Bicyclo[1.1.1]pentane (BCP) is studied extensively as a bioisosteric component of drugs. Not found in nature, this molecular unit approximates the distance of a -disubstituted benzene which is replaced in medicines as a method of improving treatments. Predicting interactions of these drugs with specific active sites requires knowledge of the non-covalent interactions engaged by this subunit. Structure determinations and computational analysis (Hirshfeld analysis, 2D fingerprint plots, DFT) of seven BCP derivatives chosen to probe specific and directional interactions. X-ray analysis revealed the presence of various non-covalent interactions including I ⋅⋅⋅ I, I ⋅⋅⋅ N, N-H ⋅⋅⋅ O, C-H ⋅⋅⋅ O, and H-C ⋅⋅⋅ H-C contacts. The preference of halogen bonding (I ⋅⋅⋅ I or I ⋅⋅⋅ N) in BCP - strictly depends upon the electronic nature and angle between bridgehead substituents. The transannular distance in co-crystals and was longer as compared to monomers and . Stronger N-H ⋅⋅⋅ O and weaker C-H ⋅⋅⋅ O contacts were observed for BCP while the O ⋅⋅⋅ H interaction was a prominent contact for BCP . The presence of 3D BCP units prevented the π ⋅⋅⋅ π stacking between phenyl rings in , , and . The BCP skeleton was often rotationally averaged, indicating fewer interactions compared to bridgehead functional groups. Using DFT analysis, geometries were optimized and molecular electrostatic potentials were calculated on the BCP surfaces. These interaction profiles may be useful for designing BCP analogs of drugs.
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http://dx.doi.org/10.1002/ejoc.202001564 | DOI Listing |
Anal Bioanal Chem
January 2025
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of Biomedical Materials, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210023, China.
Insulin bound with ligand molecules can improve its bioavailability in oral formulations. In this work, the interactions between insulin and bile acids of taurocholic acid (TCA) and glycocholic acid (GCA) are characterized using different mass spectrometry (MS) methods. Electrospray (ESI)-MS analysis revealed that GCA and TCA could interact with insulin individually or together through non-covalent bonds, and the products included mGCA-insulin, nTCA-insulin, and mGCA-nTCA-insulin complexes.
View Article and Find Full Text PDFJ Colloid Interface Sci
January 2025
School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 101408 China. Electronic address:
The exploration of pure organic ultra-long room temperature phosphorescence (RTP) materials has emerged as a research hotspot in recent years. Herein, a simple strategy for fabricating long-afterglow polymer aerogels with three-dimensional ordered structures and environmental monitoring capabilities is proposed. Based on the non-covalent interactions between pectin (PC) and melamine formaldehyde (MF), a composite aerogel (PCMF@phenanthrene) (PCMF@PA) doped with phosphorescent organic small molecules was constructed.
View Article and Find Full Text PDFPLoS One
January 2025
Manchester Cancer Research Centre, Division of Cancer Sciences, School of Medical Sciences, Faculty of Biology, Medicine and Health, University of Manchester, Manchester, United Kingdom.
Non-covalent protein-protein interactions are one of the most fundamental building blocks in cellular signalling pathways. Despite this, they have been historically hard to identify using conventional methods due to their often weak and transient nature. Using genetic code expansion and incorporation of commercially available unnatural amino acids, we have developed a highly accessible method whereby interactions between biotinylated ubiquitin-like protein (UBL) probes and their binding partners can be stabilised using ultraviolet (UV) light-induced crosslinks.
View Article and Find Full Text PDFJ Chem Phys
January 2025
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
The Effective Fragment Potential (EFP) method, a polarizable quantum mechanics-based force field for describing non-covalent interactions, is utilized to calculate protein-ligand interactions in seven inactive cyclin-dependent kinase 2-ligand complexes, employing structural data from molecular dynamics simulations to assess dynamic and solvent effects. Our results reveal high correlations between experimental binding affinities and EFP interaction energies across all the structural data considered. Using representative structures found by clustering analysis and excluding water molecules yields the highest correlation (R2 of 0.
View Article and Find Full Text PDFRSC Adv
January 2025
Dipartimento di Scienze e Innovazione Tecnologica, Università Del Piemonte Orientale A. Avogadro Viale T. Michel 11 15121 Alessandria Italy
A novel synthesis of a nanometric MCM-41 from biogenic silica obtained from rice husk is here presented. CTABr and Pluronic F127 surfactants were employed as templating agents to promote the formation of a long-range ordered 2D-hexagonal structure with cylindrical pores and to limit the particle growth at the nanoscale level thus resulting in a material with uniform particle size of 20-30 nm. The physico-chemical properties of this sample (RH-nanoMCM) were investigated through a multi-technique approach, including PXRD, Si MAS NMR, TEM, -potential and N physisorption analysis at 77 K.
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