Ramoplanin is used as a treatment for multiple antibiotic-resistant Clostridium difficile infection of the gastrointestinal tract.
CAT No: 10-101-105
CAS No:76168-82-6
Synonyms/Alias:Ramoplanin; A 16686; A16686; A-16686; MD 62198; MD62198; MD-62198; MDL62198
Ramoplanin is a glycolipodepsipeptide antibiotic compound renowned for its unique carbohydrate structure and potent activity against Gram-positive bacteria. Distinguished by its ability to bind lipid II, a key precursor in bacterial cell wall biosynthesis, Ramoplanin offers a valuable mechanism for research targeting peptidoglycan assembly. As a non-ribosomal peptide with significant carbohydrate moieties, it stands out in both microbiological and biochemical investigations. Its amphipathic nature and structural complexity also make it an excellent candidate for studies exploring the interactions between antibiotics and bacterial membranes. With growing interest in novel antimicrobial agents, Ramoplanin's distinctive properties provide researchers with a versatile tool for advancing understanding in multiple scientific domains.
Antibacterial Mechanism Studies: Ramoplanin serves as a critical research tool for elucidating the inhibition of cell wall biosynthesis in Gram-positive bacteria. By binding to lipid II, it effectively blocks the transglycosylation step, impeding the incorporation of new peptidoglycan subunits into the bacterial cell wall. This unique mode of action is particularly useful in mechanistic studies aimed at identifying potential weaknesses in bacterial cell wall synthesis. Researchers frequently employ Ramoplanin to dissect the molecular details of lipid II interactions, offering insights that inform the development of next-generation antimicrobial agents.
Antibiotic Resistance Research: The compound is highly valuable in the investigation of resistance mechanisms among Gram-positive pathogens. By using Ramoplanin as a reference molecule, scientists can explore how bacterial populations adapt to cell wall inhibitors and identify mutations conferring resistance. These studies are essential for mapping resistance pathways and for screening new derivatives with improved activity profiles. Furthermore, Ramoplanin's activity against strains resistant to other antibiotics makes it an important comparator in resistance surveillance and in the assessment of cross-resistance phenomena.
Membrane Interaction Analysis: Owing to its amphipathic structure, Ramoplanin is frequently utilized in studies examining antibiotic-membrane interactions. Its ability to associate with bacterial membranes provides a model system for probing the biophysical properties of membrane-bound antibiotics. Researchers investigate how Ramoplanin's carbohydrate and lipid components contribute to its affinity for lipid bilayers, which aids in the rational design of antibiotics with enhanced membrane-targeting capabilities. These analyses have broad implications for understanding antimicrobial selectivity and minimizing off-target effects.
Chemical Biology and Drug Design: The unique structure of Ramoplanin, featuring both peptide and carbohydrate elements, makes it a prime candidate for chemical biology research. Scientists leverage it to develop analogs or conjugates that retain or improve upon its antimicrobial properties. Structure-activity relationship (SAR) studies utilizing Ramoplanin help identify the critical features responsible for its biological activity, guiding the synthesis of novel compounds with optimized pharmacological profiles. Its role as a scaffold in drug design highlights its importance in expanding the repertoire of glycopeptide antibiotics.
Analytical Method Development: Ramoplanin is also instrumental in the development and validation of analytical techniques for detecting and quantifying glycopeptide antibiotics in complex matrices. Its distinctive chemical characteristics enable researchers to optimize chromatographic and spectrometric methods, ensuring accurate measurement in biological samples or environmental studies. These analytical advancements support quality control, pharmacokinetic research, and environmental monitoring of antibiotic residues, thereby broadening the impact of Ramoplanin beyond traditional microbiological applications.
Biotechnological Applications: In the realm of biotechnology, Ramoplanin is increasingly recognized for its potential in the engineering of novel antimicrobial peptides and the study of biosynthetic pathways. Its non-ribosomal peptide origin and modular structure provide a blueprint for synthetic biology initiatives aimed at generating new molecules with tailored activity. By serving as a model for enzymatic assembly and post-translational modifications, Ramoplanin contributes to advancements in peptide engineering, offering innovative solutions to challenges in antibiotic discovery and microbial control.
Ramoplanin is an actinomycetes-derived antibiotic with broad-spectrum activity against Gram-positive bacteria that has been evaluated in clinical trials for the treatment of gastrointestinal vancomycin-resistant enterococci (VRE) and Clostridium difficile infections. Recent studies have proposed that ramoplanin binds to bacterial membranes as a C2 symmetrical dimer that can sequester Lipid II, which causes inhibition of cell wall peptidoglycan biosynthesis and cell death. In this study, ramoplanin was shown to bind to anionic and zwitterionic membrane mimetics with a higher affinity for anionic membranes and to induce membrane depolarization of methicillin-susceptible Staphylococcus aureus (MSSA) ATCC 25923 at concentrations at or above the minimal bactericidal concentration (MBC). The ultrastructural effects of ramoplanin on S. aureus were also examined by transmission electron microscopy (TEM), and this showed dramatic changes to bacterial cell morphology. The correlation observed between membrane depolarization and bacterial cell viability suggests that this mechanism may contribute to the bactericidal activity of ramoplanin.
Cheng, M., Huang, J. X., Ramu, S., Butler, M. S., & Cooper, M. A. (2014). Ramoplanin at bactericidal concentrations induces bacterial membrane depolarization in Staphylococcus aureus. Antimicrobial agents and chemotherapy, 58(11), 6819-6827.
Ramoplanin, a novel antibiotic with activity against aerobic and anaerobic gram-positive bacteria, acts to prevent cell wall peptidoglycan formation by binding to a key intermediate moiety, lipid II. It has been fast-tracked by the US FDA for the prevention of enterococcal infections and the treatment of Clostridium difficile. The minimum inhibitory concentration(90s) have been < or = 1.0 microg/ml against gram-positive organisms examined. In carriers of vancomycin-resistant enterococci, a double-blind, placebo-controlled Phase II trial of two doses of ramoplanin versus placebo showed proof of concept. A second Phase II trial also demonstrated the equivalence of ramoplanin compared with vancomycin for the treatment of C. difficile colitis. The clinical value and place in therapy of ramoplanin is dependent upon the results of Phase III trials addressing its utility in suppressing carriage of target organisms in the gastrointestinal tract or in the nares.
Fulco, P., & Wenzel, R. P. (2006). Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent. Expert review of anti-infective therapy, 4(6), 939-945.
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