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Dopamine 4-O-Sulfate

(Synonyms: DA-4S, Dopamine 4-Sulfate) 目录号 : GC49516

An inactive metabolite of dopamine

Dopamine 4-O-Sulfate Chemical Structure

Cas No.:38339-02-5

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产品描述

Dopamine 4-O-sulfate is an inactive metabolite of the catecholamine dopamine .1,2 It is formed from dopamine by the sulfotransferase (SULT) isoform SULT1A3.3 Dopamine 4-O-sulfate is found at lower levels in the brain and circulation than dopamine 3-O-sulfate .1,3

1.Suominen, T., Uutela, P., Ketola, R.A., et al.Determination of serotonin and dopamine metabolites in human brain microdialysis and cerebrospinal fluid samples by UPLC-MS/MS: Discovery of intact glucuronide and sulfate conjugatesPLoS One8(6)e68007(2013) 2.Kyncl, J.J., Buckner, S.A., Brondyk, H., et al.Adrenergic and dopaminergic properties of dopamine sulfoconjugatesJ. Cardiovasc. Pharmacol.7(6)1198-1204(1985) 3.ItÄaho, K., Alakurtti, S., Yli-Kauhaluoma, J., et al.Regioselective sulfonation of dopamine by SULT1A3 in vitro provides a molecular explanation for the preponderance of dopamine-3-O-sulfate in human blood circulationBiochem. Pharmacol.74(3)504-510(2007)

Chemical Properties

Cas No. 38339-02-5 SDF Download SDF
别名 DA-4S, Dopamine 4-Sulfate
Canonical SMILES O=S(O)(OC1=CC=C(CCN)C=C1O)=O
分子式 C8H11NO5S 分子量 233.2
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Research Update

The separation and identification of dopamine 3-O-sulfate and Dopamine 4-O-Sulfate in urine of Parkinsonian patients

J Pharmacol Exp Ther 1975 Dec;195(3):441-52.PMID:1195131doi

A method is described for the isolation and measurement of dopamine 3-O-sulfate and Dopamine 4-O-Sulfate. The sulfate isomers of dopamine were synthesized chemically by the reaction of dopamine with sulfuric acid. The isomers were isolated by anion-exchange column chromatography and the identities of the two isomers were confirmed by gas chromatography coupled with mass spectrometry. A method is described for the assay of the two isomers by high-pressure liquid chromatography. When Parkinsonian patients were treated with 4.0 g/day of L-dopa, the amount of dopamine 3-O-sulfate excreted in the urine was 19.6 times that of Dopamine 4-O-Sulfate. When untreated Parkinsonian patients received tracer quantities of 3H-L-dopa either intravenously or orally, 3H-dopamine 3-O-sulfate was the predominant isomer but the amounts were only 3 times those of the 4-isomer. Greater quantities of both isomers were excreted when 3H-L-dopa was given orally as compared to intravenous administration. Since dopamine 3-O-sulfate is the predominant sulfate isomer, it is concluded that sulfate conjugation of dopamine could possibly compete with 3-O-methylation in determining the resultant conjugated product.

Direct measurement of dopamine O-sulfate in plasma and cerebrospinal fluid

J Chromatogr 1987 Jan 23;413:17-23.PMID:3558665DOI:10.1016/0378-4347(87)80209-8.

This paper describes a method for measurement of dopamine 3-O-sulfate (DA3S) and Dopamine 4-O-Sulfate (DA4S) in dog and human plasma and dog cerebrospinal fluid. C18 solid-phase extraction columns were utilized for sample preparation. DA3S and DA4S were separated by high-performance liquid chromatography and then quantified by dual-electrode electrochemical detection. [3H]Dopamine O-sulfate (DAS) was used as internal standard. Recovery of authentic DAS added to dog plasma and carried through the entire procedure was 49.9 +/- 6.3% for DA3S (n = 9) and 42.2 +/- 4.3% for DA4S (n = 8). The lower limit of detection (signal-to-noise ratio of 3) was 20 fmol for each DAS isomer. The within-assay coefficient of variation for DA3S in dog plasma averaged 5.8% (range 2.0-12%, n = 5). The between-assay coefficient of variation for DA3S in dog plasma was 3.8% (n = 3). DAS levels in plasma of conscious dogs were 20.3 +/- 6.9 pmol/ml DA3S and 5.91 +/- 3.5 pmol/ml DA4S (n = 5). Cerebrospinal fluid levels were 3.06 +/- 3.22 pmol/ml DA3S and 0.10 +/- 0.18 pmol/ml DA4S in dogs anesthetized with methoxyflurane and nitrous oxide (n = 3). This procedure is also appropriate for use with human plasma; DAS levels were 24.3 +/- 12.8 pmol/ml DA3S and 9.07 +/- 3.9 pmol/ml DA4S (n = 6).

Plasma levels and renal clearance of two isomers of dopamine sulfate in patients with essential hypertension

Clin Exp Hypertens A 1988;10(4):561-74.PMID:3390960DOI:10.3109/10641968809033909.

Two isomers of dopamine sulfate, dopamine 3-O-sulfate(3-O-S) and Dopamine 4-O-Sulfate(4-O-S), in the plasma and urine of patients with essential hypertension and normotensive controls were measured by HPLC-fluorometry. The plasma level of 3-O-S was significantly higher in patients with essential hypertension than in normotensive controls (20.9 +/- 2.2 pmol/ml and 16.3 +/- 1.4 pmol/ml respectively, p less than 0.05) and the plasma levels of 4-O-S were slightly increased in hypertensive patients. The plasma level of 3-O-S was correlated with the serum level of creatinine in both normotensives and hypertensives. In hypertensives, the plasma level of 3-O-S was also correlated with that of noradrenaline. However the creatinine clearances were similar in the two groups, the urinary clearance of 3-O-S was slightly lower in patients with essential hypertension than in normotensive controls. These data indicate that the plasma level of 3-O-S is elevated in essential hypertension because of the abnormality in dopaminergic metabolism and renal disturbance in its excretion.

Sample preparation procedure for determination of dopamine sulfate isomers in human urine by high-performance liquid chromatography with dual-electrode electrochemical detection

J Chromatogr 1986 Sep 5;381(2):241-8.PMID:3760083DOI:10.1016/s0378-4347(00)83590-2.

We developed a procedure utilizing small columns of solid-phase extraction material for sample preparation for the determination of dopamine sulfate (DAS) isomers in human urine. Processed sample is then subjected to high-performance liquid chromatography (HPLC) with dual-series-electrode electrochemical detection. Dopamine 3-O-sulfate (DA-3-S) and Dopamine 4-O-Sulfate (DA-4-S) were determined using two different HPLC systems. The ratio of the urinary excretion rate of DA-3-S to DA-4-S was relatively constant, but the 24-h excretion rates of total DAS varied widely among individuals. This method should prove useful in future studies concerning the metabolic and physiologic roles of DAS isomers.