S-Adenosyl-L-methionine disulfate tosylate
(Synonyms: S-腺苷-L-甲硫氨酸; Ademetionine disulfate tosylate; S-Adenosyl methionine disulfate tosylate; AdoMet disulfate tosylate) 目录号 : GC30843S-Adenosyl-L-methionine disulfate tosylate是一种甲基供体和辅因子,它参与多种生物过程,包括表观遗传调控、蛋白质的翻译后修饰和代谢。
Cas No.:97540-22-2
Sample solution is provided at 25 µL, 10mM.
S-Adenosyl-L-methionine disulfate tosylate is a methyl donor and cofactor. It is involved in a variety of biological processes, including epigenetic regulation, post-translational modification of proteins and metabolism. Preparations containing S-Adenosyl-L-methionine disulfate tosylate have been used as dietary supplements. S-Adenosyl-L-methionine disulfate tosylate also exhibits antiproliferative, pro-apoptotic and anti-metastatic effects in human cancers[1-2].
S-Adenosyl-L-methionine disulfate tosylate (300 μM) can regulate the cell cycle progression of Cal-33 and JHU-SCC-011 cells and reduce the expression of cyclins B1, E1, and D1. S-Adenosyl-L-methionine disulfate tosylate (200 μM and 300 μM) can inhibit the migration of Cal-33 and JHU-SCC-011 cells in a dose-dependent manner after 24 hours and 48 hours, respectively[2]. The combination of 5‑fluorouracil (5-FU) with 5-Adenosyl-L-methionine disulfate tosylate at 5-40 μg/ml can protect the anticancer effect of 5-FU by regulating the expression of DNA methyltransferases (DNMTs)[3].
In the elevated plus maze test, rats given S-Adenosyl-L-methionine disulfate tosylate (100 mg/kg) showed the greatest reduction in transfer latency at day 26, confirming the memory-improving effect of S-Adenosyl-L-methionine disulfate tosylate. Animals treated with 100 mg/kg S-Adenosyl-L-methionine disulfate tosylate showed decreased malondialdehyde and increased glutathione levels, suggesting that S-Adenosyl-L-methionine disulfate tosylate has antioxidant properties in the PTZ-induced rat model. The antioxidant properties of S-Adenosyl-L-methionine disulfate tosylate may improve cognitive impairment caused by oxidative stressl[4]. S-Adenosyl-L-methionine disulfate tosylate (30 mg/kg) can prevent autism spectrum disorder (ASD)-like behaviors caused by early postnatal valproic acid treatment in rat pups[5].
References:
[1] Loenen, W.A.M.S-Adenosylmethionine: Jack of all trades and master of everything?Biochem. Soc. Trans.34(2)330-333(2006).
[2] Mosca L, Minopoli M, Pagano M, Vitiello F, Carriero MV, Cacciapuoti G, Porcelli M. Effects of S-adenosyl-L-methionine on the invasion and migration of head and neck squamous cancer cells and analysis of the underlying mechanisms. Int J Oncol. 2020 May;56(5):1212-1224.
[3] Ham MS, et al. S-adenosyl methionine specifically protects the anticancer effect of 5-FU via DNMTs expression in human A549 lung cancer cells. Mol Clin Oncol. 2013 Mar;1(2):373-378.
[4] Dhediya RM, Joshi SS, Gajbhiye SV, Jalgaonkar SV, Biswas M. Evaluation of antiepileptic effect of S-adenosyl methionine and its role in memory impairment in pentylenetetrazole-induced kindling model in rats. Epilepsy Behav. 2016 Aug;61:153-157.
[5] Ornoy A, et al. S-adenosyl methionine prevents ASD like behaviors triggered by early postnatal valproic acid exposure in very young mice. Neurotoxicol Teratol. 2019 Jan-Feb;71:64-74.
S-Adenosyl-L-methionine disulfate tosylate是一种甲基供体和辅因子,它参与多种生物过程,包括表观遗传调控、蛋白质的翻译后修饰和代谢。含有S-Adenosyl-L-methionine disulfate tosylate的制剂已被用作膳食补充剂。S-Adenosyl-L-methionine disulfate tosylate还在人类癌症中表现出抗增殖、促凋亡和抗转移作用[1-2]。
S-Adenosyl-L-methionine disulfate tosylate(300μM)能够调节 Cal-33和JHU-SCC-011细胞周期进程,降低细胞周期蛋白B1、E1和D1的表达。S-Adenosyl-L-methionine disulfate tosylate(200 μM和300 μM)能够分别在24小时和48小时后以剂量依赖性方式抑制Cal-33和JHU-SCC-011细胞迁移[2]。5-40 μg/ ml的S-Adenosyl-L-methionine disulfate tosylate与5-氟尿嘧啶(5-FU)联合使用,可通过调节DNA甲基转移酶(DNMTs)的表达保护5-FU的抗癌作用[3]。
在高架十字迷宫测试中,给予S-Adenosyl-L-methionine disulfate tosylate(100 mg/kg)的大鼠在第26天时表现出最大程度的转移潜伏期缩短,证实了S-Adenosyl-L-methionine disulfate tosylate的记忆改善作用。使用100 mg/kg S-Adenosyl-L-methionine disulfate tosylate处理的动物表现出丙二醛减少和谷胱甘肽水平升高,这表明在PTZ诱导的大鼠模型中S-Adenosyl-L-methionine disulfate tosylate具有抗氧化特性,而S-Adenosyl-L-methionine disulfate tosylate的抗氧化特性可能会改善氧化应激导致的认知障碍[4]。S-Adenosyl-L-methionine disulfate tosylate(30 mg/kg)可预防幼鼠出生后早期丙戊酸处理引起的自闭症谱系障碍(ASD)样行为[5]。
Cell experiment [1]: | |
Cell lines | Cal-33 and JHU-SCC-011 cells |
Preparation Method | Cal-33 and JHU-SCC-011 cells were treated with 300 μM S-Adenosyl-L-methionine disulfate tosylate and the cells were harvested after 24 and 48 hours, respectively, for flow cytometry and western blot analysis. |
Reaction Conditions | 300μM, 24h or 48h |
Applications | S-Adenosyl-L-methionine disulfate tosylate can regulate the cell cycle progression of Cal-33 and JHU-SCC-011 cells and reduce the expression of cyclins B1, E1 and D1. |
Animal experiment [2]: | |
Animal models | Pentylenetetrazole (PTZ)-induced kindling model in rats |
Preparation Method | Out of 48 rats, 24 rats were used for standardization of the pentylenetetrazole (PTZ) kindling model. The remaining 24 rats were divided into 4 groups with 6 rats in each group as follows: 1. disease control: 0.9% normal saline 1 ml intraperitoneally (ip) + PTZ 35 mg/kg ip; 2. positive control: sodium valproate 200 mg/kg ip + PTZ 35 mg/kg ip; 3. S-Adenosyl-L-methionine disulfate tosylate 50 mg/kg oral + PTZ 35 mg/kg ip; 4. S-Adenosyl-L-methionine disulfate tosylate 100 mg/kg oral+ PTZ 35 mg/kg ip. |
Dosage form | 50 and 100 mg/kg, oral |
Applications | A higher dose of S-Adenosyl-L-methionine disulfate tosylate (100 mg/kg) exhibited an increase in seizure latency and a decrease in seizure severity score. |
References: [1] Mosca L, Minopoli M, Pagano M, Vitiello F, Carriero MV, Cacciapuoti G, Porcelli M. Effects of S-adenosyl-L-methionine on the invasion and migration of head and neck squamous cancer cells and analysis of the underlying mechanisms. Int J Oncol. 2020 May;56(5):1212-1224. [2] Dhediya RM, Joshi SS, Gajbhiye SV, Jalgaonkar SV, Biswas M. Evaluation of antiepileptic effect of S-adenosyl methionine and its role in memory impairment in pentylenetetrazole-induced kindling model in rats. Epilepsy Behav. 2016 Aug;61:153-157. |
Cas No. | 97540-22-2 | SDF | |
别名 | S-腺苷-L-甲硫氨酸; Ademetionine disulfate tosylate; S-Adenosyl methionine disulfate tosylate; AdoMet disulfate tosylate | ||
Canonical SMILES | N[C@@H](CC[S+](C[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C2N=CN=C3N)O1)O)O)C)C(O)=O.O=S(O)([O-])=O.O=S(O)(O)=O.OS(=O)(C4=CC=C(C)C=C4)=O | ||
分子式 | C22H34N6O16S4 | 分子量 | 766.8 |
溶解度 | DMSO : ≥ 50 mg/mL (65.21 mM);Water : 33.33 mg/mL (43.47 mM) | 储存条件 | Store at -20°C,protect from light, stored under nitrogen |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.3041 mL | 6.5206 mL | 13.0412 mL |
5 mM | 0.2608 mL | 1.3041 mL | 2.6082 mL |
10 mM | 0.1304 mL | 0.6521 mL | 1.3041 mL |
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