A new structure of a serotonin salt: comparison and conformational analysis of all known serotonin complexes

2013 ◽  
Vol 69 (9) ◽  
pp. 1055-1061 ◽  
Author(s):  
Denis Rychkov ◽  
Elena V. Boldyreva ◽  
Nikolay A. Tumanov
Keyword(s):  
Hydrogen Bonding ◽  
Biological Activity ◽  
Conformational Analysis ◽  
Molecular Conformation ◽  
Biological Properties ◽  
Stacking Interactions ◽  
Salt Formation ◽  
Counter Ion ◽  
Unknown Structure ◽  
Conformation Stability

Four serotonin salt structures (serotonin adipate, C10H13N2O+·C6H9O4−, is a previously unknown structure) were analysed to understand the influence of the anion on serotonin conformation. Hydrogen bonding alone favours a flat conformation, whereas additional stacking interactions between ions may possibly account for the nonplanar conformation. Since molecular conformation, stability and biological activity are interrelated, one can consider influencing the chemical and biological properties of serotonin by selecting an appropriate counter-ion for salt formation.

Biological Function and Chemistry of Endothelin. A Review

1999 ◽  
Vol 64 (8) ◽  
pp. 1211-1252 ◽  
Author(s):  
Jan Hlaváček ◽  
Renáta Marcová
Keyword(s):  
Biological Activity ◽  
Amino Acid ◽  
Biological Function ◽  
Biological Properties ◽  
Structural Basis ◽  
Amino Acid Residues ◽  
Snake Venoms ◽  
Vasoactive Peptides ◽  
Physico Chemical ◽  
Endothelin A

The first part of this review deals with the biosynthesis and a biological function of strongly vasoactive peptides named endothelins (ETs) including vasoactive intestinal contractor. Where it was useful, snake venoms sarafotoxins which are structural endothelin derivatives, were also mentioned. In the second part, an attention is paid to structural basis of the ETs biological activity, with respect to alterations of amino acid residues in the parent peptides modifying the conformation and consequently the physico-chemical and biological properties in corresponding ETs analogs. Special attention is focussed on the area of ETs receptors and their interaction with peptide and non peptide agonists and antagonists, important in designing selective inhibitors of ETs receptors potentially applicable as drugs in a medicine. A review with 182 references.

A computational characterization of the hydrogen-bonding and stacking interactions of hypoxanthine

2007 ◽  
Vol 9 (4) ◽  
pp. 497-509 ◽  
Author(s):  
Lesley R. Rutledge ◽  
Craig A. Wheaton ◽  
Stacey D. Wetmore
Keyword(s):  
Hydrogen Bonding ◽  
Stacking Interactions

3-n-Butyl-2-methoxy-1-benzothieno[3,2-d]pyrimidin-4(3H)-one

2006 ◽  
Vol 62 (4) ◽  
pp. o1319-o1320 ◽  
Author(s):  
Min-Hui Cao ◽  
Sheng-Zhen Xu ◽  
Yang-Gen Hu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Benzene Ring ◽  
Title Compound ◽  
Thiophene Ring ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Compound C ◽  
Π Stacking ◽  
Independent Molecules

The title compound, C15H16N2O2S, contains a five-membered thiophene ring fused to a benzene ring and a substituted pyrimidinone ring. All three rings in each of the independent molecules of the asymmetric unit lie in approximately the same plane. The crystal structure is stabilized by intermolecular C—H...O hydrogen bonding and π–π stacking interactions.

scholarly journals Conformational analysis and intramolecular interactions in monosubstituted phenylboranes and phenylboronic acids

2013 ◽  
Vol 9 ◽  
pp. 1127-1134 ◽  
Author(s):  
Josué M Silla ◽  
Rodrigo A Cormanich ◽  
Roberto Rittner ◽  
Matheus P Freitas
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Conformational Analysis ◽  
Conformational Equilibrium ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Interactions ◽  
Coupling Constant ◽  
Intramolecular Hydrogen ◽  
Phenylboronic Acids ◽  
Electron Donation

A 1 TS J F,H(O) coupling pathway, dictated by a hydrogen bond, in some 2-fluorobenzoic acids has been observed, while such an interaction does not occur in 2-fluorophenol. Thus, this work reports the conformational analysis of 2-fluorophenylboronic acid (1), in order to evaluate a possible intramolecular OH∙∙∙F hydrogen bond in comparison to an nF→pB interaction, which mimics the quantum nF→σ*OH hydrogen bond that would be expected in 2-fluorophenol. 2-Fluorophenylborane (3), which does not experience hydrogen bonding, was used to verify whether nF→pB interaction governs the conformational equilibrium in 1 due to a predominant OH∙∙∙F hydrogen bond or to other effects. A series of 2-X-phenylboranes (X = Cl, Br, NH2, PH2, OH and SH) were further computationally analyzed to search for electron donors to boron, capable of influencing the conformational equilibrium. Overall, the intramolecular OH∙∙∙F hydrogen bond in 1 is quite stabilizing and dictates the 1 h J F,H(O) coupling constant. Moreover, electron donation to the empty p orbital of boron (for noncoplanar BH2 moiety relative to the phenyl ring) is also significantly stabilizing for the NH2 and PH2 derivatives, but not enough to make the corresponding conformers appreciably populated, because of steric effects and the loss of πCC→pB resonance. Thus, the results found earlier for 2-fluorophenol about the lack of intramolecular hydrogen bonding are now corroborated.

Aktywność biologiczna ekstraktów z propolisu

2021 ◽  
Vol 22 (1) ◽  
Author(s):  
Magdalena Woźniak ◽  
Anna Kwiatkowska ◽  
Elżbieta Hołderna-Kędzia ◽  
Katarzyna Sosnowska ◽  
Lucyna Mrówczyńska ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Biological Activity ◽  
Phenolic Compounds ◽  
Propylene Glycol ◽  
Ethyl Alcohol ◽  
Antiradical Activity ◽  
Colorimetric Method ◽  
Biological Properties ◽  
Bioactive Substances ◽  
Dpph Test

Introduction. Propolis, also known as bee glue, is a resinous material collected by honeybees with numerous biological properties, including antibacterial, antifungal, antioxidant and anticancer effects. Due to its health-promoting properties, propolis is a component of many products, including dietary supplements, cosmetics and healthy food. Aim. The aim of the study was to determine the antibacterial, antifungal and antioxidant activity of propolis extracts, as well as to compare the biological activity of propolis extracts, depending on the solvent used – ethyl alcohol or propylene glycol. Material and methods. Two propolis extracts were used in the research – the first was prepared in ethyl alcohol, and the second in propylene glycol. The antimicrobial activity of the examined extracts was determined against S. aureus, E. coli and C. albicans. The antioxidant activity was determined on the basis of the evaluation of their antiradical activity in the DPPH· test and Fe2+ chelating activity. Moreover, the total content of phenolic compounds and flavonoids in the tested extracts was determined using the colorimetric method. Results. The tested propolis extracts, regardless of the solvent used (ethyl alcohol or propylene glycol), showed high antibacterial (against S. aureus), antifungal (against C. albicans) and antioxidant (antiradical activity in the DPPH· test and ferrous iron chelating potency in the ferrozine test) activity. Moreover, both tested extracts were characterized by a high and similar content of bioactive compounds – phenolic compounds and flavonoids. Conclusions. The results of the conducted tests showed that the solvent used did not affect determined biological activity and the content of bioactive substances in the tested propolis extracts.

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