- Structure-Activity Relationship of Peptide-Conjugated Chloramphenicol for Inhibiting Escherichia coli
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Intravenous administration of a prodrug, chloramphenicol succinate (CLsu), is ineffective. Recently, we have shown that conjugation of diglycine of CLsu (CLsuGG) not only increases the antibiotic efficacy against Escherichia coli but also reduces adverse drug effects against bone marrow stromal cells. Here, we report the synthesis of structural analogues of CLsuGG and their activities against E. coli. These analogues reveal several trends: (i) except the water-insoluble analogues, the attachment of peptides to CLsu enhances the efficacy of the prodrugs; (ii) negative charges, high steric hindrance in the side chains, or a rigid diester decreases the activities of prodrugs in comparison to CLsuGG; (iii) dipeptides apparently increase the efficacy of the prodrugs most effectively; and so forth. This work suggests that conjugating peptides to CLsu effectively modulates the properties of prodrugs. The structure-activity relationship of these new conjugates may provide useful insights for expanding the pool of antibiotics.
- Wang, Jiaqing,Shy, Adrianna,Wu, Difei,Cooper, Deani L.,Xu, Jiashu,He, Hongjian,Zhan, Wenjun,Sun, Shenghuan,Lovett, Susan T.,Xu, Bing
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- Chloramphenicol sodium succinate synthesis method
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The invention discloses a chloramphenicol sodium succinate synthesis method, which comprises: preparing chloramphenicol hemisuccinate by using chloramphenicol and succinic anhydride as raw materials,preparing chloramphenicol succinamide from the chloramphenicol hemisuccinate and ethanolamine, carrying out acidification treatment on the chloramphenicol succinamide to obtain high-purity chloramphenicol hemisuccinate monoester, and preparing chloramphenicol sodium succinate by using the chloramphenicol hemisuccinate monoester and sodium isooctanoate as raw materials. According to the present invention, the chloramphenicol sodium succinate is directly prepared by using the simple and easily-available preparation process, and has characteristics of high purity and high yield; the obtained product can be directly used so as to simplify the use process and achieve the good use effect; and the synthesis method provides the reliable method for the industrial preparation of chloramphenicol sodium succinate, has advantages of easily available raw materials, mild reaction conditions, short time, solvent recovery, simple and easy-performing operation, simple equipment and the like, and has theproduct yield of over 80%, wherein the content determined by liquid chromatography and UV-visible spectrophotometer is up to more than 99%.
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Paragraph 0086-0096; 0100-0110; 0114-0124
(2019/08/01)
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- Surface plasmon resonance assay for chloramphenicol
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We report a rapid and ultrasensitive surface plasmon resonance (SPR) assay of chloramphenicol (CAP) by using large gold nanoparticles (40 nm) for signal enhancement on a mixed self-assembled monolayer (mSAM) sensor surface. After immobilization of the target antibiotic CAP through its ovalbumin (OVA) conjugates with an oligoethylene glycol (OEG) linker on the mSAM surface, sequential binding of anti-CAP antibody and IgG/nanogold (40 nm) onto the sensor surface afforded a rapid (A limit of detection (LOD) for CAP as low as 0.74 fg/mL was achieved in aqueous buffer, and the linear working range was between 1-1000 fg/mL. While the LOD of CAP in a honey spiked-specimen is 17.5 fg/mL, the detection range is 80-5000 fg/mL. The mSAM sensor surface was also shown to be highly stable with over 400 binding/regeneration cycles performed.
- Yuan, Jing,Oliver, Richard,Aguilar, Marie-Isabel,Wu, Yinqiu
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experimental part
p. 8329 - 8333
(2009/04/07)
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- Synthesis of Ester Derivatives of Chloramphenicol by Lipase-Catalyzed Transesterification in Organic Solvents
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Regioselective esterification of chloramphenicol (1) and its synthetic analogue thiamphenicol (2) has been achieved by the action of lipase in acetone and several methyl carboxylates.Aliphatic and aromatic esters of different sizes and natures have been introduced selectively on the primary hydroxyl group of these molecules by modification of the reaction conditions (e.g., temperature, solvent, and lipase source).
- Ottolina, Gianluca,Carrea, Giacomo,Riva, Sergio
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p. 2366 - 2369
(2007/10/02)
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