The hydrophobic core effect in model bacterial membranes upon interaction with tetra-p-guanidinoethylcalix[4]arene

Korchowiec, Beata; Orlof-Naturalna, Monika; Korchowiec, Jacek; Vains, Jean-Bernard Regnouf de; Mourer, Maxime; Rogalska, Ewa

doi:10.1016/j.molliq.2021.117636

Cited by 3 publications

(3 citation statements)

References 46 publications

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“…The –O–CO– groups in POPC were practically not involved in hydrogen bond formation (compare both curves in Figure S5 ). It can be noted that the effects observed resemble the flip/flop mechanism described in the case of the CX1 calixarene derivative [ 40 , 43 ].…”

Section: Resultsmentioning

confidence: 80%

The Molecular Bases of the Interaction between a Saponin from the Roots of Gypsophila paniculata L. and Model Lipid Membranes

Korchowiec

Kwiecińska

et al. 2022

IJMS

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In view of the possible medical applications of saponins, the molecular structure of a GOTCAB saponin from the roots of Gypsophila paniculata L. was determined by NMR. The biological activity of saponins may depend on the interaction with cell membranes. To obtain more insight in the mechanism of membrane-related saponin function, an experimental and theoretical study was conducted. Ternary lipid systems composed of sphingomyelin, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, and cholesterol were used as models of mammalian cell membranes. The membrane–saponin interaction was studied experimentally by monitoring surface pressure in the monomolecular films formed at the air–aqueous subphase interface. The behavior of GOTCAB saponin in a water box and model monolayer systems was characterized by molecular dynamics simulations. The results obtained showed that, in the systems used, cholesterol had a decisive effect on the interaction between GOTCAB and phosphocholine or sphingomyelin as well as on its location within the lipid film.

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Section: Resultsmentioning

confidence: 80%

The Molecular Bases of the Interaction between a Saponin from the Roots of Gypsophila paniculata L. and Model Lipid Membranes

Korchowiec

Kwiecińska

et al. 2022

IJMS

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“…They deduced that the affinity of tetra-p-guanidinoethylcalix [4]arene toward bacterial membrane was related to the electrostatic interaction. 47 On the other hand, the conformations of the calix [4]arene skeleton also significantly affect their antibacterial activity, which was demonstrated by Mourer and co-workers using active guanidinocalix [4]arene derivatives. 48 The inversion of at least one phenolic unit led to enhanced antimicrobial effects against E. coli, S. aureus, and P. aeruginosa.…”

Section: Antibacterial Mechanisms and Design Strategiesmentioning

confidence: 97%

“…Calixarenes, a family of oligomeric phenolic macrocycles, are well-known for applications in chemical, physical, biological, and other disciplines due to their three-dimensional structural architecture, versatile conformational isomers, hydrophobic cavities, and ease of functionalization. ,− Korchowiec, Rogalska, and co-workers preorganized guanidinium moieties onto calix[4]arene to combat Gram-positive and Gram-negative bacteria. They deduced that the affinity of tetra- p -guanidinoethylcalix[4]arene toward bacterial membrane was related to the electrostatic interaction . On the other hand, the conformations of the calix[4]arene skeleton also significantly affect their antibacterial activity, which was demonstrated by Mourer and co-workers using active guanidinocalix[4]arene derivatives .…”

Section: Antibacterial Mechanisms and Design Strategiesmentioning

confidence: 99%

Macrocycle-Based Antibacterial Materials

Wang,

Ma,

et al. 2024

Chem. Mater.

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Bacterial infection, the cause of many diseases, has become one of the most severe global public health threats. The emergence of antimicrobial resistance poses a significant challenge in treating bacterial infections. Recently, synthetic macrocycles with various well-defined cavities and excellent dynamic, reversible, and directional noncovalent interactions can not only form complexation with biomarkers or drugs via host−guest recognition but also enable controlled drug delivery in response to many external stimuli, such as pH, thermal, redox, competitive binding, and light irradiation. Therefore, macrocycle-based functional materials have received increasing attention as promising candidates for precise ondemand bacteria inhibition. This Perspective provides an overview of the recent progress in the design and synthesis of macrocyclebased materials with antibacterial properties. The antibacterial mechanisms and various applications are also discussed in detail. Finally, the existing challenges and future opportunities in this emerging research field are put forward with the hope of promoting the further development of macrocycle-based antibacterial materials toward superior biomedical applications.

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Inclusion of organic cations by calix[4]resorcinarenes modified with sulfonic acid groups

Wang,

Liu,

Sun

et al. 2024

Sci. Sin.-Chim

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Calix[4]resorcinarene, as an important branch of the third generation supramolecular compounds, calixarene, have received increasing attention for their functionalized modifications in recent years. In this paper, calix[4]resorcinarenes were synthesized by using resorcinol as the starting material, and calix[4]resorcinarene sulfonic acid derivatives 2a and 2b were synthesized by introducing sulfonic acid groups at their C-2 positions with methylene as a bridge link. The inclusion behavior of 2a and 2b towards solvent molecules and organic ammonium salts was studied. The molecular structures of 2a•Me 4 NCl and 2b•MeOH were determined by X-ray single-crystal diffraction, indicating their 1:1 inclusion formation. Of which, the ammonium cations were encapsulated by dimer of 2a in 2a•Me4NCl. The 1 H NMR characterization was performed to investigate the inclusion of 2b with Et 4 NCl and n-Bu 4 NCl, the results showed that the N + head of ammonium salts are embedded to sulfonic acid groups of 2b. Ultraviolet (UV) spectrum was performed on studying the relationship of absorption of inclusion complex and concentration ratio of host and guest. Moreover, the catalytic effect of 2a•Me 4 NCl in the synthesis of triglycidyl isocyanurate was examined, and it was found to possess good catalytic properties.

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The hydrophobic core effect in model bacterial membranes upon interaction with tetra-p-guanidinoethylcalix[4]arene

Cited by 3 publications

References 46 publications

The Molecular Bases of the Interaction between a Saponin from the Roots of Gypsophila paniculata L. and Model Lipid Membranes

The Molecular Bases of the Interaction between a Saponin from the Roots of Gypsophila paniculata L. and Model Lipid Membranes

Macrocycle-Based Antibacterial Materials

Inclusion of organic cations by calix[4]resorcinarenes modified with sulfonic acid groups

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