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Visual detection of cysteine and homocysteine.

ABSTRACT: The determination of cysteine and homocysteine levels is of great current interest for the monitoring of desease states. A new colorimetric method for the simultaneous detection of l-cysteine and l-homocysteine has been developed. A fluorescein derivative reacts with the above amino acids, producing their respective thiazolidines resulting in color changes. Interference from other amino acids and proteins is minimal.

SUBMITTER: Rusin O

PROVIDER: S-EPMC3376414 | biostudies-literature | 2004 Jan

REPOSITORIES: biostudies-literature

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Visual detection of cysteine and homocysteine.

Rusin Oleksandr O St Luce Nadia N NN Agbaria Rezik A RA Escobedo Jorge O JO Jiang Shan S Warner Isiah M IM Dawan Fareed B FB Lian Kun K Strongin Robert M RM

Journal of the American Chemical Society 20040101 2

The determination of cysteine and homocysteine levels is of great current interest for the monitoring of desease states. A new colorimetric method for the simultaneous detection of l-cysteine and l-homocysteine has been developed. A fluorescein derivative reacts with the above amino acids, producing their respective thiazolidines resulting in color changes. Interference from other amino acids and proteins is minimal. ...[more]

PMID: 14719920

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Detection of homocysteine and cysteine.

Project description:At elevated levels, homocysteine (Hcy, 1) is a risk factor for cardiovascular diseases, Alzheimer's disease, neural tube defects, and osteoporosis. Both 1 and cysteine (Cys, 3) are linked to neurotoxicity. The biochemical mechanisms by which 1 and 3 are involved in disease states are relatively unclear. Herein, we describe simple methods for detecting either Hcy or Cys in the visible spectral region with the highest selectivity reported to date without using biochemical techniques or preparative separations. Simple methods and readily available reagents allow for the detection of Cys and Hcy in the range of their physiologically relevant levels. New HPLC postcolumn detection methods for biological thiols are reported. The potential biomedical relevance of the chemical mechanisms involved in the detection of 1 is described.

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A dual emission fluorescent probe enables simultaneous detection of glutathione and cysteine/homocysteine.

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| S-EPMC4074921 | biostudies-literature

A Fluorescent Cy7-Mercaptopyridine for the Selective Detection of Glutathione over Homocysteine and Cysteine.

Project description:We describe a near-infrared (NIR) fluorescent probe 1 for the selective detection of GSH over Hcy and Cys under physiological conditions. Probe 1 was composed of Cy7 as a NIR dye and 2-mercaptopyridine as a GSH-reactive site and fluorescence quencher. In the presence of GSH, the 2-mercaptopyridine functionality of probe 1 was replaced by the thiolate group of GSH through a nucleophilic substitution reaction with a fluorescence increase at 818 nm. The probe was found to be highly selective for GSH over Hcy, Cys, and other tested potential interferants, including ROS and metal ions. In addition, probe 1 successfully displayed fluorescence changes in response to changing the GSH concentrations in MDA-MB-231 cells in the presence of external agents i.e., N-acetyl-l-cysteine (NAC; as GSH inducer) or buthionine sulfoximine (BSO; as GSH inhibitor). We envision that probe 1 will serve as a promising sensing tool for monitoring the changes of the GSH level and the understanding of the roles of GSH under physiological and pathological conditions.

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Project description: Not available

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Cysteine and homocysteine as biomarker of various diseases

Project description:Abstract Cysteine and homocysteine (Hcy), both sulfur?containing amino acids (AAs), produced from methionine another sulfur?containing amino acid, which is converted to Hcy and further converted to cysteine. This article aims to highlight the link between cysteine and Hcy, and their mechanisms, important functions, play in the body and their role as a biomarker for various types of diseases. So that using cysteine and Hcy as a biomarker, we can prevent and diagnose many diseases. This review concluded that hyperhomocysteinemia (elevated levels of homocysteine) is considered as toxic for cells and is associated with different health problems. Hyperhomocysteinemia and low levels of cysteine associated with various diseases like cardiovascular diseases (CVD), ischemic stroke, neurological disorders, diabetes, cancer like lung and colorectal cancer, renal dysfunction?linked conditions, and vitiligo. Cysteine and homocysteine, both sulfur?containing amino acids (AAs) produced from methionine another sulfur?containing amino acid, which is converted to homocysteine and further converted to cysteine. The aim of this article is to highlight the link between cysteine and homocysteine, and their mechanisms, important functions, play in the body and their role as a biomarker for various different types of diseases. Hyperhomocysteinemia (elevated levels of homocysteine) is considered as toxic for cells and is associated with different health problems. Not only hyperhomocysteinemia but also low levels of cysteine in most cases is used as a biomarker for various diseases like cardiovascular diseases (CVD), ischemic stroke, neurological disorders, diabetes, cancer like lung and colorectal cancer, renal dysfunction?linked conditions, and vitiligo.

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A Simple and Effective Ratiometric Fluorescent Probe for the Selective Detection of Cysteine and Homocysteine in Aqueous Media.

Project description:Biothiols such as cysteine (Cys) and homocysteine (Hcy) are essential biomolecules participating in molecular and physiological processes in an organism. However, their selective detection remains challenging. In this study, ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate (NL) was synthesized as a ratiometric fluorescent probe for the rapid and selective detection of Cys and Hcy over glutathione (GSH) and other amino acids. The fluorescence intensity of the probe in the presence of Cys/Hcy increased about 3-fold at a concentration of 20 equiv. of the probe, compared with that in the absence of these chemicals in aqueous media. The limits of detection of the fluorescent assay were 0.911 ?M and 0.828 ?M of Cys and Hcy, respectively. ¹H-NMR and MS analyses indicated that an excited-state intramolecular proton transfer is the mechanism of fluorescence sensing. This ratiometric probe is structurally simple and highly selective. The results suggest that it has useful applications in analytical chemistry and diagnostics.

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Direct detection of homocysteine.

Project description:Homocysteine (Hcy) is a biomarker for significant disorders including Alzheimer's and cardiovascular disease. The monitoring of Hcy levels in plasma is of current concern. We describe highly selective colorimetric methods for the direct detection of Hcy. Inexpensive, commercially available materials are employed. The results show potential application for the detection of Hcy in human blood plasma.

| S-EPMC3376413 | biostudies-literature

Differences in heterocycle basicity distinguish homocysteine from cysteine using aldehyde-bearing fluorophores.

Project description:We report the detection of homocysteine over cysteine based upon characteristic differences between 5- and 6-membered heterocyclic amines formed upon reaction with aldehyde-bearing compounds. Homocysteine-derived thiazinane-4-carboxylic acids are more basic than cysteine-derived thiazolidines-4-carboxylic acids. Fluorescence enhancement in response to homocysteine is achieved by tuning pH and excitation wavelength.

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pH-Dependent Fluorescent Probe That Can Be Tuned for Cysteine or Homocysteine.

Project description:The very close structural similarities between cysteine and homocysteine present a great challenge to achieve their selective detection using regular fluorescent probes, limiting the biological and pathological studies of these two amino thiols. A coumarin-based fluorescent probe was designed featuring pH-promoted distinct turn-on followed by ratiometric fluorescence responses for Cys and turn-on fluorescence response for Hcy through two different reaction paths. These specific responses demonstrate the activity differences between Cys and Hcy qualitatively for the first time. The probe could also be used for Cys and Hcy imaging in living cells.

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Ratiometric measurement of hydrogen sulfide and cysteine/homocysteine ratios using a dual-fluorophore fragmentation strategy.

Project description:Hydrogen sulfide (H2S) is an integral signaling molecule in biology with complex generation, translocation, and metabolism processes that are intertwined with cellular thiols. Differentiating the complex interplay between H2S and biological thiols, however, remains challenging due to the difficulty of monitoring H2S and thiol levels simultaneously in complex redox environments. As a step toward unraveling the complexities of H2S and thiols in sulfur redox homeostasis, we present a dual-fluorophore fragmentation strategy that allows for the ratiometric determination of relative H2S and cysteine (Cys) or homocysteine (Hcy) concentrations, two important metabolites in H2S biosynthesis. The key design principle is based on a nitrobenzofurazan-coumarin (NBD-Coum) construct, which fragments into spectroscopically differentiable products upon nucleophilic aromatic substitution with either H2S or Cys/Hcy. Measurement of the ratio of fluorescence intensities from coumarin and the NBD-Cys or NBD-Hcy adducts generates a sigmoidal response with a dynamic range of 3 orders of magnitude. The developed scaffold displays a rapid response (<1 min) and is selective for sulfhydryl-containing nucleophiles over other reactive sulfur, oxygen, and nitrogen species, including alcohol- and amine-functionalized amino acids, polyatomic anionic sulfur species, NO, and HNO. Additionally, NBD-Coum is demonstrated to differentiate and report on different oxidative stress stimuli in simulated sulfur pools containing H2S, Cys, and cystine.

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