Desotamide
(Synonyms: Desotamide A) 目录号 : GC43424
An antibiotic
Cas No.:194660-14-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Desotamide is a cyclic hexapeptide antibiotic originally isolated from Streptomyces. It is active against S. aureus, S. pneumoniae, and methicillin-resistant S. epidermidis (MRSE; MICs = 16, 12.5, and 32 μg/ml, respectively).
| Cas No. | 194660-14-5 | SDF | |
| 别名 | Desotamide A | ||
| Canonical SMILES | O=C(N[C@@H](CC1=CNC2=C1C=CC=C2)C(N[C@@H](CC(C)C)C(N[C@@](CC(C)C)([H])C(N[C@@]3([H])[C@H](C)CC)=O)=O)=O)CNC([C@H](CC(N)=O)NC3=O)=O | ||
| 分子式 | C35H52N8O7 | 分子量 | 696.8 |
| 溶解度 | Soluble in DMSO | 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 | 1.4351 mL | 7.1757 mL | 14.3513 mL |
| 5 mM | 0.287 mL | 1.4351 mL | 2.8703 mL |
| 10 mM | 0.1435 mL | 0.7176 mL | 1.4351 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。
The Desotamide Family of Antibiotics
Antibiotics (Basel) 2020 Jul 27;9(8):452.PMID:32727132DOI:10.3390/antibiotics9080452.
Microbial natural products underpin the majority of antimicrobial compounds in clinical use and the discovery of new effective antibacterial treatments is urgently required to combat growing antimicrobial resistance. Non-ribosomal peptides are a major class of natural products to which many notable antibiotics belong. Recently, a new family of non-ribosomal peptide antibiotics were discovered-the Desotamide family. The Desotamide family consists of Desotamide, wollamide, surugamide, ulleungmycin and noursamycin/curacomycin, which are cyclic peptides ranging in size between six and ten amino acids in length. Their biosynthesis has attracted significant attention because their highly functionalised scaffolds are cyclised by a recently identified standalone cyclase. Here, we provide a concise review of the Desotamide family of antibiotics with an emphasis on their biosynthesis.
Chemical Synthesis and Structure-Activity Relationship Study Yield Desotamide a Analogues with Improved Antibacterial Activity
Mar Drugs 2021 May 24;19(6):303.PMID:34073984DOI:10.3390/md19060303.
Desotamides A, a cyclohexapeptide produced by the deep-sea-derived Streptomyces scopuliridis SCSIO ZJ46, displays notable antibacterial activities against strains of Streptococcus pnuemoniae, Staphylococcus aureus, and methicillin-resistant Staphylococcus epidermidis (MRSE). In this study, to further explore its antibacterial potential and reveal the antibacterial structure-activity relationship of desotamides, 13 cyclopeptides including 10 new synthetic Desotamide A analogues and wollamides B/B1/B2 were synthesized and evaluated for their antibacterial activities against a panel of Gram-positive and -negative pathogens. The bioactivity data reveal that residues at position II and VI greatly impact antibacterial activity. The most potent antibacterial analogues are Desotamide A4 (13) and A6 (15) where l-allo-Ile at position II was substituted with l-Ile and Gly at position VI was simultaneously replaced by d-Lys or d-Arg; desotamides A4 (13) and A6 (15) showed a 2-4-fold increase of antibacterial activities against a series of Gram-positive pathogens including the prevalent clinical drug-resistant pathogen methicillin-resistant Staphylococcus aureus (MRSA) with MIC values of 8-32 μg/mL compared to the original Desotamide A. The enhanced antibacterial activity, broad antibacterial spectrum of desotamides A4 and A6 highlighted their potential as new antibiotic leads for further development.
Solid-phase synthesis of cyclic hexapeptides wollamides A, B and Desotamide B
Tetrahedron Lett 2017 Jul 5;58(27):2675-2680.PMID:29129945DOI:10.1016/j.tetlet.2017.05.084.
Solid-phase synthesis of antibacterial cyclohexapeptides including wollamides A, B and Desotamide B has been developed. Briefly, the protected linear hexapeptides were assembled on 2-chlorotrityl chloride resin using standard Fmoc chemistry and diisopropylcarbodiimide/hydroxybenzotriazole coupling reagents, cleaved off-resin with hexafluoroisopropanol/dichloromethane to keep side-chain protecting groups intact, and cyclized in solution. Final global removal of all protecting groups using a cocktail of trifluoroacetic acid/triisopropylsilane/dichloromethane afforded the desired cyclic hexapeptides, which were characterized by 1H, 13C NMR, and HRMS. Subsequent investigation of macrocyclization parameters such as terminal residues, coupling reagents, and cyclization concentration revealed the optimized conditions for the synthesis of this class of cyclic hexapeptides.
The roles of genes associated with regulation, transportation, and macrocyclization in Desotamide biosynthesis in Streptomyces scopuliridis SCSIO ZJ46
Appl Microbiol Biotechnol 2020 Mar;104(6):2603-2610.PMID:32002605DOI:10.1007/s00253-020-10414-4.
The deep-sea-derived microbe Streptomyces scopuliridis SCSIO ZJ46 produces desotamides A-D. Notably, desotamides A and B display antibacterial activities against pathogenic Gram-positive Streptococcus pneumoniae NCTC 7466, Staphylococcus aureus ATCC 29213, and the methicillin-resistant clinical isolate Staphylococcus epidermidis (MRSE) shhs-E1. The 39-kb Desotamide biosynthetic gene cluster (dsa) has previously been identified and heterologously expressed in S. coelicolor M1152 for the purposes of assigning dsa gene functions. In this work, we identified seven genes in the dsa cluster including three regulatory genes (dsaA, dsaM, and dsaN), two transporter genes (dsaK and dsaL), and two other genes, dsaB (annotated as a phosphate synthase) and dsaJ (a PBP-type thioesterase). The DsaA and DsaN were unambiguously shown to be positive regulators of Desotamide biosynthesis, and consistent with these roles, inactivation of either gene completely abolished Desotamide production. Moreover, overexpression of dsaA or dsaN (independent of each other) was shown to improve Desotamide titers. Production of desotamides in M1152/07-6H::dsaA strain was 2.4-fold greater than that in the heterologous dsa expression strain M1152/07-6H whereas Desotamide titers from the M1152/07-6H::dsaN strain were about twice that of M1152/07-6H. In addition, inactivation of dsaB and dsaJ (independent of each other) completely abolished Desotamide production, indicating their indispensability for Desotamide assembly. These studies provide new insights into the functions and combinatorial biosynthetic potentials of seven key genes within the dsa biosynthetic gene cluster. Findings reported here are likely to facilitate further efforts aimed at assessing and developing the desotamides and related analogs for future applications.
Deep Sea Actinomycetes and Their Secondary Metabolites
Front Microbiol 2017 May 1;8:760.PMID:28507537DOI:10.3389/fmicb.2017.00760.
Deep sea is a unique and extreme environment. It is a hot spot for hunting marine actinomycetes resources and secondary metabolites. The novel deep sea actinomycete species reported from 2006 to 2016 including 21 species under 13 genera with the maximum number from Microbacterium, followed by Dermacoccus, Streptomyces and Verrucosispora, and one novel species for the other 9 genera. Eight genera of actinomycetes were reported to produce secondary metabolites, among which Streptomyces is the richest producer. Most of the compounds produced by the deep sea actinomycetes presented antimicrobial and anti-cancer cell activities. Gene clusters related to biosynthesis of Desotamide, heronamide, and lobophorin have been identified from the deep sea derived Streptomyces.