Probing vibrational activities, electronic properties, molecular docking and Hirshfeld surfaces analysis of 4-chlorophenyl ({[(1E)-3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)methanone

A promising anti-Candida agent

K. Jayasheela, Lamya H. Al-Wahaibi, S. Periandy, Hanan M. Hassan, S. Sebastian, S. Xavier, Joseph C. Daniel, Ali A. El-Emam, Mohamed I. Attia

Research output: Contribution to journalArticleResearchpeer-review

4 Citations (Scopus)

Abstract

The promising anti-Candida agent, 4-chlorophenyl ({[1E-3(1H-imidazole-1-yl)-1-phenylpropylidene}oxy)methanone (4-CPIPM) was comprehensively characterized by FT-IR, FT-Raman, UV, as well as 1H and 13C spectroscopic techniques. The theoretical calculations in the current study utilized Gaussian 09 W software with DFT approach of the B3LYP/6-311++G(d,p) method. The experimental X-ray diffraction data of the 4-CPIPM molecule were compared with the optimized structure and showed well agreement. Intermolecular electronic interactions and their stabilization energies have been analyzed by natural bond orbital method. Potential energy distribution confirmed the normal fundamental mode of vibration with the aid of MOLVIB software. The chemical shift values of the 1H and 13C spectra of the title compound were computed using gauge independent atomic orbital and the results were compared with the experimental values. The time-dependent density function theory method was used to predict the electronic, absorption wavelength and frontier molecular orbital energies. The HOMO-LUMO plots proved the charge transfer in the molecular system of the title compound through conjugated paths. The molecular electrostatic potential analysis provided the electrophilic and nucleophilic reactive sites in the title molecule which have been analyzed using Hirshfeld surface and two dimensions fingerprint plots. Non covalent interactions were also studied using reduced density gradient analysis and color filled electron density diagram. Molecular docking studies of the ligand-protein interactions along with their binding energies were carried out aiming to explain the potent anti-Candida activity of the title molecule.

Original languageEnglish
Pages (from-to)83-95
Number of pages13
JournalJournal of Molecular Structure
Volume1159
DOIs
Publication statusPublished - 5 May 2018

Fingerprint

Candida
Surface analysis
Electronic properties
Molecules
Chemical shift
Molecular orbitals
Potential energy
Binding energy
Discrete Fourier transforms
Probability density function
Gages
Carrier concentration
Charge transfer
Electrostatics
Stabilization
Ligands
Color
X ray diffraction
Wavelength
Proteins

Keywords

  • Candida albicans
  • Hirshfeld surfaces
  • Molecular docking
  • NBO
  • RDG
  • Vibrational spectra

Cite this

@article{f9cdd4aa6c884b6c824a36a6be180e51,
title = "Probing vibrational activities, electronic properties, molecular docking and Hirshfeld surfaces analysis of 4-chlorophenyl ({[(1E)-3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)methanone: A promising anti-Candida agent",
abstract = "The promising anti-Candida agent, 4-chlorophenyl ({[1E-3(1H-imidazole-1-yl)-1-phenylpropylidene}oxy)methanone (4-CPIPM) was comprehensively characterized by FT-IR, FT-Raman, UV, as well as 1H and 13C spectroscopic techniques. The theoretical calculations in the current study utilized Gaussian 09 W software with DFT approach of the B3LYP/6-311++G(d,p) method. The experimental X-ray diffraction data of the 4-CPIPM molecule were compared with the optimized structure and showed well agreement. Intermolecular electronic interactions and their stabilization energies have been analyzed by natural bond orbital method. Potential energy distribution confirmed the normal fundamental mode of vibration with the aid of MOLVIB software. The chemical shift values of the 1H and 13C spectra of the title compound were computed using gauge independent atomic orbital and the results were compared with the experimental values. The time-dependent density function theory method was used to predict the electronic, absorption wavelength and frontier molecular orbital energies. The HOMO-LUMO plots proved the charge transfer in the molecular system of the title compound through conjugated paths. The molecular electrostatic potential analysis provided the electrophilic and nucleophilic reactive sites in the title molecule which have been analyzed using Hirshfeld surface and two dimensions fingerprint plots. Non covalent interactions were also studied using reduced density gradient analysis and color filled electron density diagram. Molecular docking studies of the ligand-protein interactions along with their binding energies were carried out aiming to explain the potent anti-Candida activity of the title molecule.",
keywords = "Candida albicans, Hirshfeld surfaces, Molecular docking, NBO, RDG, Vibrational spectra",
author = "K. Jayasheela and Al-Wahaibi, {Lamya H.} and S. Periandy and Hassan, {Hanan M.} and S. Sebastian and S. Xavier and Daniel, {Joseph C.} and El-Emam, {Ali A.} and Attia, {Mohamed I.}",
year = "2018",
month = "5",
day = "5",
doi = "10.1016/j.molstruc.2018.01.042",
language = "English",
volume = "1159",
pages = "83--95",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",

}

Probing vibrational activities, electronic properties, molecular docking and Hirshfeld surfaces analysis of 4-chlorophenyl ({[(1E)-3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)methanone : A promising anti-Candida agent. / Jayasheela, K.; Al-Wahaibi, Lamya H.; Periandy, S.; Hassan, Hanan M.; Sebastian, S.; Xavier, S.; Daniel, Joseph C.; El-Emam, Ali A.; Attia, Mohamed I.

In: Journal of Molecular Structure, Vol. 1159, 05.05.2018, p. 83-95.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Probing vibrational activities, electronic properties, molecular docking and Hirshfeld surfaces analysis of 4-chlorophenyl ({[(1E)-3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)methanone

T2 - A promising anti-Candida agent

AU - Jayasheela, K.

AU - Al-Wahaibi, Lamya H.

AU - Periandy, S.

AU - Hassan, Hanan M.

AU - Sebastian, S.

AU - Xavier, S.

AU - Daniel, Joseph C.

AU - El-Emam, Ali A.

AU - Attia, Mohamed I.

PY - 2018/5/5

Y1 - 2018/5/5

N2 - The promising anti-Candida agent, 4-chlorophenyl ({[1E-3(1H-imidazole-1-yl)-1-phenylpropylidene}oxy)methanone (4-CPIPM) was comprehensively characterized by FT-IR, FT-Raman, UV, as well as 1H and 13C spectroscopic techniques. The theoretical calculations in the current study utilized Gaussian 09 W software with DFT approach of the B3LYP/6-311++G(d,p) method. The experimental X-ray diffraction data of the 4-CPIPM molecule were compared with the optimized structure and showed well agreement. Intermolecular electronic interactions and their stabilization energies have been analyzed by natural bond orbital method. Potential energy distribution confirmed the normal fundamental mode of vibration with the aid of MOLVIB software. The chemical shift values of the 1H and 13C spectra of the title compound were computed using gauge independent atomic orbital and the results were compared with the experimental values. The time-dependent density function theory method was used to predict the electronic, absorption wavelength and frontier molecular orbital energies. The HOMO-LUMO plots proved the charge transfer in the molecular system of the title compound through conjugated paths. The molecular electrostatic potential analysis provided the electrophilic and nucleophilic reactive sites in the title molecule which have been analyzed using Hirshfeld surface and two dimensions fingerprint plots. Non covalent interactions were also studied using reduced density gradient analysis and color filled electron density diagram. Molecular docking studies of the ligand-protein interactions along with their binding energies were carried out aiming to explain the potent anti-Candida activity of the title molecule.

AB - The promising anti-Candida agent, 4-chlorophenyl ({[1E-3(1H-imidazole-1-yl)-1-phenylpropylidene}oxy)methanone (4-CPIPM) was comprehensively characterized by FT-IR, FT-Raman, UV, as well as 1H and 13C spectroscopic techniques. The theoretical calculations in the current study utilized Gaussian 09 W software with DFT approach of the B3LYP/6-311++G(d,p) method. The experimental X-ray diffraction data of the 4-CPIPM molecule were compared with the optimized structure and showed well agreement. Intermolecular electronic interactions and their stabilization energies have been analyzed by natural bond orbital method. Potential energy distribution confirmed the normal fundamental mode of vibration with the aid of MOLVIB software. The chemical shift values of the 1H and 13C spectra of the title compound were computed using gauge independent atomic orbital and the results were compared with the experimental values. The time-dependent density function theory method was used to predict the electronic, absorption wavelength and frontier molecular orbital energies. The HOMO-LUMO plots proved the charge transfer in the molecular system of the title compound through conjugated paths. The molecular electrostatic potential analysis provided the electrophilic and nucleophilic reactive sites in the title molecule which have been analyzed using Hirshfeld surface and two dimensions fingerprint plots. Non covalent interactions were also studied using reduced density gradient analysis and color filled electron density diagram. Molecular docking studies of the ligand-protein interactions along with their binding energies were carried out aiming to explain the potent anti-Candida activity of the title molecule.

KW - Candida albicans

KW - Hirshfeld surfaces

KW - Molecular docking

KW - NBO

KW - RDG

KW - Vibrational spectra

UR - http://www.scopus.com/inward/record.url?scp=85041454539&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2018.01.042

DO - 10.1016/j.molstruc.2018.01.042

M3 - Article

VL - 1159

SP - 83

EP - 95

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

ER -