Oxythiamine (Hydroxythiamin)
(Synonyms: Hydroxythiamin) 目录号 : GC33316
Oxythiamine (Hydroxythiamin) 是一种抗代谢药和维生素 B1 拮抗剂，是众所周知的硫胺素拮抗剂和转酮酶抑制剂。
Cas No.:136-16-3
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: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cell experiment: | Human pancreatic carcinoma cell line MIA PaCa-2 is used throughout the study. Experiments are set up in two groups: dose and time-dependent groups. For the dose-dependent group, the cells are stimulated with 5, 50 and 500 μM Oxythiamine (OT) for 48 hours, respectively. The unstimulated cells are considered as control. For the time-dependent group, the cells are stimulated with 50 μM Oxythiamine in MEM containing natural amino acids or 50% of 15 N algal amino acid mixture for 12 and 48 h. The unstimulated cells are considered as the zero time point. Each treatment is repeated four times with 10 mL/flask. The cell pellets are then collected for further analysis[2]. |
References: [1]. Moradi H, et al. Functional thiamine deficiency in end-stage renal disease: malnutrition despite ample nutrients. Kidney Int. 2016 Aug;90(2):252-254. | |
Oxythiamine, an antimetabolite and a vitamin B1 antagonist, is a well-known thiamine antagonist and inhibitor of transketolase.
Oxythiamine, an antimetabolite and a vitamin B1 antagonist, is a well-known thiamine antagonist and inhibitor of transketolase. Oxythiamine alters protein expression in a dose dependent manner. The level of alpha-enolase is increased by Oxythiamine treatment, while expression of 14-3-3 protein beta/alpha is suppressed by Oxythiamine at a stratified dose. Oxythiamine causes dynamic changes of total protein expression in time dependent fashion. Oxythiamine suppresses expression of cellular phosphor proteins significantly[2].
[1]. Moradi H, et al. Functional thiamine deficiency in end-stage renal disease: malnutrition despite ample nutrients. Kidney Int. 2016 Aug;90(2):252-254. [2]. Wang J, et al. Inhibition of transketolase by oxythiamine altered dynamics of protein signals in pancreatic cancer cells. Exp Hematol Oncol. 2013 Jul 27;2:18.
| Cas No. | 136-16-3 | SDF | |
| 别名 | Hydroxythiamin | ||
| Canonical SMILES | CC1=C(CCO)SC=[N+]1CC2=CN=C(C)NC2=O | ||
| 分子式 | C12H16N3O2S | 分子量 | 266.34 |
| 溶解度 | DMSO : 51.67 mg/mL (194.00 mM) | 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 | 3.7546 mL | 18.773 mL | 37.546 mL |
| 5 mM | 0.7509 mL | 3.7546 mL | 7.5092 mL |
| 10 mM | 0.3755 mL | 1.8773 mL | 3.7546 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。
Investigating Oxythiamine levels in children undergoing kidney transplantation and the risk of immediate post-operative metabolic and hemodynamic decompensation
Pediatr Nephrol 2021 Apr;36(4):987-993.PMID:33067673DOI:10.1007/s00467-020-04797-9.
Background: Oxythiamine is a uremic toxin that acts as an antimetabolite to thiamine and has been associated with cases of Shoshin beriberi syndrome in adults. We sought to identify whether surgical stress and ischemia/reperfusion injury may precipitate functional thiamine deficiency in children peritransplant. Methods: We retrospectively analyzed a cohort of pediatric kidney transplant recipients. Oxythiamine levels were measured in pre-transplant serum samples by mass spectrometry and tested for association with severity of lactic acidosis in the first 24 h post-transplant. Secondary outcomes included association with hyperglycemia and indicators of dialysis adequacy (DA). Results: Forty-seven patients were included in the analysis. Median Oxythiamine levels differed by modality, measuring 0.67 nM (IQR 0.31, 0.74), 0.34 nM (IQR 0.28, 0.56), and 0.25 nM (IQR 0.17, 0.38) for peritoneal dialysis (PD), hemodialysis (HD), and no dialysis, respectively (p = 0.05). Oxythiamine was associated with 24-h lactate levels (r = 0.38, p = 0.02) and negatively associated with DA (r = - 0.44, p = 0.02). Median Oxythiamine levels were higher in patients with poor DA (0.92 nM (IQR 0.51, 1.01) vs. 0.40 nM (IQR 0.24, 0.51), p < 0.01). Sensitivity analysis showed absence of residual association of Oxythiamine with 24-h lactate or dialysis modality, but remained significant for DA (p = 0.03). One patient manifested Shoshin beriberi syndrome (Oxythiamine 2.03 nM). Conclusions: Oxythiamine levels are associated with DA at transplant. Patients on PD with no residual kidney function and low DA manifest the highest Oxythiamine levels and may be at an increased risk for developing acute Shoshin beriberi syndrome in the early post-transplant period.
The uremic toxin Oxythiamine causes functional thiamine deficiency in end-stage renal disease by inhibiting transketolase activity
Kidney Int 2016 Aug;90(2):396-403.PMID:27198804DOI:10.1016/j.kint.2016.03.010.
Decreased transketolase activity is an unexplained characteristic of patients with end-stage renal disease and is linked to impaired metabolic and immune function. Here we describe the discovery of a link to impaired functional activity of thiamine pyrophosphate cofactor through the presence, accumulation, and pyrophosphorylation of the thiamine antimetabolite Oxythiamine in renal failure. Plasma Oxythiamine was significantly increased by 4-fold in patients receiving continuous ambulatory peritoneal dialysis and 15-fold in patients receiving hemodialysis immediately before the dialysis session (healthy individuals, 0.18 [0.11-0.22] nM); continuous ambulatory peritoneal dialysis patients, 0.64 [0.48-0.94] nM; and hemodialysis patients (2.73 [1.52-5.76] nM). Oxythiamine was converted to the transketolase inhibitor Oxythiamine pyrophosphate. The red blood cell Oxythiamine pyrophosphate concentration was significantly increased by 4-fold in hemodialysis (healthy individuals, 15.9 nM and hemodialysis patients, 66.1 nM). This accounted for the significant concomitant 41% loss of transketolase activity (mU/mg hemoglobin) from 0.410 in healthy individuals to 0.240 in hemodialysis patients. This may be corrected by displacement with excess thiamine pyrophosphate and explain lifting of decreased transketolase activity by high-dose thiamine supplementation in previous studies. Oxythiamine is likely of dietary origin through cooking of acidic thiamine-containing foods. Experimentally, trace levels of Oxythiamine were not formed from thiamine degradation under physiologic conditions but rather under acidic conditions at 100(°)C. Thus, monitoring of the plasma Oxythiamine concentration in renal failure and implementation of high-dose thiamine supplements to counter it may help improve the clinical outcome of patients with renal failure.
Modification of thiamine pyrophosphate dependent enzyme activity by Oxythiamine in Saccharomyces cerevisiae cells
Can J Microbiol 2005 Oct;51(10):833-9.PMID:16333342DOI:10.1139/w05-072.
Oxythiamine is an antivitamin derivative of thiamine that after phosphorylation to Oxythiamine pyro phosphate can bind to the active centres of thiamine-dependent enzymes. In the present study, the effect of Oxythiamine on the viability of Saccharomyces cerevisiae and the activity of thiamine pyrophosphate dependent enzymes in yeast cells has been investigated. We observed a decrease in pyruvate decarboxylase specific activity on both a control and an Oxythiamine medium after the first 6 h of culture. The cytosolic enzymes transketolase and pyruvate decarboxylase decreased their specific activity in the presence of Oxythiamine but only during the beginning of the cultivation. However, after 12 h of cultivation, oxythiamine-treated cells showed higher specific activity of cytosolic enzymes. More over, it was established by SDS-PAGE that the high specific activity of pyruvate decarboxylase was followed by an increase in the amount of the enzyme protein. In contrast, the mitochondrial enzymes, pyruvate dehydrogenase and 2-oxoglutarate dehydrogenase complexes, were inhibited by Oxythiamine during the entire experiment. Our results suggest that the observed strong decrease in growth rate and viability of yeast on medium with Oxythiamine may be due to stronger inhibition of mitochondrial pyruvate dehydrogenase than of cytosolic enzymes.
[Is Oxythiamine an antivitamin?]
Biokhimiia 1995 Oct;60(10):1564-74.PMID:8555356doi
The review deals with biological and medical aspects of Oxythiamine biochemistry with special reference to the facts which contradict the traditional antivitamin conception. Alternatives to the coenzyme mechanism in interpreting the metabolic effects of this vitamin B1 derivative are discussed.
A dose- and time-dependent effect of Oxythiamine on cell growth inhibition in non-small cell lung cancer
Cogn Neurodyn 2022 Jun;16(3):633-641.PMID:35603057DOI:10.1007/s11571-021-09725-7.
The high mortality rate of non-small-cell lung cancer (NSCLC) is mostly due to the high risk of recurrence. A comprehensive understanding of proliferation mechanisms of NSCLC would remarkably contribute to blocking up the invasion and metastasis of tumor cells. In our previous study, the remarkable decreased activity of Thiamine-dependent enzymes (TDEs), involving in intermediary metabolism responsible for energy production of tumor, was found under conditions of thiamine deficiency in vivo. To explore the effect of Oxythiamine (OT), a TDEs antimetabolite, on cell growth, we co-cultured A549 cells with OT in vitro at various doses (0.1, 1, 10 and 100 μM) and time periods (6, 12, 24 and 48 h) and subsequent cell proliferation and apoptosis assays were performed respectively. Our findings demonstrated that A549 cells proliferation was significantly downregulated by OT treatment in a progressively dose as well as time dependent manner. Inhibition of TDEs resulted in antagonism of lung cancer growth by inducing cells to cease the cycle as well as apoptotic cell death. We concluded a critical role of OT, a TDEs antagonistic compound, indicating the potential target of its practical use.