Streptazolin
(Synonyms: (+)-Streptazolin) 目录号 : GC40564
A fungal metabolite
Cas No.:80152-07-4
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
Streptazolin is a fungal metabolite originally isolated from S. viridochromogenes. It increases NF-κB activity when used at concentrations ranging from 60 to 130 µg/ml, at least in part, via PI3K signaling. Streptazolin enhances TNF-α secretion induced by LPS and enhances IL-8 secretion when used alone or in combination with LPS in THP-1 Blue cells.
| Cas No. | 80152-07-4 | SDF | |
| 别名 | (+)-Streptazolin | ||
| Canonical SMILES | O=C1O[C@]([C@]2([H])C/3=CCCN21)([H])[C@@H](O)C3=C/C | ||
| 分子式 | C11H13NO3 | 分子量 | 207.2 |
| 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 | 4.8263 mL | 24.1313 mL | 48.2625 mL |
| 5 mM | 0.9653 mL | 4.8263 mL | 9.6525 mL |
| 10 mM | 0.4826 mL | 2.4131 mL | 4.8263 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。
New co-metabolites of the Streptazolin pathway
J Nat Prod 2001 Jan;64(1):42-5.PMID:11170664DOI:10.1021/np000377i.
Variation of the culture conditions of Streptomyces sp. strain A1, which produces Streptazolin (1), resulted in the isolation of four new co-metabolites: 5-O-(beta-D-xylopyranosyl)Streptazolin (3), 9-hydroxystreptazolin (4), 13-hydroxystreptazolin (5), and streptenol E (6). Their structures were established by spectroscopic and chemical methods. The possible biosynthetic relationship between the streptazolins and the streptenols is discussed.
Stereoselective total synthesis of (+)-streptazolin by using a temporary silicon-tethered RCM strategy
J Org Chem 2006 Jul 7;71(14):5221-7.PMID:16808509DOI:10.1021/jo060555y.
A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of Streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded Streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.
Streptomyces thermoviolaceus SRC3 strain as a novel source of the antibiotic adjuvant Streptazolin: A statistical approach toward the optimized production
J Microbiol Methods 2018 May;148:161-168.PMID:29665368DOI:10.1016/j.mimet.2018.04.008.
Streptomyces thermoviolaceus SRC3, a newly isolated actinobacterial strain from Algerian river sediments, exhibited a broad activity against various bacterial and yeast human pathogens (Salmonella Typhi ATCC 14028, Vibrio cholerae ATCC 14035, MRSA ATCC 43300 and Candida albicans ATCC 10231). The strain SRC3 was selected from thirty nine actinobacterial isolates and identified as S. thermoviolaceus based on morphology, cultural properties, physiological analyses and 16S rRNA gene sequencing. Culture parameters for the antibiotic production were optimized by sequential statistical strategy including Plackett-Burman design (PBD) and Response Surface Methodology (RSM). In PBD experiments, KCl, K2HPO4, MgSO4·7H2O, pH value and incubation time emerged as the most significant in affecting the output of antimicrobial activities. These factors were further optimized using Central Composite Design (CCD). The best achieved conditions were: KCl (0.01%), K2HPO4 (0.1%), MgSO4·7H2O (0.02%) and 9 days incubation for anti-S. Typhi compounds, KCl (0.051%), MgSO4·7H2O (0.05%) and 5 days incubation for C. albicans inhibitors. The metabolite responsible for the bioactivities was purified, structurally characterized (by NMR, MS, UV and IR analyses) and identified as Streptazolin, recently reported as a promising antibiotic adjuvant.
A macrophage-stimulating compound from a screen of microbial natural products
J Antibiot (Tokyo) 2015 Jan;68(1):40-6.PMID:24984798DOI:10.1038/ja.2014.83.
Rising rates of antibiotic resistance in bacterial pathogens is a medical crisis of global concern that necessitates the development of new treatment strategies. We have isolated a natural product with macrophage-stimulating activity from a screen of microbially produced bioactive molecules. Streptazolin increased bacterial killing and elaboration of immunostimulatory cytokines by macrophages in vitro. Furthermore, we show that Streptazolin stimulates the macrophage nuclear factor κB (NF-κB) pathway via phosphatidylinositide 3-kinase (PI3K) signaling, and that the conjugated diene moiety is essential for stimulatory activity. Immunostimulatory molecules like Streptazolin represent entries into new treatment paradigms to address the challenge of antibiotic resistance.
Studies on the total synthesis of Streptazolin and its related natural products: first total synthesis of (+/-)-8alpha-hydroxystreptazolone
J Org Chem 2004 Mar 19;69(6):1803-12.PMID:15058922DOI:10.1021/jo0356816.
The intramolecular Pauson-Khand reaction of 2-oxazolone derivatives with a suitable heptynyl appendage gave exclusively the corresponding 4-hydroxy-6-substituted-9-oxa-1-azatricyclo[6.2.1.0(5,11)]undec-5-ene-7,10-diones. On the basis of this newly developed Pauson-Khand reaction of 2-oxazolone-alkyne derivatives, the first total synthesis of (+/-)-8alpha-hydroxystreptazolone was accomplished in a highly stereoselective manner. In addition, (+/-)-7-epi-8alpha-hydroxystreptazolone was also synthesized.