Catecholamine sulfates: End products or metabolic intermediates?

Demassieux, S.; Bordeleau, Luc; Gravel, Denis; Carrière, S

doi:10.1016/0024-3205(87)90358-4

Cited by 22 publications

(10 citation statements)

References 15 publications

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“…In addition, scCA have been viewed recently as possible metabolic intermediates and not necessarily end-products of CA metabolism. This is supported by the finding of hydrolyzable CA sulfates in vitro by human aryl sulfatases (12) and by the observation of a decrease in scNE and scE during brief vigorous exercise in healthy subjects (11,13) or during insulin-induced hypoglycemia (14). The mechanism or physiological implication of this interesting fall in sulfate conjugates, however, has remained unclear.…”

mentioning

confidence: 67%

Sulfoconjugated and free plasma catecholamine levels at rest and during exercise in patients with idiopathic dilated cardiomyopathy

Dobnig

Leb²,

Lipp³

et al. 1995

European Journal of Endocrinology

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Plasma levels of sulfoconjugated (sc) catecholamines (CA) have been shown to be increased with activation of the sympathoadrenal system in a number of clinical settings. We evaluated the relation between scCA and clinical or hemodynamic parameters of patients with idiopathic dilated cardiomyopathy (IDC) at rest and during incremental exercise testing. Eleven healthy subjects, nine patients in New York Heart Association (NYHA) functional class I (IDC-A group) and 11 in NYHA functional class II and III (IDC-B group) performed a symptom-limited, graded bicycle exercise test. Resting, peak and various postexercise levels of plasma free and scCA were determined by high-pressure liquid chromatography. Resting CA levels obtained in the supine position were remarkable for elevations of free norepinephrine (NE) in IDC-B patients (355 +/- 157 ng/l) as compared to IDC-A patients (177 +/- 54, p = 0.006) or healthy controls (193 +/- 74, p = 0.007). Similarly, scNE was highest in IDC-B patients with 1856 +/- 1089 ng/l, followed by IDC-A (1028 +/- 187, p = 0.025) and control subjects (1109 +/- 440, p = 0.025). There was a highly significant correlation between free and scNE (r = 0.76, p < 0.0005). Whereas resting free dopamine (DA) levels were comparable in all three groups, scDA was found to be elevated clearly in IDC-B patients (8772 +/- 2097 ng/l) and significantly different to IDC-A (5786 +/- 2481, p = 0.01) or control subjects (4892 +/- 1575, p = 0.0005). The NYHA functional class and maximum exercise performance correlated best with resting scDA (r = 0.68, p = 0.001 and r = 0.56, p = 0.005, respectively). At peak exercise, IDC-B patients exhibited a significant decrease in scNE and sc epinephrine (E) (from 1856 +/- 1089 to 1495 +/- 932 ng/l, p < 0.005 and from 491 +/- 173 to 282 +/- 143 ng/l, p < 0.01) compared to controls (from 1109 +/- 444 to 1094 +/- 548 ng/l and from 379 +/- 200 to 329 +/- 134 ng/l). In IDC-B patients this decrease in scNE and scE at peak exercise was related inversely to the rise in free NE and E (r = -0.81, p < 0.005 and r = -0.68, p < 0.05). Resting hemodynamic indices generally were reflected better by some free CA rather than by conjugated forms or by parameters of clinical performance. These findings suggest that in addition to free or scNE levels, resting scDA is elevated in symptomatic patients with IDC.(ABSTRACT TRUNCATED AT 400 WORDS)

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mentioning

confidence: 67%

Sulfoconjugated and free plasma catecholamine levels at rest and during exercise in patients with idiopathic dilated cardiomyopathy

Dobnig

Leb²,

Lipp³

et al. 1995

European Journal of Endocrinology

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“…36) And dopamine sulfate is partially hydrolyzed by human arylsulfatase A, B and C in vitro, then converted to dopamine. 14) From the physiological study of free and sulfated dopamine during exercise, Yoshizumi et al found a positive relationship between free dopamine and the conjugated form in plasma, 37) which suggests that dopamine-4-Osulfate, not dopamine-3-O-sulfate, 38) acts as a reservoir of dopamine.…”

Section: Discussionmentioning

confidence: 99%

“…13) One study, however, found that sulfate conjugated dopamine has no physiological activity. 14) From the viewpoint of free radical chemistry, dopamine can serve electrons via its oxidation pathway (Chart 1). This enables dopamine to act as both an antioxidant and a prooxidant.…”

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confidence: 99%

Electron Paramagnetic Resonance Study on Free Radical Scavenging and/or Generating Activity of Dopamine-4-O-sulfate.

Kirima

Tsuchiya

Yoshizumi

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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With the increasing understanding of the cytotoxicity of free radicals and other reactive oxygen species as a major cause of human disease and aging, the roles of endogenous antioxidants have drawn attentions. Uric acid, 1) vitamin E, 2) vitamin C, 3) ubiquinone, 4) SH-compounds, 5) bilirubin, 6) and pyruvate 7) are recognized as endogenous non-enzymatic antioxidants, while catalase, superoxide dismutase and glutathione peroxidase are known to be enzymatic antioxidants.Dopamine is the immediate metabolic precursor of norepinephrine and epinephrine. Dopamine interacts with dopamine receptors, then exerts its pharmacological effects.In human and experimental animals, dopamine is present almost entirely as a sulfate conjugated form in the circulation, 8,9) and very little of the free form is presented in the plasma.10) The physiological roles of sulfate conjugated dopamine are still unclear. Pharmacologically, conjugated dopamine has convulsive effects, 11) inhibits aldosterone secretion from cultured bovine adrenal cells, 12) and induces a constriction of some vascular beds. 13) One study, however, found that sulfate conjugated dopamine has no physiological activity. 14)From the viewpoint of free radical chemistry, dopamine can serve electrons via its oxidation pathway (Chart 1). This enables dopamine to act as both an antioxidant and a prooxidant. It acts as an antioxidant by scavenging free radicals. [15][16][17] Recently, it was found that dopamine spontaneously react with molecular oxygen to produce reactive oxygen species and semiquinone dopamine radical, 18,19) which are toxic to catecholamine neurons. [20][21][22][23] However, there is no evidence that sulfate conjugated dopamine acts as an antioxidant or a prooxidant. Therefore, in the present report, we compared dopamine and dopamine-4-O-sulfate for susceptibility to enzymatic and non-enzymatic oxidization in vitro using alkaline solution, horseradish peroxidase, UV irradiation, hydroxyl radical, superoxide anion radical, and sodium periodate. ExperimentalChemicals Dopamine, hypoxanthine, xanthine oxidase (from butter milk), and peroxidase (from horseradish) were purchased from Sigma Chemical Co., (MO, U.S.A.), hydrogen peroxide from Wako Pure Chemical Industries Ltd. (Osaka, Japan), and sodium metaperiodate from Acros Organics (NJ, U.S.A.). Dopamine-4-O-sulfate was kindly donated by Kyowa Hakko Kogyo Co., Ltd. (Tokyo, Japan). Other reagents were of the highest quality available from Wako Pure Chemical Industries Ltd.Free Radical Analysis Using EPR Spectroscopy The free radical metabolites of dopamine and dopamine-4-O-sulfate were examined with an EPR spectrometer (JES-TE 300, JEOL Co., Ltd., Tokyo, Japan) equipped with a cavity and an aqueous quartz flat cell (JEOL Co., Ltd., Tokyo, Japan) at X-band (9.5 GHz). EPR data were analyzed by a computer (HP Apollo 9000 Series 400) with the software, ESPRIT 432 ( JEOL Co., Ltd., Tokyo, Japan). Typical operating conditions of the EPR spectrometer were: power, 5 mW; center field, 3360 G; sweep width, 20 G; modulat...

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“…1983). Conjugates of DA have recently attracted much attention because these metabolites were reported to be transformed to free norepinephrine (NE) by a dopamine P-hydroxylase (Buu & Kuchel 1979) and may also be converted to free DA by a deconjugation pathway (Demassieux et al 1987). In general, catecholamines (CA) administered intravenously are mainly metabolized by 0-methylation while the contribution of sulfoconjugation in relation to 0-methylation and deamination is unknown.…”

Section: Introductionmentioning

confidence: 99%

Dopamine Infusion in Healthy Subjects and Critically Ill Patients

Ratge

Steegmüller

Mikus

et al. 1990

Clin Exp Pharma Physio

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1. Little is known about the metabolism and the pharmacokinetics of dopamine (DA) in critically ill patients. To study the influence of the total administered DA dose on the disposition of free (i.e. unconjugated) and sulfoconjugated DA, plasma levels of free and sulfoconjugated DA were measured following infusion of 5 micrograms DA/kg per min for 0.5 and 3 h in six healthy volunteers and in eight critically ill patients receiving DA at the same infusion rate for 6.5 to 329 h. 2. In patients and volunteers steady state concentrations of free DA showing fairly large inter-individual variations (12.4-73.4 micrograms/L) were reached within 10 min of the beginning of the infusion. 3. DA sulfate was generated immediately. In volunteers peak values of the sulfoconjugate were observed 15-60 min after the termination of the DA infusion. In patients steady state concentrations of conjugated DA (63-80 micrograms/L) were reached within 5-10 h of DA infusion. 4. The initial half-life (t1/2 alpha), the terminal elimination half life (t1/2) and the distribution volume of free DA in the volunteers were significantly higher after 3 h of the DA infusion as compared to the shorter infusion. These parameters as well as the total plasma clearance of free DA were independent of the length of the DA infusion period in patients. The large distribution volumes of 19.8-75 L/kg indicate that DA has been taken up by peripheral tissues. 5. Substantial inter-individual variations in the patients' clearance of free DA (3.9-16.5 L/kg per h) may partly explain the variability in haemodynamic responses to DA infusion reported in clinical studies.(ABSTRACT TRUNCATED AT 250 WORDS)

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Catecholamine sulfates: End products or metabolic intermediates?

Cited by 22 publications

References 15 publications

Sulfoconjugated and free plasma catecholamine levels at rest and during exercise in patients with idiopathic dilated cardiomyopathy

Sulfoconjugated and free plasma catecholamine levels at rest and during exercise in patients with idiopathic dilated cardiomyopathy

Electron Paramagnetic Resonance Study on Free Radical Scavenging and/or Generating Activity of Dopamine-4-O-sulfate.

Dopamine Infusion in Healthy Subjects and Critically Ill Patients

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