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Efficient Activity Enhancement of a Lipase from Sporisorium reilianum for the Synthesis of a Moxifloxacin Chiral Intermediate via Rational Design

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Engineering 2022年第12期19卷 207-216页

作者： Xue Cai Jiang-Wei Shen Yu Qiang Jing Hua Zhang-Qi Ma Zhi-Qiang Liu Yu-Guo Zheng The National and Local Joint Engineering Research Center for Biomanufacturing of Chiral Chemicals Zhejiang University of TechnologyHangzhou 310014China Key Laboratory of Bioorganic Synthesis of Zhejiang Province College of Biotechnology and BioengineeringZhejiang University of TechnologyHangzhou 310014China

Lipase-catalyzed stereoselective resolution of cis-(±)-dimethyl 1-acetylpiperidine-2,3-dicarboxylate(cis-(±)-1)is an attractive route for the synthesis of(S,S)-2,8-diazobicyclo[4.3.0]nonane,an important chiral intermediate of the fluoroquinolone antibiotic,Moxifloxacin.In our previous study,a lipase from Sporisorium reilianum(SRL)was identified to possess excellent thermostability and pH stability.However,the low enzymatic activity of the SRL is a challenge that must be addressed.A rational design was initially employed for SRL tailoring according to the engineered Candida antarctica lipase B(CALB),resulting in a beneficial variant called SRL-I194N/V195L.Subsequently,two key amino acid residues in loop 6,L145 and L154,which might modulate the lid conformation between open and closed,were identified.A tetra-site variant,SRL-I194N/V195L/L145V/L154G(V13),with a significantly enhanced activity of 87.8 U∙mg^(−1) was obtained;this value was 2195-fold higher than that of wild-type SRL.Variant V13 was used to prepare optically pure(2S,3R)-dimethyl 1-acetylpiperidine-2,3-dicarboxylate((2S,3R)-1),resolving 1 mol∙L^(−1) cis-(±)-1 with a conversion of 49.9%in 2 h and absolute stereoselectivity(E>200).Excellent stability with a half-life of 92.5 h was also observed at 50℃.Overall,the study findings reveal a lipase with high activity toward cis-(±)-1 at an industrial level and may offer a general strategy for enhancing the enzyme activity of other lipases and other classes of enzymes with a lid moiety.

关键词： Lipase Sporisorium reilianum Site-directed mutagenesis Molecular dynamics simulation Rational design Moxifloxacin

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Prospective comparison of prophylactic antibiotic use between intravenous Moxifloxacin and ceftriaxone for high-risk patients with post-ERCP cholangitis

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Hepatobiliary & Pancreatic Diseases International 2017年第5期16卷 512-518页

作者： Nam Hee Kim Hong Joo Kim Ki Bae Bang Department of Internal Medicine Sungkyunkwan University Kangbuk Samsung Hospital Department of Internal Medicine Dankook University Hospital

BACKGROUND: The use of prophylactic antibiotics before endoscopic retrograde cholangiopancreatography(ERCP) is recommended by all major international gastroenterological societies, especially in the presence of an obstructed biliary system. This study compared the occurrence rate of post-procedural complications, including cholangitis and septicemia between prophylactic intravenous Moxifloxacin and ceftriaxone in patients with bile duct obstruction scheduled for therapeutic ERCP.METHODS: From November 2013 to July 2015, 86 consecutive patients with biliary obstruction with one or more factors predicting benefits of antibiotic prophylaxis prior to ERCP were included in the current randomized open-label non-inferiority trial(Clinical Trial.gov identifier NCT02098486). Intravenous Moxifloxacin(400 mg/day) or ceftriaxone(2 g/day)were given 90 minutes before ERCP, and were administered for more than 3 days if the patient developed symptoms and signs of cholangitis or septicemia. Recalcitrant cholangitis was defined as persistence of cholangitis for more than 5 days after ERCP or recurrence of cholangitis within 30 days after ERCP.RESULTS: Recalcitrant cholangitis occurred in 1(2.3%) and 2(4.8%) patients receiving intravenous Moxifloxacin and ceftriaxone group, respectively(P=0.612). Septicemia was noted in1(2.3%) and 1(2.4%) patient in intravenous Moxifloxacin and ceftriaxone group, respectively(P=1.0). The mean hospital stay was also not significantly different between the Moxifloxacin and ceftriaxone groups(8.8±7.2 vs 9.1±9.4 days, P=0.867). Antibiotic resistance of the isolated pathogens by in vitro activity assay was noted in 1(2.3%) and 2(4.8%) patients in the Moxifloxacin and ceftriaxone group, respectively(P=0.612). CONCLUSION: Intravenous Moxifloxacin is not inferior to intravenous ceftriaxone for the prophylactic treatment of post-ERCP cholangitis and cholangitis-associated morbidity.

关键词： endoscopic retrograde cholangiopancreatography cholangitis Moxifloxacin ceftriaxone recalcitrant cholangitis

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Efficacy of Moxifloxacin against Mycobacterium abscessus in Zebrafish Model in vivo

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Biomedical and Environmental Sciences 2020年第5期33卷 350-358页

作者： NIE Wen Juan XIE Zhong Yao GAO Shan TENG Tian Lu ZHOU Wen Qiang SHANG Yuan Yuan JING Wei SHI Wen Hui WANG Qing Feng HUANG Xue Rui CAI Bao Yun WANG Jun WANG Jing GUO Ru GE Qi Ping NIE Li Hui HAN Xi Qin DU Ya Dong CHU Nai Hui Tuberculosis Department Beijing Chest Hospital affiliated to Capital Medical UniversityBeijing 101149China Beijing Chest Hospital affiliated to Capital Medical University Beijing 101149China

Objective Moxifloxacin(MFX)shows good in vitro activity against Mycobacterium abscessus and can be a possible antibiotic therapy to treat M.abscessus infection;however,other studies have shown a lower or no activity.We aimed to evaluate MFX activity against M.abscessus using zebrafish(ZF)model in vivo.Methods A formulation of M.abscessus labeled with CM-Dil was micro-injected into ZF.Survival curves were determined by recording dead ZF every day.ZF were lysed,and colony-forming units(CFUs)were enumerated.Bacteria dissemination and fluorescence intensity in ZF were analyzed.Inhibition rates of MFX and azithromycin(AZM,positive control)were determined and compared.Results Significantly increased survival rate was observed with different AZM concentrations.However,increasing MFX concentration did not result in a significant decrease in ZF survival curve.No significant differences in bacterial burdens by CFU loads were observed between AZM and MFX groups at various concentrations.Bacterial fluorescence intensity in ZF was significantly correlated with AZM concentration.However,with increasing MFX concentration,fluorescence intensity decreased slightly when observed under fluorescence microscope.Transferring rates at various concentrations were comparable between the MFX and AZM groups,with no significant difference.Conclusion MFX showed limited efficacy against M.abscessus in vivo using ZF model.Its activity in vivo needs to be confirmed.

关键词： Mycobacterium abscessus Moxifloxacin Azithromycin Zebrafish

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Efficacy of 14-d vs 7-d Moxifloxacin-based triple regimens for second-line Helicobacter pylori eradication

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World Journal of Gastroenterology 2015年第18期21卷 5568-5574页

作者： Jae Jin Hwang Dong Ho Lee Ae-Ra Lee Hyuk Yoon Cheol Min Shin Young Soo Park Nayoung Kim Department of Internal Medicine Seoul National University Bundang Hospital Gyeonggi-do 463-707 South Korea

AIM: To evaluate the efficacy of the 14-d Moxifloxacinbased triple therapy for the second-line eradication of Helicobacter pylori(H. pylori) infection.METHODS: Between 2011 and 2013, we conducted a retrospective review of the medical records of 160 patients who had experienced failure of their first-line proton pump inhibitor-based eradication therapy and subsequently received the Moxifloxacin-based triple therapy as a second-line eradication treatment regimen. The patients who were treated with the Moxifloxacinbased triple therapy(oral 20 mg rabeprazole b.i.d., 1000 mg amoxicillin b.i.d., and 400 mg Moxifloxacin q.d.) for 7 d were assigned to the RAM-7 group(n = 79) while those who took them for 14 days were assigned to RAM-14 group(n = 81). The eradication rates for both groups were determined by intentionto-treat(ITT) and per-protocol(PP) analyses. ITT analysis compared the treatment groups as originally allocated while the PP analysis including only those patients who had completed the treatment as originally allocated. Successful eradication therapy for H. pylori infection was defined as the documentation of a negative 13C-urea breath test 4 wk after the end of the eradication treatment.RESULTS: The overall ITT eradication rate was 76.2%(122/160). The final ITT eradication rates were 70.8%(56/79; 95%CI: 63.3%-77.1%) in the RAM-7 group and 81.4%(66/81; 95%CI: 74.6%-88.3%) in the RAM-14 group(P = 0.034). The overall PP eradication rate was 84.1%(122/145), and the final PP eradication rates were 77.7%(56/72; 95%CI: 70.2%-85.3%) in the RAM-7 group and 90.4%(66/73; 95%CI: 82.8%-98.1%) in the RAM-14 group(P = 0.017). The H. pylori-eradication rates in the RAM-14 group were significantly higher compared with that of the RAM-7 group according to both the ITT(P = 0.034) and the PP analyses(P = 0.017). Both groups exhibited good treatment compliance(RAM-7/RAM-14 group: 100%/100%). The adverse event rates were19.4%(14/72)and 20.5%(15/73)in the RAM-7 and RAM-14 groups,respectively(P=0.441).Adverse events occurred in 14

关键词： Helicobacter pylori Treatment failure Second-line treatment Moxifloxacin Eradication rate

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Clinical efficacy and safety of Moxifloxacin versus levofloxacin plus metronidazole for community-acquired pneumonia with aspiration factors

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Chinese Medical Journal 2014年第7期127卷 1201-1205页

作者： Sun Tieying Sun Li Wang Rongmei Ren Xiaoping Sui Dong-jiang Pu Chun Ren Yajuan Liu Ying Yang Zhuo Li Fengzhi Department of Respiratory and Critical Care Medicine Beijing Hospital of the Ministry of Health Beijing 100730 China Department of Respiratory Diseases Shaanxi Provincial People's Hospital Xi'an Shaanxi 710068China Department of Respiratory Diseases Air Force General HospitalPeople's Liberation Army Beijing 100142 China

Background Community-acquired pneumonia （CAP） is a common infectious disease throughout the world and the incidence continues to grow as the population ages.Aspiration is an important pathogenic mechanism for pneumonia in the elderly and the management of patients with community-acquired pneumonia with aspiration factors is a major medical problem.Our study aimed to assess whether Moxifloxacin in comparison to levofloxacin plus metronidazole are effective and safe in the treatment of community-acquired pneumonia with aspiration factors.Methods In this prospective,multicenter,open-label,randomized controlled trial,77 patients with mild-to-moderate community-acquired pneumonia with aspiration factors were enrolled and randomly assigned to receive Moxifloxacin or levofloxacin plus metronidazole.The primary efficacy variables were clinical outcomes in evaluable patients at a follow-up visit 7 to 14 days after the end of therapy.Results Seven days after the end of therapy a clinical cure was achieved for 76.7％（23 of 37） of efficacy-evaluable patients in the Moxifloxacin group and 51.7％（15 of 40） of patients in the levofloxacin plus metronidazole group.There was a significant difference between the two groups （x2=4.002,P ＜0.05）.Bacteriological success rates were similar in the Moxifloxacin group （93.3％） and levofloxacin plus metronidazole group （96.4％）,there was no significant difference between the two groups （P ＞0.05）.The overall adverse event rate was 10.8％（4/37） in the Moxifloxacin group versus 17.5％（7/40） in the levofloxacin plus metronidazole group,there was no significant difference between the two groups （P＞0.05）.No serious adverse events were observed.Conclusions Moxifloxacin is effective and safe for treatment of community-acquired pneumonia with aspiration factors.And the regimen of Moxifloxacin monotherapy is more convenient compared with levofloxacin plus metronidazole.

关键词： pneumonia community-acquired infection Moxifloxacin levofloxacin metronidazole

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Moxifloxacin-induced multiple organ dysfunction possibly related to mutations in several genes involved in drug metabolism pathways

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Chinese Medical Journal 2013年第7期126卷 1396-1398页

作者： XIAO Yong-jiu SU Long-xiang ZHANG Xin XIE Li-xin Department of Respiratory Medicine Hainan Branch of Chinese People's Liberation Army General Hospital Sanya Hainan 572013 China Department of Respiratory Medicine L anzhou General Hospital of Lanzhou Military Area Command of Chinese People's Liberation Army Lanzhou Gansu 730050 China Medical College of Nankai University Tianjin 300071 China Department of Respiratory Medicine Chinese People's Liberation Army General Hospital Beijing 100853 China

Quinolones have been used to treat various infectious diseases. The addition of fluorine atoms has allowedfor extensive modifications of structures, which has enhanced the spectrum of activities and oral bioavailability of quinolones and resulted in the creation of fluoroquinolones） Although the adverse effects associated with fluoroquinolone antibiotics have decreased considerably and these drugs are generally well tolerated, adverse effects do sometimes occur.

关键词： Moxifloxacin multiple organ dysfunction mutations

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Efficacy of Moxifloxacin-based sequential therapy for first-line eradication of Helicobacter pylori infection in gastrointestinal disease

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World Journal of Gastroenterology 2015年第16期21卷 5032-5038页

作者： Jae Jin Hwang Dong Ho Lee Ae-Ra Lee Hyuk Yoon Cheol Min Shin Young Soo Park Nayoung Kim Department of Internal Medicine Seoul National University Bundang Hospital

AIM:To evaluate the efficacy of 14-d Moxifloxacinbased sequential therapy as first-line eradication treatment of Helicobacter pylori(H.pylori) infection.METHODS:From December 2013 to August 2014, 161 patients with confirmed H.pylori infection randomly received 14 d of Moxifloxacin-based sequential group(MOX-ST group, n = 80) or clarithromycin-based sequential group(CLA-ST group, n = 81) therapy.H.pylori infection was defined on the basis of at least one of the following three tests:a positive 13C-urea breath test; histologic evidence of H.pylori by modified Giemsa staining; or a positive rapid urease test(CLOtest; Delta West, Bentley, Australia) by gastric mucosal biopsy.Successful eradication therapy for H.pylori infection was defined as a negative 13C-urea breath test four weeks after the end of eradication treatment.Compliance was defined as good when drug intake was at least 85%.H.pylori eradication rates, patient compliance with drug treatment, adverse event rates, and factors influencing the efficacy of eradication therapy were evaluated.RESULTS:The eradication rates by intention-to-treat analysis were 91.3%(73/80;95%CI:86.2%-95.4%)in the MOX-ST group and 71.6%(58/81;95%CI:65.8%-77.4%)in the CLA-ST group(P=0.014).The eradication rates by per-protocol analysis were 93.6%(73/78;95%CI:89.1%-98.1%)in the MOX-ST group and 75.3%(58/77;95%CI:69.4%-81.8%)in the CLAST group(P=0.022).Compliance was 100%in both groups.The adverse event rates were 12.8%(10/78)and 24.6%(19/77)in the MOX-ST and CLA-ST group,respectively(P=0.038).Most of the adverse events were mild-to-moderate in intensity;there was none serious enough to cause discontinuation of treatmentin either group.In multivariate analysis,advanced age(≥60 years)was a significant independent factor related to the eradication failure in the CLA-ST group(adjusted OR=2.13,95%CI:1.97-2.29,P=0.004),whereas there was no significance in the MOX-ST group.CONCLUSION:The 14-d Moxifloxacin-based sequential therapy is effective.Moreover,it shows excellent patient compliance an

关键词： Helicobacter pylori First-line eradicationtreatment Moxifloxacin Sequential therapy Eradicationrate

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Effects of Moxifloxacin exposure on the conjunctival flora and antibiotic resistance profile following repeated intravitreal injections

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International Journal of Ophthalmology(English edition) 2014年第5期7卷 855-859页

作者： Mustafa Atas Burhan Baskan Ayse zkse Fatma Mutlu Sarιgüzel Süleyman Demircan Emine Pangal Department of Ophtalmology Kayseri Education and Research Hospital Department of Microbiology Kayseri Education and Research Hospital

AIMTo evaluate the effects of Moxifloxacin exposure on the conjunctival flora and antibiotic resistance profile following repeated intravitreal injections.

关键词： intravitreal injection Moxifloxacin endopthalmitis

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Safety of prophylactic intracameral Moxifloxacin ophthalmic solution after cataract surgery in patients with penetrating keratoplasty

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International Journal of Ophthalmology(English edition) 2014年第5期7卷 795-799页

作者： Osman Sevki Arslan Ceyhun Arici Mustafa Unal Erdogan Cicik Mehmet Serhat Mangan Eray Atalay Department of Ophthalmology Cerrahpasa Medical FacultyIstanbul University Department of Ophthalmology Medical FacultyAkdeniz University

AIM:To determine the safety of prophylactic intracameral Moxifloxacin after cataract surgery in patients with penetrating keratoplasty(PKP).METHODS:In this retrospective study of consecutive patients who had phacoemulsification cataract surgery after PKP, were treated with intracameral Moxifloxacin0.5% ophthalmic solution(0.5 mg/0.1 mL). The main outcome measures were anterior chamber reaction, best corrected visual acuity(BCVA), corneal endothelial cell count(ECC), and central corneal thickness(CCT).RESULTS:Fifty-five patients were recruited(26 males,29 females). The mean age was 54.36±4.97y(range 45-64y).All eyes had improved postoperative BCVA. The mean BCVA was 0.25 preoperatively and 0.57 postoperatively,which was statistically significant(P Moxifloxacin(0.5 mg/0.1 mL) in terms of anterior chamber reaction, CCT, ECC, and visual rehabilitation at the conclusion of cataract surgery in patients with PKP.

关键词： cataract surgery intracameral injection Moxifloxacin penetrating keratoplasty phacoemulsification

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Liquid chromatography electrospray ionization tandem mass spectrometry(LC/ESI-MS/MS) method for quantitative estimation of Moxifloxacin in human plasma

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Journal of Chinese Pharmaceutical Sciences 2014年第3期23卷 159-164页

作者： Vipul.M.Vaghela Prajesh Prajapati Hetal K.Patel A.R.College of Pharmacy and G.H.Patel Institute of Pharmacy Institute of Research and Development Gujarat Forensic Sciences University Shree Swaminarayan Sanskar Pharmacy College

A rapid and sensitive liquid chromatography tandem mass spectrometry(LC-MS/MS) method has been developed and validated for the determination of Moxifloxacin(MOXI) in human plasma. After a simple protein precipitation using acetonitrile, the post treatment samples were analysed on a C18 column interfaced with a Triple Quadropole Tandem Mass Spectrometer. Positive electrospray ionization was employed as the ionization source. The mobile phase consisted of 0.1% formic acid–acetonitrile(60:40, v/v). Ciprofloxacin(CIPRO) was used as an internal standard. The analyte and internal standard(CIPRO) were monitored in the multiple reaction monitoring mode(MRM). The mass transition ion-pair has been followed as m/z 402→358.2 for MOXI and 332→288.1 for CIPRO. The method was linear in the concentration range of 25–5000 ng/mL. The lower limit of quantification was 25 ng/mL. The intra- and inter-day precision(relative standard deviation) and accuracy(relative error) values were within 12.4%. Each plasma sample was analyzed within 3 min.

关键词： Moxifloxacin Ciprofloxacin Human plasma Liquid chromatography tandem mass spectrometry Electrospray ionization

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