| Surface modification of poly(lactic acid) nanoparticles by covalent attachment of thiol groups by means of three methods. | |
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MedLine Citation:
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PMID: 12527160 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The aim of the present work was to find a suitable method for the introduction of thiol functions on the surface of poly(DL-lactic acid) (PLA) nanoparticles. Three different approaches were investigated. The modification of the surface involves the activation of PLA carboxylic acid groups followed by the attack of a nucleophile such as cysteine (method #1) or cystamine (method #2 and #3) that provide thiol functions via an amide bond. For the conjugation with cystamine, a second reaction step is required to expose the sulfhydryl function of cystamine that is otherwise protected in a disulfide bond. 1,4-Dithio-DL-threitol (DTT) (method #2) or Tris(2-carboxyethyl)-phosphine hydrochloride (method #3) were evaluated for their ability to reduce this linkage. Method #1 allowed a maximum of 8.5+/-2.8 mmol of thiol functions per mol of PLA to be attached on the surface of the nanoparticles. Method #2 allowed the introduction of a greater number of thiol functions (up to 190+/-15 mmol per mol of PLA). However, this latter method has a major drawback: DTT interacts strongly with the nanoparticle matrix during the reduction step. Method #3 has the advantage over method #2 in that it allowed a significant number of thiol functions to be covalently bound to the particles (up to 107.6+/-0.6 mmol per mol of PLA) without the problem of undesired interaction between DTT and the nanoparticle matrix. The introduction of thiol groups onto the surface of PLA nanoparticles is possible with all three suggested methods. The method #3 provides a straight forward approach for the substitution of carboxylic acid groups with a high number of activated sulfhydryl at the surface of PLA nanoparticles. |
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Authors:
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Leila Nobs; Franz Buchegger; Robert Gurny; Eric Allémann |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: International journal of pharmaceutics Volume: 250 ISSN: 0378-5173 ISO Abbreviation: Int J Pharm Publication Date: 2003 Jan |
Date Detail:
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Created Date: 2003-01-15 Completed Date: 2003-07-24 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 7804127 Medline TA: Int J Pharm Country: Netherlands |
Other Details:
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Languages: eng Pagination: 327-37 Citation Subset: IM |
Affiliation:
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School of Pharmacy, University of Geneva, Quai Ernest-Ansermet 30, 1211 4, Geneva, Switzerland. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Lactic Acid
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chemistry* Nanotechnology / methods* Polymers / chemistry* Sulfhydryl Compounds / chemistry* Surface Properties / drug effects Technology, Pharmaceutical / methods* |
| Chemical | |
Reg. No./Substance:
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0/Polymers; 0/Sulfhydryl Compounds; 26100-51-6/poly(lactic acid); 50-21-5/Lactic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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