Stacking interactions between caffeine and methyl gallate

1996 ◽  
Vol 92 (2) ◽  
pp. 231 ◽  
Author(s):  
Nicola J. Baxter ◽  
Michael P. Williamson ◽  
Terence H. Lilley ◽  
Edwin Haslam
Keyword(s):  
Stacking Interactions ◽  
Methyl Gallate

Understanding the electron density reorganization upon stacking vs. H-bonding interaction in methyl gallate–caffeine complexes

RSC Advances ◽  
2014 ◽  
Vol 4 (48) ◽  
pp. 25018-25027 ◽  
Author(s):  
Laura Estévez ◽  
Marta Sánchez-Lozano ◽  
Ricardo A. Mosquera
Keyword(s):  
Hydrogen Bonds ◽  
Electron Density ◽  
Stacking Interactions ◽  
Methyl Gallate ◽  
Qtaim Analysis ◽  
Cooperative Effects ◽  
Bonding Interaction

QTAIM analysis of selected subcomplexes contained in methyl gallate-caffeine crystal indicate: a) significant differences between electron density reorganization involved in H-bonds and stacking interactions; b) cooperative effects are only significant when bond paths associated to homomonomeric hydrogen bonds are found.

Intrinsic Stacking Interactions of Natural and Artificial Nucleobases

2019 ◽  
Author(s):  
Drew P. Harding ◽  
Laura J. Kingsley ◽  
Glen Spraggon ◽  
Steven Wheeler
Keyword(s):  
Gas Phase ◽  
Electrostatic Interactions ◽  
Density Functional ◽  
Molecular Descriptors ◽  
Stacking Interactions ◽  
Interaction Energies ◽  
Functional Theory ◽  
Binding Partner ◽  
Heavy Atoms ◽  
Wide Range

The intrinsic (gas-phase) stacking energies of natural and artificial nucleobases were explored using density functional theory (DFT) and correlated ab initio methods. Ranking the stacking strength of natural nucleobase dimers revealed a preference in binding partner similar to that seen from experiments, namely G > C > A > T > U. Decomposition of these interaction energies using symmetry-adapted perturbation theory (SAPT) showed that these dispersion dominated interactions are modulated by electrostatics. Artificial nucleobases showed a similar stacking preference for natural nucleobases and were also modulated by electrostatic interactions. A robust predictive multivariate model was developed that quantitively predicts the maximum stacking interaction between natural and a wide range of artificial nucleobases using molecular descriptors based on computed electrostatic potentials (ESPs) and the number of heavy atoms. This model should find utility in designing artificial nucleobase analogs that exhibit stacking interactions comparable to those of natural nucleobases. Further analysis of the descriptors in this model unveil the origin of superior stacking abilities of certain nucleobases, including cytosine and guanine.

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz
Keyword(s):  
Noncovalent Interactions ◽  
Interaction Model ◽  
Alder Reaction ◽  
Diels Alder ◽  
Stacking Interactions ◽  
Pi Stacking ◽  
Diels Alder Reaction ◽  
Double Decker ◽  
Anthracene Molecule ◽  
New Strategies

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

A Chemical Perspective to the Anti-Amyloid Action of Compounds and a Nanoparticle Based Assay for Screening Amyloid Inhibitors

2020 ◽  
Author(s):  
Nidhi Gour ◽  
Bharti Koshti
Keyword(s):  
Memory Loss ◽  
Cost Effective ◽  
Structural Motif ◽  
Rapid Screening ◽  
Stacking Interactions ◽  
Aromatic Rings ◽  
Amyloid Fibers ◽  
Aromatic Stacking ◽  
Cost Effective Technique ◽  
The Brain

Aggregation of amyloid beeta 1-42 (Aβ<sub>42</sub>) peptide causes the formation of clustered deposits knows as amyloid plaques in the brain which leads to neuronal dysfunction and memory loss and associated with many neurological disorders including Alzheimer’s and Parkinson’s. Aβ<sub>42</sub> has core structural motif with phenylalanine at the 19 and 20 positions. The diphenylalanine (FF) residue plays a crucial role in the formation of amyloid fibers and serves as model peptide for studying Aβ<sub>42 </sub>aggregation. FF self-assembles to well-ordered tubular morphology via aromatic pi-pi stackings. Our studies, suggest that the aromatic rings present in the anti-amyloidogenic compounds may interact with the pi-pi stacking interactions present in the FF. Even the compounds which do not have aromatic rings, like cyclodextrin and cucurbituril show anti-amyloid property due to the binding of aromatic ring inside the guest cavity. Hence, our studies also suggest that compounds which may have a functional moiety capable of interacting with the aromatic stacking interactions might be tested for their anti-amyloidogenic properties. Further, in this manuscript, we have proposed two novel nanoparticle based assays for the rapid screening of amyloid inhibitors. In the first assay, interaction between biotin-tagged FF peptide and the streptavidin labelled gold nanoparticles (s-AuNPs) were used. In another assay, thiol-Au interactions were used to develop an assay for detection of amyloid inhibitors. It is envisaged that the proposed analytical method will provide a simple, facile and cost effective technique for the screening of amyloid inhibitors and may be of immense practical implications to find the therapeutic remedies for the diseases associated with the protein aggregation.

Predicting the Strength of Stacking Interactions Between Heterocycles and Aromatic Amino Acid Side Chains

2019 ◽  
Author(s):  
Andrea N. Bootsma ◽  
Analise C. Doney ◽  
Steven Wheeler
Keyword(s):  
Amino Acid ◽  
Binding Sites ◽  
Aromatic Amino Acid ◽  
Aromatic Amino Acids ◽  
Biologically Active ◽  
Side Chains ◽  
Stacking Interactions ◽  
Inhibitor Binding ◽  
Protein Binding Sites ◽  
Amino Acid Side Chains

<p>Despite the ubiquity of stacking interactions between heterocycles and aromatic amino acids in biological systems, our ability to predict their strength, even qualitatively, is limited. Based on rigorous <i>ab initio</i> data, we have devised a simple predictive model of the strength of stacking interactions between heterocycles commonly found in biologically active molecules and the amino acid side chains Phe, Tyr, and Trp. This model provides rapid predictions of the stacking ability of a given heterocycle based on readily-computed heterocycle descriptors. We show that the values of these descriptors, and therefore the strength of stacking interactions with aromatic amino acid side chains, follow simple predictable trends and can be modulated by changing the number and distribution of heteroatoms within the heterocycle. This provides a simple conceptual model for understanding stacking interactions in protein binding sites and optimizing inhibitor binding in drug design.</p>

Self-Recognizing π-π Stacking Interactions Designed for the Generation of Ultrastable Mesoporous Hydrogen-Bonded Organic Frameworks

2019 ◽  
Author(s):  
KAIKAI MA ◽  
Peng Li ◽  
John Xin ◽  
Yongwei Chen ◽  
Zhijie Chen ◽  
...  
Keyword(s):  
Pore Size ◽  
Fiber Composite ◽  
Aqueous Media ◽  
Stacking Interactions ◽  
Mustard Gas ◽  
X Ray Diffraction ◽  
X Ray ◽  
Expansion Strategy ◽  
Π Stacking ◽  
Hydrogen Bonded

Creating crystalline porous materials with large pores is typically challenging due to undesired interpen-etration, staggered stacking, or weakened framework stability. Here, we report a pore size expansion strategy by self-recognizing π-π stacking interactions in a series of two-dimensional (2D) hydrogen–bonded organic frameworks (HOFs), HOF-10x (x=0,1,2), self-assembled from pyrene-based tectons with systematic elongation of π-conjugated molecular arms. This strategy successfully avoids interpene-tration or staggered stacking and expands the pore size of HOF materials to access mesoporous HOF-102, which features a surface area of ~ 2,500 m2/g and the largest pore volume (1.3 cm3/g) to date among all reported HOFs. More importantly, HOF-102 shows significantly enhanced thermal and chemical stability as evidenced by powder x-ray diffraction and N2 isotherms after treatments in chal-lenging conditions. Such stability enables the adsorption of dyes and cytochrome c from aqueous media by HOF-102 and affords a processible HOF-102/fiber composite for the efficient photochemical detox-ification of a mustard gas simulant.

Anticancer Activity of Methyl Gallate in RC-58T/h/SA#4 Primary Human Prostate Cancer Cells

2014 ◽  
Vol 43 (3) ◽  
pp. 367-373 ◽  
Author(s):  
Soon Jae Kwon ◽  
Ju Hye Lee ◽  
Jae Yong Kim ◽  
Kwang Deog Moon ◽  
Sung Tae Yee ◽  
...  
Keyword(s):  
Prostate Cancer ◽  
Anticancer Activity ◽  
Cancer Cells ◽  
Human Prostate ◽  
Human Prostate Cancer ◽  
Methyl Gallate ◽  
Prostate Cancer Cells

scholarly journals Anti-quorum quenching activity of methyl gallate isolated from galls of Guiera senegalensis J. F. Gmel (Combretaceae)

2019 ◽  
Vol 13 (16) ◽  
pp. 290-297 ◽  
Author(s):  
Ouedraogo Vincent ◽  
Alexandre Eric Djifaby Sombié Pierre ◽  
Compaoré Moussa ◽  
Kiendrébéogo Martin
Keyword(s):  
Quorum Quenching ◽  
Methyl Gallate ◽  
Guiera Senegalensis

Examination of Aggregation Induced Enhanced Emission in a Propeller Shaped Chiral- Nonconjugated Blue Emitter from Restricted Intramolecular Rotation and J Type π⋯π Stacking Interactions

2021 ◽  
Author(s):  
Gul Yakali
Keyword(s):  
Thin Film ◽  
Small Molecules ◽  
Solid Phase ◽  
Stacking Interactions ◽  
Optoelectronic Materials ◽  
Π Stacking ◽  
Intramolecular Rotation

Fluorescent organic small molecules with the property of aggregation induced enhanced emission in the solid phase (crystall or thin film) have great attention for the design of optoelectronic materials. Generally,...

X-ray Crystal Structure of Gallium Tris- (8-hydroxyquinoline):  Intermolecular π−π Stacking Interactions in the Solid State

1999 ◽  
Vol 11 (3) ◽  
pp. 530-532 ◽  
Author(s):  
Yue Wang ◽  
Weixing Zhang ◽  
Yanqin Li ◽  
Ling Ye ◽  
Guangdi Yang
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Stacking Interactions ◽  
X Ray ◽  
Π Stacking
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