Hygrolidin
(Synonyms: Antibiotic 1166C) 目录号 : GC43882
A macrocyclic lactone
Cas No.:83329-73-1
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
Hygrolidin is a macrocyclic lactone originally isolated from S. hygroscopicus. It inhibits proliferation of a variety of cancer cell lines, including DLD-1 colon cancer, LNCaP prostate cancer, and K562 leukemia cells (IC50s = 2.9, 5.2, and 33 ng/ml, respectively). Hygrolidin induces the expression and levels of p21 in DLD-1 cells, but not WI-38 fibroblasts, and leads to cell accumulation in the G1 and S phases without inducing apoptosis. It has antiparasitic activity against T. cruzi, L. donovani, and T. b. brucei but also induces cytotoxicity in HepG2 cells (IC50s = 1.1, 72.5, 77, and 24.5 nM, respectively).
| Cas No. | 83329-73-1 | SDF | |
| 别名 | Antibiotic 1166C | ||
| Canonical SMILES | C/C1=C\C=C\[C@H](OC)[C@]([C@@H](C)[C@@H](O)[C@H](C)[C@]2(O)O[C@H](CC)[C@H](C)[C@H](OC(/C=C/C(O)=O)=O)C2)([H])OC(/C(C)=C\C(C)=C/[C@@H](C)[C@@H](O)[C@@H](C)C1)=O | ||
| 分子式 | C38H58O11 | 分子量 | 690.9 |
| 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 | 1.4474 mL | 7.2369 mL | 14.4739 mL |
| 5 mM | 0.2895 mL | 1.4474 mL | 2.8948 mL |
| 10 mM | 0.1447 mL | 0.7237 mL | 1.4474 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。
Hygrolidin induces p21 expression and abrogates cell cycle progression at G1 and S phases
Biochem Biophys Res Commun 2002 Oct 18;298(1):178-83.PMID:12379237DOI:10.1016/s0006-291x(02)02416-6.
Hygrolidin family antibiotics showed selective cytotoxicity against both cyclin E- and cyclin A-overexpressing cells. Among them, Hygrolidin was the most potent and inhibited growth of solid tumor-derived cell lines such as DLD-1 human colon cancer cells efficiently more than that of hematopoietic tumor cells and normal fibroblasts. FACS analysis revealed that Hygrolidin increased cells in G1 and S phases in DLD-1 cells. While Hygrolidin decreased amounts of cyclin-dependent kinase (cdk) 4, cyclin D, and cyclin B, it increased cyclin E and p21 levels. Hygrolidin-induced p21 bound to and inhibit cyclin A-cdk2 complex more strongly than cyclin E-cdk2 complex. Furthermore, Hygrolidin was found to increase p21 mRNA in DLD-1 cells, but not in normal fibroblasts. Thus, Hygrolidin inhibited tumor cell growth through induction of p21. In respect to p21 induction, inhibition of vacuolar-type (H+)-ATPase by Hygrolidin was suggested to be involved.
Catenulisporidins A and B, 16-membered macrolides of the Hygrolidin family produced by the chemically underexplored actinobacterium Catenulispora species
Bioorg Med Chem Lett 2020 Apr 1;30(7):127005.PMID:32046902DOI:10.1016/j.bmcl.2020.127005.
Two new macrolide metabolites of the Hygrolidin family, catenulisporidins A and B (1 and 2), together with a known compound Hygrolidin (3), were isolated from the culture broth of the rare actinobacterium Catenulispora sp. KCB13F192. Their structures were elucidated on the basis of HRESIMS spectrometric and NMR spectroscopic analyses. Catenulisporidins A and B are the first example of natural Hygrolidin and bafilomycin derivatives featuring a modified macrolide ring, and catenulisporidin A possesses a tetrahydrofuran ring through an ether linkage between C-7 and C-10. In cell-based fluorescent imaging and immunoblot assays, the three compounds were shown to inhibit autophagic flux in HeLa cells.
Inhibition of pinocytosis by Hygrolidin family antibiotics: possible correlation with their selective effects on oncogene-expressed cells
J Antibiot (Tokyo) 1991 Mar;44(3):344-8.PMID:1851149DOI:10.7164/antibiotics.44.344.
A fermentation broth of Streptomyces sp. SIPI-A4-0044 inhibited in vitro growth of src or ras oncogene-expressed (onc+) cells more strongly than that of oncogene-unexpressed (onc-) counterparts. The active components were isolated and identified as Hygrolidin family antibiotics (HGL). In mixed cultures consisting of onc+ and onc- cells, at an appropriate ratio, HGL showed selective toxicity to focus like structures of onc+ cells, leaving monolayer areas of onc- cells little damaged. HGL rapidly inhibited pinocytosis, or the influx of neutral red into the cells, at concentrations partially inhibitory to the cell growth. In contrast, HGL only slightly inhibited the influx of 2-deoxyglucose, nucleosides and leucine and the syntheses of DNA, RNA and protein even at high concentrations. Upon prolonged exposure to sublethal concentrations of HGL, onc- cells but not onc+ cells recovered pinocytotic activity and resumed growth.
Screening for microbial potentiators of neutral lipid degradation in CHO-K1 cells
Drug Discov Ther 2022 Dec 26;16(6):273-279.PMID:36450503DOI:10.5582/ddt.2022.01087.
A cell-based assay was conducted to screen microbial culture broths for potentiators of neutral lipid degradation in Chinese Hamster Ovary K1 cells. A total of 5,363 microbial cultures from fungi and actinomycetes were screened in this assay. Brefeldin A (1) from fungal cultures was found to promote the degradation of triacylglycerol (TG) with an EC50 of 2.6 µM. Beauveriolides I (2), III (3), beauverolides A (4), B (5), and K (6) from fungal cultures showed potentiating effect on cholesteryl ester (CE) degradation with EC50s ranging from 0.02 to 0.13 µM. Among these compounds, 2 and 6 exhibited the strongest activities (EC50, 0.02 µM). From actinomycete cultures, oxohygrolidin (7) (EC50 for TG and CE, > 1.7 and 0.8 µM, respectively) and Hygrolidin (8) (EC50 for TG and CE, 0.08 and 0.004 µM, respectively) promoted degradation of CE more preferably than TG.
Structures and total syntheses of the plecomacrolides
Curr Med Chem 2005;12(17):1947-93.PMID:16101499DOI:10.2174/0929867054546591.
The plecomacrolides are a large family of natural products typically featured with a 16- or 18-membered macrolactone possessing two conjugated diene units and a hemiacetal side chain. The macrocycle skeleton is connected with the side chain through a three-carbon linker, forming a biologically important intramolecular hydrogen bonding network among the lactone/linker/hemiacetal structural motif. Many members of the plecomacrolides act as selective inhibitors of vacuolar H+-ATPases (V-ATPases) and they are considered to have the potential for treatment of postmenopausal osteoporosis. Significant progress has been achieved in recent years in the area of plecomacrolide total synthesis. These include the total synthesis of bafilomycin A1 by Evans, Toshima, Hanessian, and Roush, of bafilomycin V1 by Marshall, of Hygrolidin by Hashimoto and Yonemitsu, of concanamycin F by Paterson and Toshima, and of formamicin by Roush. The synthetic strategies and key transformations used in the total synthesis are discussed.