Bekanamycin (Kanamycin B)
(Synonyms: 卡那霉素; Kanamycin B) 目录号 : GC32080
An aminoglycoside antibiotic
Cas No.:4696-76-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Bekanamycin is an aminoglycoside antibiotic.1 It is active against S. aureus, E. coli, P. aeruginosa, and P. rettgeri (MICs = 0.78-25 ?g/ml). Bekanamycin binds to the ribosomal decoding A site to interfere with bacterial protein synthesis.2
1.Umezawa, H., Umezawa, S., Tsuchiya, T., et al.3',4'-Dideoxy-kanamycin B active against kanamycin-resistant Escherichia coli and Pseudomonas aeruginosaJ. Antibiot. (Tokyo)24(7)485-487(1971) 2.Salian, S., Matt, T., Akbergenov, R., et al.Structure-activity relationships among the kanamycin aminoglycosides: Role of ring I hydroxyl and amino groupsAntimicrob. Agents Chemother.56(12)6104-6108(2012)
| Cas No. | 4696-76-8 | SDF | |
| 别名 | 卡那霉素; Kanamycin B | ||
| Canonical SMILES | O[C@H]1[C@](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@@]3([H])O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)([H])O[C@H](CO)[C@@H](O)[C@@H]1N | ||
| 分子式 | C18H37N5O10 | 分子量 | 483.51 |
| 溶解度 | Water : ≥ 37 mg/mL (76.52 mM) | 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 | 2.0682 mL | 10.341 mL | 20.6821 mL |
| 5 mM | 0.4136 mL | 2.0682 mL | 4.1364 mL |
| 10 mM | 0.2068 mL | 1.0341 mL | 2.0682 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。
Modulation of Kanamycin B and kanamycin A biosynthesis in Streptomyces kanamyceticus via metabolic engineering
PLoS One 2017 Jul 28;12(7):e0181971.PMID:28753625DOI:10.1371/journal.pone.0181971.
Both kanamycin A and Kanamycin B, antibiotic components produced by Streptomyces kanamyceticus, have medical value. Two different pathways for kanamycin biosynthesis have been reported by two research groups. In this study, to obtain an optimal kanamycin A-producing strain and a kanamycin B-high-yield strain, we first examined the native kanamycin biosynthetic pathway in vivo. Based on the proposed parallel biosynthetic pathway, kanN disruption should lead to kanamycin A accumulation; however, the kanN-disruption strain produced neither kanamycin A nor Kanamycin B. We then tested the function of kanJ and kanK. The main metabolite of the kanJ-disruption strain was identified as Kanamycin B. These results clarified that kanamycin biosynthesis does not proceed through the parallel pathway and that synthesis of kanamycin A from Kanamycin B is catalyzed by KanJ and KanK in S. kanamyceticus. As expected, the Kanamycin B yield of the kanJ-disruption strain was 3268±255 μg/mL, 12-fold higher than that of the original strain. To improve the purity of kanamycin A and reduce the yield of Kanamycin B in the fermentation broth, four different kanJ- and kanK-overexpressing strains were constructed through either homologous recombination or site-specific integration. The overexpressing strain containing three copies of kanJ and kanK in its genome exhibited the lowest Kanamycin B yield (128±20 μg/mL), which was 54% lower than that of the original strain. Our experimental results demonstrate that kanamycin A is derived from KanJ-and-KanK-catalyzed conversion of Kanamycin B in S. kanamyceticus. Moreover, based on the clarified biosynthetic pathway, we obtained a kanamycin B-high-yield strain and an optimized kanamycin A-producing strain with minimal byproduct.
HPLC-ELSD determination of Kanamycin B in the presence of kanamycin A in fermentation broth
Biomed Chromatogr 2015 Mar;29(3):396-401.PMID:25042110DOI:10.1002/bmc.3289.
A novel method for the direct determination of Kanamycin B in the presence of kanamycin A in fermentation broth using high performance liquid chromatography with evaporative light scattering detector (HPLC-ELSD) was developed. An Agilent Technologies C18 column was utilized, evaporation temperature of 40°C and nitrogen pressure of 3.5 bar, the optimized mobile phase was water-acetonitrile (65:35, v/v), containing 11.6 mm heptafluorobutyric acid (isocratic elution with flow rate of 0.5 mL/min) with the gain 11. Kanamycin B was eluted at 5.6 min with an asymmetry factor of 1.827. The method showed good linearity over the concentration range of 0.05 to 0.80 mg/mL for the Kanamycin B (r(2) = 0.9987). The intra-day and inter-day coefficients of variation obtained from Kanamycin B were less than 4.3%. Mean recovery of Kanamycin B from spiked fermentation broth was 95%. The developed method was applied to the determination of Kanamycin B without any interference from other constituents in the fermentation broth. This method offers simple, rapid and quantitative detection of Kanamycin B.
Construction of Kanamycin B overproducing strain by genetic engineering of Streptomyces tenebrarius
Appl Microbiol Biotechnol 2011 Feb;89(3):723-31.PMID:20936279DOI:10.1007/s00253-010-2908-5.
Genetic engineering as an important approach to strain optimization has received wide recognition. Recent advances in the studies on the biosynthetic pathways and gene clusters of Streptomyces make stain optimization by genetic alteration possible. Kanamycin B is a key intermediate in the manufacture of the important medicines dibekacin and arbekacin, which belong to a class of antibiotics known as the aminoglycosides. Kanamycin could be prepared by carbamoylkanamycin B hydrolysis. However, carbamoylkanamycin B production in Streptomyces tenebrarius H6 is very low. Therefore, we tried to obtain high kanamycin B-producing strains that produced Kanamycin B as a main component. In our work, aprD3 and aprD4 were clarified to be responsible for deoxygenation in apramycin and tobramycin biosynthesis. Based on this information, genes aprD3, aprQ (deduced apramycin biosynthetic gene), and aprD4 were disrupted to optimize the production of carbamoylkanamycin B. Compared with wild-type strain, mutant strain SPU313 (ΔaprD3, ΔaprQ, and ΔaprD4) produced carbamoylkanamycin B as a single antibiotic, whose production increased approximately fivefold. To construct a strain producing Kanamycin B instead of carbamoylkanamycin B, the carbamoyl-transfer gene tacA was inactivated in strain SPU313. Mutant strain SPU314 (ΔaprD3, ΔaprQ, ΔaprD4, and ΔtacA) specifically produced Kanamycin B, which was proven by LC-MS. This work demonstrated careful genetic engineering could significantly improve production and eliminate undesired products.
Comparative ototoxicity of kanamycin A and Kanamycin B in the guinea pig
Acta Otolaryngol 1987 Jan-Feb;103(1-2):73-80.PMID:3564930DOI:10.3109/00016488709134700.
It has previously been shown that simple compounds with multiple amine groups are ototoxic, the degree of ototoxicity depending on the number of amine groups in the molecule. The relationship between the number of amino groups and ototoxicity in aminoglycoside was studied using kanamycin A and Kanamycin B, which contain 4 and 5 amino groups respectively. Forty-five pigmented guinea pigs were injected intratympanically with 0.1 ml of different concentrations of kanamycin A and Kanamycin B. The animals were sacrificed 4 days after injection and the organ of Corti was studied by scanning electron microscopy. It was found that on an equimolar basis, Kanamycin B (with 5 amino groups) is more cochleotoxic than kanamycin A (with 4 amino groups). The greater cochleotoxic potential of Kanamycin B may be explained by the higher cationic nature of the molecule due to protonation of the amino--NH2 groups at physiological pH, resulting in a greater affinity between the drug and the cell membrane.
Genome-wide identification of Kanamycin B binding RNA in Escherichia coli
BMC Genomics 2023 Mar 16;24(1):120.PMID:36927548DOI:10.1186/s12864-023-09234-3.
Background: The aminoglycosides are established antibiotics that inhibit bacterial protein synthesis by binding to ribosomal RNA. Additional non-antibiotic aminoglycoside cellular functions have also been identified through aminoglycoside interactions with cellular RNAs. The full extent, however, of genome-wide aminoglycoside RNA interactions in Escherichia coli has not been determined. Here, we report genome-wide identification and verification of the aminoglycoside Kanamycin B binding to Escherichia coli RNAs. Immobilized Kanamycin B beads in pull-down assays were used for transcriptome-profiling analysis (RNA-seq). Results: Over two hundred Kanamycin B binding RNAs were identified. Functional classification analysis of the RNA sequence related genes revealed a wide range of cellular functions. Small RNA fragments (ncRNA, tRNA and rRNA) or small mRNA was used to verify the binding with Kanamycin B in vitro. Kanamycin B and ibsC mRNA was analysed by chemical probing. Conclusions: The results will provide biochemical evidence and understanding of potential extra-antibiotic cellular functions of aminoglycosides in Escherichia coli.