N-Phenylthiourea
(Synonyms: 苯基硫脲) 目录号 : GC47805
A tyrosinase inhibitor and building block
Cas No.:103-85-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
N-Phenylthiourea is a tyrosinase inhibitor (Ki = 0.21 μM in an enzyme assay using L-DOPA as a substrate) and building block.1,2 It increases the susceptibility of SK-MEL-188 melanoma cells in melanogenesis-inducing conditions to γ-radiation-induced cytotoxicity when used at a concentration of 0.01 μM.3 N-Phenylthiourea has been used as a precursor in the synthesis of compounds with antibacterial and antifungal activities.2 It has also been used as a genetic marker for taste because only some people detect it as a bitter taste.4
1.Ryanzanova, A.D., Alekseev, A.A., and Slepneva, I.A.The phenylthiourea is a competitive inhibitor of the enzymatic oxidation of DOPA by phenoloxidaseJ. Enzyme Inhib. Med. Chem.27(1)78-83(2012) 2.Soni, B., Bhandari, A.A., Ranawat, M.S., et al.Synthesis and antimicrobial activity of 2-substituted benzothiazole containing azomethine linkagePharmacophore2(1)24-33(2011) 3.Bro?yna, A.A., VanMiddlesworth, L., and Slominski, A.T.Inhibition of melanogenesis as a radiation sensitizer for melanoma therapyInt. J. Cancer123(6)1448-1456(2008) 4.Drewnowski, A., and Rock, C.L.The influence of genetic taste markers on food acceptanceAm. J. Clin. Nutr.62(3)506-511(1995)
| Cas No. | 103-85-5 | SDF | |
| 别名 | 苯基硫脲 | ||
| Canonical SMILES | NC(NC1=CC=CC=C1)=S | ||
| 分子式 | C7H8N2S | 分子量 | 152.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml | 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 | 6.5703 mL | 32.8515 mL | 65.703 mL |
| 5 mM | 1.3141 mL | 6.5703 mL | 13.1406 mL |
| 10 mM | 0.657 mL | 3.2852 mL | 6.5703 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。
Experimental and theoretical study of corrosion inhibition performance of N-Phenylthiourea for mild steel in hydrochloric acid and sodium chloride solution
J Mol Model 2019 Jun 27;25(7):204.PMID:31250118DOI:10.1007/s00894-019-4084-6.
The corrosion inhibition performance of N-Phenylthiourea for mild steel in solutions of 1.0 M hydrochloric and 3.5% wt. sodium chloride was investigated using tandem potentiodynamic polarization curves, scanning electron microscope analysis and quantum chemical calculations. The inhibition efficiency values of N-Phenylthiourea in acidic solution and in salt solution were 94.95% and 55.70%, respectively. The results show that the corrosion inhibitor ability of N-Phenylthiourea was better than that of urotropine under the same conditions. The adsorption of N-Phenylthiourea on the mild steel electrode surface obeys the Langmuir adsorption isotherm in acidic solution and modified Langmuir adsorption isotherm in salt solution. The results of quantum chemical calculations and molecular dynamics simulations were found to be in accord with experimental data. Graphical abstract Corrosion inhibition performance of N-Phenylthiourea for mild steel in hydrochloric acid and sodium chloride solution Figure A contains poor quality and small text inside the artwork. Please do not re-use the file that we have rejected or attempt to increase its resolution and re-save. It is originally poor, therefore, increasing the resolution will not solve the quality problem. We suggest that you provide us the original format. We prefer replacement figures containing vector/editable objects rather than embedded images. Preferred file formats are eps, ai, tiff and pdf.Figure A now has been prepared. The font size of text is increased except for the SEM image.
Emergence of hydrogen bonds from molecular dynamics simulation of substituted N-phenylthiourea-catechol oxidase complex
Arch Pharm Res 2017 Jan;40(1):57-68.PMID:27878514DOI:10.1007/s12272-016-0866-x.
A series of N-Phenylthiourea derivatives was built starting from the X-ray structure in the molecular mechanics framework and the interaction profile in the complex with the catechol oxidase was traced using molecular dynamics simulation. The results showed that the geometry and interactions between ligand and receptor were highly related to the position of the substituted side chains of phenyl moiety. At the end of molecular dynamics run, a concentrated multicenter hydrogen bond was created between the substituted ligand and receptor. The conformation of the ligand itself were also restricted in the receptor pocket. Furthermore, the simulation time of 50 ns were found to be long enough to explore the relevant conformational space and the stationary behavior of the molecular dynamic could be observed.
Comparative analysis of goitrogenic effects of phenylthiourea and methimazole in zebrafish embryos
Reprod Toxicol 2015 Nov;57:10-20.PMID:25962731DOI:10.1016/j.reprotox.2015.04.012.
Craniofacial malformations, reduced locomotion and induction of genes encoding for enzymes involved in thyroid hormone synthesis were assessed using methimazole and N-Phenylthiourea in zebrafish embryos. Gene expression, the most sensitive endpoint (EC50_MMI=372-765μM, EC50_PTU=7.6-8.6μM), was analysed in wild-type and in a transgenic strain, tg(tg:mCherry), expressing mCherry fluorescence protein under the control of the thyroglobulin gene. Reduction of locomotion and craniofacial malformations were observed at one or two orders of magnitude above concentrations affecting gene expression, respectively. Both effects could be linked to the malformations caused by reduced thyroxin levels. Our results show that due to the presence of the autoregulatory loop of the hypothalamus-pituitary-thyroid axis, various molecular initiating events of thyroid disruption are amenable for the zebrafish embryo. We propose the tg(tg:mCherry) bioassay as a sensitive tool in medium scale screening of goitrogens, given the minimal effort for sample preparation and analysis of gene expression.
Synthesis and cytostatic properties of daunorubicin derivatives, containing N-Phenylthiourea or N-ethylthiourea moieties in the 3'-position
J Antibiot (Tokyo) 1991 Feb;44(2):192-9.PMID:1901311DOI:10.7164/antibiotics.44.192.
A series of phenylthiourea and ethylthiourea derivatives of daunorubicin and its congeners was prepared by reaction of the 3'-amino group of the antibiotic with phenylisothiocyanate or ethylisothiocyanate. S-Methylation yielded S-methylisothiouromium salts which when reacted with amines resulted in an intramolecular cyclization with the participation of the neighboring 4'-OH group. The structures and predominant conformations of the thiourea derivatives and daunorubicino(3'-N,4'-O-d)oxazolines were determined by 1H and 13C NMR. Cytostatic activities of the thiourea and oxazoline derivatives were compared with the cytostatic activities of N-methylurea and N-methyl-N-nitrosourea containing daunorubicin and its congeners. Carminomycin derivatives were endowed with the highest cytostatic activity.
A unique NH-spacer for N-benzamidothiourea based anion sensors. Substituent effect on anion sensing of the ICT dual fluorescent N-(p-dimethylaminobenzamido)-N'-arylthioureas
Org Biomol Chem 2006 Feb 21;4(4):624-30.PMID:16467936DOI:10.1039/b513969d.
A series of N-(p-dimethylaminobenzamido)-N'-(substituted-phenyl)thioureas (substituent = p-CH3, H, p-Cl, p-Br, m-Br, m-NO2, and p-NO2) were designed as anion sensors in order to better understand the -NH-spacer via a substituent effect investigation. In these molecules the dual fluorescent intramolecular charge transfer (ICT) fluorophore p-dimethylaminobenzamide as the signal reporter was linked to the anion-binding site, the thiourea moiety, via an N-N single bond. Correlation of the NMR signals of the aromatic and -NH protons with substituents in these molecules indicated that the N-N single bond stopped the ground-state electronic communication between the signal reporter and the anion-binding site. Dual fluorescence was observed in highly polar solvents such as acetonitrile with the former five derivatives. The fact that the CT emission wavelength and the CT to LE emission intensity ratio of the sensors were independent of the substituent existing in the anion-binding moiety suggested that the substituent electronic effect could not be communicated to the CT fluorophore in the excited-state either. Yet in acetonitrile both the CT dual fluorescence and the absorption of the sensors were found to be highly sensitive toward anions. A conformation change around the N-N bond in the sensor molecules was suggested to occur upon anion binding that established the electronic communication between the signal reporter and the anion-binding site. The anion binding constants of the N-(p-dimethylaminobenzamido)thiourea sensors were found higher than those of the corresponding traditional N-Phenylthiourea counterparts and the substituent effect on the anion binding constant was much higher than that in the latter. "-NH-" was shown to be a unique spacer that affords N-benzamidothiourea allosteric anion sensors.