Assaleh, Mohamed H.

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  • Assaleh, Mohamed H. (3)
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Author's Bibliography

In vitro activity of novel cinnamic acids hydrazides against clinically important pathogens

Assaleh, Mohamed H.; Jeremić, Sanja; Cvijetić, Ilija; Marinković, Aleksandar; Prlainović, Nevena

(Elsevier B.V., 2022)

TY  - JOUR
AU  - Assaleh, Mohamed H.
AU  - Jeremić, Sanja
AU  - Cvijetić, Ilija
AU  - Marinković, Aleksandar
AU  - Prlainović, Nevena
PY  - 2022
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5111
AB  - Antimicrobial-resistance (AMR) has become the greatest concern and highly challenging issue when treating nosocomial infections. The exigency to develop new potent compounds continues to increase worldwide, whereby derivatives of natural products are becoming more attractive. In the present paper, the microbiological assessment of a series of 12 cinnamide hydrazides, four of them completely novel, against clinically relevant pathogens has discovered several derivatives with promising in vitro activities against Acinetobacter baumannii, one of the most dreaded opportunistic pathogens in hospitals. The compounds were synthesized by combining one of three different natural acids (cinnamic, 4-chloro or 4-methoxy) with four monothiocarbohydrazones (MTCHs) - an important class of synthetic organic molecules. Their structure was confirmed by elemental microanalysis, as well as ATR-FTIR, 1H and 13C NMR spectra, with the addition of 2D NMR spectra for novel compounds. The hybrids of cinnamic acids and pyridine derivatives are particularly active compounds with the lowest MIC50 value of 10.4 µM for p-chloro cinnamic acid and acetyl pyridine derivatives. An alignment-independent 3D QSAR model identified pharmacophoric hotspots and suggested several structural modifications that might improve the potency of this class of compounds against A. baumannii. The compounds are strong iron-chelating agents forming complexes with a stability constant between 107 and 109. The synthesized derivatives represent a promising class of antibacterial compounds with activities comparable to the commonly used antibiotics.
PB  - Elsevier B.V.
T2  - Journal of Molecular Structure
T1  - In vitro activity of novel cinnamic acids hydrazides against clinically important pathogens
SP  - 133016
VL  - 1262
DO  - 10.1016/j.molstruc.2022.133016
ER  - 
@article{
author = "Assaleh, Mohamed H. and Jeremić, Sanja and Cvijetić, Ilija and Marinković, Aleksandar and Prlainović, Nevena",
year = "2022",
abstract = "Antimicrobial-resistance (AMR) has become the greatest concern and highly challenging issue when treating nosocomial infections. The exigency to develop new potent compounds continues to increase worldwide, whereby derivatives of natural products are becoming more attractive. In the present paper, the microbiological assessment of a series of 12 cinnamide hydrazides, four of them completely novel, against clinically relevant pathogens has discovered several derivatives with promising in vitro activities against Acinetobacter baumannii, one of the most dreaded opportunistic pathogens in hospitals. The compounds were synthesized by combining one of three different natural acids (cinnamic, 4-chloro or 4-methoxy) with four monothiocarbohydrazones (MTCHs) - an important class of synthetic organic molecules. Their structure was confirmed by elemental microanalysis, as well as ATR-FTIR, 1H and 13C NMR spectra, with the addition of 2D NMR spectra for novel compounds. The hybrids of cinnamic acids and pyridine derivatives are particularly active compounds with the lowest MIC50 value of 10.4 µM for p-chloro cinnamic acid and acetyl pyridine derivatives. An alignment-independent 3D QSAR model identified pharmacophoric hotspots and suggested several structural modifications that might improve the potency of this class of compounds against A. baumannii. The compounds are strong iron-chelating agents forming complexes with a stability constant between 107 and 109. The synthesized derivatives represent a promising class of antibacterial compounds with activities comparable to the commonly used antibiotics.",
publisher = "Elsevier B.V.",
journal = "Journal of Molecular Structure",
title = "In vitro activity of novel cinnamic acids hydrazides against clinically important pathogens",
pages = "133016",
volume = "1262",
doi = "10.1016/j.molstruc.2022.133016"
}
Assaleh, M. H., Jeremić, S., Cvijetić, I., Marinković, A.,& Prlainović, N.. (2022). In vitro activity of novel cinnamic acids hydrazides against clinically important pathogens. in Journal of Molecular Structure
Elsevier B.V.., 1262, 133016.
https://doi.org/10.1016/j.molstruc.2022.133016
Assaleh MH, Jeremić S, Cvijetić I, Marinković A, Prlainović N. In vitro activity of novel cinnamic acids hydrazides against clinically important pathogens. in Journal of Molecular Structure. 2022;1262:133016.
doi:10.1016/j.molstruc.2022.133016 .
Assaleh, Mohamed H., Jeremić, Sanja, Cvijetić, Ilija, Marinković, Aleksandar, Prlainović, Nevena, "In vitro activity of novel cinnamic acids hydrazides against clinically important pathogens" in Journal of Molecular Structure, 1262 (2022):133016,
https://doi.org/10.1016/j.molstruc.2022.133016 . .

Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid

Assaleh, Mohamed H.; Bjelogrlic, Snezana K.; Prlainović, Nevena; Cvijetić, Ilija; Bozic, Aleksandra; Aranđelović, Irena; Vukovic, Dragana; Marinković, Aleksandar

(2022)

TY  - JOUR
AU  - Assaleh, Mohamed H.
AU  - Bjelogrlic, Snezana K.
AU  - Prlainović, Nevena
AU  - Cvijetić, Ilija
AU  - Bozic, Aleksandra
AU  - Aranđelović, Irena
AU  - Vukovic, Dragana
AU  - Marinković, Aleksandar
PY  - 2022
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4986
AB  - A series of twelve novel hybrids of cinnamic acid and thiocarbohydrazones were designed, synthesized in high yield using a simple coupling strategy via acid chlorides, and evaluated for their impact against Mycobacterium tuberculosis (Mtb) and cancer cells survival. Among them, compound 3 demonstrated strong anti-Mtb activity by reducing bacilli survival for>90 % in all three treated Mtb isolates, whereas isoniazid and rifampicin did not. Moreover, compound 3 didn't affect vitality of HepG-2 cells, implying on advantageous hepatotoxicity profile compared to current therapeutic options for tuberculosis. Compounds 2a and 3b displayed as strong inducers of apoptosis in A549 cells, both activating intrinsic caspase pathway and cell cycle arrest at the G0/ G1 phase. Subsequent analyses disclosed differences in their activities, where 3b has ability to induce production of mitochondrial superoxide anions, while 2a significantly inhibited cellular mobility. More importantly, 3b considerably affected viability of HepG-2 and HaCaT cells, whereas 2a had moderate impact only on the later. Molecular modeling studies indicated high permeability and good absorption through the human intestine, and moderate aqueous solubility with poor blood-brain barrier permeability. In summary, our results reveal that novel compounds 3 and 2a represent promising agents for tuberculosis and cancer treatment, respectively, indicating that fur-ther investigation needs to be performed to clarify the mechanisms of their anti-Mtb and anticancer activity. (c) 2021 The Authors. Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
T2  - Arabian Journal of Chemistry
T1  - Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid
IS  - 1
SP  - 103532
VL  - 15
DO  - 10.1016/j.arabjc.2021.103532
ER  - 
@article{
author = "Assaleh, Mohamed H. and Bjelogrlic, Snezana K. and Prlainović, Nevena and Cvijetić, Ilija and Bozic, Aleksandra and Aranđelović, Irena and Vukovic, Dragana and Marinković, Aleksandar",
year = "2022",
abstract = "A series of twelve novel hybrids of cinnamic acid and thiocarbohydrazones were designed, synthesized in high yield using a simple coupling strategy via acid chlorides, and evaluated for their impact against Mycobacterium tuberculosis (Mtb) and cancer cells survival. Among them, compound 3 demonstrated strong anti-Mtb activity by reducing bacilli survival for>90 % in all three treated Mtb isolates, whereas isoniazid and rifampicin did not. Moreover, compound 3 didn't affect vitality of HepG-2 cells, implying on advantageous hepatotoxicity profile compared to current therapeutic options for tuberculosis. Compounds 2a and 3b displayed as strong inducers of apoptosis in A549 cells, both activating intrinsic caspase pathway and cell cycle arrest at the G0/ G1 phase. Subsequent analyses disclosed differences in their activities, where 3b has ability to induce production of mitochondrial superoxide anions, while 2a significantly inhibited cellular mobility. More importantly, 3b considerably affected viability of HepG-2 and HaCaT cells, whereas 2a had moderate impact only on the later. Molecular modeling studies indicated high permeability and good absorption through the human intestine, and moderate aqueous solubility with poor blood-brain barrier permeability. In summary, our results reveal that novel compounds 3 and 2a represent promising agents for tuberculosis and cancer treatment, respectively, indicating that fur-ther investigation needs to be performed to clarify the mechanisms of their anti-Mtb and anticancer activity. (c) 2021 The Authors. Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).",
journal = "Arabian Journal of Chemistry",
title = "Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid",
number = "1",
pages = "103532",
volume = "15",
doi = "10.1016/j.arabjc.2021.103532"
}
Assaleh, M. H., Bjelogrlic, S. K., Prlainović, N., Cvijetić, I., Bozic, A., Aranđelović, I., Vukovic, D.,& Marinković, A.. (2022). Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid. in Arabian Journal of Chemistry, 15(1), 103532.
https://doi.org/10.1016/j.arabjc.2021.103532
Assaleh MH, Bjelogrlic SK, Prlainović N, Cvijetić I, Bozic A, Aranđelović I, Vukovic D, Marinković A. Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid. in Arabian Journal of Chemistry. 2022;15(1):103532.
doi:10.1016/j.arabjc.2021.103532 .
Assaleh, Mohamed H., Bjelogrlic, Snezana K., Prlainović, Nevena, Cvijetić, Ilija, Bozic, Aleksandra, Aranđelović, Irena, Vukovic, Dragana, Marinković, Aleksandar, "Antimycobacterial and anticancer activity of newly designed cinnamic acid hydrazides with favorable toxicity profile: Antimycobacterial and anticancer activity of newly designed cinnamic acid" in Arabian Journal of Chemistry, 15, no. 1 (2022):103532,
https://doi.org/10.1016/j.arabjc.2021.103532 . .
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Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study

Assaleh, Mohamed H.; Božić, Aleksandra R.; Bjelogrlić, Snežana K.; Milošević, Milena D.; Simić, Milena R.; Marinković, Aleksandar; Cvijetić, Ilija

(Springer/Plenum Publishers, New York, 2019)

TY  - JOUR
AU  - Assaleh, Mohamed H.
AU  - Božić, Aleksandra R.
AU  - Bjelogrlić, Snežana K.
AU  - Milošević, Milena D.
AU  - Simić, Milena R.
AU  - Marinković, Aleksandar
AU  - Cvijetić, Ilija
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4147
AB  - Thiocarbohydrazones (TCHs) and structurally related molecules are versatile organic compounds which exert antioxidant, anticancer, and other beneficial health effects. The combination of UV/Vis, NMR spectroscopy, and quantum chemical calculations was used to rationalize the experimentally observed increase in the radical scavenging activity upon the addition of water in DMSO solution of TCHs. Mono- and bis(salicylaldehyde) TCHs (compounds 1 and 2) undergo water-induced E-to-Z isomerization which is followed by disruption of intramolecular hydrogen bond, ground state destabilization, and 11 kcal/mol decrease in the bond dissociation enthalpy (BDE). Electron spin delocalization is more pronounced in Z-isomers of 1 and 2. On the other hand, 2-acetylpyridine TCHs (compounds 3 and 4) undergo thione-to-thiol tautomerism which also decreases the BDE and facilitates the hydrogen atom transfer to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.). The appearance of thiolic -SH group as another reactive site toward free radicals improves the antioxidant activity of 3 and 4. The spin density of 3- and 4-thiol radicals is delocalized over the entire thiocarbohydrazide moiety compared to more localized spin of thione radicals. Additional stabilization of thiol radicals corroborates with the increased antioxidant activity. This study provides the new insights on the solution structure of TCHs, and also highlights the importance of solution structure determination when studying the structure-antioxidant relationships of isomerizable compounds.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study
EP  - 2457
IS  - 6
SP  - 2447
VL  - 30
DO  - 10.1007/s11224-019-01371-4
ER  - 
@article{
author = "Assaleh, Mohamed H. and Božić, Aleksandra R. and Bjelogrlić, Snežana K. and Milošević, Milena D. and Simić, Milena R. and Marinković, Aleksandar and Cvijetić, Ilija",
year = "2019",
abstract = "Thiocarbohydrazones (TCHs) and structurally related molecules are versatile organic compounds which exert antioxidant, anticancer, and other beneficial health effects. The combination of UV/Vis, NMR spectroscopy, and quantum chemical calculations was used to rationalize the experimentally observed increase in the radical scavenging activity upon the addition of water in DMSO solution of TCHs. Mono- and bis(salicylaldehyde) TCHs (compounds 1 and 2) undergo water-induced E-to-Z isomerization which is followed by disruption of intramolecular hydrogen bond, ground state destabilization, and 11 kcal/mol decrease in the bond dissociation enthalpy (BDE). Electron spin delocalization is more pronounced in Z-isomers of 1 and 2. On the other hand, 2-acetylpyridine TCHs (compounds 3 and 4) undergo thione-to-thiol tautomerism which also decreases the BDE and facilitates the hydrogen atom transfer to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.). The appearance of thiolic -SH group as another reactive site toward free radicals improves the antioxidant activity of 3 and 4. The spin density of 3- and 4-thiol radicals is delocalized over the entire thiocarbohydrazide moiety compared to more localized spin of thione radicals. Additional stabilization of thiol radicals corroborates with the increased antioxidant activity. This study provides the new insights on the solution structure of TCHs, and also highlights the importance of solution structure determination when studying the structure-antioxidant relationships of isomerizable compounds.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study",
pages = "2457-2447",
number = "6",
volume = "30",
doi = "10.1007/s11224-019-01371-4"
}
Assaleh, M. H., Božić, A. R., Bjelogrlić, S. K., Milošević, M. D., Simić, M. R., Marinković, A.,& Cvijetić, I.. (2019). Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study. in Structural Chemistry
Springer/Plenum Publishers, New York., 30(6), 2447-2457.
https://doi.org/10.1007/s11224-019-01371-4
Assaleh MH, Božić AR, Bjelogrlić SK, Milošević MD, Simić MR, Marinković A, Cvijetić I. Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study. in Structural Chemistry. 2019;30(6):2447-2457.
doi:10.1007/s11224-019-01371-4 .
Assaleh, Mohamed H., Božić, Aleksandra R., Bjelogrlić, Snežana K., Milošević, Milena D., Simić, Milena R., Marinković, Aleksandar, Cvijetić, Ilija, "Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study" in Structural Chemistry, 30, no. 6 (2019):2447-2457,
https://doi.org/10.1007/s11224-019-01371-4 . .
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