1-Methyladenine
(Synonyms: 1-甲基腺嘌呤) 目录号 : GC33646
1-甲基腺嘌呤是在N-1位被甲基取代的腺嘌呤，是 DNA 烷基化损伤的产物，可通过氧化去甲基化损伤逆转进行修复。
Cas No.:5142-22-3
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
1-Methyladenine is a product of alkylation damage in DNA which can be repaired by damage reversal by oxidative demethylation.
[1]. Falnes P?, et al. Repair of 3-methylthymine and 1-methylguanine lesions by bacterial and human AlkB proteins. Nucleic Acids Res. 2004 Dec 1;32(21):6260-7. Print 2004. [2]. Yang H, et al. Effect of 1-methyladenine on double-helical DNA structures. FEBS Lett. 2008 May 14;582(11):1629-33.
| Cas No. | 5142-22-3 | SDF | |
| 别名 | 1-甲基腺嘌呤 | ||
| Canonical SMILES | NC1=C2N=CN=C2N=CN1C | ||
| 分子式 | C6H7N5 | 分子量 | 149.15 |
| 溶解度 | Water: 5.2 mg/mL (34.86 mM; ultrasonic and warming and heat to 80°C) | 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 | 6.7047 mL | 33.5233 mL | 67.0466 mL |
| 5 mM | 1.3409 mL | 6.7047 mL | 13.4093 mL |
| 10 mM | 0.6705 mL | 3.3523 mL | 6.7047 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。
Immunophotoaffinity labeling of binders of 1-Methyladenine, the oocyte maturation-inducing hormone of starfish
Biochem Biophys Res Commun 2017 Mar 25;485(1):41-46.PMID:28174006DOI:10.1016/j.bbrc.2017.02.009.
Starfish oocytes are arrested at the prophase stage of the first meiotic division in the ovary and resume meiosis by the stimulus of 1-Methyladenine (1-MeAde), the oocyte maturation-inducing hormone of starfish. Putative 1-MeAde receptors on the oocyte surface have been suggested, but not yet been biochemically characterized. Immunophotoaffinity labeling, i.e., photoaffinity labeling combined with immunochemical detection, was attempted to detect unknown 1-MeAde binders including putative maturation-inducing hormone receptors in starfish oocytes. When the oocyte crude membrane fraction or its Triton X-100/EDTA extract was incubated with N6-[6-(5-azido-2-nitrobenzoyl)aminohexyl]carboxamidomethyl-1-methyladenine and then photo-irradiated, followed by western blotting with antibody that was raised against a 1-MeAde hapten, a single band with Mr of 47.5 K was detected. The band was lost when extract was heated at 100 °C. A similar 47.5 K band was detected in the crude membrane fraction of testis as well. Upon labeling with whole cells, this band was detected in immature and maturing oocytes, but only faintly in mature oocytes. As judged from these results, this 1-MeAde binder might be a possible candidate of the starfish maturation-inducing hormone receptors.
Affinity chromatography of a binder of 1-Methyladenine, the maturation-inducing hormone for starfish oocytes
Biochem Biophys Res Commun 2017 May 13;486(4):1055-1061.PMID:28366629DOI:10.1016/j.bbrc.2017.03.161.
Starfish oocytes are arrested at the prophase stage of the first meiotic division in the ovary. They resume meiosis by the stimulus of 1-Methyladenine (1-MeAde), the maturation-inducing hormone for starfish oocytes. Putative 1-MeAde receptors have been suggested to be present on the oocyte surface, but not yet been characterized biochemically. As reported recently (T. Toraya, T. Kida, A. Kuyama, S. Matsuda, S. Tanaka, Y. Komatsu, T. Tsurukai, Biochem. Biophys. Res. Commun. 485 (2017) 41-46), it became possible to detect unknown 1-MeAde binders of starfish oocytes by immunophotoaffinity labeling, i.e., photoaffinity labeling combined with immunochemical detection. We designed and synthesized water-soluble and insoluble polymer-bound 1-MeAde derivatives. A water-soluble polymer-bound 1-MeAde derivative, in which 1-MeAde is bound to dextran through an N6-substituent, triggered the germinal-vesicle breakdown toward follicle-free oocytes, dejellied oocytes, and denuded oocytes. This is consistent with the idea that putative 1-MeAde receptors are located on the cell surface of starfish oocytes. A water-insoluble polymer-bound 1-MeAde derivative, in which 1-MeAde is bound to Sepharose 4B through an N6-substituent, served as an effective affinity adsorbent for the partial purification of a 1-MeAde binder with Mr of 47.5 K that might be a possible candidate of the maturation-inducing hormone receptors of starfish oocytes.
1-Methyladenine production from ATP by starfish ovarian follicle cells
Biochim Biophys Acta 1999 Jun 28;1428(1):13-20.PMID:10366755DOI:10.1016/s0304-4165(99)00041-0.
1-Methyladenine (1-MeAde), the oocyte maturation-inducing substance in starfish, is produced by ovarian follicle cells upon stimulation with a gonad-stimulating substance (GSS) released from the radial nerves. We have shown previously that GSS causes a reduction in the intracellular levels of ATP coincident with 1-MeAde production. The present study examined whether the adenine molecule of 1-MeAde is directly derived from ATP. When isolated follicle cells from the starfish Asterina pectinifera were preloaded with [U-14C]adenine or [U-14C]adenosine, there was an increase in the intracellular levels of radiolabeled adenine nucleotides, particularly ATP. Following further incubation with GSS, the intracellular levels of radiolabeled ATP decreased, concomitant with a marked increase in the levels of [14C]1-MeAde in the medium. The amount of ATP consumed under the influence of GSS was similar to the amount of 1-MeAde produced. However, there was no change in the levels of ADP and AMP regardless of the presence or absence of GSS. These findings strongly suggest that 1-MeAde is synthesized from ATP as a substrate in follicle cells under the influence of GSS. Furthermore, using [methyl-3H]methionine, the methyl group of 1-MeAde was found to be derived from methionine. Thus GSS appears to stimulate the synthesis of 1-MeAde from ATP via the methylation process in starfish ovarian follicle cells.
Synthesis of Some 1-Methyladenine Analogs and Their Biological Activities on Starfish Oocyte Maturation
Biosci Biotechnol Biochem 1998;62(1):72-7.PMID:27393355DOI:10.1271/bbb.62.72.
Starfish oocytes are naturally arrested at the prophase stage of the first meiotic division and resume meiosis in response to the maturation-inducing hormone 1-Methyladenine. Five analogs of 1-Methyladenine including three novel ones were synthesized and tested for biological activities as 1-Methyladenine agonists or antagonists in triggering reinitiation of meiosis of starfish Asterina pectinifera oocytes, as well as for competition in binding to putative 1-Methyladenine receptors with respect to 1-Methyladenine. 1-Ethyladenine was an effective agonist, but 1-propyladenine served as a weak antagonist to 1-Methyladenine, indicating strict specificity for a relatively small N-1 substituent. Analogs in which carboxymethyl or methyl group substitutes for a hydrogen of 6-amino group still retained oocyte maturation-inducing activity, but to a much lesser degree. The results of the competitive binding assay with cortices of oocytes demonstrated that these agonists or antagonist inhibited the binding of [(3)H]1-Methyladenine to receptors. 8-methylamino-1-methyladenine competed only weakly with [(3)H]1-Methyladenine for the binding to cortices, although it behaved as a potent antagonist.
Oocyte Maturation in Starfish
Cells 2020 Feb 19;9(2):476.PMID:32092921DOI:10.3390/cells9020476.
Oocyte maturation is a process that occurs in the ovaries, where an immature oocyte resumes meiosis to attain competence for normal fertilization after ovulation/spawning. In starfish, the hormone 1-Methyladenine binds to an unidentified receptor on the plasma membrane of oocytes, inducing a conformational change in the heterotrimeric GTP-binding protein α-subunit (Gα), so that the α-subunit binds GTP in exchange of GDP on the plasma membrane. The GTP-binding protein βγ-subunit (Gβγ) is released from Gα, and the released Gβγ activates phosphatidylinositol-3 kinase (PI3K), followed by the target of rapamycin kinase complex2 (TORC2) and 3-phosphoinositide-dependent protein kinase 1 (PDK1)-dependent phosphorylation of serum- and glucocorticoid-regulated kinase (SGK) of ovarian oocytes. Thereafter, SGK activates Na+/H+ exchanger (NHE) to increase the intracellular pH (pHi) from ~6.7 to ~6.9. Moreover, SGK phosphorylates Cdc25 and Myt1, thereby inducing the de-phosphorylation and activation of cyclin B-Cdk1, causing germinal vesicle breakdown (GVBD). Both pHi increase and GVBD are required for spindle assembly at metaphase I, followed by MI arrest at pHi 6.9 until spawning. Due to MI arrest or SGK-dependent pHi control, spawned oocytes can be fertilized normally.