Thiochrome
(Synonyms: 硫色素) 目录号 : GC38950
Thiochrome 是硫胺素的天然氧化产物和代谢产物，一种选择性的 M4 受体的乙酰胆碱 (ACh) 亲和力增强剂。Thiochrome 与 Ach 在 M1 至 M3 受体上具有中性协同作用。
Cas No.:92-35-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Thiochrome, a natural oxidation product and metabolite of thiamine, is a selective M4 muscarinic receptor of acetylcholine (ACh) affinity enhancer. Thiochrome has neutral cooperativity with ACh at M1 to M3 receptors[1][2].
Thiochrome can increase the intensity of the reproduction process of the representatives of one-cell organisms worms, crustaceans, insects and fishes[1].
[1]. Petrov SA, et al. Administration of Thiamine and Thiochrome Enhanced Reproduction of Chlorella, Drosophila melanogaster, and Danio. J Nutr Sci Vitaminol (Tokyo). 2016;62(1):6-11. [2]. Lazareno S, et al. Thiochrome enhances acetylcholine affinity at muscarinic M4 receptors: receptor subtype selectivity via cooperativity rather than affinity. Mol Pharmacol. 2004 Jan;65(1):257-66.
| Cas No. | 92-35-3 | SDF | |
| 别名 | 硫色素 | ||
| Canonical SMILES | OCCC1=C(C)N2CC3=CN=C(C)N=C3N=C2S1 | ||
| 分子式 | C12H14N4OS | 分子量 | 262.33 |
| 溶解度 | DMSO: 25 mg/mL (95.30 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。 |
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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 | 3.812 mL | 19.06 mL | 38.1199 mL |
| 5 mM | 0.7624 mL | 3.812 mL | 7.624 mL |
| 10 mM | 0.3812 mL | 1.906 mL | 3.812 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。
Administration of Thiamine and Thiochrome Enhanced Reproduction of Chlorella, Drosophila melanogaster, and Danio
J Nutr Sci Vitaminol (Tokyo) 2016;62(1):6-11.PMID:27117845DOI:10.3177/jnsv.62.6.
Thiochrome, a natural metabolite of thiamine, has scarcely attracted the attention of researchers, since many of them considered it to be a biologically inactive substance. We examined a possible effect of Thiochrome upon the reproduction of the organisms of Chlorella, Drosophila, and Danio. We added thiamine or Thiochrome to the culture medium or to the aquaria. Our data showed that the number of cells and organisms were increased in the presence of thiamine and Thiochrome. We suggest possible effect(s) of thiamine and Thiochrome on the reproduction of these organisms.
Photolysis of Thiochrome in aqueous solution: A kinetic study
J Photochem Photobiol B 2020 Jan;203:111766.PMID:31927488DOI:10.1016/j.jphotobiol.2019.111766.
The photolysis of Thiochrome (THC), an oxidation product of thiamine (vitamin B1) (THE), used for its fluorimetric assay, has been studied in the pH range 7.0-12.0. THC undergoes photooxidation to oxodihydrothiochrome (ODTHC) which is oxidized to a non-fluorescent compound (OP1) on UV irradiation. The kinetics of the consecutive first-order reactions: THC→k1ODTHC→k2OP1, has been evaluated and the values of first-order rate constants, k1 (0.58-4.20 × 10-5, s-1) and k2 (0.05-2.03 × 10-5, s-1), at pH 7.0-12.0 have been determined. The rates of degradation of THC and ODTHC are enhanced with pH and the second-order rate constants k1' and k2' for the OH- ion-catalyzed reaction are in the range of 0.002-58.3 M-1 s-1. The quantum yields of the photolysis of THC and ODTHC in the pH range 7.0-12.0 have been determined. THC, ODTHC and OP1 have been identified by chromatographic, spectrometric and fluorimetric methods. THC and ODTHC have similar fluorescence characteristics and emit at 450 and 445 nm, respectively. THC, ODTHC and OP1 with distinct absorption maxima (370, 344 and 290 nm, respectively) have been determined by a newly developed and validated multicomponent spectrometric method during the photolysis reactions. The on-line formation of THC by the photooxidation of THE may lead to the degradation of THC and give erroneous results in the fluorimetric assay of THE. A scheme for the photolysis reactions of THC in aqueous solution is presented.
Development of carbon dot-thiochrome-based sensing system for ratiometric fluorescence detection of D-penicillamine
Anal Bioanal Chem 2021 Sep;413(23):5779-5787.PMID:34312692DOI:10.1007/s00216-021-03552-9.
A simple and rapid ratiometric fluorescent sensing system for D-penicillamine (D-PA) determination is developed based on yellow carbon dots (Y-CDs) combined with Thiochrome (oxVB1) for the first time. The oxidization of thiamine (VB1) can be catalyzed by Alkaline-hydrolyzed artemisinin (a-ART) to form oxVB1, which leads to the occurrence of fluorescence emission peak at 466 nm. Furthermore, the oxidation reaction between a-ART and VB1 could be inhibited by D-PA, and accompanied with the decrease of fluorescence at 466 nm. However, the fluorescence peak of Y-CDs as an internal reference at 566 nm was almost unchanged. The ratiometric signal changes contributed to a robust and sensitive D-PA sensing. Under the optimal condition, a good linear response for the D-PA detection was obtained in the ranges of 0.5-50 μM with a detection limit of 0.33 μM. In addition, Y-CDs and thiochrome-based sensing system was applied to D-PA determination in real samples and obtained acceptable results. We developed a new carbon dots/Thiochrome fluorescent nanoprobe for ratiometric fluorescence sensing of D-penicillamine.
Thiochrome enhances acetylcholine affinity at muscarinic M4 receptors: receptor subtype selectivity via cooperativity rather than affinity
Mol Pharmacol 2004 Jan;65(1):257-66.PMID:14722259DOI:10.1124/mol.65.1.257.
Thiochrome (2,7-dimethyl-5H-thiachromine-8-ethanol), an oxidation product and metabolite of thiamine, has little effect on the equilibrium binding of l-[3H]N-methyl scopolamine ([3H]NMS) to the five human muscarinic receptor subtypes (M1-M5) at concentrations up to 0.3 mM. In contrast, it inhibits [3H]NMS dissociation from M1 to M4 receptors at submillimolar concentrations and from M5 receptors at 1 mM. These results suggest that Thiochrome binds allosterically to muscarinic receptors and has approximately neutral cooperativity with [3H]NMS at M1 to M4 and possibly M5 receptors. Thiochrome increases the affinity of acetylcholine (ACh) 3- to 5-fold for inhibiting [3H]NMS binding to M4 receptors but has no effect on ACh affinity at M1 to M3 or M5 receptors. Thiochrome (0.1 mM) also increases the direct binding of [3H]ACh to M4 receptors but decreases it slightly at M2 receptors. In agreement with the binding data, Thiochrome does not affect the potency of ACh for stimulating the binding of guanosine 5'-O-(3-[35S]thiotriphosphate) ([35S]GTPgammaS) to membranes containing M1 to M3 receptors, but it increases ACh potency 3.5-fold at M4 receptors. It also selectively reduces the release of [3H]ACh from potassium-stimulated slices of rat striatum, which contain autoinhibitory presynaptic M4 receptors, but not from hippocampal slices, which contain presynaptic M2 receptors. We conclude that Thiochrome is a selective M4 muscarinic receptor enhancer of ACh affinity and has neutral cooperativity with ACh at M1 to M3 receptors; it therefore demonstrates a powerful new form of selectivity, "absolute subtype selectivity", which is derived from cooperativity rather than from affinity.
How is vitamin B1 oxidized to Thiochrome? Elementary processes revealed by a DFT study
Org Biomol Chem 2021 May 26;19(20):4529-4536.PMID:33929469DOI:10.1039/d1ob00677k.
The oxidation reaction of thiamine (vitamin B1) to Thiochrome was investigated by DFT calculations. Three reaction systems, [A] thiamine + methyl peroxy radical + (H2O)8, [B] thiamine + cyanogen bromide + HO-(H2O)8 and [C] thiamine + mercury(ii) chloride + HO-(H2O)8, were investigated. wB97X-D/6-311+G** for [A] and [B] and wB97X-D/SDD&6-311(+)G** for [C] geometry optimizations were carried out with the solvent effect (water). The effect is of the self-consistent reaction field (SCRF) with the polarizable continuum model (PCM). In [A], the H3C-O2˙ adduct of thiamine undergoes simultaneous cleavage of the C-H and O-O bonds, leading to a very stable 2(3H)-thiazolone intermediate. The same intermediate was obtained after the cleavage of the C-H and O-H bonds of the HO adduct of thiamine in [B] and [C]. After the formation of the key intermediate, the N-protonated Thiochrome was afforded via three steps. In reflection of the water-soluble character of vitamin B1, proton transfers along hydrogen bonds of the water cluster enhance those steps.