7-Amino-4-methyl-3-coumarinylacetic Acid
(Synonyms: 7-氨基-4-甲基-3-香豆素醋酸) 目录号 : GC45986
A fluorescent protein labeling agent
Cas No.:106562-32-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
7-Amino-4-methyl-3-coumarinylacetic acid (AMCA) is fluorescent protein labeling agent.1 It contains an N-hydroxysuccinimide ester that reacts with lysine residues to form photostable amide links. Upon activation with UV light, AMCA displays emission maxima of 400-460 nm. It has commonly been used in multiplex immunophenotyping applications.2,3,4
|1. Khalfan, H., Abuknesha, R., Rand-Weaver, M., et al. Aminomethyl coumarin acetic acid: A new fluorescent labelling agent for proteins. Histochem. J. 18(9), 497-499 (1986).|2. Ferri, G.-L., Gaudio, R.M., Castello, I.F., et al. Quadruple immunofluorescence: A direct visualization method. J. Histochem. Cytochem. 45(2), 155-158 (1997).|3. Nederlof, P.M., Robinson, D., Abuknesha, R., et al. Three-color fluorescence in situ hybridization for the simultaneous detection of multiple nucleic acid sequences. Cytometry 10(1), 20-27 (1989).|4. Gothot, A., Grosdent, J.-C., and Paulus, J.-M. A strategy for multiple immunophenotyping by image cytometry: Model studies using latex microbeads labeled with seven streptavidin-bound fluorochromes. Cytometry 24(3), 214-225 (1996).
| Cas No. | 106562-32-7 | SDF | |
| 别名 | 7-氨基-4-甲基-3-香豆素醋酸 | ||
| Canonical SMILES | NC1=CC=C2C(OC(C(CC(O)=O)=C2C)=O)=C1 | ||
| 分子式 | C12H11NO4 | 分子量 | 233.2 |
| 溶解度 | DMF: 2mg/mL,DMSO: 3mg/mL,DMSO:PBS (pH 7.2) (1:6): 0.14mg/mL | 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 | 4.2882 mL | 21.4408 mL | 42.8816 mL |
| 5 mM | 0.8576 mL | 4.2882 mL | 8.5763 mL |
| 10 mM | 0.4288 mL | 2.1441 mL | 4.2882 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。
Analysis of fluorescence quenching of coumarin derivatives by 4-hydroxy-TEMPO in aqueous solution
J Fluoresc 2014 May;24(3):713-8.PMID:24337873DOI:10.1007/s10895-013-1342-3.
The fluorescence quenching of different coumarin derivatives (7-hydroxy-4-methylcoumarin, 5,7-dimethoxycoumarin, 7-Amino-4-methyl-3-coumarinylacetic Acid, 7-ethoxy-4-methylcoumarin, 7-methoxycoumarin, 7-hydroxycoumarin, 7-hydroxy-4-methyl-3-coumarinylacetic acid and 7-amino-4-methylcoumarin) by 4-hydroxy-TEMPO in aqueous solutions at the room temperature was studied with the use of UV-Vis absorption spectroscopy as well as a steady-state and time-resolved fluorescence spectroscopy. In order to understand the mechanism of quenching the absorption and fluorescence emission spectra of all coumarins along with fluorescence decays were recorded under the action of 4-hydroxy-TEMPO. The Stern-Volmer plots (both from time-averaged and time-resolved measurements) displayed no positive (upward) deviation from a linearity. The fluorescence quenching mechanism was found to be entirely dynamic, what was additionally confirmed by the registration of Stern-Volmer plots at different temperatures. The Stern-Volmer quenching constants and bimolecular quenching rate constants were obtained for all coumarins studied at the room temperature. The findings demonstrate the possibility of developing an analytical method for the quantitative determination of the free radicals' scavenger, 4-hydroxy-TEMPO.
A combined spectroscopic and TDDFT investigation of the solute-solvent interactions of two coumarin derivatives
Luminescence 2017 Nov;32(7):1328-1338.PMID:28581184DOI:10.1002/bio.3329.
The UV/Vis absorption and fluorescence characteristics of 3-cyano-7-hydroxycoumarin [CHC] and 7-Amino-4-methyl-3-coumarinylacetic Acid [AMCA-H] were studied at room temperature in several neat solvents and binary solvent mixtures of 1,4-dioxane/acetonitrile. The effects of solvent on the spectral properties are analyzed using single and multi-parameter solvent polarity scales. Both general solute/solvent interactions and hydrogen bond interactions are operative in these systems. The solvation of CHC and AMCA-H dyes in 1,4-dioxane/acetonitrile solvent mixtures has been studied. The solutes CHC and AMCA-H are preferentially solvated by acetonitrile and a synergistic effect is observed for both molecules in dioxane/acetonitrile solvent mixtures. In addition, using the solvatochromic method the ground- and the excited-state dipole moments of both the dyes were calculated. The ground- and excited-state dipole moments, absorption and emission maxima and HOMO-LUMO gap were also estimated theoretically using B3LYP/6-311+ G (d,p) level of theory in the gaseous phase, dioxane and acetonitrile solvents. Furthermore, changes in dipole moment values were also calculated using the variation of Stokes shift with the molecular-microscopic empirical solvent polarity parameter ( ETN). The observed excited-state dipole moments are larger than their ground-state counterparts, indicating a substantial redistribution of the electron densities in a more dipolar excited state for both coumarins investigated.
Effects of surface treatments on trapping with DC insulator-based dielectrophoresis
Analyst 2019 Dec 2;144(24):7478-7488.PMID:31720589DOI:10.1039/c9an01186b.
A central challenge in measuring the biophysical properties of cells with electrokinetic approaches is the assignment of these biophysical properties to specific biological characteristics. Changes in the electrokinetic behavior of cells may come from mutations, altered gene expression levels, post-translation modifications, or environmental effects. Here we assess the electrokinetic behavior of chemically surface-modified bacterial cells in order to gain insight into the biophysical properties that are specifically affected by changes in surface chemistry. Using E. coli as a scaffold, an amine coupling reaction was used to covalently attach glycine, spermine, bovine serum albumin (protein), or 7-Amino-4-methyl-3-coumarinylacetic Acid (fluorescent dye) to the free carboxylic acid groups on the surface of the cells. These populations, along with unlabeled control cells, were subject to electrokinetic and dielectrophoretic measurements to quantify any changes in the biophysical properties upon alteration. The properties associated with each electrokinetic force are discussed relative to the specific reactant used. We conclude that relatively modest and superficial changes to cell surfaces can cause measurable changes in their biophysical properties.
Synthesis and fluorescent labeling of beta-amyloid peptides
J Pept Sci 2001 Aug;7(8):397-401.PMID:11548055DOI:10.1002/psc.346.
Fluorescent cell analytical techniques require the incorporation of a fluorophore into the target molecule without causing a significant change in the native conformation. Many short peptides have a limited number of reactive groups that can be labeled without affecting the biological activity. In this work we present several methods for labeling beta-amyloid peptides (betaA[25-35], betaA[1-40]) and their derivatives (LPFFD, RIIGL and RVVIA) with different chromophores exclusively at the N-terminus. In the case of liquid-phase labeling, fluorescein isothiocyanate was used. The side-chain amino function of Lys, if present in the sequence, was protected with an Fmoc group, whereby the hydrophobic character of the peptide was further increased. The labeling reaction was carried out in an appropriate deaggregating solvent, DMSO. For solid-phase labeling, 5(6)-carboxyfluorescein and 7-Amino-4-methyl-3-coumarinylacetic Acid were applied. Several cleavage cocktails were tested for removal of the labeled amyloid peptides from the resin in order to completely suppress the oxidation of Met.
Synthesis of Abeta[1-42] and its derivatives with improved efficiency
J Pept Sci 2007 Feb;13(2):94-9.PMID:17103463DOI:10.1002/psc.801.
It has been proved that the principal component of senile plaques is aggregates of beta-amyloid peptide (Abeta) in cases of one of the most common forms of age-related neurodegenerative disorders, Alzheimer's disease (AD). Although the synthetic methods for the synthesis of Abeta peptides have been developed since their first syntheses, Abeta[1-42] is still problematic to prepare. The highly hydrophobic composition of Abeta[1-42] results in aggregation between resin-bound peptide chains or intrachain aggregation which leads to a decrease in the rates of deprotection and repetitive incomplete coupling reactions during 9-flurenylmethoxycarbonyl (Fmoc) synthesis. In order to avoid aggregation and/or disrupt internal aggregation during stepwise Fmoc solid phase synthesis and to improve the quality of crude products, several attempts have been made. Since highly pure Abeta peptides in large quantities are used in biological experiments, we wanted to develop a method for a rational synthesis of human Abeta[1-42] with high purity and adequate yield. This paper reports a convenient methodology with a novel solvent system for the synthesis of Abeta[1-42], its N-terminally truncated derivatives Abeta[4-42] and Abeta[5-42], and Abeta[1-42] labeled with 7-Amino-4-methyl-3-coumarinylacetic Acid (AMCA) at the N-terminus using Fmoc strategy. The use of 10% anisole in Dimethylformamide/Dichloromethane (DMF/DCM) can substantially improve the purity and yield of crude Abeta[1-42] and has been shown to be an optimal coupling condition for the synthesis of Abeta[1-42]. Anisole is a cheap and simple aid in the synthesis of 'difficult sequences' where other solvents are less successful in the prevention of aggregation during the synthesis.