Dihydrotetrodecamycin
(Synonyms: 二氢四环癸霉素) 目录号 : GC47230
A fungal metabolite with antibacterial activity
Cas No.:166403-10-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >70.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Dihydrotetrodecamycin is a fungal metabolite originally isolated from S. nashvillensis that has antibacterial activity.1,2 It is active against the piscine pathogenic bacterium P. piscicida.
1.Tsuchida, T., Linuma, H., Nishida, C., et al.Tetrodecamycin and dihydrotetrodecamycin, new antimicrobial antibiotics against Pasteurella piscicida produced by Streptomyces nashvillensis MJ885-mF8. I. Taxonomy, fermentation, isolation, characterization and biological activitiesJ. Antibiot. (Tokyo)48(10)1104-1109(1995) 2.Tsuchida, T., Linuma, H., Nakamura, K.T., et al.Derivatives of tetrodecamycinJ. Antibiot. (Tokyo)48(11)1330-1335(1995)
| Cas No. | 166403-10-7 | SDF | |
| 别名 | 二氢四环癸霉素 | ||
| Canonical SMILES | CC12C(C)C(OC(C(C)OC3=O)=C3C2=O)C(O)C4(O)CCCCC41 | ||
| 分子式 | C18H24O6 | 分子量 | 336.4 |
| 溶解度 | Dichloromethane: 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 | 2.9727 mL | 14.8633 mL | 29.7265 mL |
| 5 mM | 0.5945 mL | 2.9727 mL | 5.9453 mL |
| 10 mM | 0.2973 mL | 1.4863 mL | 2.9727 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。
Tetrodecadazinone, a novel tetrodecamycin-pyridazinone hybrid with anti-liver fibrosis activity from Streptomyces sp. HU051
Bioorg Chem 2022 Feb;119:105573.PMID:34952245DOI:10.1016/j.bioorg.2021.105573.
Tetrodecadazinone (1), a novel tetrodecamycin-pyridazinone hybrid possessing a new 1,2-dimethyl-1-(2-methylnonyl)decahydronaphthalene skeleton, and 4-hydroxydihydrotetrodecamycin (2) were separated from a culture of Streptomyces sp. HU051, together with a known compound, Dihydrotetrodecamycin (3). Diverse spectroscopic approaches were applied to assign the structures of 1-3, and the structure of 1 was further confirmed by single crystal X-ray diffraction analysis. Compound 1 is the first example of a pyridazinone-containing natural product. Biosynthetically, 1 is proposed to be derived from a Michael addition reaction of a PKS-derived tetrodecamycin and a piperazic-acid-derived pyridazinone. Biological evaluation revealed 1 could reduce the expressions of extracellular matrix proteins (fibronectin and collagen I) and α-smooth muscle actin (α-SMA) in transforming growth factor-β (TGF-β1)-activated LX-2 cells. Preliminary mechanism study showed 1 exerted its anti-liver fibrosis effect by regulating TGF-β1/Smad2/3 signaling pathway.
Tetrodecamycin and Dihydrotetrodecamycin, new antimicrobial antibiotics against Pasteurella piscicida produced by Streptomyces nashvillensis MJ885-mF8. II. Structure determination
J Antibiot (Tokyo) 1995 Oct;48(10):1110-4.PMID:7490216DOI:10.7164/antibiotics.48.1110.
Novel antimicrobial antibiotics against Pasteurella piscicida, tetrodecamycin (1) and weakly active Dihydrotetrodecamycin (2) were isolated from a culture broth of Streptomyces nashvillensis MJ885-mF8. The planar structure of 1 was determined to be 2-acyl-4-ylidene tetronic acid alkyl ether containing decaline ring by various NMR spectral data of 1 and its acetyl derivative (3). The structure of 2 was elucidated by comparison with the spectral data of 1 and confirmed by catalytic reduction of 1 into 2. The X-ray crystallography of 2 showed the relative stereochemistry. Their absolute configurations were determined by using modified Mosher's method.
Tetrodecamycin and Dihydrotetrodecamycin, new antimicrobial antibiotics against Pasteurella piscicida produced by Streptomyces nashvillensis MJ885-mF8. I. Taxonomy, fermentation, isolation, characterization and biological activities
J Antibiot (Tokyo) 1995 Oct;48(10):1104-9.PMID:7490215DOI:10.7164/antibiotics.48.1104.
The novel antimicrobial antibiotic against Pasteurella piscicida, tetrodecamycin (1) and weakly active Dihydrotetrodecamycin (2) were isolated from the fermentation broth of Streptomyces nashvillensis MJ885-mF8. They were purified by adsorption on Diaion HP-20, silica gel column chromatography and crystallization. The MICs of 1 were 6.25 approximately 12.5 micrograms/liter and 1.56 approximately 6.25 micrograms/ml against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and 12 strains of P. piscicida, respectively.
Biosynthetic Genes for the Tetrodecamycin Antibiotics
J Bacteriol 2016 Jun 27;198(14):1965-1973.PMID:27137499DOI:10.1128/JB.00140-16.
We recently described 13-deoxytetrodecamycin, a new member of the tetrodecamycin family of antibiotics. A defining feature of these molecules is the presence of a five-membered lactone called a tetronate ring. By sequencing the genome of a producer strain, Streptomyces sp. strain WAC04657, and searching for a gene previously implicated in tetronate ring formation, we identified the biosynthetic genes responsible for producing 13-deoxytetrodecamycin (the ted genes). Using the ted cluster in WAC04657 as a reference, we found related clusters in three other organisms: Streptomyces atroolivaceus ATCC 19725, Streptomyces globisporus NRRL B-2293, and Streptomyces sp. strain LaPpAH-202. Comparing the four clusters allowed us to identify the cluster boundaries. Genetic manipulation of the cluster confirmed the involvement of the ted genes in 13-deoxytetrodecamycin biosynthesis and revealed several additional molecules produced through the ted biosynthetic pathway, including tetrodecamycin, Dihydrotetrodecamycin, and another, W5.9, a novel molecule. Comparison of the bioactivities of these four molecules suggests that they may act through the covalent modification of their target(s). Importance: The tetrodecamycins are a distinct subgroup of the tetronate family of secondary metabolites. Little is known about their biosynthesis or mechanisms of action, making them an attractive subject for investigation. In this paper we present the biosynthetic gene cluster for 13-deoxytetrodecamycin in Streptomyces sp. strain WAC04657. We identify related clusters in several other organisms and show that they produce related molecules.