • Herbicides
  • Imazapyr
  • Inclusion complex
  • Molecular dynamics

ASJC Scopus subject areas

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

Cite this

@article{cefe84957510442da4ca4590cb79e787,
title = "The binding interaction of imazapyr with cucurbit[n]uril (n = 6–8): Combined experimental and molecular modeling study",
abstract = "The inclusion complexes of imazapyr (IMA) with cucurbit[n]uril, CB[n] (n = 6–8), have been investigated. Fluorescence spectroscopy, MALDI-TOF, and 1HNMR were used to investigate and characterize the inclusion complexation of IMA and CB[n] in solutions. Whereas the solid state complexes have been characterized by Fourier transform infrared spectroscopy (FTIR), and powder X-ray diffraction (PXRD). IMA was found to form 1:1 complexes with CB[n] with association constants ranging from 5.80 × 102–2.65 × 103. The guest molecule IMA was found to encapsulate into the larger cavities of CB[7] and CB[8], whereas with CB[6] the molecule remains outside the cavity. Molecular dynamic (MD) simulations were used to follow the inclusion process at an atomistic level to study the mechanism and stability of inclusion. The results obtained showed that inclusion complexes of IMA with both CB[7] and CB[8] are highly stable in aqueous media, but the CB[6] smaller cavity size prohibited the formation of an inclusion complex with IMA. The results clearly show that in addition to hydrophobic effects the presence of hydrogen bonding has added greatly to the stability of these complexes.",
keywords = "Cucurbit[n]uril, Herbicides, Imazapyr, Inclusion complex, Molecular dynamics",
author = "Mokhtar, {Maali Saad} and Suliman, {Fakhr Eldin O.} and Elbashir, {Abdalla A.}",
year = "2018",
month = "4",
day = "5",
doi = "10.1016/j.saa.2018.01.007",
language = "English",
volume = "194",
pages = "67--75",
journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",
issn = "1386-1425",
publisher = "Elsevier",

}

TY - JOUR

T1 - The binding interaction of imazapyr with cucurbit[n]uril (n = 6–8)

T2 - Combined experimental and molecular modeling study

AU - Mokhtar, Maali Saad

AU - Suliman, Fakhr Eldin O.

AU - Elbashir, Abdalla A.

PY - 2018/4/5

Y1 - 2018/4/5

N2 - The inclusion complexes of imazapyr (IMA) with cucurbit[n]uril, CB[n] (n = 6–8), have been investigated. Fluorescence spectroscopy, MALDI-TOF, and 1HNMR were used to investigate and characterize the inclusion complexation of IMA and CB[n] in solutions. Whereas the solid state complexes have been characterized by Fourier transform infrared spectroscopy (FTIR), and powder X-ray diffraction (PXRD). IMA was found to form 1:1 complexes with CB[n] with association constants ranging from 5.80 × 102–2.65 × 103. The guest molecule IMA was found to encapsulate into the larger cavities of CB[7] and CB[8], whereas with CB[6] the molecule remains outside the cavity. Molecular dynamic (MD) simulations were used to follow the inclusion process at an atomistic level to study the mechanism and stability of inclusion. The results obtained showed that inclusion complexes of IMA with both CB[7] and CB[8] are highly stable in aqueous media, but the CB[6] smaller cavity size prohibited the formation of an inclusion complex with IMA. The results clearly show that in addition to hydrophobic effects the presence of hydrogen bonding has added greatly to the stability of these complexes.

AB - The inclusion complexes of imazapyr (IMA) with cucurbit[n]uril, CB[n] (n = 6–8), have been investigated. Fluorescence spectroscopy, MALDI-TOF, and 1HNMR were used to investigate and characterize the inclusion complexation of IMA and CB[n] in solutions. Whereas the solid state complexes have been characterized by Fourier transform infrared spectroscopy (FTIR), and powder X-ray diffraction (PXRD). IMA was found to form 1:1 complexes with CB[n] with association constants ranging from 5.80 × 102–2.65 × 103. The guest molecule IMA was found to encapsulate into the larger cavities of CB[7] and CB[8], whereas with CB[6] the molecule remains outside the cavity. Molecular dynamic (MD) simulations were used to follow the inclusion process at an atomistic level to study the mechanism and stability of inclusion. The results obtained showed that inclusion complexes of IMA with both CB[7] and CB[8] are highly stable in aqueous media, but the CB[6] smaller cavity size prohibited the formation of an inclusion complex with IMA. The results clearly show that in addition to hydrophobic effects the presence of hydrogen bonding has added greatly to the stability of these complexes.

KW - Cucurbit[n]uril

KW - Herbicides

KW - Imazapyr

KW - Inclusion complex

KW - Molecular dynamics

UR - http://www.scopus.com/inward/record.url?scp=85040111696&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85040111696&partnerID=8YFLogxK

U2 - 10.1016/j.saa.2018.01.007

DO - 10.1016/j.saa.2018.01.007

M3 - Article

VL - 194

SP - 67

EP - 75

JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

SN - 1386-1425

ER -