Pyridoxatin
目录号 : GC44786
A fungal metabolite with diverse biological activities
Cas No.:135529-30-5
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
Pyridoxatin is a fungal metabolite originally isolated from Acremonium with diverse biological activities. It inhibits production of thiobarbituric acid reactive substance (TBARS) in vitro (IC50 = 0.55 μg/ml). Pyridoxatin inhibits hemolysis induced by the free radical generator AAPH in rat erythrocytes (IC50 = 1.95 μg/ml). It is active against C. albicans (MIC = 1.64 μg/ml). Pyridoxatin is cytotoxic in a panel of 21 cancer cell lines (EC50s = 0.10-7.04 μg/ml). It also inhibits gelatinase A (IC50 = 15.2 μM).
| Cas No. | 135529-30-5 | SDF | |
| Canonical SMILES | C[C@H]1C[C@@H](C=C)[C@H](C2=C(O)C=CN(O)C2=O)[C@@H](C)C1 | ||
| 分子式 | C15H21NO3 | 分子量 | 263.3 |
| 溶解度 | DMSO: 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 | 3.7979 mL | 18.9897 mL | 37.9795 mL |
| 5 mM | 0.7596 mL | 3.7979 mL | 7.5959 mL |
| 10 mM | 0.3798 mL | 1.899 mL | 3.7979 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。
Lichen endophyte derived Pyridoxatin inactivates Candida growth by interfering with ergosterol biosynthesis
Biochim Biophys Acta 2015 Sep;1850(9):1762-71.PMID:25960388DOI:10.1016/j.bbagen.2015.05.005.
Background: This study is to characterize the antifungal effects of Pyridoxatin (PYR), a small natural product isolated from an endolichenic fungus. Methods: The susceptibility tests in vitro and in vivo by using Caenorhabditis elegans as an infectious model were performed to evaluate the antifungal efficacy of PYR against Candida species. The cytotoxicity of PYR against normal human cells was tested using MTT assay. The transcriptional levels of genes related to sterol synthesis and cell cycle regulation were measured using real-time quantitative PCR (qPCR). The contents ergosterol, squalene, lanosterol were detected by liquid chromatography/tandem mass spectrometry (LC/MS). Results: PYR was effective against four tested Candida species with its minimal inhibitory concentrations (MICs) ranging from 1-4μg/ml. No obvious cytotoxicity was observed for PYR against normal human cells. PYR inhibited the growth of Candida albicans, preventing the biofilm formation. And the antifungal action was independent on efflux pumps. The in vivo test showed PYR greatly prolonged the survival of infected C. elegans. qPCR results revealed that most of the genes related to sterol biosynthesis were considerably down-regulated in PYR-treated cells. Determination of the sterol content found that PYR inhibited the ergosterol synthesis dose dependently and caused the accumulation of squalene and lanosterol. Moreover, analysis of the structure-activity relationship revealed the heterocyclic hydroxamic acid in PYR was the key group for the antifungal action. Conclusions: PYR interferes with the ergosterol synthesis to exert antifungal action. General significance: The elucidated mechanism provides possible applications of PYR in fighting clinical relevant fungal infections.
Antioxidant activity and cellular uptake of the hydroxamate-based fungal iron chelators Pyridoxatin, desferriastechrome and desferricoprogen
Biometals 2019 Aug;32(4):707-715.PMID:31152280DOI:10.1007/s10534-019-00202-7.
The hydroxamate class of compounds is well known for its pharmacological applications, especially in the context of chelation therapy. In this work we investigate the performance of the fungal hydroxamates Pyridoxatin (PYR), desferriastechrome (DAC) and desferricoprogen (DCO) as mitigators of stress caused by iron overload (IO) both in buffered medium and in cells. Desferrioxamine (DFO), the gold standard for IO treatment, was used as comparison. It was observed that all the fungal chelators (in aqueous medium) or PYR and DAC (in cells) are powerful iron scavengers. However only PYR and DCO (in aqueous medium) or PYR (in cells) were also antioxidant against two forms of iron-dependent oxidative stress (ascorbate or peroxide oxidation). These findings reveal that PYR is an interesting alternative to DFO for iron chelation therapy, since it has the advantage of being cell permeable and thus potentially orally active.
Chaunopyran A: Co-Cultivation of Marine Mollusk-Derived Fungi Activates a Rare Class of 2-Alkenyl-Tetrahydropyran
J Nat Prod 2017 Apr 28;80(4):1167-1172.PMID:28383912DOI:10.1021/acs.jnatprod.7b00144.
Co-cultivation of Chaunopycnis sp. (CMB-MF028) and Trichoderma hamatum (CMB-MF030), fungal strains co-isolated from the inner tissue of an intertidal rock platform mollusc (Siphonaria sp), resulted in transcriptional activation of a rare class of 2-alkenyl-tetrahydropyran, chaunopyran A (7), and biotransformation and deactivation of the antifungal Pyridoxatin (1), to methyl-pyridoxatin (8). This study illustrates the complexity of offensive and counter-offensive molecular defenses encountered during fungal co-cultivation, and the opportunities for activating new, otherwise transcriptionally silent secondary metabolites.
Tetramic Acids and Pyridone Alkaloids from the Endolichenic Fungus Tolypocladium cylindrosporum
J Nat Prod 2015 Sep 25;78(9):2155-60.PMID:26356746DOI:10.1021/np501018w.
Three new tetramic acid derivatives, tolypocladenols A1, A2, and B (1-3), a new pyridone alkaloid, tolypyridone A (4), and a new coumarin derivative, 3,8-dihydroxy-4-(4-hydroxyphenyl)-6-methylcoumarin (5), together with four known compounds (6-9) were isolated from the endolichenic fungus Tolypocladium cylindrosporum, which inhabits the lichen Lethariella zahlbruckneri. Structures of these compounds were determined by comprehensive analysis of spectroscopic data and single-crystal X-ray diffraction determination. Bioassay of the isolated compounds found that Pyridoxatin (7) was cytotoxic to human cancer cells by induction of G0/G1 cell cycle arrest and apoptosis.
Isolation and Characterization of Aphidicolin Derivatives from Tolypocladium inflatum
Molecules 2017 Jul 12;22(7):1168.PMID:28704971DOI:10.3390/molecules22071168.
Inflatin G (1), a new aphidicolin analogue, together with seven known compounds inflatin A (2), inflatin B (3), aphidicolin (4), aphidicolin-17-monoacetate (5), gulypyrone A (6), Pyridoxatin rotamers A (7) and B (8), were isolated from the ascomycete fungus Tolypocladium inflatum. Their structures were determined through NMR analyses and the circular dichroism data of the in situ formed [Rh₂(OCOCF₃)₄] complexes. Compounds 1, 4, 5, 7, and 8 showed modest cytotoxicity against four human cancer cell lines A549, CNE1-MP1, A375, and MCF-7.