In vitro cytotoxic effects, in silico studies, some metabolic enzymes inhibition, and vibrational spectral analysis of novel β-amino alcohol compounds

Taş, Ayça; Tüzün, Burak; Khalilov, Ali N.; Taslimi, Parham; Ağbektas, Tugba; Çakmak, Neşe Keklikçioğlu

doi:10.1016/j.molstruc.2022.134282

Cited by 13 publications

(5 citation statements)

References 67 publications

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“…istry (Montes et al, 2018), drug design and development (Tas et al, 2023) and materials sciences (Yin et al, 2020). The thiazole core is the most common five-membered heteroaromatic ring system in azole heterocycles (Yadigarov et al, 2009;Khalilov, 2021).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one

Huseynov,

Akkurt,

Brito

et al. 2023

Acta Cryst E

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In the title compound, C6H8N2OS, all atoms except for the methyl H atoms are coplanar, with a maximum deviation of 0.026 (4) Å. In the crystal, pairs of molecules are linked by N—H...N hydrogen bonds, forming R 2 2(8) ring motifs. Dimers are connected by N—H...O hydrogen bonds, forming layers parallel to the (102) plane. Consolidating the molecular packing, these layers are connected by C—H...π interactions between the center of the 1,3-thiazole ring and the H atom of the methyl group attached to it, as well as C=O...π interactions between the center of the 1,3-thiazole ring and the O atom of the carboxyl group. According to a Hirshfeld surface study, H...H (37.6%), O...H/H...O (16.8%), S...H/H...S (15.4%), N...H/H...N (13.0%) and C...H/H...C (7.6%) interactions are the most significant contributors to the crystal packing.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one

Huseynov,

Akkurt,

Brito

et al. 2023

Acta Cryst E

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“…Heterocyclic systems account for many important organic compounds (Maharramov et al, 2011b;Abdelhamid et al, 2014). In particular, five-and six-membered heterocycles are applied in different branches of chemistry, including sustainable chemistry (Montes et al, 2018), drug design and development (Khalilov et al, 2021;Tas et al, 2023) or material science (Yin et al, 2020). The thiazole core is one of the most common five-membered heteroaromatic ring systems (Yadigarov et al, 2009;Khalilov, 2021).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2-amino-5-{(1E)-1-[(carbamothioylamino)imino]ethyl}-4-methyl-1,3-thiazol-3-ium chloride monohydrate

et al. 2023

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In the hydrated title salt, C7H12N5S2 +·Cl−·H2O, the asymmetric unit comprises one 2-amino-5-{(1E)-1-[(carbamothioylamino)imino]ethyl}-4-methyl-1,3-thiazol-3-ium cation, one chloride anion and one water molecule of crystallization. The cation is nearly flat (r.m.s. deviation of non-H atoms is 0.0814 Å), with the largest deviation of 0.1484 (14) Å observed for one of the methyl C atoms. In the crystal, the cations are linked by O—H...Cl, N—H...Cl, N—H...O, N—H...S and C—H...S hydrogen bonds, forming a tri-periodic network. The most important contributions to the crystal packing are from H...H (35.4%), S...H/H...S (24.4%), N...H/H...N (8.7%), Cl...H/H...Cl (8.2%) and C...H/H...C (7.7%) interactions.

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“…Furthermore, the usage of cholinesterase inhibitors may be constrained due to a number of side effects, such as nausea, vomiting, diarrhea, and bradycardia. Therefore, it is necessary to create new medications that focus on many disease-related factors while having fewer side effects (Tas et al 2023, Tokalı et al 2023b Surface Analysis by FTIR After the interaction of p-CA with LA-5 and LGG, changes in the cell components on the surface of the bacteria were analyzed by comparing the changes in their FTIR spectra with the control.…”

Section: Ache/bche Activity Determination and Inhibition Studiesmentioning

confidence: 99%

Effects of p-coumaric acid on Probiotic Properties of Lactobacillus acidophilus LA-5 and Lacticaseibacillus rhamnosus GG

DEREBASİ,

BULUT,

ERDEN

et al. 2023

Preprint

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p-coumaric acid (p-CA) is one of the most abundant phenolic compounds in nature and human diet. Probiotic bacteria are microorganisms conferring health benefits on host when administered in adequate amounts. The synbiotic interaction of these two contents, found in gastrointestinal tract, and effect of this interaction on intestines are not known. Thus, this study aimed to investigate synbiotic relationship between p-CA and Lactobacillus acidophilus LA-5 (LA-5), Lacticaseibacillus rhamnosus GG (LGG). They were grown in the presence of different concentrations of p-CA and effects of p-CA on probiotic properties, as well as in vitro effects on AChE and BChE activities were examined. Results indicated p-CA did not negatively affect bacterial growth, but increased auto-aggregation of both probiotics. While p-CA increased co-aggregation of LA-5 and LGG against Escherichia coli, it decreased co-aggregation against Staphylococcus aureus. Probiotics grown with p-CA were more resistant to pepsin. While p-CA increased the resistance of LA-5 to bile salt, it decreased the resistance of LGG. The combinations of bacteria and p-CA efficiently suppressed AChE and BChE with inhibition (%) 11.31-68.06 and 13.47-65.14, respectively. Furthermore, surface analysis was conducted using FTIR to investigate the interaction of p-coumaric acid with LA-5 and LGG, and changes in cell components on the bacterial surface were analyzed. The results, recorded in range of 4000-600 cm⁻¹ with resolution of 4 cm⁻¹, demonstrated that p-CA significantly affected only the phosphate/CH ratio for both bacteria. These results indicate the addition of p-CA to the probiotic growth may enhance the probiotic properties of bacteria.

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In vitro cytotoxic effects, in silico studies, some metabolic enzymes inhibition, and vibrational spectral analysis of novel β-amino alcohol compounds

Cited by 13 publications

References 67 publications

Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one

Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one

Crystal structure and Hirshfeld surface analysis of 2-amino-5-{(1E)-1-[(carbamothioylamino)imino]ethyl}-4-methyl-1,3-thiazol-3-ium chloride monohydrate

Effects of p-coumaric acid on Probiotic Properties of Lactobacillus acidophilus LA-5 and Lacticaseibacillus rhamnosus GG

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