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Xanthopterin Sale

(Synonyms: 黄蝶呤) 目录号 : GC37940

Xanthopterin,一种非共轭的蝶啶化合物,是东方大黄蜂翅膀中黄色颗粒的主要成分,在 386/456 nm 处产生特征性的激发光最大值。 Xanthopterin (XPT) 引起大鼠肾脏生长和肥大。Xanthopterin抑制 RNA 合成。

Xanthopterin Chemical Structure

Cas No.:119-44-8

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产品描述

Xanthopterin, an unconjugated pteridine compound, is the main component of the yellow granule in the Oriental hornet bear wings, produces a characteristic excitation/emission maximum at 386/456 nm[2]. Xanthopterin (XPT) causes renal growth and hypertrophy in rat[1].Xanthopterin inhibits RNA synthesis[4].

Xanthopterin (7.8-250 mM; 24 hours) show a significant reduction in mitochondrial activity with respect to controls (IC50=109 mM)[2]. Cell Viability Assay[2] Cell Line: MCF-7 cells

[1]. Xanthopterin (XPT), an unconjugated pteridine compound, affects cell growth and differentiation. When injected into rats, XPT has caused changes that have been interpreted as renal growth and hypertrophy. [2]. Lord JL, et al. Cytotoxicity of xanthopterin and isoxanthopterin in MCF-7 cells. Cancer Lett. 2005 May 10;222(1):119-24. [3]. Plotkin M, et al. Xanthopterin in the Oriental hornet (Vespa orientalis): light absorbance is increased with maturation of yellow pigment granules. Photochem Photobiol. 2009 Jul-Aug;85(4):955-61. [4]. Ziegler I, et al. Pterins and the regulation of lymphocyte activation on the mode of xanthopterin action. Hoppe Seylers Z Physiol Chem. 1984 Jun;365(6):667-73.

Chemical Properties

Cas No. 119-44-8 SDF
别名 黄蝶呤
Canonical SMILES O=C1NC2=C(N=C1)NC(N)=NC2=O
分子式 C6H5N5O2 分子量 179.14
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Research Update

A study of Xanthopterin in chronic renal failure

Am J Nephrol 1992;12(4):224-8.PMID:1481869DOI:10.1159/000168450.

Xanthopterin, a metabolic end product of the nonconjugated pterins dihydrobiopterin and tetrahydrobiopterin, is present in many organs and is known to inhibit the proliferation and growth of conconavalin-stimulated lymphocytes. We have developed a simple fluorometric method to measure Xanthopterin in the blood and have validated the method by high pressure liquid chromatography (HPLC). Serum levels were 14 +/- 7 nmol/l in normal subjects and 141 +/- 51 nmol/l in hemodialysis patients (p < 0.02). Intermediate levels from patients with renal insufficiency not on dialysis correlated with serum creatinine levels (p < 0.001). Xanthopterin (MW 179) was cleared by hemodialysis at a slightly lower rate than creatinine. It is bound to protein, but the binding, 90 +/- 5% in normal subjects, is decreased in uremia to 60 +/- 15%, p < 0.01. Red cell levels of Xanthopterin were five times higher than those of plasma in normal subjects (69 +/- 15 vs. 14 +/- 7 nmol/l, p < 0.001), but uremic patients had lower levels in red cells than in plasma (101 +/- 24 vs. 141 +/- 51 nmol/l, p < 0.05). Slight or moderate hemolysis induced by mechanical stress increased plasma Xanthopterin levels by 35%, the effect being more pronounced when hemolysis was severe. We conclude that Xanthopterin is increased and its binding to protein is decreased in chronic renal failure. The altered ratio of red cell/plasma Xanthopterin levels may reflect an abnormality of the red cell membrane in uremia. We are conducting further studies to amplify our preliminary findings that Xanthopterin inhibits cellular growth in vitro.

Simultaneous determination of Xanthopterin and isoxanthopterin in human urine by synchronous fluorescence spectroscopy

J Fluoresc 2010 Nov;20(6):1191-8.PMID:20419340DOI:10.1007/s10895-010-0667-4.

A simple, rapid, sensitive and selective method for simultaneously determining Xanthopterin and isoxanthopterin content in human urine has been developed using synchronous fluorescence spectroscopy based on their intrinsic fluorescence. The synchronous fluorescence spectra were obtained with Δλ = 65 nm in a pH 8.5 KH(2)PO(4)-NaOH buffer solution. The detected wavelengths of quantitative analysis were set at 410 nm for Xanthopterin and 325 nm for isoxanthopterin, respectively. Pretreatment of urine samples only was filtrated through a 0.45 μm membrane filter, which was free from the tedious separation procedures. Under optimized conditions, the limits of detection (LOD) were 0.94 ng/mL for Xanthopterin and 0.48 ng/mL for isoxanthopterin. The recoveries ranged from 88.0% to 103.8 % for healthy and cancer urine samples, with coefficient of variation between 2.09% and 7.06%. The proposed method has been successfully applied to the simultaneous analysis for Xanthopterin and isoxanthopterin in human urine. The results showed that the average level of isoxanthopterin was significantly elevated in urine excreted by stomach cancer patients (P < 0.01), while no significant change of Xanthopterin level was found between stomach cancer patients and healthy individuals. This potentially indicates that an increase in amounts of isoxanthopterin can be associated with the presence of stomach cancer.

Pterins and the regulation of lymphocyte activation on the mode of Xanthopterin action

Hoppe Seylers Z Physiol Chem 1984 Jun;365(6):667-73.PMID:6207092DOI:10.1515/bchm2.1984.365.1.667.

Some intermediates of pterin anabolism amplify the lectin-induced lymphocyte stimulation while the catabolites Xanthopterin and isoxanthopterin terminate their proliferation (Ziegler, I. et al., Cancer Res. 43, 5356 (1983). In the present investigation, we analysed the effect of Xanthopterin on total RNA synthesis and on DNA synthesis in both concanavalin A-stimulated lymphocytes and in the lymphoblastoid cell line L 1210. The time courses at various inhibitor concentrations indicated that Xanthopterin inhibits RNA synthesis prior to DNA synthesis. Further analysis of the RNA species was performed by double-labeling and subsequent polyacrylamide-gel electrophoresis. Pulse and pulse-chase experiments revealed that an inhibition of 45 S pre-RNA is closer to the target of Xanthopterin inhibition than is DNA synthesis.

Cytotoxicity of Xanthopterin and isoxanthopterin in MCF-7 cells

Cancer Lett 2005 May 10;222(1):119-24.PMID:15837549DOI:10.1016/j.canlet.2004.09.009.

Human mammary carcinoma MCF-7 cell line responsiveness to the pteridines Xanthopterin and isoxanthopterin was studied using the MTS assay for measurement of cell viability. The pteridines were tested at concentrations ranging from 7.8 to 500 microM singly and in 11 isoxanthopterin:Xanthopterin ratios. IC50s of Xanthopterin and isoxanthopterin were 109+/-13 microM (mean+/-SEM of y estimate) and 103+/-9 microM, respectively. The IC50 values for pteridine mixtures were similar although 3:1 and 4:1 isoxanthopterin:Xanthopterin ratios seemed slightly more cytotoxic than other mixtures. However, ANOVA revealed no statistical differences in the cytotoxicity of mixtures.

Xanthopterin in the Oriental hornet (Vespa orientalis): light absorbance is increased with maturation of yellow pigment granules

Photochem Photobiol 2009 Jul-Aug;85(4):955-61.PMID:19222794DOI:10.1111/j.1751-1097.2008.00526.x.

The Oriental hornet bears both brown and yellow colors on its cuticle. The brown component is contributed by the pigment melanin, which is dispersed in the brown cuticle and provides protection against insolation, while the yellow-colored part contains within pockets in the cuticle granules possessing a yellow pigment. These yellow granules (YG) are formed about 2 days prior to eclosion of the imago, and their production continues for about 3 days posteclosion. Xanthopterin is the main component of the granule and lends it its yellow color. Xanthopterin produces a characteristic excitation/emission maximum at 386/456 nm. Characterization by use of mass spectrometry showed the compound to have a molecular ion of 179, as expected from Xanthopterin. Spectroscopic examination of the absorption of an entire stripe of yellow cuticle in the course of its metamorphosis revealed that the absorption steadily increases throughout the process to a maximal level of absorption about 3 days posteclosion. In the absence of the YG, the cuticle is permeable to the passage of all wavelengths within the visible range and to the UV range (290-750 nm) in all age groups of hornets. The newly ecloded hornets depart the nest to engage in activities requiring exposure to insolation only as the process of granule formation terminates, namely, when the layer of YG in the cuticle suffices to absorb all the harmful UV radiation.