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Leucomycin Sale

(Synonyms: 吉他霉素; Kitasamycin) 目录号 : GC39183

Kitasamycin (Leucomycin) is a macrolide antibiotic. It has antimicrobial activity against a wide spectrum of pathogens.

Leucomycin Chemical Structure

Cas No.:1392-21-8

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产品描述

Kitasamycin (Leucomycin) is a macrolide antibiotic. It has antimicrobial activity against a wide spectrum of pathogens.

Chemical Properties

Cas No. 1392-21-8 SDF
别名 吉他霉素; Kitasamycin
Canonical SMILES [Leucomycin]
分子式 C40H67NO14 分子量 785.96
溶解度 60mg/ml in DMSO (Need ultrasonic) 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 1.2723 mL 6.3616 mL 12.7233 mL
5 mM 0.2545 mL 1.2723 mL 2.5447 mL
10 mM 0.1272 mL 0.6362 mL 1.2723 mL
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Research Update

Quantitative analysis of impurities in Leucomycin bulk drugs and tablets: A high performance liquid chromatography-charged aerosol detection method and its conversion to ultraviolet detection method

J Pharm Biomed Anal 2021 Aug 5;202:114148.PMID:34052548DOI:10.1016/j.jpba.2021.114148.

Toxic impurities were found in Leucomycin and its preparation, however the content determination of impurities was challengeable due to the lacking of their reference standards. In this study, we developed high-performance liquid chromatography method coupled with charged aerosol detection (CAD) for the quantification of related substance of Leucomycin (kitasamycin) bulk drugs and tablets, however, the CAD was not yet popular. In order to carry out quantitation work conveniently in the laboratory without CAD instruments, a high-performance liquid chromatography method coupled with ultraviolet (UV) detection was developed with the assistant of the HPLC-CAD results. The relative response of impurities on CAD chromatogram was used for guiding the establishment of HPLC-UV method, which could achieve the quantitation task in the absence of impurity reference standards. The developed HPLC-UV method was validated according to the ICH guideline and showed good precision, reproducibility and linearity with determination coefficient higher than 0.9999. The limit of detection and quantitation were 0.3 and 0.5 μg mL-1, respectively. The recoveries were 92.9 %-101.5 % at the spiked concentration levels of 0.1 %, 0.8 %, 1.0 and 1.2 % with relative standard deviations (RSDs, n = 3) lower than 2.0 %. Finally, the developed HPLC-CAD and -UV methods were compared by the determination of impurities in several batches of Leucomycin bulk drugs and tablets. The results demonstrated that the developed HPLC-UV method was simple and reliable. This study developed methods to quantify the related substance in Leucomycin and tablets, and discussed a strategy of the conversion of HPLC-CAD method to HPLC-UV method. The developed methods could be considered for implementation into pharmacopeial monographs in the future.

Inhibition of the biosynthesis of Leucomycin, a macrolide antibiotic, by cerulenin

J Biochem 1977 Apr;81(4):1127-32.PMID:881413DOI:10.1093/oxfordjournals.jbchem.a131537.

Cerulenin, an inhibitor of fatty acid synthesis, specifically inhibits the biosynthesis of Leucomycin, a 16-membered macrolide antibiotic, in both growing cells and resting cells of Streptomyces kitasatoensis. In growing cells, the production of Leucomycin was inhibited as long as cerulenin remained in the culture. In resting cells, 50 percent inhibition was achieved with a cerulenin concentration of 1.5 microgram/ml. Cells in which Leucomycin synthesis was inhibited for 9 h remained capable of Leucomycin synthesis upon removal of the inhibitor. Cerulenin specifically inhibits the incorporation of [14C]acetate into Leucomycin but does not affect total protein or RNA synthesis. The uptake of [14C]acetate was not inhibited under conditions which completely inhibited the incorporation of acetate into Leucomycin. Since cerulenin is known to block the condensation of malonyl-CoA subunits in the formation of fatty acids, it can be concluded that the aglycone of Leucomycin is synthesized via the polyketide pathway by condensation steps similar to those involved in fatty acid biosynthesis.

Preparation and biological evaluation of novel Leucomycin analogs derived from nitroso Diels-Alder reactions

Org Biomol Chem 2010 Feb 7;8(3):691-7.PMID:20090988DOI:10.1039/b922450e.

A series of 10,13-disubstituted 16-membered macrolides was synthesized using nitroso Diels-Alder reactions of Leucomycin A7. Despite the extensive constituent functionalities in Leucomycin, the hetero cycloaddition reactions proceeded in a highly regio- and stereoselective fashion. Subsequent chemical modifications of the nitroso cycloadducts, including N-O bond reduction, were also conducted. Most Leucomycin derivatives retained antibiotic profiles similar to Leucomycin A7, and, in contrast to Leucomycin itself, several exhibited moderate antiproliferative and cytotoxic activity.

9-epi-leucomycin A5. Synthesis and antimicrobial activity

J Antibiot (Tokyo) 1981 Dec;34(12):1577-80.PMID:7333970DOI:10.7164/antibiotics.34.1577.

9-epi-Leucomycin A5 has been obtained from Leucomycin A5 (I) by the following reaction sequence. Leucomycin A5 (I) was treated with Collins reagent (CrO3-pyridine) in the presence of water (13%) to provide 9-dehydroleucomycin A5 (II) in 95% yield. The formyl group was internally protected by the reaction of II with acetic anhydride-K2CO3 to afford 18,2'-di-O-acetyl-9-dehydroleucomycin A5-3,18-hemiacetal (III). Sodium borohydride reaction of II provided a 1 : 1 mixture of natural I and its 9-epimer, 9-epi-leucomycin A5 (IV), which were separated by silica gel chromatography. It was observed that the antimicrobial activities of both enantiomers were virtually identical with some tests strains but that of IV is reduced in comparison with I in some bacteria such as Staphylococcus epidermidis sp-al-1 and Streptococcus pyogenes N. Y. 5.

Synthesis and biological evaluation of novel Leucomycin analogues modified at the C-3 position. I. Epimerization and methylation of the 3-hydroxyl group

J Antibiot (Tokyo) 2003 Apr;56(4):399-414.PMID:12817814DOI:10.7164/antibiotics.56.399.

The synthesis and biological evaluation of sixteen-membered macrolides modified at the C-3 position are described. 3-Epi-leucomycin A7 (9), 3-O-acyl-3-epi-leucomycin A7 analogues (11a-11e), 3-O-acylleucomycin A7 analogues (13b-13e) and 3-O-methylleucomycin analogues (16a, 16b and 22) were synthesized via fully protected intermediates (7, 5a, 5b and 20). After appropriate modification, subsequent deprotections were performed to furnish a variety of Leucomycin analogues. Methylation of the 3-hydroxyl group was found to improve the pharmacoprofile of Leucomycin antibiotics. 3-O-Methylrokitamycin (16b) showed enhanced antibacterial activity in vitro and 3,3''-di-O-methyl-4''-O-(3-methylbutyl)Leucomycin V (22) exhibited improved metabolic stability in rat plasma in vitro.