2-Aminopurine
(Synonyms: 2-氨基嘌呤) 目录号 : GC61906
2-Aminopurine 是鸟苷和腺苷的荧光类似物，是一种广泛使用的基于荧光衰变的 DNA 结构探针。当将 2-Aminopurine 插入寡核苷酸时，其荧光会通过与天然碱基堆积而被高度淬灭。2-Aminopurine 已被用于探测核酸的结构和动力学。
Cas No.:452-06-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Aminopurine, a fluorescent analog of guanosine and adenosine, is a widely used fluorescence-decay-based probe of DNA structure. When 2-Aminopurine is inserted in anoligonucleotide, its fluorescence is highly quenched by stacking with the natural bases. 2-Aminopurine has been used to probe nucleic acid structure and dynamics[1][2].
2-Aminopurine (2AP) is not valuable as afluorescent label because its fluorescence is highly quenched by stacking with the natural bases, when it is inserted in anoligonucleotide. However, it is this very susceptibility to interbase quenching that makes 2AP an exquisitely sensitivefluorescent probe of nucleic acid structure[1]. 2-Aminopurine differs from adenine (6-aminopurine) only in the position of the exocyclic amine group, and yet its fluorescence intensity is one thousand times that of adenine[1].
References:
[1]. J M Jean, et al. 2-Aminopurine fluorescence quenching and lifetimes: role of base stacking. Proc Natl Acad Sci U S A. 2001 Jan 2;98(1):37-41.
[2]. Dehong Tan, et al. Decreased glycation and structural protection properties of γ-glutamyl-S-allyl-cysteine peptide isolated from fresh garlic scales (Allium sativum L.). Nat Prod Res. 2015;29(23):2219-22.
| Cas No. | 452-06-2 | SDF | |
| 别名 | 2-氨基嘌呤 | ||
| Canonical SMILES | NC1=NC=C2NC=NC2=N1 | ||
| 分子式 | C5H5N5 | 分子量 | 135.13 |
| 溶解度 | DMSO : 5 mg/mL (37.00 mM)|Water : 1.35 mg/mL (9.99 mM) | 储存条件 | Store at 2-8°C, protect from light |
| 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 | 7.4003 mL | 37.0014 mL | 74.0028 mL |
| 5 mM | 1.4801 mL | 7.4003 mL | 14.8006 mL |
| 10 mM | 0.74 mL | 3.7001 mL | 7.4003 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。
Transcriptional Perturbations of 2,6-Diaminopurine and 2-Aminopurine
ACS Chem Biol 2022 Jul 15;17(7):1672-1676.PMID:PMC9354233DOI:10.1021/acschembio.2c00369.
2,6-Diaminopurine (Z) is a naturally occurring adenine (A) analog that bacteriophages employ in place of A in their genetic alphabet. Recent discoveries of biogenesis pathways of Z in bacteriophages have stimulated substantial research interest in this DNA modification. Here, we systematically examined the effects of Z on the efficiency and fidelity of DNA transcription. Our results showed that Z exhibited no mutagenic yet substantial inhibitory effects on transcription mediated by purified T7 RNA polymerase and by human RNA polymerase II in HeLa nuclear extracts and in human cells. A structurally related adenine analog, 2-Aminopurine (2AP), strongly blocked T7 RNA polymerase but did not impede human RNA polymerase II in vitro or in human cells, where no mutant transcript could be detected. The lack of mutagenic consequence and the presence of a strong blockage effect of Z on transcription suggest a role of Z in transcriptional regulation. Z is also subjected to removal by transcription-coupled nucleotide-excision repair (TC-NER), but not global-genome NER in human cells. Our findings provide new insight into the effects of Z on transcription and its potential biological functions.
2-Aminopurine Fluorescence Spectroscopy for Probing a Glucose Binding Aptamer
Chembiochem 2022 Jun 20;23(12):e202200127.PMID:35468257DOI:10.1002/cbic.202200127.
Glucose is the most important analyte for biosensors. Recently a DNA aptamer was reported allowing binding-based detection. However, due to a relatively weak binding affinity, it is difficult to perform binding assays to understand the property of this aptamer. In this work, we replaced the only adenine base in the aptamer binding pocket with a 2-Aminopurine (2AP) and used fluorescence spectroscopy to study glucose binding. In the selection buffer, glucose increased the 2AP fluorescence with a Kd of 15.0 mM glucose, which was comparable with the 10 mM Kd previously reported using the strand displacement assay. The binding required two Na+ ions or one Mg2+ that cannot be replaced by Li+ or K+ . The binding was weaker at higher temperature and its van't Hoff plot indicated enthalpy-driven binding. While other monosaccharides failed to achieve saturated binding even at high concentrations, two glucose-containing disaccharides, namely trehalose and sucrose, reached a similar fluorescence level as glucose although with over 10-fold higher Kd values. Detection limits in both the selection buffer (0.9 mM) and in artificial interstitial fluids (6.0 mM) were measured.
2-Aminopurine modified DNA probe for rapid and sensitive detection of l-cysteine
Talanta 2019 Sep 1;202:520-525.PMID:31171216DOI:10.1016/j.talanta.2019.05.007.
A rapid, cost-effective and quencher-free fluorescence-based analytical method for sensitive detection of l-cysteine (Cys) based on 2-Aminopurine (2-AP) labeled DNA probe and exonuclease I (Exo I) activity was developed. 2-AP labeled DNA probe includes two thymine (T)-T mismatches, which can bind with Hg2+ to form T-Hg2+-T pairing bases, resulting in stable hairpin with five base pairs in its stem. The target Cys can remove Hg2+ from the stem of the hairpin probe based on the high affinity of Cys with Hg2+, leading to the unfolding of the hairpin probe. At last, by adding Exo I, the resulted single-stranded DNA (ssDNA) will be digested to release free 2-AP with strong fluorescence. Under the optimal conditions, the sensing system exhibited a good and wider linear range from 0.4 to 400 nM (R2 = 0.997) and a detection limit as low as 0.16 nM for Cys. Furthermore, other amino acids without reductive sulfur group did not generate obvious change in fluorescence signals. Finally, the sensor can be used in diluted real samples with a good recovery rate, showing promising application in food, environmental and medical analysis.
2-Aminopurine as a probe for quadruplex loop structures
Methods Mol Biol 2010;608:121-36.PMID:20012419DOI:10.1007/978-1-59745-363-9_8.
Fluorescent reporter groups have served for many years as sensitive probes of macromolecular structure. Such probes can be especially useful in comparative studies such as detection of conformational changes and discrimination among structural models. Spectroscopic methods such as fluorescence are attractive because they are rapid, require small amounts of material, are nondestructive, can be carried out with commonly available equipment, and are relatively inexpensive. In addition, there is a rich library of theoretical and practical materials available to aid in data interpretation.The intrinsic fluorescence of most nucleic acids is too low to be useful in structural studies. Thus, it is necessary to incorporate a suitable reporter group to utilize fluorescence methods involving polynucleotide structure. A highly fluorescent adenine analog, 2-Aminopurine, has long served in this capacity. The present article describes our use of 2-Aminopurine as a probe of loop structures in quadruplex DNA. In particular, we show how knowledge of the relative intensity of 2-Aminopurine emission as well as its sensitivity to exogenous quenching molecules such as acrylamide can aid in comparing crystal and solution structures of an oligonucleotide model of the human telomere and in discrimination among models containing tandem repeats of the telomeric quadruplex.
DNA nanodevices monitored with fluorogenic looped-out 2-Aminopurine
Analyst 2018 Feb 26;143(5):1268-1273.PMID:29445799DOI:10.1039/c7an01953j.
We report several DNA nanodevices monitored with fluorogenic looped-out 2-Aminopurine. It is found that looped-out 2-AP, an analogue of adenine, in split parallel G-quadruplexes, triplexes and duplexes always shows much higher fluorescence intensity than that in single- or double-stranded DNAs, due to the weaker quenching effects derived from the reduced base stacking environments. Taking advantage of these traits, we introduce a new strategy to monitor the behaviours of DNA nanodevices via the fluorescence signal output by utilizing changes in the base stacking environment of 2-AP. As proof-of-principle experiments, two nanoplatforms for detecting disease genes, as well as a triplex nanoswitch, are constructed and monitored by fluorogenic looped-out 2-AP, illustrating that fluorogenic looped-out 2-AP holds great promise for reading the behaviours of diverse DNA nanodevices. Compared with conventional fluorescence labelling, looped-out 2-AP as a reporter shows good photostability and can be quenched by base-pairing, thereby providing an efficient quencher-free methodology for monitoring DNA nanodevices.