FAPy-adenine
(Synonyms: 4,6-二氨基-5-甲酰胺基嘧啶) 目录号 : GC60160
FAPy-adenine 是一种氧化的 DNA 碱基。FAPy-adenine 在阿尔茨海默病脑中呈上升趋势。氧化核苷是肿瘤、衰老和神经退行性疾病的生化标志物。
Cas No.:5122-36-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
FAPy-adenine is an oxidized DNA base. Fapy-adenine shows an increased trend levels in the Alzheimer's disease brain. Oxidized nucleosides are biochemical markers for tumors, aging, and neurodegenerative diseases[1][2][3].
In the absence of the external field the FAPy-adenine is able to form pairs with all four canonical nucleic acid bases. In contrast, in the presence of the external field the mispairing abilities of FAPy-adenine become insignificant since the most stable dimers are formed with thymine[1].
The nuclear DNA damage by oxygen-derived radicals is increased in Alzheimer's disease and support the concept that the brain is under increased oxidative stress in Alzheimer's disease[1].
[1]. Gabbita SP, et al. Increased nuclear DNA oxidation in the brain in Alzheimer's disease. [2]. Cysewski P, et al. Theoretical description of the coding potential of diamino-5-formamidopyrimidines. Z Naturforsch C J Biosci. 1999 Mar-Apr;54(3-4):239-45. [3]. Lee SH, et al. A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7.
| Cas No. | 5122-36-1 | SDF | |
| 别名 | 4,6-二氨基-5-甲酰胺基嘧啶 | ||
| Canonical SMILES | O=CNC1=C(N)N=CN=C1N | ||
| 分子式 | C5H7N5O | 分子量 | 153.14 |
| 溶解度 | 储存条件 | ||
| 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 | 6.53 mL | 32.6499 mL | 65.2997 mL |
| 5 mM | 1.306 mL | 6.53 mL | 13.0599 mL |
| 10 mM | 0.653 mL | 3.265 mL | 6.53 mL |
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| 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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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。
SOS-dependent A-->G transitions induced by hydroxyl radical generating system hypoxanthine/xanthine oxidase/Fe3+/EDTA are accompanied by the increase of FAPy-adenine content in M13 mp18 phage DNA
Mutat Res 1999 May 14;434(1):41-52.PMID:10377947DOI:10.1016/s0921-8777(99)00012-9.
Gas chromatography/isotope dilution-mass spectrometry with selected ion monitoring (GC/IDMS-SIM) was used to measure oxidised bases in hypoxanthine/xanthine oxidase/Fe3+/EDTA modified ss M13 mp18 phage DNA. A dose-dependent increase of oxidised bases content in DNA was observed with the biggest augmentation of FapyGua, thymine glycol and FapyAde. The amount of 8-OH-Gua was relatively high both in non-oxidised and oxidised DNA, and increased to the same extent as FapyAde and ThyGly. DNA oxidation caused a dramatic decrease in phage survival after transfection to E. coli. Survival was improved 2.8-fold after induction of the SOS system by UV irradiation of bacteria and mutation frequency of the lacZ gene in SOS conditions increased 7-fold over that in non-irradiated bacteria. Spectrum of mutations was different from those reported previously and mutations were distributed rather randomly within M13 lacZ sequence, which was in contrast to previous findings, where with non-chelated metal ions other types of mutations were found in several clusters. Thus, conditions of DNA oxidation and accessibility of metal ions for DNA bases might be important factors for generating different DNA damages and mutations. Major base substitutions found both in SOS-induced and non-induced E. coli but with higher mutation frequency in SOS-induced cells were C-->A (approximately 20-fold increase in SOS-conditions), G-->A (9-fold increase) and G-->C (4.5-fold increase). Very few G-->T transitions were found. A particularly large group of A-->G transitions appeared only in SOS-induced bacteria and was accompanied by augmentation of FapyAde content in the phage DNA with undetectable 2-OH-Ade. It is then possible that imidazole ring-opened adenine mimics guanine during DNA replication and pairs with cytosine yielding A-->G transitions in SOS-induced bacteria.
Theoretical description of the coding potential of diamino-5-formamidopyrimidines
Z Naturforsch C J Biosci 1999 Mar-Apr;54(3-4):239-45.PMID:10349742DOI:10.1515/znc-1999-3-414.
The results of geometry optimisation of possible Watson-Crick-like pairs of 2,6-diamino-4-oxy-5-formamidopyrimidine (FAPy-adenine) or 4,6-diamino-5-formamidopyrimidine (fapy-guanine) were presented. In the absence of the external field the FAPy-adenine is able to form pairs with all four canonical nucleic acid bases. However, pairs with guanine, cytosine and thymine the most stable are. Thus, the potential miscoding abilities may be observed. In contrast, in the presence of the external field the mispairing abilities of FAPy-adenine become insignificant since the most stable dimers are formed with thymine. The pairing properties of fapy-guanine are complex and depend on its tatomeric form. In the absence of an external field the 4-enol-6-keto-diamino tautomer of fapyG is able to form stable dimers with thymine and cytosine, while the 4,6-diketo-diamino tautomer forms the most stable pairs with cytosine and guanine. The presence of the water solvent does not significantly alter the pairing abilities of fapy-guanine. However, pairs with thymine are at least as stable as the Watson-Crick GC pair. Thus, in polar conditions the mispairing potential of fapyG will be extended and may be enriched by potential GC-->AT transition.
Urinary Metabolomic Study in a Healthy Children Population and Metabolic Biomarker Discovery of Attention-Deficit/Hyperactivity Disorder (ADHD)
Front Psychiatry 2022 May 20;13:819498.PMID:35669266DOI:10.3389/fpsyt.2022.819498.
Objectives: Knowledge of the urinary metabolomic profiles of healthy children and adolescents plays a promising role in the field of pediatrics. Metabolomics has also been used to diagnose disease, discover novel biomarkers, and elucidate pathophysiological pathways. Attention-deficit/hyperactivity disorder (ADHD) is one of the most common psychiatric disorders in childhood. However, large-sample urinary metabolomic studies in children with ADHD are relatively rare. In this study, we aimed to identify specific biomarkers for ADHD diagnosis in children and adolescents by urinary metabolomic profiling. Methods: We explored the urine metabolome in 363 healthy children aged 1-18 years and 76 patients with ADHD using high-resolution mass spectrometry. Results: Metabolic pathways, such as arachidonic acid metabolism, steroid hormone biosynthesis, and catecholamine biosynthesis, were found to be related to sex and age in healthy children. The urinary metabolites displaying the largest differences between patients with ADHD and healthy controls belonged to the tyrosine, leucine, and fatty acid metabolic pathways. A metabolite panel consisting of FAPy-adenine, 3-methylazelaic acid, and phenylacetylglutamine was discovered to have good predictive ability for ADHD, with a receiver operating characteristic area under the curve (ROC-AUC) of 0.918. A panel of FAPy-adenine, N-acetylaspartylglutamic acid, dopamine 4-sulfate, aminocaproic acid, and asparaginyl-leucine was used to establish a robust model for ADHD comorbid tic disorders and controls with an AUC of 0.918.
Flavonoid effects on DNA oxidation at low concentrations relevant to physiological levels
Food Chem Toxicol 2008 Jan;46(1):96-104.PMID:17707569DOI:10.1016/j.fct.2007.07.002.
Flavonoids, which are abundant in fruits and vegetables, are known to have many beneficial health effects. Antioxidant activity is likely to be a main function but has been mostly studied at high flavonoid concentrations which are not feasible at the intracellular level. In this experiment, several flavonoids (e.g., catechin, quercetin, myricetin, luteolin, morin and cyanidin) were examined at low physiologically relevant concentrations. Calf thymus DNA was treated with different flavonoids at concentrations of 0.1, 1, 10 and 100 microM using Fenton conditions to induce oxidation and several oxidative adducts including 8-hydroxy guanine (7,8-dihydro-8-oxo-2'-deoxyguanosine; 8-OH guanine) were analyzed using gas chromatography-mass spectrometry-selective ion monitoring (GC-MS-SIM). Catechin, quercetin and cyanidin inhibited 8-OH guanine formation by 92%, 33% and 45%, respectively, at low concentrations (0.1 microM). In addition catechin and quercetin showed antioxidant activities on 8-OH guanine formation over all concentrations. When the oxidative DNA adduct 4,6-diamino-5-formamidopyrimidine (FAPy-adenine) was measured, however, the highest concentrations of catechin and quercetin actually increased adduct formation. These results indicate that flavonoids can act as antioxidants at low concentrations relevant to physiological levels. However measuring only one oxidative DNA adduct as a biomarker may result in misleading conclusions regarding antioxidant activities of natural products.
Increased nuclear DNA oxidation in the brain in Alzheimer's disease
J Neurochem 1998 Nov;71(5):2034-40.PMID:9798928DOI:10.1046/j.1471-4159.1998.71052034.x.
Multiple lines of evidence indicate that oxidative stress is a contributor to neuronal death in Alzheimer's disease (AD). The oxidative damage that occurs to DNA may play a role in both normal aging and neurodegenerative diseases, including AD. This is a study of the oxidative damage that occurs in nuclear DNA in the brains of AD patients and cognitively intact, prospectively evaluated, age-matched control subjects. Nuclear DNA from frontal, temporal, and parietal lobes and cerebellum was isolated from 11 control subjects and 9 AD subjects, and oxidized purine and pyrimidine bases were quantitated using gas chromatography/mass spectrometry. Stable isotope-labeled oxidized base analogues were used as internal standards to measure 5-hydroxyuracil, 5-hydroxycytosine, 8-hydroxyadenine, 4,6-diamino-5-formamidopyrimidine (FAPy-adenine), 8-hydroxyguanine, and 2,6-diamino-4-hydroxy-5-formamidopyrimidine (Fapy-guanine). Statistically significant elevations of 5-hydroxycytosine, 5-hydroxyuracil, 8-hydroxyadenine, and 8-hydroxyguanine were found in AD brain compared with control subjects (p < 0.05). There was an increased trend in the levels of FAPy-adenine in the AD brain, and Fapy-guanine showed a trend toward higher levels in control brains compared with AD. A generally higher level of oxidative DNA damage was present in neocortical regions than cerebellum. No significant correlation was observed between the oxidized bases and neurofibrillary tangle and senile plaque counts. Our results demonstrate that nuclear DNA damage by oxygen-derived radicals is increased in AD and support the concept that the brain is under increased oxidative stress in AD.