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Telomycin

(Synonyms: 远霉素) 目录号 : GC45008

A macrocyclic peptide lactone antibiotic

Telomycin Chemical Structure

Cas No.:19246-24-3

规格 价格 库存 购买数量
500μg
¥6,082.00
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2.5mg
¥19,769.00
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产品描述

Telomycin is a macrocyclic peptide lactone antibiotic originally isolated from Streptomyces. It is active against Gram-positive bacteria, including S. aureus, methicillin-resistant S. aureus (MRSA), and E. faecium (MICs = 4, 2, and 16 µg/ml, respectively). Telomycin eradicates B. anserina spirochetosis infection in chicks.

Chemical Properties

Cas No. 19246-24-3 SDF
别名 远霉素
分子式 C59H77N13O19 分子量 1272.3
溶解度 DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble,Water: slightly soluble 储存条件 Store at -20°C
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1 mM 0.786 mL 3.9299 mL 7.8598 mL
5 mM 0.1572 mL 0.786 mL 1.572 mL
10 mM 0.0786 mL 0.393 mL 0.786 mL
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Research Update

Biosynthetic Studies of Telomycin Reveal New Lipopeptides with Enhanced Activity

J Am Chem Soc 2015 Jun 24;137(24):7692-705.PMID:26043159DOI:10.1021/jacs.5b01794.

Telomycin (TEM) is a cyclic depsipeptide antibiotic active against Gram-positive bacteria. In this study, five new natural Telomycin analogues produced by Streptomyces canus ATCC 12646 were identified. To understand the biosynthetic machinery of Telomycin and to generate more analogues by pathway engineering, the TEM biosynthesis gene cluster has been characterized from S. canus ATCC 12646: it spans approximately 80.5 kb and consists of 34 genes encoding fatty acid ligase, nonribosomal peptide synthetases (NRPSs), regulators, transporters, and tailoring enzymes. The gene cluster was heterologously expressed in Streptomyces albus J1074 setting the stage for convenient biosynthetic engineering, mutasynthesis, and production optimization. Moreover, in-frame deletions of one hydroxylase and two P450 monooxygenase genes resulted in the production of novel Telomycin derivatives, revealing these genes to be responsible for the specific modification by hydroxylation of three amino acids found in the TEM backbone. Surprisingly, natural lipopeptide Telomycin precursors were identified when characterizing an unusual precursor deacylation mechanism during Telomycin maturation. By in vivo gene inactivation and in vitro biochemical characterization of the recombinant enzyme Tem25, the maturation process was shown to involve the cleavage of previously unknown Telomycin precursor-lipopeptides, to yield 6-methylheptanoic acid and telomycins. These lipopeptides were isolated from an inactivation mutant of tem25 encoding a (de)acylase, structurally elucidated, and then shown to be deacylated by recombinant Tem25. The TEM precursor and several semisynthetic lipopeptide TEM derivatives showed rapid bactericidal killing and were active against several multidrug-resistant (MDR) Gram-positive pathogens, opening the path to future chemical optimization of Telomycin for pharmaceutical application.

Streptomyces coeruleorubidus as a potential biocontrol agent for Newcastle disease virus

BMC Vet Res 2022 Jun 24;18(1):241.PMID:35751117DOI:10.1186/s12917-022-03349-7.

Background: Newcastle disease virus (NDV) is a severe disease that affects domestic and wild birds. Controlled antibiotics derived from probiotics have been examined as prospective solutions for preserving seroconversion in NDV-vaccinated fowl. In this study, the secondary metabolite "Telomycin" was extracted from Streptomyces coeruleorubidus (S. coeruleorubidus) isolated from Egypt's cultivated soil. The structure of Telomycin was determined by the elucidation of spectroscopic analysis, including nuclear magnetic resonance (NMR) and mass spectrometry (MS) spectra, and comparison with the literature. The antiviral activity of the secondary metabolite was tested by checking its effect on NDV hemagglutination activity (HA). Moreover, HA of NDV was tested after inoculation of NDV (control) and a combination of Telomycin and NDV in 10- days- specific pathogen-free embryonated chicken eggs (SPF-ECE) daily candling. Histopathological examination was performed for chorioallantoic membranes and liver of SPF-ECE. Results: S. coeruleorubidus secondary metabolite "Telomycin" showed complete hemagglutination inhibition (HI) activity of NDV strain (MN635617) with log106 infectivity titers (EID50/mL). The HA of NDV strain was 8 log2 and 9 log2 with 0.5% and 0.75% of chicken RBCs, respectively. Preserved structures of chorioallantoic-membranes (CAM) with dilated capillary networks were observed in the treated group inoculated with Telomycin and NDV. Histological changes in SPF-ECE liver were examined after inoculation in ova to further characterize the Telomycin effect. Telomycin and NDV mixture inoculated group showed preserved cytoarchitecture of hepatocytes with the presence of perivascular foci of lymphocytes. The group that was inoculated with Telomycin alone showed normal histology of hepatic acini, central veins, and portal triads. Conclusion: S. coeruleorubidus Telomycin is a promising bioactive agent that might be a biological weapon against a deadly chicken NDV that costs farmers a lot of money.

Draft Genome Sequence of Streptomyces canus ATCC 12647, a Producer of Telomycin

Genome Announc 2016 Mar 24;4(2):e00173-16.PMID:27013049DOI:10.1128/genomeA.00173-16.

We present here the genome sequence ofStreptomyces canusATCC 12647, a producer of the antibiotic Telomycin, noted for its unique antibacterial activity against cardiolipin. Genomic analysis using the bioinformatics tool PRISM revealed the presence of multiple biosynthetic gene clusters, including those for Telomycin and other natural products of potential pharmacological interest.

Structure and Antibacterial Activity of Ambobactin, a New Telomycin-Like Cyclic Depsipeptide Antibiotic Produced by Streptomyces ambofaciens F3

Molecules 2015 Sep 9;20(9):16278-89.PMID:26370952DOI:10.3390/molecules200916278.

A new telomycin-like cyclic depsipeptide, ambobactin (1), was isolated from the metabolites of Streptomyces ambofaciens F3, an endophyte of Platycladus orientalis. Its structure was elucidated on the basis of extensive spectroscopic analysis and advanced Marfey's method. Ambobactin is structurally related with Telomycin, except that the configuration of the 3-methyltryptophanes in their structures is different. It exhibited strong antibacterial activity against both Gram-positive and Gram-negative bacteria. Furthermore, this investigation revealed that S. ambofaciens F3 is a new producer of telomycin-like antibiotics.

Micromonospora schwarzwaldensis sp. nov., a producer of Telomycin, isolated from soil

Int J Syst Evol Microbiol 2013 Oct;63(Pt 10):3812-3817.PMID:23667141DOI:10.1099/ijs.0.051623-0.

A Gram-stain-positive, spore-forming actinomycete strain (HKI0641(T)) was isolated from a soil sample collected in the Black Forest, Germany. During screening for antimicrobial natural products this bacterium was identified as a producer of the antibiotic Telomycin. Morphological characteristics and chemotaxonomic data indicated that the strain belonged to the genus Micromonospora. The peptidoglycan of strain HKI0641(T) contained meso-diaminopimelic acid, and the fatty acid profile consisted predominantly of anteiso-C15 : 0, iso-C15 : 0, iso-C16 : 0 and C16 : 0. MK-10(H4), MK-10(H2) and MK-10 were identified as the major menaquinones. To determine the taxonomic positioning of strain HKI0641(T), we computed a binary tanglegram of two rooted phylogenetic trees that were based upon 16S rRNA and gyrB gene sequences. The comparative analysis of the two common classification methods strongly supported the phylogenetic affiliation with the genus Micromonospora, but it also revealed discrepancies in the assignment at the level of the genomic species. 16S rRNA gene sequence analysis identified Micromonospora coxensis DSM 45161(T) (99.1 % sequence similarity) and Micromonospora marina DSM 45555(T) (99.0 %) as the nearest taxonomic neighbours, whereas the gyrB sequence of strain HKI0641(T) indicated a closer relationship to Micromonospora aurantiaca DSM 43813(T) (95.1 %). By means of DNA-DNA hybridization experiments, it was possible to resolve this issue and to clearly differentiate strain HKI0641(T) from other species of the genus Micromonospora. The type strains of the aforementioned species of the genus Micromonospora could be further distinguished from strain HKI0641(T) by several phenotypic properties, such as colony colour, NaCl tolerance and the utilization of carbon sources. The isolate was therefore assigned to a novel species of the genus Micromonospora, for which the name Micromonospora schwarzwaldensis sp. nov. is proposed. The type strain is HKI0641(T) ( = DSM 45708(T) = CIP 110415(T)).