Chapter 13. Antibacterial Agents

Jaynes, Burton H.; Dirlam, John P.; Hecker, Scott J.

doi:10.1016/s0065-7743(08)60452-2

Cited by 7 publications

(6 citation statements)

References 67 publications

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“…Biogenetically oriented approaches toward their total syntheses based on the construction of a suitable seco-acid derivative, followed by its macrolactonization, have been explored . The development of new methodologies for macrolactonizations and asymmetric synthesis 2 and the discovery of new semisynthetic erythromycin A derivatives with better bioavailability and efficiency have recently renewed the interest in the development of more efficient routes to this family of biologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

et al. 1998

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A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog−Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki−Hiyama−Kishi coupling reaction.

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Section: Introductionmentioning

confidence: 99%

Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

et al. 1998

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“…In an early example, E-0702, a semisynthetic iron-chelating antipseudomonal cephalosporin derivative, was proposed to be incorporated into microbial cells by the tonB -dependent iron transport system (Watanabe et al 1987; Katsu et al 1982). Subsequently, many other catechol (e.g., LB10522 and several conjugates reported by the HKI) and hydroxypyridone-substituted cephalosporin derivatives were prepared and shown to have significant antipseudomonal activity, presumably because of iron chelation facilitated uptake by otherwise resistant microbes (Heinisch et al 2002; Jaynes et al 1996). …”

Section: Siderophore-mediated Drug Delivery (“Trojan Horse” Antibiotics)mentioning

confidence: 99%

Utilization of microbial iron assimilation processes for the development of new antibiotics and inspiration for the design of new anticancer agents

et al. 2009

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Pathogenic microbes rapidly develop resistance to antibiotics. To keep ahead in the “microbial war”, extensive interdisciplinary research is needed. A primary cause of drug resistance is the overuse of antibiotics that can result in alteration of microbial permeability, alteration of drug target binding sites, induction of enzymes that destroy antibiotics (ie., beta-lactamase) and even induction of efflux mechanisms. A combination of chemical syntheses, microbiological and biochemical studies demonstrate that the known critical dependence of iron assimilation by microbes for growth and virulence can be exploited for the development of new approaches to antibiotic therapy. Iron recognition and active transport relies on the biosyntheses and use of microbe-selective iron-chelating compounds called siderophores. Our studies, and those of others, demonstrate that siderophores and analogs can be used for iron transport-mediated drug delivery (“Trojan Horse” antibiotics) and induction of iron limitation/starvation (Development of new agents to block iron assimilation). Recent extensions of the use of siderophores for the development of novel potent and selective anticancer agents are also described.

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“…Unfortunately, clarithromycin and azithromycin, like erythromycin and other 14-membered macrolides, have relatively poor activity against macrolideresistant bacteria in which resistance results from plasmid and transposon-mediated methylation of 23S rRNA (MLS phenotype) [23][24][25]. The above situation has resulted in the development of further macrolides with which to address the problems of resistance [24].…”

Section: Ketolidesmentioning

confidence: 99%

Protein synthesis as a target for antibacterial drugs: current status and future opportunities

Chopra

1998

Expert Opinion on Investigational Drugs

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The discovery and development of clinically useful antibiotic classes, such as the aminoglycosides, macrolides and tetracyclines, have clearly demonstrated that bacterial protein synthesis is a suitable target for drug intervention. New information on the binding of classical protein synthesis inhibitors to ribosomal RNA provides a rational explanation for their selective action against bacteria and also explains why chromosomal point mutations conferring resistance by structural changes at the target site are relatively rare in the majority of bacteria. These principles will be helpful when considering strategies for the screening or design of novel protein synthesis inhibitors that could be developed as new antibiotics. Recent progress in the discovery and development of bacterial protein synthesis inhibitors is illustrated by consideration of the glycylcyclines, ketolides, oxazolidinones and streptogramins.

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Chapter 13. Antibacterial Agents

Cited by 7 publications

References 67 publications

Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

Utilization of microbial iron assimilation processes for the development of new antibiotics and inspiration for the design of new anticancer agents

Protein synthesis as a target for antibacterial drugs: current status and future opportunities

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