Xanthine
(Synonyms: 黄嘌呤) 目录号 : GC33846
A purine base
Cas No.:69-89-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Xanthine is a purine base and intermediate in the biosynthesis of uric acid .1,2 It is formed during mammalian purine catabolism in the liver via oxidation of hypoxanthine by xanthine oxidase (XO), which also oxidizes xanthine to produce uric acid.1,3 Xanthine is also formed from guanine, xanthosine, or hypoxanthine during purine catabolism in plants.4 It has been found in a variety of commercial foodstuffs, including beer yeast, mushrooms, vegetables, fish, and beef.5 Urinary xanthine levels are decreased in patients with primary gout.6 Xanthine has also been used in the synthesis of xanthine derivatives that have anticancer or anti-inflammatory activities in vitro.7
1.Dawson, J., and Walters, M.Uric acid and xanthine oxidase: Future therapeutic targets in the prevention of cardiovascular disease?Br. J. Clin. Pharmac.62(6)633-644(2006) 2.Wu, S., Jia, S., and Dong, X.Study on detection methods for xanthine in food and biological samplesInt. J. Curr. Res. Chem. Pharm. Sci.3(8)(2016) 3.Garcia-Gil, M., Camici, M., Allegrini, S., et al.Emerging role of purine metabolizing enzymes in brain function and tumorsInt. J. Mol. Sci.19(11)3598(2018) 4.Zrenner, R., Stitt, M., Sonnewald, U., et al.Pyrimidine and purine biosynthesis and degradation in plantsAnnu. Rev. Plant Biol.57805-836(2006) 5.Kaneko, K., Aoyagi, Y., Fukuuchi, T., et al.Total purine and purine base content of common foodstuffs for facilitating nutritional therapy for gout and hyperuricemiaBiol. Pharm. Bull.37(5)709-721(2014) 6.Puig, J.G., Mateos, F.A., Jiménez, M.L., et al.Renal excretion of hypoxanthine and xanthine in primary goutAm. J. Med.85(4)533-537(1988) 7.Singh, N., Shreshtha, A.K., Thakur, M.S., et al.Xanthine scaffold: Scope and potential in drug developmentHeliyon4(10)e00829(2018)
| Cas No. | 69-89-6 | SDF | |
| 别名 | 黄嘌呤 | ||
| Canonical SMILES | O=C(N1)NC2=C(N=CN2)C1=O | ||
| 分子式 | C5H4N4O2 | 分子量 | 152.11 |
| 溶解度 | 1M NaOH : 50 mg/mL (328.71 mM);DMSO : 3.33 mg/mL (21.89 mM; ultrasonic and warming and heat to 60°C) | 储存条件 | Store at 2-8°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 | 6.5742 mL | 32.8709 mL | 65.7419 mL |
| 5 mM | 1.3148 mL | 6.5742 mL | 13.1484 mL |
| 10 mM | 0.6574 mL | 3.2871 mL | 6.5742 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。
Super-Robust Xanthine-Sodium Complexes on Au(111)
Angew Chem Int Ed Engl 2022 Apr 11;61(16):e202200064.PMID:35133710DOI:10.1002/anie.202200064.
A widely accepted theory is that life originated from the hydrothermal environment in the primordial ocean. Nevertheless, the low desorption temperature from inorganic substrates and the fragileness of hydrogen-bonded nucleobases do not support the required thermal stability in such an environment. Herein, we report the super-robust complexes of Xanthine, one of the precursors for the primitive nucleic acids, with Na. We demonstrate that the well-defined xanthine-Na complexes can only form when the temperature is ≥430 K, and the complexes keep adsorbed even at ≈720 K, presenting as the most thermally stable organic polymer ever reported on Au(111). This work not only justifies the necessity of high-temperature, Na-rich environment for the prebiotic biosynthesis but also reveals the robustness of the xanthine-Na complexes upon the harsh environment. Moreover, the complexes can induce significant electron transfer with the metal as inert as Au and hence lift the Au atoms up.
Xanthine oxidoreductase activity is correlated with hepatic steatosis
Sci Rep 2022 Jul 19;12(1):12282.PMID:35854080DOI:10.1038/s41598-022-16688-0.
The enzyme Xanthine oxidoreductase (XOR) catalyzes the synthesis of uric acid (UA) from hypoxanthine and Xanthine, which are products of purine metabolism starting from ribose-5-phosphate. Several studies suggested a relationship between hyperuricemia and hepatic steatosis; however, few previous studies have directly examined the relationship between XOR activity and hepatic steatosis. A total of 223 subjects with one or more cardiovascular risk factors were enrolled. The liver-to-spleen (L/S) ratio on computed tomography and the hepatic steatosis index (HSI) were used to assess hepatic steatosis. We used a newly developed highly sensitive assay based on [13C2, 15N2] Xanthine and liquid chromatography/triple quadrupole mass spectrometry to measure plasma XOR activity. Subjects with the L/S ratio of < 1.1 and the HSI of < 36 had increased XOR activity and serum UA levels. Independent of insulin resistance and serum UA levels, multivariate logistic regression analysis revealed that plasma XOR activity was associated with the risk of hepatic steatosis as assessed by the L/S ratio and HSI. According to the findings of this study, plasma XOR activity is associated with hepatic steatosis independent of insulin resistance and serum UA levels.
Xanthine, xanthosine and its nucleotides: solution structures of neutral and ionic forms, and relevance to substrate properties in various enzyme systems and metabolic pathways
Acta Biochim Pol 2004;51(2):493-531.PMID:15218545doi
The 6-oxopurine Xanthine (Xan, neutral form 2,6-diketopurine) differs from the corresponding 6-oxopurines guanine (Gua) and hypoxanthine (Hyp) in that, at physiological pH, it consists of a approximately 1:1 equilibrium mixture of the neutral and monoanionic forms, the latter due to ionization of N(3)-H, in striking contrast to dissociation of the N(1)-H in both Gua and Hyp at higher pH. In xanthosine (Xao) and its nucleotides the Xanthine ring is predominantly, or exclusively, a similar monoanion at physiological pH. The foregoing has, somewhat surprisingly, been widely overlooked in studies on the properties of these compounds in various enzyme systems and metabolic pathways, including, amongst others, Xanthine oxidase, purine phosphoribosyltransferases, IMP dehydrogenases, purine nucleoside phosphorylases, nucleoside hydrolases, the enzymes involved in the biosynthesis of caffeine, the development of Xanthine nucleotide-directed G proteins, the pharmacological properties of alkylxanthines. We here review the acid/base properties of Xanthine, its nucleosides and nucleotides, their N-alkyl derivatives and other analogues, and their relevance to studies on the foregoing. Included also is a survey of the pH-dependent helical forms of polyxanthylic acid, poly(X), its ability to form helical complexes with a broad range of other synthetic homopolynucleotides, the base pairing properties of Xanthine in synthetic oligonucleotides, and in damaged DNA, as well as enzymes involved in circumventing the existence of Xanthine in natural DNA.
Biosensing methods for Xanthine determination: a review
Enzyme Microb Technol 2014 Apr 10;57:55-62.PMID:24629268DOI:10.1016/j.enzmictec.2013.12.006.
Xanthine (3,7-dihydro-purine-2,6-dione) is generated from guanine by guanine deaminase and hypoxanthine by Xanthine oxidase (XOD). The determination of Xanthine in meat indicates its freshness, while its level in serum/urine provides valuable information about diagnosis and medical management of certain metabolic disorders such as xanthinuria, hyperurecemia, gout and renal failure. Although chromatographic methods such a HPLC, capillary electrophoresis and mass spectrometry are available for quantification of Xanthine in biological materials, these suffer from certain limitations such as complexity, time consuming sample preparation and requirement of expensive apparatus and trained persons to operate. Immobilized XOD based biosensors have emerged as simple, rapid, sensitive and economic tools for determination of Xanthine in food industries and clinical diagnosis. This review article describes the various immobilization methods of XOD and different matrices used for construction of Xanthine biosensors, their classification, analytical performance and applications along with their merits and demerits. The future perspectives for improvement of present Xanthine biosensors are also discussed.
Xanthine interference with dipyridamole-thallium-201 myocardial imaging
Ann Pharmacother 1995 Apr;29(4):425-7.PMID:7633022DOI:10.1177/106002809502900414.
Both theophylline and caffeine have been shown to antagonize adenosine and are associated with false-negative test results with dipyridamole-T1-201 imaging. This has led to recommendations for theophylline and caffeine abstinence for at least 24 hours prior to dipyridamole-T1-201 imaging. Because pentoxifylline and its metabolites are structurally similar to theophylline and caffeine, and pentoxifylline has adenosine antagonistic properties, one might presume that pentoxifylline may also attenuate the diagnostic yield of dipyridamole-T1-201 imaging. To the best of our knowledge, the pharmacodynamic interaction between pentoxifylline and dipyridamole and its effects on dipyridamole-T1-201 imaging in patients have never been studied adequately. However, a single study in 7 dogs does suggest that there may be no significant interaction. In addition, we must also consider the nonacute nature of the clinical use of pentoxifylline in peripheral vascular disease and the critical need for accurate dipyridamole-T1-201 imaging results and the cost associated with this procedure. Until such information is available in humans, it would be prudent to discontinue pentoxifylline, in addition to caffeinated foods, caffeine-containing drug products, and theophylline, at least 24 hours prior to dipyridamole-T1-201 imaging.