Article
Chemistry, Physical
Andrzej Olczak, Jaroslaw Sukiennik, Beata Olszewska, Monika Stefaniak, Krzysztof Walczynski, Malgorzata Szczesio
Summary: Seven new low-temperature structures of 4-n-propylpiperazine derivatives, potential H3 receptor antagonists, have been determined, displaying N-H···Br hydrogen bonding and laying the foundation for the search for new non-imidazole histamine H3 receptor antagonists.
Review
Chemistry, Multidisciplinary
Mo Wang, Zhenfeng Zhang, Wanbin Zhang
Summary: This article introduces the development of chiral bicyclic imidazole catalysts by our research group, including their design, synthesis, and application. By using different skeletons and substituents, a series of highly active and selective catalysts were successfully prepared and applied in asymmetric synthesis reactions. This research provides important insights and guidance for exploring new organocatalysts and related reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Dazhi Feng, Lihua Liu, Yuqi Shi, Pian Du, Shengtao Xu, Zheying Zhu, Jinyi Xu, Hong Yao
Summary: Bicyclic peptides, with two loops within their structure, have emerged as powerful tools in the development of new peptide drugs due to their potential to bind to challenged drug targets with antibody-like affinity and selectivity. They also possess small molecule-like access to chemical synthesis, enabling large-scale synthesis and screening. This perspective provides an overview of the structure types, synthesis, and applications of bicyclic peptides in current drug development and discusses future challenges.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Timofey D. Moseev, Egor A. Nikiforov, Mikhail V. Varaksin, Valery N. Charushin, Oleg N. Chupakhin
Summary: The study successfully utilized the methodology of nucleophilic substitution of hydrogen to synthesize azaheterocyclic derivatives of phenols of various architectures, resulting in the preparation of 26 novel imidazole-linked polyphenolic compounds. This straightforward method enables the development of novel bifunctional derivatives with both phenolic and imidazole scaffolds, which are of particular interest for versatile applications in medicinal chemistry and materials science.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qian Wang, Kumchok C. Mgimpatsang, Xin Li, Alexander Domling
Summary: A Cu-catalyzed cascade reaction was successfully designed to access highly substituted isoquinolone-4-carboxylic acid using ammonia and 2-halobenzoic acids as crucial building blocks. Privileged polysubstituted isoquinolin-1(2H)-ones were constructed in a combinatorial format with generally moderate to good yields. The protocol showed broad substrate scope and good functional group tolerance, making it possible to access free 4-carboxy-isoquinolone using a convergent multicomponent reaction protocol for the first time.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Muxing Zhou, Tatiana Gridneva, Zhenfeng Zhang, Ende He, Yangang Liu, Wanbin Zhang
Summary: This study presents an efficient route for the synthesis of chiral phthalidyl ester prodrugs using a chiral bicyclic imidazole organocatalyst and a continuous injection process. Computational studies suggest a general base catalytic mechanism different from the widely accepted nucleophilic catalytic mechanism. Analysis of key transition states reveals that CH-pi interactions, rather than previously considered cation/pi-pi interactions, play a dominant role in stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Mikhail Khvotchev, Mikhail Soloviev
Summary: In this review, the recent advances in the development of functional peptides that can modify SNARE-binding interfaces and modulate SNARE function are discussed. The authors evaluate two systems based on peptide-nucleic acids (PNAs) and coiled coil peptides, and review how the self-assembly of SNARE motifs can be used to drive the assembly of complex re-engineered polypeptides.
Article
Engineering, Multidisciplinary
Xiaoxiao Zheng, Yubing Xue, Changhao Dai, Hongwei Yang, Guangbin Cheng
Summary: A series of 5,7-fused bicyclic imidazole-diazepine compounds were developed with high yields by only two efficient steps. These compounds have a stable energetic skeleton with multiple modifiable sites, exhibiting high decomposition temperatures and low mechanical sensitivities. Among them, compound 4 has superior thermochemical stability and mechanical sensitivities compared to a typical heat-resistant energetic material.
DEFENCE TECHNOLOGY
(2023)
Article
Chemistry, Inorganic & Nuclear
Ritu Yadav, Bindusagar Das, Ashi Singh, Ankita Anmol, Ankita Sharma, Chinmoy Majumder
Summary: This study reports the synthesis and characterization of BICAAC-stabilized phosphinidenes. X-ray crystallography and NMR spectroscopy were used to characterize the compounds, and theoretical calculations indicated the presence of characteristic double bonds.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Ritu Yadav, Bindusagar Das, Ashi Singh, Ankita Anmol, Ankita Sharma, Chinmoy Majumder
Summary: In this study, the synthesis and characterization of bicyclic (alkyl)(amino)carbene (BICAAC)-stabilized phosphinidenes were reported. The compounds were obtained through reactions between trihalophosphine and BICAAC, and their structures were confirmed by X-ray crystallography and NMR spectroscopy. Theoretical calculations revealed the presence of predominant C(carbene)-P double bond characteristic in these compounds.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Physical
Francisco de Azambuja, Alexandra Loosen, Dragan Conic, Maxime van den Besselaar, Jeremy N. Harvey, Tatjana N. Parac-Vogt
Summary: The study explores the catalytic activity of Zr-6-based metal-organic frameworks in peptide bond formation, showing good stability and recyclability in dipeptide cyclization reactions without the need for additional activators. The results indicate that the catalyst can be applied to substrates with bulky and Lewis basic groups, and the reaction is driven by a mechanism involving Lewis acid activation of carboxylate groups towards amine addition.
Article
Chemistry, Multidisciplinary
Alexandra Hindle, Krzysztof Baj, Jonathan A. Iggo, Daniel J. Cox, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: A convergent approach to diazabicyclic scaffolds containing twisted amides or anilines is achieved through photocatalysed hydroamination and subsequent cyclisation of cyclic enecarbamates. The modular synthesis enables variation of the degree of twist and consequently the properties of the amides and anilines.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Analytical
Jia Kong, Jinyao Hu, Jia Li, Jiaxing Zhang, Yuhe Shen, Tianli Yue, Xihui Shen, Yuefei Wang, Zhonghong Li, Yinqiang Xia
Summary: Reconstructing miniaturized peptides to mimic specific protein functions is appealing but challenging. In this study, we propose a practical approach to construct a mimetic peptide of redox-sensitive green fluorescent protein-2 (roGFP2) by rethreading aromatic residues adjacent to the chromophore fragment. By fine-tuning the residues, we designed a mini tetrapeptide (Cys-Phe-Phe-His) that acts as a hydrogen peroxide sensor using ratiometric fluorescence. The roGFP2 mimetic tetrapeptide, with its assembly-induced emissions, is biocompatible, photostable, and exhibits competitive fluorescent properties compared to roGFP2. We demonstrated the ability of the ratiometric tetrapeptide to sense hydrogen peroxide in acidic chambers, providing a promising approach for artificially designing miniaturized peptides with desired functions.
ANALYTICAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Lucia De Rosa, Donatella Diana, Rossella Di Stasi, Alessandra Romanelli, Michele F. M. Sciacca, Danilo Milardi, Carla Isernia, Roberto Fattorusso, Luca D. D'Andrea
Summary: Replacing leucine 10 in the QK peptide with different hydrophobic amino acids leads to changes in helical content and thermal stability, depending on the type of interaction that could be established between Leu7 and the residue in position 10. Interestingly, the changes in helical content and thermal stability are not always correlated, highlighting the complex nature of these interactions.
BIOORGANIC CHEMISTRY
(2021)
Article
Materials Science, Multidisciplinary
Na Li, Ying Ma, Niuniu Chen, Xiaoyu Tang, Shanshan Lv
Summary: This study investigates the effect of microwave on the stability of peptide bonds in silk protein, and finds that microwave irradiation causes minor damage and negligible cleavage of the peptide bonds compared to conventional heating methods, making it suitable for silk protein dissolution.
ADVANCED FIBER MATERIALS
(2022)
Article
Chemistry, Medicinal
Shibin Zhao, Julian Maceren, Mia Chung, Samantha Stone, Raphael Geiben, Melissa L. Boby, Bradley S. Sherborne, Derek S. Tan
Summary: Antibiotic resistance is a major threat to public health, with Gram-negative bacteria presenting unique challenges due to their low permeability and efflux pumps. Limited understanding of the chemical rules for overcoming these barriers hinders antibacterial drug discovery. Efforts to address this issue, such as screening compound libraries and using cheminformatic analysis, have led to the design of sulfamidoadenosines with diverse substituents, showing potential utility in accumulation in Escherichia coli.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Jichun Li, Qing Li, Shuai Xia, Jiahuang Tu, Longbo Zheng, Qian Wang, Shibo Jiang, Chao Wang
Summary: This study successfully developed a short peptide mimetic as a MERS-CoV fusion inhibitor by reproducing the key recognition features of the HR2 helix. The resulting 23-mer lipopeptide showed comparable inhibitory effect to the 36-mer HR2 peptide HR2P-M2. This has important implications for developing short peptide-based antiviral agents to treat MERS-CoV infection.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Krista Jaunsleine, Linda Supe, Jana Spura, Sten van Beek, Anna Sandstrom, Jessica Olsen, Carina Halleskog, Tore Bengtsson, Ilga Mutule, Benjamin Pelcman
Summary: Beta(2)-adrenergic receptor agonists can stimulate glucose uptake by skeletal muscle cells and are therefore potential treatments for type 2 diabetes. The chirality of compounds has a significant impact on the activity of these agonists. This study found that certain synthesized compounds showed higher glucose uptake activity. These findings provide important information for the design of novel beta(2)AR agonists for T2D treatment.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Xin Xu, Jia Chen, Guan Wang, Xiaojuan Zhang, Qiang Li, Xiaobo Zhou, Fengying Guo, Min Li
Summary: The study focuses on EZH2, a promising therapeutic target for various types of cancers. Researchers designed and synthesized a series of novel derivatives aiming to enhance the EZH2 inhibition activity. Among them, compound 28 displayed potent EZH2 inhibition activity and showed high anti-proliferative effects in lymphoma cell lines and xenograft mouse models. The study suggests that compound 28 has potential as a therapeutic candidate for EZH2-associated cancers.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Wei Zhang, Wei Liu, Ya-Dong Zhao, Li-Zi Xing, Ji Xu, Rui-Jun Li, Yun-Xiao Zhang
Summary: This study developed a series of aromatic amide derivatives based on Rhein and investigated their inhibitory activity against alpha-Syn aggregation. Two of these compounds showed promising potential in treating Parkinson's disease by stabilizing alpha-Syn's conformation and disassembling alpha-Syn oligomers and fibrils.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Mani Sharma, S. S. S. S. Sudha Ambadipudi, Neeraj Kumar Chouhan, V. Lakshma Nayak, Srihari Pabbaraja, Sai Balaji Andugulapati, Ramakrishna Sistla
Summary: Therapeutically active lipids in drug delivery systems can enhance the safety and efficacy of treatment. The liposome formulation created using synthesized biologically active lipids showed additive anti-cancer effects and reduced tumorigenic potential.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)