Novel Parallel Stacking Interactions of Aromatic Molecules

2014 ◽  
pp. 375-404
Keyword(s):  
Stacking Interactions ◽  
Aromatic Molecules

Suppressing π–π stacking interactions for enhanced solid-state emission of flat aromatic molecules via edge functionalization with picket-fence-type groups

2020 ◽  
Vol 8 (48) ◽  
pp. 17289-17296
Author(s):  
Hye Jin Cho ◽  
Sang Won Kim ◽  
Sungjin Kim ◽  
Sangback Lee ◽  
Juhyen Lee ◽  
...  
Keyword(s):  
Solid State ◽  
Light Emitting Diodes ◽  
Organic Light Emitting Diodes ◽  
Stacking Interactions ◽  
Light Emitting ◽  
Aromatic Molecules ◽  
Organic Light ◽  
Π Stacking ◽  
Picket Fence ◽  
Π Stacking Interaction

Picket-fence-type substituents effectively suppress the π–π stacking interaction of flat aromatic molecules and enhance solid-state emission for application in organic light-emitting diodes.

Relation between structure and enthalpy for stacking interactions of aromatic molecules

2010 ◽  
Vol 108 (15) ◽  
pp. 1941-1947 ◽  
Author(s):  
Adrian Hernandez Santiago ◽  
Salvador Rosas Castilla ◽  
Albino Morales Rodriguez ◽  
Elena Aleskerova ◽  
Anastasia Lantushenko ◽  
...  
Keyword(s):  
Stacking Interactions ◽  
Aromatic Molecules

Nitrosubstituted aromatic molecules as universal nucleobases: Computational analysis of stacking interactions

2006 ◽  
Vol 428 (1-3) ◽  
pp. 157-166 ◽  
Author(s):  
Craig A. Wheaton ◽  
Sarah L. Dobrowolski ◽  
Andrea L. Millen ◽  
Stacey D. Wetmore
Keyword(s):  
Computational Analysis ◽  
Stacking Interactions ◽  
Aromatic Molecules

Perylene bisimide cyclophanes as receptors for planar transition structures – Catalysis of stereoinversions by shape-complementarity and noncovalent π–π interactions

2021 ◽  
Author(s):  
Asja A. Kroeger ◽  
Amir Karton
Keyword(s):  
Stacking Interactions ◽  
Π Interactions ◽  
Perylene Bisimide ◽  
Aromatic Molecules ◽  
Shape Complementarity ◽  
Π Stacking ◽  
Transition Structures ◽  
Planar Transition

Perylene bisimide (PBI) cyclophanes have been shown to form ideal hosts for large aromatic molecules, offering rigid cavities and ideal monomer spacing for π–π stacking interactions between host and guest....

scholarly journals Methylxanthines (caffeine, pentoxifylline and theophylline) decrease the mutagenic effect of daunomycin, doxorubicin and mitoxantrone.

2005 ◽  
Vol 52 (4) ◽  
pp. 923-926 ◽  
Author(s):  
Jacek Piosik ◽  
Anna Gwizdek-Wiśniewska ◽  
Katarzyna Ulanowska ◽  
Jakub Ochociński ◽  
Agata Czyz ◽  
...  
Keyword(s):  
Aromatic Compounds ◽  
Mutagenic Effect ◽  
Spectrophotometric Titration ◽  
Stacking Interactions ◽  
Electron Systems ◽  
Cytotoxic Effects ◽  
Aromatic Molecules ◽  
Mixed Aggregates ◽  
Polycyclic Aromatic

Previously performed experiments showed that methylxanthines, especially caffeine, may protect cells against cytostatic or cytotoxic effects of several aromatic compounds. One of the proposed mechanisms of this protection is based on stacking interactions between pi electron systems of polycyclic aromatic molecules. In this work, we demonstrate that caffeine and other methylxanthines--pentoxifylline and theophylline--significantly decrease mutagenicity of the anticancer aromatic drugs daunomycin, doxorubicin and mitoxantrone. The spectrophotometric titration of these aromatic compounds by methylxanthines indicated formation of mixed aggregates. The concentrations of free active forms of the drugs decreased when the concentrations of methylxanthines increased in the mixture. Therefore, likely methylxanthines may play a role of scavengers of the free active forms of daunomycin, doxorubicin and mitoxantrone.

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>

Sign in / Sign up

Export Citation Format

Share Document