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DL-Cystathionine (hydrochloride) Sale

(Synonyms: DL-Allocystathionine) 目录号 : GC43486

An intermediate in cysteine synthesis

DL-Cystathionine (hydrochloride) Chemical Structure

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产品描述

DL-Cystathionine is an intermediate in the synthesis of cysteine that is produced from homocysteine and serine by the action of cystathionine-β-synthase (CBS). CBS can also mediate the condensation of cysteine with homocysteine to produce cystathionine and hydrogen sulfide. An excess of cystathionine in the urine, resulting from a congenital deficiency of cystathionase or an acquired deficiency of vitamin B6, is a hallmark of cystathioninuria.

Chemical Properties

Cas No. SDF
别名 DL-Allocystathionine
Canonical SMILES OC(C(N)CCSCC(N)C(O)=O)=O.Cl.Cl
分子式 C7H14N2O4S•2HCl 分子量 295.2
溶解度 PBS (pH 7.2): 0.25 mg/mL 储存条件 Store at -20°C
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1 mM 3.3875 mL 16.9377 mL 33.8753 mL
5 mM 0.6775 mL 3.3875 mL 6.7751 mL
10 mM 0.3388 mL 1.6938 mL 3.3875 mL
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Research Update

A sensitive UPLC-MS/MS method for simultaneous quantification of one-carbon metabolites & co-factors in human plasma

J Pharm Biomed Anal 2022 Sep 20;219:114944.PMID:35863169DOI:10.1016/j.jpba.2022.114944.

One-carbon metabolism is an important metabolic pathway involved in many diseases, such as congenital malformations, tumours, cardiovascular diseases, anaemia, depression, cognitive diseases and liver disease. However, the current methods have specific defects in detecting and qualifying the related compounds of one-carbon metabolism. In this study, a validated method was established to simultaneously quantify 22 one-carbon metabolites & co-factors in human plasma and applied to the study of correlation between one-carbon metabolism and colorectal cancer in human plasma samples, which were from 44 healthy subjects and 55 colorectal cancer patients. The method used ultra-high performance liquid chromatography coupled with triple quadrupole mass spectrometry (UPLC-MS/MS), and the analytes included betaine, L-carnitine, L-cystathionine, L-cysteine, dimethylglycine, DL-homocysteic acid, homocysteine, methionine, pyridoxal hydrochloride, pyridoxamine dihydrochloride, pyridoxine dihydrochloride, S-(5'-Adenosyl)-L-homocysteine, serine, choline chloride, folic acid, glycine, pyridoxal phosphate monohydrate, riboflavin, taurine, 5-methyltetrahydrofolate, S-(5'-adenosyl)-L-methionine disulfate salt, trimethylamine oxide. The developed method was successfully applied to the quantification of 22 one-carbon metabolites & co-factors in human plasma from colorectal cancer patients and healthy individuals. The plasma concentrations of dimethylglycine was significantly decreased in the patients compared with the healthy individuals, while L-cystathionine was increased.

Studies on a 2,3-diaminopropionate: ammonia-lyase from a Pseudomonad

Hoppe Seylers Z Physiol Chem 1975 Feb;356(2):193-201.PMID:240767DOI:10.1515/bchm2.1975.356.1.193.

2,3-Diaminopropionate:ammonia-lyase, an induced enzyme in a Pseudomonas isolate, has been purified 40-fold and found to be homogeneous by disc gel electrophoresis and by ultracentrifugation. Some of its properties have been studied. The optimum pH and temperature for activity are 8 and 40 degrees C, respectively. The enzyme shows a high degree of substrate specificity, acting only on 2,3-diaminopropionate; the D-isomer is only one-eighth as effective as the L-form. L-Homoserine and DL-Cystathionine are not substrates, and 3-cyanolalanine does not inhibit its activity. It is a pyridoxal phosphate enzyme which requires free enzyme sulphhydryls for activity. The Km values for L-2,3-diaminopropionate and pyridoxal phosphate are 1mM and 25 muM, respectively. The molecular weight of the enzyme is about 80 000 as determined by gel filtration. On treatment with 0.5M urea or guanidine by hydrochloride, the enzyme dissociates into inactive subunits with an approximate molecular weight of 45 000. One mole of the active enzyme binds one mole of pyridoxal phosphate. The bacterial enzyme seems to be quite different in many of its properties from the rat liver enzyme which also exhibits the substrate specificity of cystathionine gamma-lyase.

Possible mechanisms of action of Caesalpinia pyramidalis against ethanol-induced gastric damage

J Ethnopharmacol 2015 Jun 20;168:79-86.PMID:25843020DOI:10.1016/j.jep.2015.03.054.

Ethnopharmacological relevance: Caesalpinia pyramidalis Tul. (Fabaceae), known as "catingueira", is an endemic tree of the Northeast region of Brazil. This plant, mainly inner bark and flowers, has been used in traditional medicine to treat gastritis, heartburn, indigestion, stomachache, dysenteries, and diarrheas. Materials and methods: The ethanol extract of C. pyramidalis inner bark was used in rats via oral route, at the doses of 30, 100, and 300 mg/kg, in the ethanol-induced ulcer model and some of the mechanisms underlying to the gastroprotective effect of this plant investigated. Results: The ethanol extract of C. pyramidalis inner bark (100 mg/kg) produced reduction (P < 0.001) on the total lesion area in the ethanol-induced gastric damage. The gastroprotective response caused by the ethanol extract (100 mg/kg) was significantly attenuated (P < 0.05) by intraperitoneal treatment of rats with DL-Propargylglycine (PAG, a cystathionine-γ-lyase inhibitor; 25 mg/kg), but not by Nw-nitro-L-arginine methyl ester hydrochloride (L-NAME, an inhibitor of nitric oxide synthase; 70 mg/kg), and confirmed by microscopic evidence. The ethanol extract significantly decreased the number of mucosal mast cells compared to vehicle-treated group. The inflammatory cells of the ethanol extract (100 mg/kg)-treated ulcerated rats exhibited an upregulation of interleukin (IL)-4 protein expression and downregulation of inducible nitric oxide synthase (iNOS) expression, observed by immunohistochemistry and flow cytometer. Conclusions: The present results suggest that the ethanol extract of C. pyramidalis produced dose-related gastroprotective response on ethanol-induce ulcer in rats through mechanisms that involved an interaction with endogenous hydrogen sulfide and reduction of inflammatory process with imbalance between pro-inflammatory and anti-inflammatory mediators, supporting the popular usage of this plant.

Fetal Hypothyroidism Impairs Aortic Vasorelaxation Responses in Adulthood: Involvement of Hydrogen Sulfide and Nitric Oxide Cross talk

J Cardiovasc Pharmacol 2021 Feb 1;77(2):238-244.PMID:33165144DOI:10.1097/FJC.0000000000000948.

Thyroid hormones have a wide range of effects on growth, differentiation, evolution, metabolism, and physiological function of all tissues, including the vascular bed. In this study, the effect of fetal hypothyroidism on impairment of aortic vasorelaxation responses in adulthood was investigated with emphasis on possible involvement of hydrogen sulfide (H2S)/nitric oxide interaction. Two groups of female rats were selected. After mating and observation of vaginal plaque, one group received propylthiouracil (200 ppm in drinking water) until the end of pregnancy and another group had no propylthiouracil treatment during the fetal period. In adult rats, aortic relaxation responses to l-arginine and GYY4137 were assessed in the presence or absence of Nω-nitro-L-arginine methyl ester hydrochloride and dl-propargylglycine in addition to the biochemical measurement of thyroid hormones and some related factors. Obtained findings showed a lower vasorelaxation response for GYY4137 and l-arginine in the fetal hypothyroidism group, and preincubation with Nω-nitro-L-arginine methyl ester hydrochloride or dl-propargylglycine did not significantly aggravate this weakened relaxation response. In addition, aortic levels of sirtuin 3, endothelial nitric oxide synthase, cystathionine gamma-lyase, and H2S were significantly lower in the fetal hypothyroidism group. Meanwhile, no significant changes were obtained regarding serum levels of thyroid hormones including free triiodothyronine;, total triiodothyronine, free thyroxine, total thyroxine, and thyroid-stimulating hormone in adult rats. It can be concluded that hypothyroidism in the fetal period has inappropriate effects on the differentiation and development of vascular bed with subsequent functional abnormality that persists into adulthood, and part of this vascular abnormality is mediated through weakened interaction and/or cross talk between H2S and nitric oxide.

The roles of nitric oxide and hydrogen sulfide in the anti-atherosclerotic effect of atorvastatin

J Cardiovasc Med (Hagerstown) 2015 Jan;16(1):22-8.PMID:24933195DOI:10.2459/JCM.0000000000000012.

Aims: To investigate antiatherosclerosis effect of atorvastatin (ATV) in a rat atherosclerosis model, and to explore roles of nitric oxide and hydrogen sulfide (H2S) in this event. Methods: After being fed a high-fat diet, the rats were treated with ATV, ATV combined with cystathionine-γ-lyase (CSE) inhibitor DL-propargylglycine, and ATV combined with endothelial nitric oxide synthase (eNOS) inhibitor N'-nitro-L-arginine-methyl ester hydrochloride from 9 to 12 weeks, respectively. At the end of the experiment, the animals were sacrificed. Pathologic changes of aortic arch were observed to assay the degree of atherosclerotic lesions. Serum total cholesterol (TC), triglyceride, low-density lipoprotein cholesterol (LDL-C), and high-density lipoprotein cholesterol were determined. Further, nitric oxide, total nitric oxide synthase and eNOS, and H2S and CSE were also measured. Results: Compared with the normal control group, serum TC, triglyceride, and LDL-C levels in the model group were significantly elevated (P < 0.05). Pathological result suggested typical atherosclerotic lesions after the high-fat diet. The serum nitric oxide, eNOS, H2S, and CSE significantly decreased (P < 0.05). Quantitative reverse transcription polymerase chain reaction (qRT-PCR) showed that mRNA levels of eNOS and CSE in the aortic arch of the model rats were significantly downregulated (P < 0.05). Actually, ATV significantly ameliorated atherosclerotic lesions. ATV also significantly downregulated increased serum TC and LDL-C, and upregulated decreased serum nitric oxide and eNOS. However, it had no significant effects on serum H2S and CSE (P > 0.05). ATV combined with DL-propargylglycine significantly reduced serum H2S and CSE, and increased serum nitric oxide and eNOS as compared to single ATV treatment (P < 0.05). ATV combined with N'-nitro-L-arginine-methyl ester hydrochloride significantly increased serum TC, LDL-C, H2S, and CSE, and decreased nitric oxide and eNOS as compared to the single ATV (P < 0.05). Conclusions: ATV significantly ameliorates atherosclerotic lesions and enhances the activity of serum nitric oxide system, but not H2S system. The blockage of nitric oxide pathway, but not H2S pathway, significantly weakens antiatherosclerosis of ATV.