Viridicatumtoxin
(Synonyms: NSC 159628) 目录号 : GC40215
A mycotoxin with diverse biological activities
Cas No.:39277-41-3
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
Viridicatumtoxin in a mycotoxin originally isolated from Penicillium that has diverse biological activities, including antimicrobial, cytotoxic, and toxic properties. It inhibits the growth of B. subtilis, M. luteus, C. perfringens, B. fragilis, and methicillin-resistant S. aureus (MRSA; MICs = 0.39-1.56 µg/ml), as well as C. albicans, S. cerevisiae, M. racemosus, A. niger, and P. chrysogenum (MICs = 6.2-25 µg/ml), but has no activity against M. smegmatis, E. coli, K. pneumoniae, P. aeruginosa, or S. marcescens (MICs = >100 µg/ml). Viridicatumtoxin inhibits the production of polyprenyl alcohols by S. aureus undecaprenyl pyrophosphate (UPP) synthase, E. coli octaprenyl pyrophosphate synthase (OPS), and S. cerevisiae dehydrodolichyl pyrophosphate (DedoIPP) synthase in vitro (IC50s = 3.1, 21, and 71 µM, respectively). It has cytotoxic effects against human Jurkat T (IC50 = 4.92 µM), chronic lymphocytic leukemia (CLL; LC50 = 0.7-3.5 nM), and bone marrow-derived HS-5 stromal cells. Viridicatumtoxin is toxic to rats and mice when administered intraperitoneally (LD50s = 80 and 90 mg/kg, respectively) and to rats when administered via gastric intubation (LD50 = 122.4 mg/kg), but not to rats or mice when administered orally or through subcutaneous injection.
| Cas No. | 39277-41-3 | SDF | |
| 别名 | NSC 159628 | ||
| Canonical SMILES | O[C@@H]1[C@]2(O)[C@](C(C(C(N)=O)=C(O)C2)=O)(O)C(C3=C(O)C4=C(O)C=C(OC)C5=C4C(C[C@]56C(C)(C)CCC=C6C)=C31)=O | ||
| 分子式 | C30H31NO10 | 分子量 | 565.6 |
| 溶解度 | DMF: 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 | 1.768 mL | 8.8402 mL | 17.6803 mL |
| 5 mM | 0.3536 mL | 1.768 mL | 3.5361 mL |
| 10 mM | 0.1768 mL | 0.884 mL | 1.768 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。
Viridicatumtoxin mycotoxicosis in mice and rats
Toxicol Lett 1984 Sep;22(3):287-91.PMID:6485002DOI:10.1016/0378-4274(84)90103-6.
LD50 studies of Viridicatumtoxin were done in rats and mice using oral, intraperitoneal (i.p.), and subcutaneous (s.c.) routes. Mice were given oral doses of Viridicatumtoxin up to 350 mg/kg body weight and rats were given doses of Viridicatumtoxin up to 150 mg/kg. No deaths occurred in the animals dosed by the oral route. Hepatic alterations of hydropic change and necrosis of centrolobular hepatocytes were observed in mice given 250, 300, or 350 mg/kg viridicatum toxin and were more severe in the mice given the higher doses. No histopathologic alterations were present in the rats dosed orally. Mice were given doses of Viridicatumtoxin up to 300 mg/kg, s.c., and rats up to 400 mg/kg. No deaths occurred in the animals dosed by this route. Microscopic alterations in both mice and rats were limited to the injection sites and consisted of coagulation necrosis. The single-dose, 72-h i.p. LD50 for the mouse and the rat was 70 mg/kg and 80 mg/kg respectively. Histopathologic alterations in mice given Viridicatumtoxin i.p. included fibrinous peritonitis, large subcapsular areas of hepatic necrosis, single-cell hepatocytic necrosis, splenic lymphoid depletion, and vacuolar degeneration of the myocardium. Rats had splenic lymphoid depletion and fibrinous peritonitis.
Viridicatumtoxin B, a new anti-MRSA agent from Penicillium sp. FR11
J Antibiot (Tokyo) 2008 Oct;61(10):633-7.PMID:19168978DOI:10.1038/ja.2008.84.
A new tetracycline-type antibiotic named Viridicatumtoxin B along with the known compound Viridicatumtoxin has been isolated from the mycelium of liquid fermentation cultures of Penicillium sp. FR11. The structure of Viridicatumtoxin B was determined on the basis of MS and NMR data. Viridicatumtoxin B inhibited the growth of Staphylococcus aureus including methicillin-resistant S. aureus and quinolone-resistant S. aureus with MIC (microg/ml) of 0.5, which is similar with that of vancomycin, but 8-64 times higher activity than that of tetracycline.
Identification of the Viridicatumtoxin and griseofulvin gene clusters from Penicillium aethiopicum
Chem Biol 2010 May 28;17(5):483-94.PMID:20534346DOI:10.1016/j.chembiol.2010.03.015.
Penicillium aethiopicum produces two structurally interesting and biologically active polyketides: the tetracycline-like Viridicatumtoxin 1 and the classic antifungal agent griseofulvin 2. Here, we report the concurrent discovery of the two corresponding biosynthetic gene clusters (vrt and gsf) by 454 shotgun sequencing. Gene deletions confirmed that two nonreducing PKSs (NRPKSs), vrtA and gsfA, are required for the biosynthesis of 1 and 2, respectively. Both PKSs share similar domain architectures and lack a C-terminal thioesterase domain. We identified gsfI as the chlorinase involved in the biosynthesis of 2, because deletion of gsfI resulted in the accumulation of decholorogriseofulvin 3. Comparative analysis with the P. chrysogenum genome revealed that both clusters are embedded within conserved syntenic regions of P. aethiopicum chromosomes. Discovery of the vrt and gsf clusters provided the basis for genetic and biochemical studies of the pathways.
Total synthesis and structural revision of Viridicatumtoxin B
Angew Chem Int Ed Engl 2013 Aug 12;52(33):8736-41.PMID:23893651DOI:10.1002/anie.201304691.
Will the real Viridicatumtoxin B please stand up: Total synthesis of Viridicatumtoxin B resulted in its structural revision and opens the way for analogue construction and biological evaluation of this complex tetracycline antibiotic. The highly convergent strategy employed allows for swift construction of the entire carbocyclic framework of the molecule.
Total synthesis of Viridicatumtoxin B and analogues thereof: strategy evolution, structural revision, and biological evaluation
J Am Chem Soc 2014 Aug 27;136(34):12137-60.PMID:25317739DOI:10.1021/ja506472u.
The details of the total synthesis of Viridicatumtoxin B (1) are described. Initial synthetic strategies toward this intriguing tetracycline antibiotic resulted in the development of key alkylation and Lewis acid-mediated spirocyclization reactions to form the hindered EF spirojunction, as well as Michael-Dieckmann reactions to set the A and C rings. The use of an aromatic A-ring substrate, however, was found to be unsuitable for the introduction of the requisite hydroxyl groups at carbons 4a and 12a. Applying these previous tactics, we developed stepwise approaches to oxidize carbons 12a and 4a based on enol- and enolate-based oxidations, respectively, the latter of which was accomplished after systematic investigations that revealed critical reactivity patterns. The herein described synthetic strategy resulted in the total synthesis of Viridicatumtoxin B (1), which, in turn, formed the basis for the revision of its originally assigned structure. The developed chemistry facilitated the synthesis of a series of Viridicatumtoxin analogues, which were evaluated against Gram-positive and Gram-negative bacterial strains, including drug-resistant pathogens, revealing the first structure-activity relationships within this structural type.