6-Formylpterin
(Synonyms: 2-氨基-4-氧代-3,4-二氢蝶啶-6-甲醛) 目录号 : GC42578
An intracellular generator of hydrogen peroxide
Cas No.:712-30-1
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 oxidase (XO) generates reactive oxygen species, including hydrogen peroxide (H2O2), as it oxidizes specific substrates in the presence of water and oxygen. 6-Formylpterin is an oxidized pterin produced by photolytic breakdown of folic acid. It binds to one of two active sites on XO nearly quantitatively and irreversibly and prevents the metabolism of other substrates at the second site, resulting in "hetero-substrate" inhibition at nanomolar concentrations. However, 6-formylpterin itself is converted by XO to 6-carboxylpterin and H2O2 and the turnover rate of this reaction can actually be accelerated by prior binding of a hetero-substrate to XO. In this way, 6-formylpterin acts as an intracellular generator of H2O2 in cells expressing XO, altering cellular function.
| Cas No. | 712-30-1 | SDF | |
| 别名 | 2-氨基-4-氧代-3,4-二氢蝶啶-6-甲醛 | ||
| Canonical SMILES | O=C1C2=C(N=CC(C=O)=N2)N=C(N)N1 | ||
| 分子式 | C7H5N5O2 | 分子量 | 191.1 |
| 溶解度 | Soluble in DMSO | 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 | 5.2329 mL | 26.1643 mL | 52.3286 mL |
| 5 mM | 1.0466 mL | 5.2329 mL | 10.4657 mL |
| 10 mM | 0.5233 mL | 2.6164 mL | 5.2329 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。
Properties and reactivity of the folic acid and folate photoproduct 6-Formylpterin
Free Radic Biol Med 2021 Aug 1;171:1-10.PMID:33965562DOI:10.1016/j.freeradbiomed.2021.05.002.
Folates (vitamin B9) are essential components of our diet and our gut microbiota. They are omnipresent in our cells and blood. Folates are necessary for DNA synthesis, methylation, and other vital bioprocesses. Folic acid (FA), as the synthetic form of folates, is largely found in supplements and fortified foods. FA and folate drugs are also extensively used as therapeutics. Therefore, we are continuously exposed to the pterin derivatives, and their photo-degradation products, such as 6-Formylpterin (6-FPT) and pterin-6-carboxylic acid. During ultraviolet radiation, these two photolytic products generate reactive oxygen species (ROS) responsible for the cellular oxidative stress. 6-FPT can exhibit variable pro/anti-oxidative roles depending on the cell type and its environment (acting as a cell protector in normal cells, or as an enhancer of drug-induced cell death in cancer cells). The ROS-modulating capacity of 6-FPT is well-known, whereas its intrinsic reactivity has been much less investigated. Here, we have reviewed the properties of 6-FPT and highlighted its capacity to form covalent adducts with the ROS-scavenging drug edaravone (used to treat stroke and amyotrophic lateral sclerosis) as well as its implication in immune surveillance. 6-FPT and its analogue acetyl-6-FPT function as small molecule antigens, recognized by the major histocompatibility complex-related class I-like molecule, MR1, for presentation to mucosal-associated invariant T (MAIT) cells. As modulators of the MR1/MAIT machinery, 6-FPT derivatives could play a significant immuno-regulatory role in different diseases. This brief review shed light on the multiple properties and cellular activities of 6-FPT, well beyond its primary ROS-generating activity.
6-Formylpterin, a xanthine oxidase inhibitor, intracellularly generates reactive oxygen species involved in apoptosis and cell proliferation
Free Radic Biol Med 2001 Feb 1;30(3):248-59.PMID:11165871DOI:10.1016/s0891-5849(00)00465-2.
The chemical property of 6-Formylpterin and its biological functions were examined. Polarographic studies revealed that 6-Formylpterin reacted with NAD(P)H and consumed oxygen. In contrast, other conjugated pterins, such as biopterin and neopterin, showed no consumption of oxygen. The production analysis using high-performance liquid chromatography documented that 6-Formylpterin catalyzes the conversion from NADH to NAD. Electroparamagnetic resonance spin trapping experiments demonstrated that this reaction is accompanied with the generation of reactive oxygen species (ROS), superoxide anion and hydrogen peroxide. When 6-Formylpterin was administered to HL-60 cells, intracellular ROS generation was observed and apoptosis was induced. In contrast, other conjugated pterins induced neither intracellular ROS generation nor apoptosis in HL-60 cells. The intracellular ROS generation by 6-Formylpterin was observed in other cells, such as PanC-1 cells and Jurkat cells. 6-Formylpterin suppressed cell proliferation in PanC-1 cells and inhibited Fas-mediated apoptosis in Jurkat cells. These findings indicate that, among conjugated pterins, 6-Formylpterin has the unique property to transfer electron from NAD(P)H to oxygen and that the property brings about intracellular ROS generation, which exerts various biological functions such as induction of apoptosis, suppression of cell proliferation, and inhibition of Fas-mediated apoptosis.
Fluorescence of pterin, 6-Formylpterin, 6-carboxypterin and folic acid in aqueous solution: pH effects
Photochem Photobiol Sci 2002 Jun;1(6):421-6.PMID:12856711DOI:10.1039/b202114e.
Steady-state and time-resolved studies have been performed on four compounds of the pterin family (pterin, 6-carboxypterin, 6-Formylpterin and folic acid) in aqueous solution, using the single photon counting technique. The fluorescence characteristics (spectra, quantum yields, lifetimes) of these compounds and their dependence on the pH have been investigated. Most pterins can exist in two acid-base forms over the pH range between 3 and 13. Emission spectra and excitation spectra were obtained for both forms of each compound studied. Fluorescence quantum yields (phi(F)) in acidic and basic media were measured. The phi(F) of folic acid (< 0.005 in both media) is very low compared to those of pterin (0.27 in basic media and 0.33 in acidic media), 6-carboxypterin (0.18 in basic media and 0.28 in acidic media) and 6-Formylpterin (0.07 in basic media and 0.12 in acidic media). The variation in integrated fluorescence intensity and fluorescence lifetimes (tau(F)) was analysed as a function of pH. Dynamic quenching by OH- was observed and the corresponding bimolecular rate constants for quenching of fluorescence (k(q)) were calculated. The reported values for k(q) (M(-1) s(-1)) are 3.6 x 10(9), 1.9 x 10(9) and 1.1 x 10(10) M(-1) s(-1) for pterin, 6-carboxypterin and 6-Formylpterin, respectively.
Novel 6-Formylpterin derivatives: chemical synthesis and O2 to ROS conversion activities
Org Biomol Chem 2006 May 7;4(9):1811-6.PMID:16633574DOI:10.1039/b602778d.
6-Formylpterin (6FP) has been demonstrated to have strong neuroprotective effects against transient ischemia-reperfusion injury in gerbils. Also it has been shown that in rats, 6FP protected retinal neurons even when it was administered after the ischemic insult. Since there is a significant need for such a compound that effectively suppresses the events caused by the lack of oxygen supply, 6FP has attracted further investigation. Unfortunately, however, 6FP is hardly soluble in water at neutral pH and in organic solvents because of its self-assembling ability. Although a several mM solution of 6FP is available in alkaline water, it is unstable. In the present study, a novel chemical derivatization of 6FP has been developed which maintains the formyl group on the 6-position of 6FP, which is essential for the physiological activities of 6FP, and increases solubility in water and organic solvents. In the method, the 2- and 3-positions of 6FP were modified by a three component coupling reaction: 6FP was subjected to the reaction with acid chloride and N,N-dimethylformamide. The derivatives synthesized here, 2-(N,N-dimethylaminomethyleneamino)-6-formyl-3-pivaloylpteridine-4-one 1, 2-(N,N-dimethylaminomethyleneamino)-6-formyl-3-isobutyrylpteridine-4-one 2, and 2-(N,N-dimethylaminomethyleneamino)-6-formyl-3-o-toluoylpteridine-4-one 3, showed high solubility in water (1.0-5.6 mM) and organic solvents. The O(2) conversion property has also been determined for the derivative 1. Using an oxygen electrode, it has been found that O(2) is consumed in the presence of 1 and NADH at around pH 7.4 and that the rate of O(2) consumption is enhanced by UV-A irradiation. Electron paramagnetic resonance (EPR) analysis coupled with DMPO spin trapping has also revealed that in the presence of NADH, 1 converts O(2) to O(2)(-), which is further reduced to OH. By UV-A illumination in the analogous systems, (1)O(2) formation was observed. These results are similar to those reported previously for 6FP.
Effects of 6-Formylpterin, a xanthine oxidase inhibitor and a superoxide scavenger, on production of nitric oxide in RAW 264.7 macrophages
Biochim Biophys Acta 2000 Mar 6;1474(1):93-9.PMID:10699495DOI:10.1016/s0304-4165(99)00210-x.
As well as superoxide generated from neutrophils, nitric oxide (NO) produced by inducible nitric oxide synthase (iNOS) in macrophages plays an important role in inflammation. We previously showed that 6-Formylpterin, a xanthine oxidase inhibitor, has a superoxide scavenging activity. In the present study, to elucidate other pharmacological activities of 6-Formylpterin, we investigated the effects of 6-Formylpterin on production of nitric oxide (NO) in the murine macrophage cell line RAW 264.7 stimulated by lipopolysaccharide (LPS) and interferon-gamma (INF-gamma). 6-Formylpterin suppressed the expression of iNOS, and it also inhibited the catalytic activity of iNOS, which collectively resulted in the inhibition of NO production in the stimulated macrophages. However, 6-Formylpterin did not scavenge the released NO from an NO donor, S-nitroso-N-acetylpenicillamine (SNAP). These results indicate that 6-Formylpterin inhibits pathological NO generation from macrophages during inflammation, but that it does not disturb the physiological action of NO released from other sources.