Acetomycin
(Synonyms: 醋霉素) 目录号 : GC46783
A γ-lactone microbial metabolite
Cas No.:510-18-9
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Acetomycin is a γ-lactone microbial metabolite originally isolated from S. ramulosus that has anticancer activity.1 It inhibits proliferation of HCT-8 human colon and L1210 mouse leukemia cancer cells (IC50s = 1.5 and 2.2 µg/ml, respectively)
1.Mamber, S.W., Mitulski, J.D., Hamelehle, K.L., et al.Biological effects of acetomycin. I. Activity against tumor cells in vitro and in vivoJ. Antibiot. (Tokyo)49(1)73-76(1987)
| Cas No. | 510-18-9 | SDF | |
| 别名 | 醋霉素 | ||
| Canonical SMILES | O=C(C)O[C@@H]([C@@H](C)[C@@]1(C)C(C)=O)OC1=O | ||
| 分子式 | C10H14O5 | 分子量 | 214.2 |
| 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.6685 mL | 23.3427 mL | 46.6853 mL |
| 5 mM | 0.9337 mL | 4.6685 mL | 9.3371 mL |
| 10 mM | 0.4669 mL | 2.3343 mL | 4.6685 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。
Biological effects of Acetomycin. II. Inactivation by esterases in vitro
J Antibiot (Tokyo) 1987 Jan;40(1):77-80.PMID:3558119DOI:10.7164/antibiotics.40.77.
Acetomycin has antitumor activity in vitro but not in vivo. HCT-8 human colon adenocarcinoma assays in the presence of a drug metabolizing system (rat liver S9 fraction) demonstrated that liver enzymes inactivated Acetomycin. The structure of Acetomycin suggested that an esterase could be the key inactivating enzyme. Assays with porcine liver esterase (EC 3.1.1.1) showed that this enzyme rapidly abolishes the activity of Acetomycin against HCT-8 cells. The potential utility of Acetomycin as an antitumor agent thus depends on finding a means of preventing esterase inactivation.
Biological effects of Acetomycin. I. Activity against tumor cells in vitro and in vivo
J Antibiot (Tokyo) 1987 Jan;40(1):73-6.PMID:3558118DOI:10.7164/antibiotics.40.73.
The antibiotic Acetomycin was active in vitro against HCT-8 human colon adenocarcinoma cells (IC50, 1.5 microgram/ml) and L1210 murine leukemia cells (IC50, 2.2 micrograms/ml). Acetomycin also had marked activity in the human tumor stem cell assay, with a 33% overall response rate (less than or equal to 30% survival) against 49 primary tumors. However, Acetomycin was inactive in four in vivo tumor assay systems (L1210 and P388 leukemias, B16 melanoma and the MX-1 mammary xenograft system). This lack of in vivo activity may result from metabolic inactivation of Acetomycin.
Total synthesis of (+/-)-acetomycin and design of esterase-resistant analogs
Chem Pharm Bull (Tokyo) 1999 Apr;47(4):517-23.PMID:10319430DOI:10.1248/cpb.47.517.
The synthesis of Acetomycin and related analogs was investigated. Acetomycin was synthesized from diethyl allyl(methyl)malonate in 6.5% yield over 18 steps. The total number of steps was improved compared to our previous synthesis; i.e., four steps shorter, and the total yield was 4.5% greater than the previous synthesis. Acetomycin analogs with benzoyloxy and pivaloyloxy groups, instead of an acetoxy group at the 5-position of the gamma-butyrolactone ring were designed as esterase-resistant models and prepared similarly. Although they showed a similar level of cytotoxicity as Acetomycin in vitro, they were not resistant to porcine liver esterase, and lost cytotoxicity in vivo.
The structure of Acetomycin. Spectroscopic characterization and X-ray analysis of a bromo derivative
J Antibiot (Tokyo) 1985 Dec;38(12):1684-90.PMID:4093332DOI:10.7164/antibiotics.38.1684.
Acetomycin (1a), known since 1958, has been further characterized by NMR and CD spectra. The 3-acetyl side chain of 1a is reduced selectively by sodium cyanoborohydride yielding the diastereomeric alcohols 2a and 3a, which were esterified to the crystalline bromoacetates 2c and 3c. The structure and absolute configuration of 3c was determined by X-ray analysis. From these data the absolute configuration of 1a followed as 3S, 4S, 5R.
The structure and absolute configuration of Acetomycin
Acta Crystallogr C 1988 May 15;44 ( Pt 5):919-21.PMID:3271088DOI:10.1107/s0108270188001337.
C10H14O5, Mr = 214.22, orthorhombic, P2(1)2(1)2(1), a = 14.1084 (6), b = 10.6443 (3), c = 7.1970 (1) A, V = 1080.80 (6) A3, Z = 4, D chi = 1.317 Mg m-3, Cu K alpha, lambda = 1.5418 A, mu = 0.8571 mm-1, F(000) = 456, T = 293 K, R = 0.052 for 816 observed [3 sigma (I)] Friedel pairs. The determined absolute configuration may be described as 3S, 4R, 5R, the five-membered ring having an envelope conformation, with the bulky substituents at cis positions. The bond lengths and angles are in agreement with those of the bromoacetoxy derivative.