Thiol-responsive micelles based on nonionic gemini surfactants with a cystine disulfide spacer

Hyun Chul Kim; Eunjoo Kim; Se Guen Lee; Sung Jun Lee; Hyunmin Kim; Sang Won Jeong

doi:10.1002/pola.27036

Thiol-responsive micelles based on nonionic gemini surfactants with a cystine disulfide spacer

Hyun Chul Kim, Eunjoo Kim, Se Guen Lee, Sung Jun Lee, Hyunmin Kim, Sang Won Jeong

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

Thiol-responsive micelles consisting of novel nonionic gemini surfactants with a cystine disulfide spacer are reported. The gemini surfactants, (C ₁₈-Cys-mPEG)₂ and ((C₁₈)₂-Lys-Cys- mPEG)₂, were synthesized from polyethylene glycol, cysteine, and stearic acid, and their structures were confirmed by ¹H NMR and gel permeation chromatography. (C₁₈-Cys-mPEG)₂ and ((C ₁₈)₂-Lys-Cys-mPEG)₂ formed micelles with average diameters of 13 and 22 nm above the critical micelle concentration of 6.5 and 4.7 μg mL^-1, respectively. The micelles of ((C ₁₈)₂-Lys-Cys-mPEG)₂ containing more stearoyl groups showed encapsulated more hydrophobic indomethacin (IMC) with higher entrapment efficiencies than those of (C₁₈-Cys-mPEG)₂. The gemini surfactant micelles exhibited an accelerated release of encapsulated IMC with the concentration of the reducing agent, glutathione (GSH), whereas they were unaffected by the presence of reduced GSH (GSSG). The 3-(4,5- dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl) -2H-tetrazolium studies revealed the noncytotoxic nature of the gemini surfactant micelles.

Original language	English
Pages (from-to)	582-589
Number of pages	8
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	52
Issue number	4
DOIs	https://doi.org/10.1002/pola.27036
State	Published - 15 Feb 2014

Keywords

biodegradable
disulfide-thiol exchange
drug delivery systems
micelles
stimuli-sensitive polymers
surfactants

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title = "Thiol-responsive micelles based on nonionic gemini surfactants with a cystine disulfide spacer",

abstract = "Thiol-responsive micelles consisting of novel nonionic gemini surfactants with a cystine disulfide spacer are reported. The gemini surfactants, (C 18-Cys-mPEG)2 and ((C18)2-Lys-Cys- mPEG)2, were synthesized from polyethylene glycol, cysteine, and stearic acid, and their structures were confirmed by 1H NMR and gel permeation chromatography. (C18-Cys-mPEG)2 and ((C 18)2-Lys-Cys-mPEG)2 formed micelles with average diameters of 13 and 22 nm above the critical micelle concentration of 6.5 and 4.7 μg mL-1, respectively. The micelles of ((C 18)2-Lys-Cys-mPEG)2 containing more stearoyl groups showed encapsulated more hydrophobic indomethacin (IMC) with higher entrapment efficiencies than those of (C18-Cys-mPEG)2. The gemini surfactant micelles exhibited an accelerated release of encapsulated IMC with the concentration of the reducing agent, glutathione (GSH), whereas they were unaffected by the presence of reduced GSH (GSSG). The 3-(4,5- dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl) -2H-tetrazolium studies revealed the noncytotoxic nature of the gemini surfactant micelles.",

keywords = "biodegradable, disulfide-thiol exchange, drug delivery systems, micelles, stimuli-sensitive polymers, surfactants",

author = "Kim, {Hyun Chul} and Eunjoo Kim and Lee, {Se Guen} and Lee, {Sung Jun} and Hyunmin Kim and Jeong, {Sang Won}",

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AU - Kim, Hyun Chul

AU - Kim, Eunjoo

AU - Lee, Se Guen

AU - Lee, Sung Jun

AU - Kim, Hyunmin

AU - Jeong, Sang Won

PY - 2014/2/15

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N2 - Thiol-responsive micelles consisting of novel nonionic gemini surfactants with a cystine disulfide spacer are reported. The gemini surfactants, (C 18-Cys-mPEG)2 and ((C18)2-Lys-Cys- mPEG)2, were synthesized from polyethylene glycol, cysteine, and stearic acid, and their structures were confirmed by 1H NMR and gel permeation chromatography. (C18-Cys-mPEG)2 and ((C 18)2-Lys-Cys-mPEG)2 formed micelles with average diameters of 13 and 22 nm above the critical micelle concentration of 6.5 and 4.7 μg mL-1, respectively. The micelles of ((C 18)2-Lys-Cys-mPEG)2 containing more stearoyl groups showed encapsulated more hydrophobic indomethacin (IMC) with higher entrapment efficiencies than those of (C18-Cys-mPEG)2. The gemini surfactant micelles exhibited an accelerated release of encapsulated IMC with the concentration of the reducing agent, glutathione (GSH), whereas they were unaffected by the presence of reduced GSH (GSSG). The 3-(4,5- dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl) -2H-tetrazolium studies revealed the noncytotoxic nature of the gemini surfactant micelles.

AB - Thiol-responsive micelles consisting of novel nonionic gemini surfactants with a cystine disulfide spacer are reported. The gemini surfactants, (C 18-Cys-mPEG)2 and ((C18)2-Lys-Cys- mPEG)2, were synthesized from polyethylene glycol, cysteine, and stearic acid, and their structures were confirmed by 1H NMR and gel permeation chromatography. (C18-Cys-mPEG)2 and ((C 18)2-Lys-Cys-mPEG)2 formed micelles with average diameters of 13 and 22 nm above the critical micelle concentration of 6.5 and 4.7 μg mL-1, respectively. The micelles of ((C 18)2-Lys-Cys-mPEG)2 containing more stearoyl groups showed encapsulated more hydrophobic indomethacin (IMC) with higher entrapment efficiencies than those of (C18-Cys-mPEG)2. The gemini surfactant micelles exhibited an accelerated release of encapsulated IMC with the concentration of the reducing agent, glutathione (GSH), whereas they were unaffected by the presence of reduced GSH (GSSG). The 3-(4,5- dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl) -2H-tetrazolium studies revealed the noncytotoxic nature of the gemini surfactant micelles.

KW - biodegradable

KW - disulfide-thiol exchange

KW - drug delivery systems

KW - micelles

KW - stimuli-sensitive polymers

KW - surfactants

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JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 4

ER -

Thiol-responsive micelles based on nonionic gemini surfactants with a cystine disulfide spacer

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