磺胺基氟喹诺酮类的作用模式。
Mode of action of sulfanilyl fluoroquinolones.
作者信息
Alovero F, Nieto M, Mazzieri M R, Then R, Manzo R H
机构信息
Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Argentina.
出版信息
Antimicrob Agents Chemother. 1998 Jun;42(6):1495-8. doi: 10.1128/AAC.42.6.1495.
Abstract
The mode of action of sulfanilyl fluoroquinolones (NSFQs) was investigated with NSFQ-104, NSFQ-105, and some structurally related compounds. Evidence arising from interactions with p-aminobenzoic acid and trimethoprim suggested that a sulfonamidelike mechanism of action makes little or no contribution to the in vitro activity of NSFQs. NSFQ-105 showed an activity that inhibits gyrase-catalyzed DNA supercoiling that is similar to the activity of other fluoroquinolones. Also, NSFQ-105 uptake was decreased by the presence of Mg2+ and increased by a lower pH. These results indicate that NSFQs having only one ionizable group could exhibit more favorable kinetics of access to the bacterial cell than zwitterionic fluoroquinolones.
摘要
利用NSFQ - 104、NSFQ - 105以及一些结构相关的化合物对磺胺基氟喹诺酮类（NSFQs）的作用模式进行了研究。与对氨基苯甲酸和甲氧苄啶相互作用产生的证据表明，类似磺胺酰胺的作用机制对NSFQs的体外活性贡献很小或没有贡献。NSFQ - 105表现出抑制回旋酶催化的DNA超螺旋的活性，这与其他氟喹诺酮类的活性相似。此外，Mg2 +的存在会降低NSFQ - 105的摄取，而较低的pH值会增加其摄取。这些结果表明，与两性离子氟喹诺酮类相比，仅具有一个可电离基团的NSFQs在进入细菌细胞时可能表现出更有利的动力学。
相似文献
1
Mode of action of sulfanilyl fluoroquinolones.磺胺基氟喹诺酮类的作用模式。
Antimicrob Agents Chemother. 1998 Jun;42(6):1495-8. doi: 10.1128/AAC.42.6.1495.
2
In-vitro activity of new sulphanilil fluoroquinolones against Staphylococcus aureus.
J Antimicrob Chemother. 1994 Aug;34(2):261-5. doi: 10.1093/jac/34.2.261.
3
Hydrophilicity of quinolones is not an exclusive factor for decreased activity in efflux-mediated resistant mutants of Staphylococcus aureus.喹诺酮类药物的亲水性并非金黄色葡萄球菌外排介导耐药突变体活性降低的唯一因素。
Antimicrob Agents Chemother. 1996 Aug;40(8):1835-42. doi: 10.1128/AAC.40.8.1835.
4
Antibacterial activities and inhibitory effects of sitafloxacin (DU-6859a) and its optical isomers against type II topoisomerases.司帕沙星（DU-6859a）及其光学异构体对II型拓扑异构酶的抗菌活性和抑制作用。
Antimicrob Agents Chemother. 1998 May;42(5):1284-7. doi: 10.1128/AAC.42.5.1284.
5
Mechanisms and frequency of resistance to temafloxacin.
Am J Med. 1991 Dec 30;91(6A):27S-30S. doi: 10.1016/0002-9343(91)90306-i.
6
In vitro susceptibility of mycoplasmas to a new quinolone, BAY Y 3118.支原体对新型喹诺酮BAY Y 3118的体外敏感性
Drugs. 1995;49 Suppl 2:243-5. doi: 10.2165/00003495-199500492-00056.
7
Antibacterial activity of a 1,8-naphthyridine quinolone, PD 131628.1,8-萘啶喹诺酮PD 131628的抗菌活性
J Med Microbiol. 1992 May;36(5):353-7. doi: 10.1099/00222615-36-5-353.
8
Effect of hydrophobicity and molecular mass on the accumulation of fluoroquinolones by Staphylococcus aureus.疏水性和分子量对金黄色葡萄球菌积累氟喹诺酮类药物的影响。
J Antimicrob Chemother. 2001 Mar;47(3):261-70. doi: 10.1093/jac/47.3.261.
9
The bactericidal activity of sparfloxacin.
J Antimicrob Chemother. 1992 Nov;30(5):625-32. doi: 10.1093/jac/30.5.625.
10
Role of the extended alpha4 domain of Staphylococcus aureus gyrase A protein in determining low sensitivity to quinolones.金黄色葡萄球菌gyrase A蛋白的延伸α4结构域在决定对喹诺酮类药物低敏感性中的作用。
Antimicrob Agents Chemother. 2006 Feb;50(2):600-6. doi: 10.1128/AAC.50.2.600-606.2006.
引用本文的文献
1
Synthesis, Antibacterial Evaluation and QSAR of α-Substituted-N₄-Acetamides of Ciprofloxacin and Norfloxacin.α-取代-N4-乙酰基环丙沙星和诺氟沙星的合成、抗菌评价及定量构效关系研究。
Antibiotics (Basel). 2014 Jun 25;3(3):244-69. doi: 10.3390/antibiotics3030244.
2
A Hybrid Drug Limits Resistance by Evading the Action of the Multiple Antibiotic Resistance Pathway.一种混合药物通过规避多重抗生素耐药途径的作用来限制耐药性。
Mol Biol Evol. 2016 Feb;33(2):492-500. doi: 10.1093/molbev/msv243. Epub 2015 Nov 3.
3
Pharmacological characterization of 7-(4-(Piperazin-1-yl)) ciprofloxacin derivatives: antibacterial activity, cellular accumulation, susceptibility to efflux transporters, and intracellular activity.7-(4-(哌嗪-1-基))环丙沙星衍生物的药理学特征：抗菌活性、细胞内积累、对外排转运蛋白的敏感性和细胞内活性。
Pharm Res. 2014 May;31(5):1290-301. doi: 10.1007/s11095-013-1250-x. Epub 2013 Dec 5.
4
Contrasting effects of acidic pH on the extracellular and intracellular activities of the anti-gram-positive fluoroquinolones moxifloxacin and delafloxacin against Staphylococcus aureus.酸性 pH 值对抗革兰氏阳性菌氟喹诺酮类药物莫西沙星和德拉沙星对金黄色葡萄球菌的细胞外和细胞内活性的对比影响。
Antimicrob Agents Chemother. 2011 Feb;55(2):649-58. doi: 10.1128/AAC.01201-10. Epub 2010 Dec 6.
5
Prospects for aminoacyl-tRNA synthetase inhibitors as new antimicrobial agents.氨酰-tRNA合成酶抑制剂作为新型抗菌药物的前景。
Antimicrob Agents Chemother. 2005 Dec;49(12):4821-33. doi: 10.1128/AAC.49.12.4821-4833.2005.
6
Small-colony mutants of Staphylococcus aureus allow selection of gyrase-mediated resistance to dual-target fluoroquinolones.金黄色葡萄球菌的小菌落突变体有助于筛选出由回旋酶介导的对双靶点氟喹诺酮类药物的耐药性。
Antimicrob Agents Chemother. 2002 Aug;46(8):2498-506. doi: 10.1128/AAC.46.8.2498-2506.2002.
7
Engineering the specificity of antibacterial fluoroquinolones: benzenesulfonamide modifications at C-7 of ciprofloxacin change its primary target in Streptococcus pneumoniae from topoisomerase IV to gyrase.设计抗菌氟喹诺酮类药物的特异性：环丙沙星C-7位的苯磺酰胺修饰将其在肺炎链球菌中的主要靶点从拓扑异构酶IV转变为回旋酶。
Antimicrob Agents Chemother. 2000 Feb;44(2):320-5. doi: 10.1128/AAC.44.2.320-325.2000.
8
Activity of newer fluoroquinolones in vitro against gram-positive bacteria.新型氟喹诺酮类药物对革兰氏阳性菌的体外活性。
Drugs. 1999;58 Suppl 2:23-8. doi: 10.2165/00003495-199958002-00005.
本文引用的文献
1
Penetration of lipophilic agents with multiple protonation sites into bacterial cells: tetracyclines and fluoroquinolones as examples.具有多个质子化位点的亲脂性药物进入细菌细胞的机制：以四环素和氟喹诺酮类药物为例
Antimicrob Agents Chemother. 1993 Jul;37(7):1393-9. doi: 10.1128/AAC.37.7.1393.
2
In-vitro activity of new sulphanilil fluoroquinolones against Staphylococcus aureus.
J Antimicrob Chemother. 1994 Aug;34(2):261-5. doi: 10.1093/jac/34.2.261.
3
Effect of pyrimido[1,6-a]benzimidazoles, quinolones, and Ca2+ on the DNA gyrase-mediated cleavage reaction.嘧啶并[1,6 - a]苯并咪唑、喹诺酮类和Ca2+对DNA回旋酶介导的切割反应的影响。
Antimicrob Agents Chemother. 1995 Jan;39(1):163-9. doi: 10.1128/AAC.39.1.163.
4
Effect of magnesium complexation by fluoroquinolones on their antibacterial properties.氟喹诺酮类药物与镁络合对其抗菌性能的影响。
Antimicrob Agents Chemother. 1994 Dec;38(12):2810-6. doi: 10.1128/AAC.38.12.2810.
5
Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids.喹诺酮类抗菌剂。8-取代喹啉-3-羧酸和1,8-萘啶-3-羧酸的合成及构效关系
J Med Chem. 1988 May;31(5):983-91. doi: 10.1021/jm00400a016.
6
Synergistic effect of quinolones and oxacillin on methicillin-resistant Staphylococcus species.喹诺酮类药物与苯唑西林对耐甲氧西林葡萄球菌属的协同作用。
Antimicrob Agents Chemother. 1989 Dec;33(12):2037-41. doi: 10.1128/AAC.33.12.2037.
7
Fluorometric assay for fleroxacin uptake by bacterial cells.细菌细胞摄取氟罗沙星的荧光测定法。
Antimicrob Agents Chemother. 1989 Jan;33(1):27-9. doi: 10.1128/AAC.33.1.27.
8
Uptake of sparfloxacin and norfloxacin by clinical isolates of Staphylococcus aureus.金黄色葡萄球菌临床分离株对司帕沙星和诺氟沙星的摄取情况。
Antimicrob Agents Chemother. 1991 Feb;35(2):368-70. doi: 10.1128/AAC.35.2.368.
9
Molecular modeling and quantitative structure-activity analysis of antibacterial sulfanilamides and sulfones.抗菌磺胺类药物和砜类的分子建模与定量构效分析
Prog Drug Res. 1991;36:361-417. doi: 10.1007/978-3-0348-7136-5_5.
10
Transport of pefloxacin across the bacterial cytoplasmic membrane in quinolone-susceptible Staphylococcus aureus.培氟沙星在喹诺酮敏感金黄色葡萄球菌中跨细菌细胞质膜的转运
Antimicrob Agents Chemother. 1992 Nov;36(11):2506-11. doi: 10.1128/AAC.36.11.2506.
Zotero 插件