Design of Stimuli-Responsive Dynamic Covalent Delivery Systems for Volatile Compounds (Part 1): Controlled Hydrolysis of Micellar Amphiphilic Imines in Water.

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Abstrakt

Tytuł:: Design of Stimuli-Responsive Dynamic Covalent Delivery Systems for Volatile Compounds (Part 1): Controlled Hydrolysis of Micellar Amphiphilic Imines in Water.
Autorzy:: Lutz E; SAMS Research Group, Institut Charles Sadron, CNRS, University of Strasbourg, 23 rue du Loess, BP 84047, 67034, Strasbourg Cedex 2, France.
Moulin E; SAMS Research Group, Institut Charles Sadron, CNRS, University of Strasbourg, 23 rue du Loess, BP 84047, 67034, Strasbourg Cedex 2, France.
Tchakalova V; Firmenich SA, Corporate R&D Division, Rue de la Bergère 7, 1242, Satigny, Switzerland.
Benczédi D; Firmenich SA, Corporate R&D Division, Rue de la Bergère 7, 1242, Satigny, Switzerland.
Herrmann A; Firmenich SA, Corporate R&D Division, Rue de la Bergère 7, 1242, Satigny, Switzerland.
Giuseppone N; SAMS Research Group, Institut Charles Sadron, CNRS, University of Strasbourg, 23 rue du Loess, BP 84047, 67034, Strasbourg Cedex 2, France.
Źródło:: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Sep 20; Vol. 27 (53), pp. 13457-13467. Date of Electronic Publication: 2021 Aug 06.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Original Publication: Weinheim, Germany : Wiley-VCH
MeSH Terms:: Imines*
Micelles*
Hydrolysis ; Hydrophobic and Hydrophilic Interactions ; Water
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Parts of this publication are the subject of a patent application: E. Lutz, N. Giuseppone, A. Herrmann, V. Tchakalova, D. Benczédi (Firmenich SA & CNRS), WO 2018/134410, 2018.
V. Tchakalova, E. Lutz, S. Lamboley, E. Moulin, D. Benczédi, N. Giuseppone, A. Herrmann, Chem. Eur. J. 2021, 27, DOI: 10.1002/chem.202102051 (following publication).
Contributed Indexing:: Keywords: amphiphiles; dynamic covalent chemistry; imines; micelles; self-assembly
Substance Nomenclature:: 0 (Imines)
0 (Micelles)
059QF0KO0R (Water)
Entry Date(s):: Date Created: 20210716 Date Completed: 20210921 Latest Revision: 20210921
Update Code:: 20240105
DOI:: 10.1002/chem.202102049
PMID:: 34270124
: Czasopismo naukowe

Pełny tekst

Despite their intrinsic hydrolysable character, imine bonds can become remarkably stable in water when self-assembled in amphiphilic micellar structures. In this work, we systematically studied some of these structures and the influence of various parameters that can be used to take control of their hydrolysis, including pH, concentration, the position of the imine function in the amphiphilic structure, relative lengths of the linked hydrophilic and hydrophobic moieties. Thermodynamic and kinetic data led us to the rational design of stable imines in water, partly based on the location of the imine function within the hydrophobic part of the amphiphile and on a predictable quantitative term that we define as the total hydrophilic-lipophilic balance (HLB). In addition, we show that such stable systems are also stimuli-responsive and therefore, of potential interest in trapping and releasing micellar components on demand.
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