Zinpyr-1
(Synonyms: 9-(2-羧基苯基)-2,7-二氯-4,5-双[二(2-吡啶基)氨基甲基]-6-羟基-3-黄原酮,ZP-1) 目录号 : GC45182A fluorescent probe for zinc detection
Cas No.:288574-78-7
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Zinpyr-1 is a cell-permeable, fluorescein-based probe for zinc detection.[1] It undergoes a shift in excitation from 515 to 507 nm with increasing zinc concentrations using an emission filter over 513-558 nm.[1][2]
Reference:
[1]. Walkup, G.K., Burdette, S.C., Lippard, S.J., et al. A new cell-permeable fluorescent probe for Zn2+. J. Am. Chem. Soc. 122(23), 5644-5645 (2000).
[2]. Burdette, S.C., Walkup, G.K., Spingler, B., et al. Fluorescent sensors for Zn2+ based on a fluorescein platform: synthesis, properties and intracellular distribution. J. Am. Chem. Soc. 123(32), 7831-7841 (2001).
| Cas No. | 288574-78-7 | SDF | |
| 别名 | 9-(2-羧基苯基)-2,7-二氯-4,5-双[二(2-吡啶基)氨基甲基]-6-羟基-3-黄原酮,ZP-1 | ||
| 化学名 | 4',5'-bis[[bis(2-pyridinylmethyl)amino]methyl]-2',7'-dichloro-3',6'-dihydroxy-spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one | ||
| Canonical SMILES | O=C1C(Cl)=CC(C(O2)=C1C[NH+](CC3=CC=CC=N3)CC4=NC=CC=C4)=C(C5=CC=CC=C5C([O-])=O)C6=C2C(C[NH+](CC7=CC=CC=N7)CC8=NC=CC=C8)=C([O-])C(Cl)=C6 | ||
| 分子式 | C46H36Cl2N6O5 | 分子量 | 823.7 |
| 溶解度 | 0.5mg/mL in DMF | 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 | 1.214 mL | 6.0702 mL | 12.1403 mL |
| 5 mM | 0.2428 mL | 1.214 mL | 2.4281 mL |
| 10 mM | 0.1214 mL | 0.607 mL | 1.214 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。
A Zinpyr-1-based Fluorimetric Microassay for Free Zinc in Human Serum
Int J Mol Sci 2019 Aug 16;20(16):4006.PMID:31426452DOI:10.3390/ijms20164006.
Zinc is an essential trace element, making it crucial to have a reliable biomarker for evaluating an individual's zinc status. The total serum zinc concentration, which is presently the most commonly used biomarker, is not ideal for this purpose, but a superior alternative is still missing. The free zinc concentration, which describes the fraction of zinc that is only loosely bound and easily exchangeable, has been proposed for this purpose, as it reflects the highly bioavailable part of serum zinc. This report presents a fluorescence-based method for determining the free zinc concentration in human serum samples, using the fluorescent probe Zinpyr-1. The assay has been applied on 154 commercially obtained human serum samples. Measured free zinc concentrations ranged from 0.09 to 0.42 nM with a mean of 0.22 ± 0.05 nM. It did not correlate with age or the total serum concentrations of zinc, manganese, iron or selenium. A negative correlation between the concentration of free zinc and total copper has been seen for sera from females. In addition, the free zinc concentration in sera from females (0.21 ± 0.05 nM) was significantly lower than in males (0.23 ± 0.06 nM). The assay uses a sample volume of less than 10 µL, is rapid and cost-effective and allows us to address questions regarding factors influencing the free serum zinc concentration, its connection with the body's zinc status, and its suitability as a future biomarker for an individual's zinc status.
The use of the zinc-fluorophore, Zinpyr-1, in the study of zinc homeostasis in Arabidopsis roots
New Phytol 2007;174(1):39-45.PMID:17335495DOI:10.1111/j.1469-8137.2007.02030.x.
* The usefulness of the zinc (Zn)-fluorophore, Zinpyr-1, to examine the localization of Zn in the roots of Arabidopsis has been investigated. * In wild-type roots Zinpyr-1 fluorescence was predominantly in the xylem. The fluorescence signal was abolished by the application of the Zn-chelator, N,N,N',N-tetrakis(2-pyridylmethyl)ethylenediamine (TPEN), and was increased by increasing exogenous Zn in the medium, indicating that fluorescence reflected relative Zn concentrations. * In the hma2, hma4 double mutant, which is deficient in root to shoot Zn translocation, Zinpyr-1 fluorescence was low in the xylem and high in the adjacent pericycle cells in which HMA2 and HMA4 are specifically expressed in a wild type. Zinpyr-1 fluorescence was also increased in the endodermis. * These results show that Zinpyr-1 can be used to examine the effects of mutations in Zn transporters on the localization of Zn in Arabidopsis roots and should be a useful addition to the tools available for studying Zn homeostasis in plants.
Application of Zinpyr-1 for the investigation of zinc signals in Escherichia coli
Biometals 2013 Feb;26(1):167-77.PMID:23324851DOI:10.1007/s10534-012-9604-0.
Changes of the pico- to nanomolar concentration of free intracellular Zn(2+) are part of the signal transduction in mammalian cells. These zinc signals regulate the enzymatic activity of target proteins such as protein tyrosine phosphatases. For Escherichia coli, previous studies have reported diverging concentrations from femto- to picomolar, raising the question if Zn(2+) could also have a function in bacterial signaling. This manuscript explores the use of the low molecular weight fluorescent probe Zinpyr-1 in E. coli. The probe detects free Zn(2+) in these bacteria. Comparable to mammalian cells, other metal ions, especially Hg(2+) and Cd(2+), interfere with the detection of Zn(2+). Moreover, experiments in E. coli were particularly prone to artifacts based on cellular autofluorescence, necessitating corrections that are not required in mammalian cells. Based on measurements in lysates of E. coli and the mammalian cell line Jurkat, similar values between 0.1 and 0.2 nM free Zn(2+) were found. For E. coli, this corresponds to less than one free zinc ion per cell. Moreover, phosphatase inhibition by Zn(2+) was only observed in Jurkat, but not E. coli. This excludes a function for zinc signals as a regulator of bacterial phosphatases. Still, changes in the free Zn(2+) concentration were observed in response to elevated extracellular Zn(2+) and pH, or to addition of the detergent NP-40, suggesting that other processes could be controlled by the free intracellular Zn(2+) concentration.
Ternary Zn(II) Complexes of Fluorescent Zinc Probes Zinpyr-1 and Zinbo-5 with the Low Molecular Weight Component of Exchangeable Cellular Zinc Pool
Inorg Chem 2019 Nov 4;58(21):14741-14751.PMID:31646867DOI:10.1021/acs.inorgchem.9b02419.
The intracellular exchangeable Zn(II) is usually measured with synthetic fluorescent zinc sensors. 4',5'-Bis[bis(2-pyridylmethyl)aminomethyl]-2',7'-dichlorofluorescein (Zinpyr-1) is a sensor containing the fluorescein platform and a duplicated chelating unit. Its advantages include brightness and a relatively high affinity for Zn(II), Kd = 0.7 nM. 2-(4,5-Dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole (Zinbo-5) is a member of a growing family of ratiometric synthetic Zn(II) probes, offering a possibility to determine Zn(II) concentration independently of the sensor concentration. Cells, however, contain high, millimolar or nearly millimolar concentrations of low molecular weight ligands (LMWLs) capable of binding Zn(II) ions. Previously, we demonstrated that such LMWLs can perturb the performance of some fluorescent zinc sensors by competition and formation of ternary Zn(sensor) (LMWL) complexes. Here we tested Zinpyr-1 and Zinbo-5 in this respect. Despite structural differences, both sensors formed such ternary complexes. We determined their stability constants CKtern and performed numerical simulations of Zn(II) distributions at physiological concentrations of selected LMWLs. Glutamic acid was found to provide the strongest ternary complexes with either of the studied sensors. Zn(Zinpyr-1)(Glu) was an absolutely dominant Zn(II)/Zinpyr-1 species (more than 96% of the exchangeable Zn(II)), and Zn(Zinbo-5)(Glu) was the most abundant one (more than 40%) in these simulations. Our results indicate that under cellular conditions these sensors are able to report Zn(II) complexed to LMWLs rather than free Zn2+ ions. On the other hand, the specific affinity of Zn(Zinpyr-1) and Zn(Zinbo-5) for Glu creates interesting opportunities for determining glutamic acid in biological samples.
Analogues of Zinpyr-1 provide insight into the mechanism of zinc sensing
Inorg Chem 2006 Aug 7;45(16):6474-8.PMID:16878961DOI:10.1021/ic060378j.
Three compounds structurally related to the fluorescent zinc sensor Zinpyr-1 (ZP1) have been synthesized and characterized. In each of these ZinAlkylPyr (ZAP) analogues, an alkyl group (methyl, benzyl) replaces one of the metal-binding picolyl moieties in ZP1. The methyl-for-picolyl substitutions in ZAP1 and ZAP2 have a negligible effect on the optical spectrum of the fluorophore but elevate the quantum yields (Phi = 0.82 (ZAP1), 0.74 (ZAP2)) to values near that of Zn2+-saturated ZP1 (Phi = 0.92). The benzyl-for-picolyl substitution in ZAP3 similarly enhances the quantum yield (Phi = 0.52) relative to that of metal-free ZP1 (Phi = 0.38). As previously observed for methylated ZP1 sensors, methylation of the 6-position of the pyridyl ring diminishes the emission by lowering both the molar extinction coefficient and the quantum yield. Although these new ZAP compounds cannot detect Zn2+ fluorimetrically at neutral pH, complexation of Zn2+ does occur, as evidenced by sizable changes in the optical spectra. The ZAP1-3 probes can detect Zn2+ fluorimetrically at pH 9, indicating that proton-induced background emission obscures any Zn2+-induced fluorescence at pH 7. The tertiary amine groups in ZAP1-3 are less basic than those in ZP1, which implies that the additional pyridine rings are responsible for the emissive response to Zn2+ at pH 7.0.