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Clusteroluminescence from Cluster Excitons in Small Heterocyclics Free of Aromatic Rings.

ABSTRACT: The study of nonconventional luminescence is important for revealing the luminescence of natural systems and has gradually drawn the attention of researchers in recent years. However, the underlying mechanism is still inexplicable. Herein, the luminescence behavior of two series of simple, heteroatom-containing small molecules without aromatic rings, i.e., maleimide and succinimide derivatives, are studied to gain further mechanistic insight into the nonconventional luminescence process. It has been unveiled that all the molecules exhibit bright and visible luminescence in concentrated solution and solid state and the formation of clusters is the root cause for such behaviors, which can effectively increase the possibility of both the nonradiative n-π* and favorable π-π* transitions and stabilize the excitons formed in the excited state. The distinctive luminescent phenomena and intriguing mechanism presented in this work will be significant for understanding the mechanism of clusteroluminescence and provide new strategies for the rational design of novel luminescent materials.

SUBMITTER: He B

PROVIDER: S-EPMC8025018 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Clusteroluminescence from Cluster Excitons in Small Heterocyclics Free of Aromatic Rings.

He Benzhao B Zhang Jing J Zhang Jianyu J Zhang Haoke H Wu Xiuying X Chen Xu X Kei Konnie H S KHS Qin Anjun A Sung Herman H Y HHY Lam Jacky W Y JWY Tang Ben Zhong BZ

Advanced science (Weinheim, Baden-Wurttemberg, Germany) 20210211 7

The study of nonconventional luminescence is important for revealing the luminescence of natural systems and has gradually drawn the attention of researchers in recent years. However, the underlying mechanism is still inexplicable. Herein, the luminescence behavior of two series of simple, heteroatom-containing small molecules without aromatic rings, i.e., maleimide and succinimide derivatives, are studied to gain further mechanistic insight into the nonconventional luminescence process. It has ...[more]

PMID: 33854902

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Project description:Protein kinases are key enzymes in many signal transduction pathways, and play a crucial role in cellular proliferation, differentiation, and various cell regulatory processes. However, aberrant function of kinases has been associated with cancers and many other diseases. Consequently, competitive inhibition of the ATP binding site of protein kinases has emerged as an effective means of curing these diseases. Over the past three decades, thousands of protein kinase inhibitors (PKIs) with varying molecular frames have been developed. Large-scale data mining of the Protein Data Bank resulted in a database of 2139 non-redundant high-resolution X-ray crystal structures of PKIs bound to protein kinases. This provided us with a unique opportunity to study molecular determinants for the molecular recognition of PKIs. A chemoinformatic analysis of 2139 PKIs resulted in findings that PKIs are "flat" molecules with high aromatic ring counts and low fractions of sp3 carbon. All but one PKI possessed one or more aromatic rings. More importantly, it was found that the average weighted hydrogen bond count is inversely proportional to the number of aromatic rings. Based on this linear relationship, we put forward the exchange rule of hydrogen bonding interactions and non-bonded π-interactions. Specifically, a loss of binding affinity caused by a decrease in hydrogen bonding interactions is compensated by a gain in binding affinity acquired by an increase in aromatic ring-originated non-bonded interactions (i.e., π-π stacking interactions, CH-π interactions, cation-π interactions, etc.), and vice versa. The very existence of this inverse relationship strongly suggests that both hydrogen bonding and aromatic ring-originated non-bonded interactions are responsible for the molecular recognition of PKIs. As an illustration, two representative PKI-kinase complexes were employed to examine the relative importance of different modes of non-bonded interactions for the molecular recognition of PKIs. For this purpose, two FDA-approved PKI drugs, ibrutinib and lenvatinib, were chosen. The binding pockets of both PKIs were thoroughly examined to identify all non-bonded intermolecular interactions. Subsequently, the strengths of interaction energies between ibrutinib and its interacting residues in tyrosine kinase BTK were quantified by means of the double hybrid DFT method B2PLYP. The resulting energetics for the binding of ibrutinib in tyrosine kinase BTK showed that CH-π interactions and π-π stacking interactions between aromatic rings of the drug and hydrophobic residues in its binding pocket dominate the binding interactions. Thus, this work establishes that, in addition to hydrogen bonding, aromatic rings function as important molecular determinants for the molecular recognition of PKIs. In conclusion, our findings support the following pharmacophore model for ATP-competitive kinase inhibitors: a small molecule features a scaffold of one or more aromatic rings which is linked with one or more hydrophilic functional groups. The former has the structural role of acting as a scaffold and the functional role of participating in aromatic ring-originated non-bonded interactions with multiple hydrophobic regions in the ATP binding pocket of kinases. The latter ensure water solubility and form hydrogen bonds with the hinge region and other hydrophilic residues of the ATP binding pocket.

Dataset Information

Clusteroluminescence from Cluster Excitons in Small Heterocyclics Free of Aromatic Rings.

Publications

Clusteroluminescence from Cluster Excitons in Small Heterocyclics Free of Aromatic Rings.

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