Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens

Dong, Fengying; Li, Lingmeng; Lin, Lin; He, Dannong; Chen, Jingwen; Wei, Wei; Wei, Dongzhi

doi:10.3390/molecules22091523

Cited by 11 publications

(6 citation statements)

References 31 publications

(42 reference statements)

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“…After analysis through conventional bacterial identification methods, the No. 1 unknown bacterial strain was identified as Gram-positive bacteria of Bacillus , having protease, lipase, and amylase activity, which might be utilized to generate antimicrobial substances such as bioactive peptides (Daroit et al, 2012) and chloramphenicol esters (Dong et al, 2017) to inhibit bacterial biofilm formation (Vaikundamoorthy et al, 2018). Bosshard et al (2003) demonstrated that 95–99% similarity for 16S rRNA gene sequencing between two bacteria hints toward a similar species, while >99% indicates the same bacterium.…”

Section: Discussionmentioning

confidence: 99%

A Newly Isolated Bacillus subtilis Strain Named WS-1 Inhibited Diarrhea and Death Caused by Pathogenic Escherichia coli in Newborn Piglets

et al. 2019

Front. Microbiol.

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Bacillus subtilis is recognized as a safe and reliable human and animal probiotic and is associated with bioactivities such as production of vitamin and immune stimulation. Additionally, it has great potential to be used as an alternative to antimicrobial drugs, which is significant in the context of antibiotic abuse in food animal production. In this study, we isolated one strain of B. subtilis , named WS-1, from apparently healthy pigs growing with sick cohorts on one Escherichia coli endemic commercial pig farm in Guangdong, China. WS-1 can strongly inhibit the growth of pathogenic E. coli in vitro . The B. subtilis strain WS-1 showed typical Bacillus characteristics by endospore staining, biochemical test, enzyme activity analysis, and 16S rRNA sequence analysis. Genomic analysis showed that the B. subtilis strain WS-1 shares 100% genomic synteny with B. subtilis with a size of 4,088,167 bp. Importantly, inoculation of newborn piglets with 1.5 × 10 10 CFU of B. subtilis strain WS-1 by oral feeding was able to clearly inhibit diarrhea ( p < 0.05) and death ( p < 0.05) caused by pathogenic E. coli in piglets. Furthermore, histopathological results showed that the WS-1 strain could protect small intestine from lesions caused by E. coli infection. Collectively, these findings suggest that the probiotic B. subtilis strain WS-1 acts as a potential biocontrol agent protecting pigs from pathogenic E. coli infection. Importance: In this work, one B. subtilis strain (WS-1) was successfully isolated from apparently healthy pigs growing with sick cohorts on one E. coli endemic commercial pig farm in Guangdong, China. The B. subtilis strain WS-1 was identified to inhibit the growth of pathogenic E. coli both in vitro and in vivo , indicating its potential application in protecting newborn piglets from diarrhea caused by E. coli infections. The isolation and characterization will help better understand this bacterium, and the strain WS-1 can be further explored as an alternative to antimicrobial drugs to protect human and animal health.

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Section: Discussionmentioning

confidence: 99%

A Newly Isolated Bacillus subtilis Strain Named WS-1 Inhibited Diarrhea and Death Caused by Pathogenic Escherichia coli in Newborn Piglets

et al. 2019

Front. Microbiol.

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“…Lipid fractions (1 µL) in hexane prepared were spotted on the line of origin and run for 30 min in a solvent tank comprising 2 solvents of different ratios i.e., hexane/ ethyl acetate (70:30,v/v%) at room temperature. The ZF-1 UV analyzer visualized the spots at 254 nm [42].…”

Section: Chloramphenicol Palmitate Characterizationmentioning

confidence: 99%

Immobilization of a Novel ESTBAS Esterase from Bacillus altitudinis onto an Epoxy Resin: Characterization and Regioselective Synthesis of Chloramphenicol Palmitate

et al. 2019

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Novel gene estBAS from Bacillus altitudinis, encoding a 216-amino acid esterase (EstBAS) with a signal peptide (SP), was expressed in Escherichia coli. EstBASΔSP showed the highest activity toward p-nitrophenyl hexanoate at 50 °C and pH 8.0 and had a half-life (T1/2) of 6 h at 50 °C. EstBASΔSP was immobilized onto a novel epoxy resin (Lx-105s) with a high loading of 96 mg/g. Fourier transform infrared (FTIR) spectroscopy showed that EstBASΔSP was successfully immobilized onto Lx-105s. In addition, immobilization improved its enzymatic performance by widening the tolerable ranges of pH and temperature. The optimum temperature of immobilized EstBASΔSP (Lx-EstBASΔSP) was higher, 60 °C, and overall thermostability improved. T1/2 of Lx-EstBASΔSP and free EstBASΔSP at 60 °C was 105 and 28 min, respectively. Lx-EstBASΔSP was used as a biocatalyst to synthesize chloramphenicol palmitate by regioselective modification at the primary hydroxyl group. Conversion efficiency reached 94.7% at 0.15 M substrate concentration after 24 h. Lx-EstBASΔSP was stable and could be reused for seven cycles, after which it retained over 80% of the original activity.

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“…Other research has demonstrated that Lip BA (lipase cloned from Bacillus amyloliquefaciens ) can be useful for the synthesis of chloramphenicol esters ( 20 ) with different carbon chain lengths ( Scheme 2 ) [ 10 ]. The vinyl propionate proved to be the best among the acyl donors with different carbon chain lengths, as it allowed CAM ester with the highest yield, conversion (98%), and purity (99%) to be obtained under the same reaction conditions.…”

Section: New Cam Derivativesmentioning

confidence: 99%

Recent Trends in Synthesis of Chloramphenicol New Derivatives

Tevyashova¹

2021

Antibiotics

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Chloramphenicol (CAM), the bacteriostatic broad-spectrum antibiotic, isolated from Streptomyces venezuelae during the “golden era” of antibiotic discovery, nowadays has limited clinical potential due to adverse side effects and frequent antimicrobial resistance. Numerous CAM analogs were synthesized in order to find the derivatives with improved pharmacological properties and activity on resistant bacterial strains. This work aims to summarize the most recent achievements in obtaining new CAM analogs reported during the last five years. Current investigations are mainly focused on elucidating the molecular basis of the mode of CAM action and determining the mechanisms of resistance to this class of antibiotics or on studies of the possible use of the CAM scaffold to search for therapeutic agents with different CAM modes of action—such as selective antiproliferative agents or bacterial cell wall biosynthesis inhibitors. Hopefully, a deeper understanding of the CAM interactions with the target and its specificity will generate research ideas for developing new effective drugs.

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Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens

Cited by 11 publications

References 31 publications

A Newly Isolated Bacillus subtilis Strain Named WS-1 Inhibited Diarrhea and Death Caused by Pathogenic Escherichia coli in Newborn Piglets

A Newly Isolated Bacillus subtilis Strain Named WS-1 Inhibited Diarrhea and Death Caused by Pathogenic Escherichia coli in Newborn Piglets

Immobilization of a Novel ESTBAS Esterase from Bacillus altitudinis onto an Epoxy Resin: Characterization and Regioselective Synthesis of Chloramphenicol Palmitate

Recent Trends in Synthesis of Chloramphenicol New Derivatives

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