Midecamycin (SF-837)
(Synonyms: 麦迪霉素; SF-837; Antibiotic SF-837) 目录号 : GC32126
Midecamycin (Espinomycin A, Medecamycin A1, Platenomycin B1, Rubimycin, Turimycin P3) is a naturally occuring macrolide antibiotic that acts by inhibiting bacterial protein synthesis.
Cas No.:35457-80-8
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
Midecamycin (Espinomycin A, Medecamycin A1, Platenomycin B1, Rubimycin, Turimycin P3) is a naturally occuring macrolide antibiotic that acts by inhibiting bacterial protein synthesis.
| Cas No. | 35457-80-8 | SDF | |
| 别名 | 麦迪霉素; SF-837; Antibiotic SF-837 | ||
| Canonical SMILES | O[C@H]1[C@](O[C@H](C)[C@@H](O[C@@](O[C@@H](C)[C@@H]2OC(CC)=O)([H])C[C@]2(O)C)[C@@H]1N(C)C)([H])O[C@@H]([C@H](C[C@H]([C@H](/C=C/C=C/C3)O)C)CC=O)[C@H]([C@](CC(O[C@@H]3C)=O)([H])OC(CC)=O)OC | ||
| 分子式 | C41H67NO15 | 分子量 | 813.97 |
| 溶解度 | DMSO : ≥ 36 mg/mL (44.23 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 | 1.2285 mL | 6.1427 mL | 12.2855 mL |
| 5 mM | 0.2457 mL | 1.2285 mL | 2.4571 mL |
| 10 mM | 0.1229 mL | 0.6143 mL | 1.2285 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。
Midecamycin Is Inactivated by Several Different Sugar Moieties at Its Inactivation Site
Int J Mol Sci 2021 Nov 23;22(23):12636.PMID:34884439DOI:10.3390/ijms222312636.
Glycosylation inactivation is one of the important macrolide resistance mechanisms. The accumulated evidences attributed glycosylation inactivation to a glucosylation modification at the inactivation sites of macrolides. Whether other glycosylation modifications lead to macrolides inactivation is unclear. Herein, we demonstrated that varied glycosylation modifications could cause inactivation of Midecamycin, a 16-membered macrolide antibiotic used clinically and agriculturally. Specifically, an actinomycetic glycosyltransferase (GT) OleD was selected for its glycodiversification capacity towards Midecamycin. OleD was demonstrated to recognize UDP-D-glucose, UDP-D-xylose, UDP-galactose, UDP-rhamnose and UDP-N-acetylglucosamine to yield corresponding Midecamycin 2'-O-glycosides, most of which displayed low yields. Protein engineering of OleD was thus performed to improve its conversions towards sugar donors. Q327F was the most favorable variant with seven times the conversion enhancement towards UDP-N-acetylglucosamine. Likewise, Q327A exhibited 30% conversion enhancement towards UDP-D-xylose. Potent biocatalysts for Midecamycin glycosylation were thus obtained through protein engineering. Wild OleD, Q327F and Q327A were used as biocatalysts for scale-up preparation of Midecamycin 2'-O-glucopyranoside, Midecamycin 2'-O-GlcNAc and Midecamycin 2'-O-xylopyranoside. In contrast to Midecamycin, these Midecamycin 2'-O-glycosides displayed no antimicrobial activities. These evidences suggested that besides glucosylation, other glycosylation patterns also could inactivate Midecamycin, providing a new inactivation mechanism for Midecamycin resistance. Cumulatively, glycosylation inactivation of Midecamycin was independent of the type of attached sugar moieties at its inactivation site.
Modifications of a macrolide antibiotic Midecamycin (SF-837). I. Synthesis and structure of 9,3''-diacetylmidecamycin
J Antibiot (Tokyo) 1976 May;29(5):536-48.PMID:956042DOI:10.7164/antibiotics.29.536.
9,3''-Diacetylmidecamycin (12) was synthesized from 4''-depropionyl-9,2',4''-triacetylmidecamycin (8) by heating the latter with propionic anhydride in pyridine followed by removal of 2'-acetyl group, with or without 18-enolpropionyl group. Direct acetylation of midecamycin (1) led to the formation of the 3'',4''-positional isomer (6). The structure of 12 was determined by mass, NMR and chemical degradation. The location of 3''-acetyl group was shown by the stereospecific 3 leads to 1 acetyl migration catalyzed by a base of 3-O-acetyl-4-O-propionyl-L-mycarose (13), and comparison of NMR and mass fragmentation with the 3,4-positional isomer (15). The latter's structure was independently supported by the nuclear Overhauser effect between methyl and propionyl group at C-3. The intramolecular 4 leads to 3 acyl shift that was taken place in the forced acylation of the mycarose moiety was found to be affected by the anomeric configuration, nature of aglycones and reaction temperature. Reverse 3 leads to 4 acyl migration occurred in acidic hydrolysis.
[Diagnosis and treatment of acute tonsillopharyngitis. Consensus document update]
An Pediatr (Engl Ed) 2020 Sep;93(3):206.e1-206.e8.PMID:32605870DOI:10.1016/j.anpedi.2020.05.004.
An update of the Spanish consensus document on the diagnosis and treatment of acute tonsillopharyngitis is presented. Clinical scores should not be used to prescribe antibiotics, unless microbiological tests are not available or there is a child at risk of rheumatic fever. There is no score better than those set out in the previous consensus. Microbiological tests are recommended in proposed cases, regardless of the result of the scores. Penicillin is the treatment of choice, prescribed twice a day for 10 days. Amoxicillin is the first alternative, prescribed once or twice a day for the same time. First-generation cephalosporins are the treatment of choice in children with non-immediate reaction to penicillin or amoxicillin. Josamycin and Midecamycin are the best options for children with immediate penicillin allergic reactions, when non-beta-lactam antibiotics should be used. In microbiological treatment failure, and in streptococcal carriers, the treatments proposed in the previous consensus are still applicable.
Macrolides allergy
Curr Pharm Des 2008;14(27):2840-62.PMID:18991703DOI:10.2174/138161208786369812.
Macrolides are characterised by their basic structure which is made up of a lactonic cycle with 2 osidic chains. They are classified according to the number of carbon atoms in the cycle : 14 membered macrolides (erythromicin, roxithromycin, dirithromycin, clarithromycin), 15 membered (azithromycin) and 16 membered (spiramycin, josamycin, Midecamycin) macrolides. Epidemiological studies show that macrolides are amongst the safest antibiotics, but in these series, no drug allergy work up was performed. An immediate IgE dependent hypersensitivity has been shown with erythromycin in some cases. The mechanism is unknown and the skin tests are negative in most other cases. It would appear that the macrolide allergies are unlikely to be class allergies. Eviction is the treatment of choice. Desensitization has been successful in a few cases.
Direct electrochemistry and voltammetric determination of Midecamycin at a multi-walled carbon nanotube coated gold electrode
Colloids Surf B Biointerfaces 2011 Aug 1;86(1):247-50.PMID:21543194DOI:10.1016/j.colsurfb.2011.03.037.
Macrolide antibiotics generally shows slow electron-transfer rate and produces insensitive redox peaks at conventional electrodes. In this paper, we studied the electrochemical behavior of Midecamycin, one of macrolide antibiotics, at a multi-walled carbon nanotube (MWNT) modified gold electrode. It was found that MWNT could adsorb Midecamycin and promote its direct electron-transfer. Hence Midecamycin exhibited a more sensitive anodic peak at the modified electrode. The electrochemical process showed the feature of a mixed-control system of diffusion and adsorption. Under the optimized conditions (i.e. pH 7.0 phosphate supporting electrolyte, 5 μl 0.5 mg ml⁻¿multi-walled carbon nanotube suspension for Ø = 2.0 mm electrode, accumulation at -0.8 V for 150 s), the anodic peak current was linear to Midecamycin concentration in the range of 5 × 10⁻⁷ to 2 × 10⁻⁵M, with a correlation coefficient of 0.998. For a 5×10⁻⁶ M Midecamycin solution, ten repetitive measurements gave a relative standard deviation of 2.2%. This method was successfully applied to the determination of Midecamycin in medicine tablet and the recovery was 97.5-104.0%.