1 / 1

Synthesis of Biomimetic Channels with Amphiphilic Cyclodextrins:

Artificial channels. Natural channels. Crown ethers: Lehn and coll., Tetrahedron lett. 1988. Resorcen: hemi-channels Kokube et al ., Angew, 1994. Cyclic Peptides association Ghadiri et al ., Nature, 1993. An antimicrobial: The Gramicidine A. An ionic channel: KcsA

dixie
Download Presentation

Synthesis of Biomimetic Channels with Amphiphilic Cyclodextrins:

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript


  1. Artificial channels Natural channels Crown ethers: Lehn and coll., Tetrahedron lett. 1988 Resorcen: hemi-channels Kokube et al., Angew, 1994 Cyclic Peptides association Ghadiri et al., Nature, 1993 Anantimicrobial: The Gramicidine A Anionic channel: KcsA MacKinnon et al., Science, 1998 A toxin: α-hémolysine Song et al., Science, 1996 Aim of the work and tools… Biomimetic artificial channels Advantages of cyclodextrins Permanent channel • To increase our understanding of natural ion channels • Possible avenues to novel non natural antimicrobials How? Using cyclodextrins as pore-forming molecules hydrophobic • Compatible geometry with lipid bilayer • Variation of the pore size • Selective modification of the hydroxyl groups to form amphiphilic molecules hydrophilic hydrophilic hemi-channel (or transient channels) hydrophilic Hemi-channels synthesized from per-2,3-heptyl-β-CD (A) and per-6-PEO-2,3-heptyl- β-CD (B1 and B2): MALDI-TOF and 13C NMR characterizations of compound B1: Electrical measurements of various CD pores inserted in lipid bilayer membranes h, i, 6 A B1 B2 Measured current vs time for a negative voltage g j 3,5 a f k b cd e Water solubility improved by the PEO chains Formation of well-defined transient pores 1 2,4 Strategy to synthesize transmembranar channels ESI-MS and 2D NMR characterizations of compound C: A B C Compound C (per-2,6-di-O-hydroxypropyl-3-O-methyl-()-CD)obtained with good yields Synthesis of Biomimetic Channels with Amphiphilic Cyclodextrins: From Hemi to Transmembranar Channels Z. Eskandani, N. Badi, C. Huin, L. Auvray, P. Guégan, Laboratoire Matériaux Polymères aux Interfaces UMR CNRS 7581, Université d’Evry-Val-d’Essonne, 91025 Evry Cedex, France contact : pguegan@univ-evry.fr Conclusion and prospects 1) Formation of hemi-channels proved by electrical measurments 2) Transmembranar channels formation is expected with the further molecules obtainedfrom the ethylene oxide anionic polymerisation initiated by the per-2,6-di-O-hydroxypropyl-3-O-methyl-()-CD)

More Related