Kijanimicin
(Synonyms: NSC 329515) 目录号 : GC44004
An broad spectrum antibiotic
Cas No.:78798-08-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Kijanimicin is an antibiotic first isolated from the fermentation broth of A. kijaniata SCC 1256. It is active against a broad spectrum of microorganisms in vitro including P. acnes (MIC = 0.86 µg/ml), B. subtilis (MIC Enterobacter sp. (MIC = 64 µg/ml), Trichophyton sp. (MIC = 17.5 µg/ml), and Microsporum sp. (MIC = 17.5 µg/ml). At 250 mg/kg, kijanimicin was also shown to be effective in mice against P. berghei, a protozoan parasite that causes malaria in certain rodents.
| Cas No. | 78798-08-0 | SDF | |
| 别名 | NSC 329515 | ||
| Canonical SMILES | O[C@H]([C@H](O)C1)[C@H](C)O[C@@]1([H])O[C@H](C2)[C@@H](O[C@]3([H])C[C@@H](O)[C@@H](OC)[C@H](C)O3)[C@H](C)O[C@@]2([H])O[C@H](C4)[C@@H](O)[C@H](C)O[C@@]4([H])O[C@@H]5[C@]6([H])[C@@]([C@@](C(C7=C8O)=O)(C)[C@@](/C(C)=C\C[C@H](O[C@]9([H])O[C@H](C)[C@H](NC | ||
| 分子式 | C67H100N2O24 | 分子量 | 1317.5 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 0.759 mL | 3.7951 mL | 7.5901 mL |
| 5 mM | 0.1518 mL | 0.759 mL | 1.518 mL |
| 10 mM | 0.0759 mL | 0.3795 mL | 0.759 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Improved synthesis of the Kijanimicin oligodeoxytetrasaccharide
Carbohydr Res 2019 Jan 1;471:19-27.PMID:30412829DOI:10.1016/j.carres.2018.10.014.
By sequential synthesis the four 2,6-dideoxy saccharide moieties of the Kijanimicin tetrasaccharide could be stereoselectively assembled. For formation of all required 2-deoxy α-glycoside linkages various S-(hexopyranosyl)-phosphorodithioates as donor structures could be convincingly employed. The terminal 2-deoxy β-glycoside linkage was stereoselectively formed following the dibromomethyl methyl ether approach. The target octadeoxy-tetrasaccha-ride could be obtained via nine subsequent steps in 5% overall yield.
Synthesis of the α-Linked Digitoxose Trisaccharide Fragment of Kijanimicin: An Unexpected Application of Glycosyl Sulfonates
Org Lett 2022 Jan 21;24(2):731-735.PMID:35005969DOI:10.1021/acs.orglett.1c04190.
Previously, we demonstrated that glycosyl tosylates are effective for the synthesis of β-glycosides of gluco-configured 2-deoxy sugars. Here, we show the same sulfonate system can be used for the selective synthesis of α-glycosides containing the allo-configured 2-deoxy sugar digitoxose. As with previous work, optimal selectivity is obtained through matching the donor with the appropriate arylsulfonyl chloride promoter. The utility of this method is demonstrated through the synthesis of the α-linked digitoxose trisaccharide fragment of Kijanimicin.
Kijanimicin (Sch 25663), a novel antibiotic produced by Actinomadura kijaniata SCC 1256. Fermentation, isolation, characterization and biological properties
J Antibiot (Tokyo) 1981 Sep;34(9):1101-6.PMID:7328052DOI:10.7164/antibiotics.34.1101.
A novel antibiotic complex has been isolated form the fermentation broth of a new species of Actinomadura, A. kijaniata SCC 1256. The complex was separated form the broth by a solvent extraction procedure and consists of 1 major component, designated Kijanimicin, and 3 minor components. Kijanimicin was isolated form the complex by column chromatography and/or preparative high pressure liquid chromatography. Structurally the compound is a unique, large acid enol antibiotic and possesses an unusual in vitro spectrum of activity against some Gram-positive and anaerobic microorganisms. In vivo it has also shown interesting activity against malaria.
Elucidation of the Kijanimicin gene cluster: insights into the biosynthesis of spirotetronate antibiotics and nitrosugars
J Am Chem Soc 2007 Nov 28;129(47):14670-83.PMID:17985890DOI:10.1021/ja0744854.
The antibiotic Kijanimicin produced by the actinomycete Actinomadura kijaniata has a broad spectrum of bioactivities as well as a number of interesting biosynthetic features. To understand the molecular basis for its formation and to develop a combinatorial biosynthetic system for this class of compounds, a 107.6 kb segment of the A. kijaniata chromosome containing the Kijanimicin biosynthetic locus was identified, cloned, and sequenced. The complete pathway for the formation of TDP-l-digitoxose, one of the two sugar donors used in construction of Kijanimicin, was elucidated through biochemical analysis of four enzymes encoded in the gene cluster. Sequence analysis indicates that the aglycone kijanolide is formed by the combined action of a modular Type-I polyketide synthase, a conserved set of enzymes involved in formation, attachment, and intramolecular cyclization of a glycerate-derived three-carbon unit, which forms the core of the spirotetronate moiety. The genes involved in the biosynthesis of the unusual deoxysugar d-kijanose [2,3,4,6-tetradeoxy-4-(methylcarbamyl)-3-C-methyl-3-nitro-d-xylo-hexopyranose], including one encoding a flavoenzyme predicted to catalyze the formation of the nitro group, have also been identified. This work has implications for the biosynthesis of other spirotetronate antibiotics and nitrosugar-bearing natural products, as well as for future mechanistic and biosynthetic engineering efforts.
Lobophorin C and D, new Kijanimicin derivatives from a marine sponge-associated actinomycetal strain AZS17
Mar Drugs 2011 Mar 17;9(3):359-68.PMID:21556165DOI:10.3390/md9030359.
Marine sponge Hymeniacidon sp. was collected from coastal waters of the East China Sea to isolate symbiotic microorganisms. The resulting sponge-associated actinomycete, Streptomyces carnosus strain AZS17, was cultivated in a 20 L volume of medium for production of bioactive secondary metabolites. Bioassay-guided isolation and purification by varied chromatographic methods yielded two new compounds of Kijanimicin derivatives, AS7-2 and AS9-12. Their structures were elucidated by spectroscopy and comparison with literatures. Results showed these two compounds were structurally similar to the previously reported compounds lobophorin A and B, yet differed in specific bond forms, stereochemistry and optical activities. The two novel compounds were named lobophorin C and D. In vitro cytotoxicity investigation by MTT assay indicated their selective activities. Lobophorin C displayed potent cytotoxic activity against the human liver cancer cell line 7402, while lobophorin D showed significant inhibitory effect on human breast cancer cells MDA-MB 435.