PMID- 37570673
OWN - NLM
STAT- MEDLINE
DCOM- 20230814
LR  - 20230814
IS  - 1420-3049 (Electronic)
IS  - 1420-3049 (Linking)
VI  - 28
IP  - 15
DP  - 2023 Jul 28
TI  - Experimental and Theoretical Biological Probing of Schiff Bases as Esterase 
      Inhibitors: Structural, Spectral and Molecular Insights.
LID - 10.3390/molecules28155703 [doi]
LID - 5703
AB  - The present study was designed to evaluate the in vitro and in silico potential 
      of the Schiff bases (Z)-4-ethoxy-N-((5-nitrothiophen-2-yl)methylene)benzenamine 
      (1) and (Z)-2,4-diiodo-6-((2-methyl-3-nitrophenylimino)methyl)phenol (2). These 
      Schiff bases were synthesized according to a reported method using ethanol as a 
      solvent, and each reaction was monitored on a TLC until completion of the 
      reaction. The structures of both compounds were elucidated using spectroscopic 
      techniques such as UV-Vis, FTIR, (1)H NMR and (13)C NMR. Molecular structure was 
      determined using single-crystal XRD, which revealed that compounds 1 and 2 were 
      monoclinic and triclinic, respectively. Hirshfeld surface analysis (HS) and 2D 
      fingerprint plots were used to determine the intermolecular interactions along 
      the contact contribution in the crystalline molecules. The structures of both 
      compounds were optimized through a hybrid functional method B3LYP using the 
      6-31G(d,p) basis set, and various structural parameters were studied. The 
      experimental and theoretical parameters (bond angle and bond length) of the 
      compounds were compared with each other and are in close agreement. The in vitro 
      esterase potential of the synthesized compounds was checked using a 
      spectrophotometric model, while in silico molecular docking studies were 
      performed with AutoDock against two enzymes of the esterase family. The docking 
      studies and the in vitro assessment predicted that such molecules could be used 
      as enzyme inhibitors against the tested enzymes: acetylcholine esterase (AChE) 
      and butyrylcholine esterase (BChE).
FAU - Raza, Muhammad Asam
AU  - Raza MA
AUID- ORCID: 0000-0002-6723-2637
AD  - Department of Chemistry, Hafiz Hayat Campus, University of Gujrat, Gujrat 50700, 
      Pakistan.
FAU - Mumtaz, Muhammad Waseem
AU  - Mumtaz MW
AD  - Department of Chemistry, Hafiz Hayat Campus, University of Gujrat, Gujrat 50700, 
      Pakistan.
FAU - Ozturk, Seyhan
AU  - Ozturk S
AUID- ORCID: 0000-0003-4638-5578
AD  - Department of Chemistry, Faculty of Sciences, Ondokuz Mayis University, Samsun 
      55139, Turkiye.
FAU - Latif, Muhammad
AU  - Latif M
AUID- ORCID: 0000-0003-4858-3324
AD  - Department of Biochemistry and Molecular Medicine, College of Medicine, Taibah 
      University, Madinah 42318, Saudi Arabia.
AD  - Centre for Genetics and Inherited Diseases (CGID), Taibah University, Madinah 
      42318, Saudi Arabia.
FAU - Aisha
AU  - Aisha
AD  - Department of Chemistry, Hafiz Hayat Campus, University of Gujrat, Gujrat 50700, 
      Pakistan.
FAU - Ashraf, Adnan
AU  - Ashraf A
AD  - Department of Chemistry, University of Lahore, Lahore 54000, Pakistan.
FAU - Dege, Necmi
AU  - Dege N
AUID- ORCID: 0000-0003-0660-4721
AD  - Department of Physics, Faculty of Sciences, Ondokuz Mayis University, Samsun 
      55139, Turkiye.
FAU - Dogan, Onur Erman
AU  - Dogan OE
AUID- ORCID: 0000-0002-1956-7918
AD  - Department of Chemistry, Faculty of Sciences, Ondokuz Mayis University, Samsun 
      55139, Turkiye.
FAU - Agar, Erbil
AU  - Agar E
AD  - Department of Chemistry, Faculty of Sciences, Ondokuz Mayis University, Samsun 
      55139, Turkiye.
FAU - Rehman, Shafiq Ur
AU  - Rehman SU
AUID- ORCID: 0000-0001-7094-0194
AD  - Department of Chemistry, University of Central Punjab, Lahore 54590, Pakistan.
FAU - Noor, Awal
AU  - Noor A
AUID- ORCID: 0000-0003-2075-1840
AD  - Department of Basic Sciences, Preparatory Year Deanship, King Faisal University, 
      Al Hassa 31982, Saudi Arabia.
LA  - eng
GR  - 3016/King Faisal University/
PT  - Journal Article
DEP - 20230728
PL  - Switzerland
TA  - Molecules
JT  - Molecules (Basel, Switzerland)
JID - 100964009
RN  - 0 (Schiff Bases)
RN  - 0 (Enzyme Inhibitors)
RN  - EC 3.1.- (Esterases)
SB  - IM
MH  - Molecular Docking Simulation
MH  - Crystallography, X-Ray
MH  - *Schiff Bases/chemistry
MH  - Magnetic Resonance Spectroscopy
MH  - *Enzyme Inhibitors
MH  - Esterases
PMC - PMC10419919
OTO - NOTNLM
OT  - Hirshfeld surface analysis
OT  - Schiff base
OT  - crystal structure
OT  - density functional theory
OT  - molecular docking
COIS- All authors declared that they have no conflict of interest.
EDAT- 2023/08/12 10:48
MHDA- 2023/08/14 06:42
PMCR- 2023/07/28
CRDT- 2023/08/12 01:17
PHST- 2023/06/23 00:00 [received]
PHST- 2023/07/14 00:00 [revised]
PHST- 2023/07/19 00:00 [accepted]
PHST- 2023/08/14 06:42 [medline]
PHST- 2023/08/12 10:48 [pubmed]
PHST- 2023/08/12 01:17 [entrez]
PHST- 2023/07/28 00:00 [pmc-release]
AID - molecules28155703 [pii]
AID - molecules-28-05703 [pii]
AID - 10.3390/molecules28155703 [doi]
PST - epublish
SO  - Molecules. 2023 Jul 28;28(15):5703. doi: 10.3390/molecules28155703.