Abstract:
:This report describes the synthesis and evaluation of glycosylated polyacrylate nanoparticles that have covalently-bound antibiotics within their framework. The requisite glycosylated drug monomers were prepared from one of three known antibiotics, an N-sec-butylthio beta-lactam, ciprofloxacin, and a penicillin, by acylation with 3-O-acryloyl-1,2-O-isopropylidene-5,6 bis((chlorosuccinyl)oxy)-d-glucofuranose (7) or 6-O-acetyl-3-O-acryloyl-1,2-O-isopropylidene-5-(chlorosuccinyl)oxy-alpha-d-glucofuranose (10). These acrylated monomers were subjected to emulsion polymerization in a 7:3 (w:w) mixture of butyl acrylate-styrene in the presence of sodium dodecyl sulfate as surfactant (3 weight %) and potassium persulfate as a radical initiator (1 weight %). The resulting nanoparticle emulsions were characterized by dynamic light scattering and found to have similar diameters ( approximately 40 nm) and size distributions to those of our previously studied systems. Microbiological testing showed that the N-sec-butylthio beta-lactam and ciprofloxacin nanoparticles both have powerful in vitro activities against methicillin-resistant Staphylococcus aureus and Bacillus anthracis, while the penicillin-bound nanoparticles have no antimicrobial activity. This indicates the need for matching a suitable antibiotic with the nanoparticle carrier. Overall, the study shows that even relatively large, polar acrylate monomers (MW>1000 amu) can be efficiently incorporated into the nanoparticle matrix by emulsion polymerization, providing opportunities for further advances in nanomedicine.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Abeylath SC,Turos E,Dickey S,Lim DVdoi
10.1016/j.bmc.2007.11.052subject
Has Abstractpub_date
2008-03-01 00:00:00pages
2412-8issue
5eissn
0968-0896issn
1464-3391pii
S0968-0896(07)01020-6journal_volume
16pub_type
杂志文章abstract::A series of methyllycaconitine (1a, MLA) analogs was synthesized where the (S)-2-methylsuccinimidobenzoyl group in MLA was replaced with a (R)-2-methyl, 2,2-dimethyl-, 2,3-dimethyl, 2-phenyl-, and 2-cyclohexylsuccinimidobenzoyl (1b-f) group. The analogs 1b-f were evaluated for their inhibition of [(125)I]iodo-MLA bind...
journal_title:Bioorganic & medicinal chemistry
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journal_title:Bioorganic & medicinal chemistry
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更新日期:2013-06-01 00:00:00
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更新日期:2007-06-01 00:00:00
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journal_title:Bioorganic & medicinal chemistry
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更新日期:2013-08-01 00:00:00
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journal_title:Bioorganic & medicinal chemistry
pub_type: 杂志文章
doi:10.1016/j.bmc.2006.10.022
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journal_title:Bioorganic & medicinal chemistry
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journal_title:Bioorganic & medicinal chemistry
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journal_title:Bioorganic & medicinal chemistry
pub_type: 杂志文章
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journal_title:Bioorganic & medicinal chemistry
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journal_title:Bioorganic & medicinal chemistry
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journal_title:Bioorganic & medicinal chemistry
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journal_title:Bioorganic & medicinal chemistry
pub_type: 杂志文章
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更新日期:2006-09-15 00:00:00
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journal_title:Bioorganic & medicinal chemistry
pub_type: 杂志文章
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更新日期:2018-02-01 00:00:00
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journal_title:Bioorganic & medicinal chemistry
pub_type: 杂志文章
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更新日期:2007-11-01 00:00:00
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journal_title:Bioorganic & medicinal chemistry
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更新日期:2019-06-15 00:00:00