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Cellular Uptake Mediated by Cyclic Oligochalcogenides.

Rémi Martinent¹, Quentin Laurent², Naomi Sakai²

¹Department of Organic Chemistry, University of Geneva, Geneva, Switzerland, SCS-DSM Award for best poster presentation in Medicinal Chemistry;,

|April 13, 2019

Summary

This summary is machine-generated.

Cyclic oligochalcogenides (COCs) offer innovative cellular entry strategies. Optimized ring tension enhances dynamic covalent chemistry for cell penetration, overcoming endosomal capture for cytosolic delivery.

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Area of Science:

Chemical biology
Molecular delivery systems

Background:

Cellular uptake remains a significant hurdle in chemical biology.
Cyclic oligochalcogenides (COCs) are novel molecular tools for cell entry.
Dynamic covalent chemistry is key to COC-mediated transport.

Purpose of the Study:

To explore innovative strategies for cellular uptake using COCs.
To investigate the role of ring tension in COC transport dynamics.
To understand the mechanism of cytosolic delivery beyond endosomal capture.

Main Methods:

Utilizing dynamic covalent exchange chemistry with varying ring tensions.
Investigating the chemical properties of chalcogenols for membrane crossing.
Hypothesizing and examining the 'walking' mechanism along disulfide tracks.

Main Results:

Increased ring tension enhances the speed and selectivity of COC-mediated transport.
Dynamic covalent COC opening generates acidic chalcogenols.
The proposed mechanism involves chalcogenol deprotonation and disulfide track interaction.

Conclusions:

COCs represent a promising approach for efficient cellular and cytosolic delivery.
The mechanism of cytosolic entry involves specific chemical triggers and interactions with membrane proteins.
Further research is needed to assess the compatibility of diselenolanes for delivering larger molecules.