scholarly journals Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

2019 ◽  
Vol 15 ◽  
pp. 2419-2427
Author(s):  
Sachin S Burade ◽  
Sushil V Pawar ◽  
Tanmoy Saha ◽  
Navanath Kumbhar ◽  
Amol S Kotmale ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Amino Acid ◽  
Molecular Modeling ◽  
Intramolecular Cyclization ◽  
Membered Ring ◽  
Conformational Study ◽  
Oxazole Ring ◽  
Solution State ◽  
Modeling Studies ◽  
Molecular Modeling Studies

The intramolecular cyclization of a C-3-tetrasubstituted furanoid sugar amino acid-derived linear tetrapeptide afforded an oxazolone pseudo-peptide with the formation of an oxazole ring at the C-terminus. A conformational study of the oxazolone pseudo-peptide showed intramolecular C=O···HN(II) hydrogen bonding in a seven-membered ring leading to a γ-turn conformation. This fact was supported by a solution-state NMR and molecular modeling studies. The oxazolone pseudotetrapeptide was found to be a better Cl−-selective transporter for which an anion–anion antiport mechanism was established.

scholarly journals Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

2019 ◽  
Author(s):  
Sachin S Burade ◽  
Sushil V Pawar ◽  
Tanmoy Saha ◽  
Navnath M Kumbhar ◽  
Amol S Kotmale ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Amino Acid ◽  
Molecular Modeling ◽  
Ion Selectivity ◽  
Conformational Study ◽  
Oxazole Ring ◽  
Selective Transport ◽  
Molecular Modeling Studies ◽  
Oxazolone Ring

The C3-tetrasubstituted furanoid sugar amino acid derived linear amino acid dipeptide 8 and tetrapeptide 9 on intra-molecular cyclization afforded oxazolone pseudo-peptides 1 and 2a, respectively, with formation of oxazole ring at the C-terminus. Conformational study of 2a showed seven membered intramolecular C=O×××HN (II) hydrogen bonding leading to the γ-turn conformation which is absent in the precursor tetrapeptide 9 thus indicating the role of oxazolone ring in γ-turn formation in 2a. This fact was supported by the molecular modeling studies. The oxazolone ring containing pseudo-tetrapeptide 2a was found to be better ion transporter than pseudodi-peptide1.The ion selectivity of 2a indicated Cl-anion-selective transport via the antiport mechanism.

Interaction of Artemisinin and Its Related Compounds with Hydroxypropyl‐β‐cyclodextrin iN Solution State: Experimental and Molecular‐modeling Studies

2003 ◽  
Vol 92 (3) ◽  
pp. 649-655 ◽  
Author(s):  
Ashok C. Illapakurthy ◽  
Yogesh A. Sabnis ◽  
Bonnie A. Avery ◽  
Mitchell A. Avery ◽  
Christy M. Wyandt
Keyword(s):  
Molecular Modeling ◽  
Solution State ◽  
Modeling Studies ◽  
Molecular Modeling Studies ◽  
Related Compounds

p-Trifluoroacetophenone Oxime Ester Derivatives: Synthesis, Antimicrobial and Cytotoxic Evaluation and Molecular Modeling Studies

2020 ◽  
Vol 17 (2) ◽  
pp. 169-183 ◽  
Author(s):  
İrem Bozbey ◽  
Suat Sari ◽  
Emine Şalva ◽  
Didem Kart ◽  
Arzu Karakurt
Keyword(s):  
Molecular Modeling ◽  
Neuroblastoma Cell ◽  
Neuroblastoma Cells ◽  
Cytotoxic Agents ◽  
Human Neuroblastoma Cell ◽  
Human Neuroblastoma ◽  
Modeling Studies ◽  
Broth Microdilution Method ◽  
Molecular Modeling Studies

Background: Azole antifungals are among the first-line drugs clinically used for the treatment of systemic candidiasis, a deadly type of fungal infection that threatens mostly immunecompromised and hospitalized patients. Some azole derivatives were also reported to have antiproliferative effects on cancer cells. Objective: In this study, 1-(4-trifluoromethylphenyl)-2-(1H-imidazol-1-yl)ethanone (3), its oxime (4), and a series of its novel oxime ester derivatives (5a-v) were synthesized and tested for their in vitro antimicrobial activities against certain ATCC standard strains of Candida sp. fungi and bacteria. The compounds were also tested for their cytotoxic effects against mouse fibroblast and human neuroblastoma cell lines. Molecular modeling studies were performed to provide insights into their possible mechanisms for antifungal and antibacterial actions. Methods: The compounds were synthesized by the reaction of various oximes with acyl chlorides. Antimicrobial activity of the compounds was determined according to the broth microdilution method. For the determination of cytotoxic effect, we used MTS assay. Molecular docking and QM/MM studies were performed to predict the binding mechanisms of the active compounds in the catalytic site of C. albicans CYP51 (CACYP51) and S. aureus flavohemoglobin (SAFH), the latter of which was created via homology modeling. Results: 5d, 5l, and 5t showed moderate antifungal activity against C. albicans, while 3, 5c, and 5r showed significant antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa. Most of the compounds showed approximately 40-50% inhibition against the human neuroblastoma cells at 100 µM. In this line, 3 was the most potent with an IC50 value of 82.18 μM followed by 5a, 5o, and 5t. 3 and 5a were highly selective to the neuroblastoma cells. Molecular modelling results supported the hypothesis that our compounds were inhibitors of CAYP51 and SAFH. Conclusion: This study supports that oxime ester derivatives may be used for the development of new antimicrobial and cytotoxic agents.

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