Mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine
Using the density functional theory, the possible non-covalent interactions and six mechanisms of covalent functionalization of the drug penicillamine with functionalized carbon nanotubes (CNT) were investigated. Quantum molecular descriptors of the non-covalent configurations were studied. It was d...
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doaj-bb7305e4cb2f4645910a83d68c33d4362020-11-24T23:03:29ZengSerbian Chemical Society Journal of the Serbian Chemical Society0352-51391820-74212018-01-0183216717910.2298/JSC170218072S0352-51391700072SMechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamineShaki Hosein0Morsali Ali1Raissi Heidar2Hakimi Mohammad3Beyramabadi Ali S.4Payame Noor University, Department of Chemistry, Tehran, IranMashhad Branch, Islamic Azad University, Department of Chemistry, Mashhad, Iran + Mashhad Branch, Islamic Azad University, Research Center for Animal Development Applied Biology, Mashhad, IranUniversity of Birjand, Department of Chemistry, Birjand, IranPayame Noor University, Department of Chemistry, Tehran, IranMashhad Branch, Islamic Azad University, Department of Chemistry, Mashhad, Iran + Mashhad Branch, Islamic Azad University, Research Center for Animal Development Applied Biology, Mashhad, IranUsing the density functional theory, the possible non-covalent interactions and six mechanisms of covalent functionalization of the drug penicillamine with functionalized carbon nanotubes (CNT) were investigated. Quantum molecular descriptors of the non-covalent configurations were studied. It was determined that binding of the drug penicillamine with functionalized CNT is thermodynamically viable. COOH functionalized CNT (NTCOOH) has more binding energy than COCl functionalized CNT (NTCOCl) and could act as a favorable system for penicillamine drug delivery within biological and chemical systems (non-covalent). NTCOOH and NTCOCl can bond to the NH2, OH and SH groups of penicillamine through OH (COOH mechanism) and Cl (COCl mechanism) groups, respectively. The activation energies, activation enthalpies and activation Gibbs energies of six pathways were calculated and compared with each other. The activation parameters related to the COOH mechanism are higher than those related to the COCl mechanism and therefore, the COCl mechanism is suitable for covalent functionalization. These results could be generalized to other similar drugs.http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391700072S.pdfdensity functional theoryquantum molecular descriptorscovalent and non-covalent functionalizationreaction mechanisms |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Shaki Hosein Morsali Ali Raissi Heidar Hakimi Mohammad Beyramabadi Ali S. |
spellingShingle |
Shaki Hosein Morsali Ali Raissi Heidar Hakimi Mohammad Beyramabadi Ali S. Mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine Journal of the Serbian Chemical Society density functional theory quantum molecular descriptors covalent and non-covalent functionalization reaction mechanisms |
author_facet |
Shaki Hosein Morsali Ali Raissi Heidar Hakimi Mohammad Beyramabadi Ali S. |
author_sort |
Shaki Hosein |
title |
Mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine |
title_short |
Mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine |
title_full |
Mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine |
title_fullStr |
Mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine |
title_full_unstemmed |
Mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine |
title_sort |
mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine |
publisher |
Serbian Chemical Society |
series |
Journal of the Serbian Chemical Society |
issn |
0352-5139 1820-7421 |
publishDate |
2018-01-01 |
description |
Using the density functional theory, the possible non-covalent interactions and six mechanisms of covalent functionalization of the drug penicillamine with functionalized carbon nanotubes (CNT) were investigated. Quantum molecular descriptors of the non-covalent configurations were studied. It was determined that binding of the drug penicillamine with functionalized CNT is thermodynamically viable. COOH functionalized CNT (NTCOOH) has more binding energy than COCl functionalized CNT (NTCOCl) and could act as a favorable system for penicillamine drug delivery within biological and chemical systems (non-covalent). NTCOOH and NTCOCl can bond to the NH2, OH and SH groups of penicillamine through OH (COOH mechanism) and Cl (COCl mechanism) groups, respectively. The activation energies, activation enthalpies and activation Gibbs energies of six pathways were calculated and compared with each other. The activation parameters related to the COOH mechanism are higher than those related to the COCl mechanism and therefore, the COCl mechanism is suitable for covalent functionalization. These results could be generalized to other similar drugs. |
topic |
density functional theory quantum molecular descriptors covalent and non-covalent functionalization reaction mechanisms |
url |
http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391700072S.pdf |
work_keys_str_mv |
AT shakihosein mechanisticenergeticandstructuralstudiesofsinglewalledcarbonnanotubesfunctionalizedwithpenicillamine AT morsaliali mechanisticenergeticandstructuralstudiesofsinglewalledcarbonnanotubesfunctionalizedwithpenicillamine AT raissiheidar mechanisticenergeticandstructuralstudiesofsinglewalledcarbonnanotubesfunctionalizedwithpenicillamine AT hakimimohammad mechanisticenergeticandstructuralstudiesofsinglewalledcarbonnanotubesfunctionalizedwithpenicillamine AT beyramabadialis mechanisticenergeticandstructuralstudiesofsinglewalledcarbonnanotubesfunctionalizedwithpenicillamine |
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