Chemical structure and biological activity of catecholamines

Pratesi, P

doi:10.1351/pac196306030435

Cited by 12 publications

(3 citation statements)

References 5 publications

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“…Few chemical reactions have been hypothesized to account for catecholamine binding to biological receptive sites. Separate lines of evidence suggest that in some systems the CAT moiety of catecholamines is important in mediating physiological effects (Pratesi, 1963;Woodruff, 197 1, 1978;Pinnock, 1983). However, only a few potential CATbased chemical interactions such as metal complexation (Maas and Colburn, 1965;Rajan et al, 1971;Bogges and Martin, 1975;Kaiser and Jain, 1985;Youdim, 1985), complexation with nucleotides (Granot and Fiat, 1977;Grol, 1979), amine side-chain acidbase reactivity (Katz et al, 1977;Kaiser and Jain, 1985;Strader et al, 1987Strader et al, , 1989Dohlman et al, 1988), and CAT hydrogen bonding (Strader et al, 1989) have been suggested as potential chemical mechanisms.…”

Section: Biochemical Considerationsmentioning

confidence: 99%

Interactions Between the Argininyl Moieties of Neurotensin and the Catechol Protons of Dopamine

Schenk

Morocco

Ziemba

1991

Journal of Neurochemistry

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The interaction between dopamine and neurotensin as well as other Arg-containing peptides was studied to provide more chemical details of how dopamine binds to the neuropeptide neurotensin. The stoichiometry of 1:1, dopamine to neurotensin, was confirmed by additional electroanalytical and ultraviolet-visible spectroscopic studies. By analyses of the 205- to 340-nm difference spectra of fixed concentrations of dopamine in the presence of increasing amounts of neurotensin, the dissociation constant of the interaction was found to be 5.9 x 10(-8) mol/L. This finding confirmed (by a second physical method) the previously reported KD value obtained by electroanalytical techniques. The associations between dopamine and neurotensin as well as the neurotensin fragment Pro7-Arg8-Arg9-Pro10 were found to be pH dependent when the dissociation constant was measured as a function of pH (in 150 mmol/L NaCl). The results of studies of the formal potential of dopamine in the presence of Arg and Arg-containing peptides confirmed that catechol protons are directly involved in the association and that the chemical species of dopamine associated with neurotensin is a catecholate form. The (pseudo)-first-order rate constant of dissociation of the complex at pH 7.6, measured by the chronoamperometric and rotating disk electroanalytical techniques, was found to be approximately 10(5) s-1, indicating that the rate of formation of the complex is under diffusion control. A hypothetical chemical structure of the neurotensin-dopamine complex is suggested.

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Section: Biochemical Considerationsmentioning

confidence: 99%

Interactions Between the Argininyl Moieties of Neurotensin and the Catechol Protons of Dopamine

Schenk

Morocco

Ziemba

1991

Journal of Neurochemistry

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“…It was therefore considered of interest to investigate more closely the relative nicotine-like properties of the quaternary derivatives of tyramine and dopamine and of the quaternary derivative of noradrenaline (2; R=W=OH), which has recently been reported to be practically free from adrenergic effects (Pratesi, 1962). Some experiments with ethyltrimethylammonium and choline were also included for comparison.…”

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confidence: 99%

Relative Actions of Quaternary Methyl Derivatives of Tyramine, Dopamine and Noradrenaline

Cuthbert

1964

British Journal of Pharmacology and Chemotherapy

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Tyramine methiodide and dopamine methobromide have greater pressor effect (three-to five-times) in the spinal cat than the parent amines. Noradrenaline methochloride has little pressor effect. Dopamine methobromide is about four times as potent as nicotine; tyramine methiodide is about equiactive to nicotine; and noradrenaline methochloride has only one-tenth the potency of nicotine. Their pressor effects are usually abolished by hexamethonium but in some experiments the effect of noradrenaline methochloride persisted and was then abolished by tolazoline. Injected intravenously into the cat anaesthetized with chloralose, each of the three quaternary derivatives contracts the nictitating membrane; dopamine methobromide is again the most active, having more than six times the potency of nicotine. When the contractions of the nictitating membrane are induced by continuous stimulation of the preganglionic fibres of the cervical sympathetic nerve, intravenous injection of the quaternary derivatives of tyramine and dopamine has a biphasic effect; there is a block on which a contraction of the membrane appears to be superimposed. Noradrenaline methochloride produces only a further contraction of the membrane.On the isolated rectus abdominis muscle preparation of the frog, dopamine methobromide is the most active in contracting the muscle, being about twelve times as active as nicotine; noradrenaline methochloride is weakest, having only onehundredth the activity of nicotine. These effects are antagonized by hexamethonium. On the isolated phrenic nerve-diaphragm preparation of the rat, the quaternary derivatives of tyramine and dopamine each have neuromuscular blocking properties, 0.7-and 3-times respectively that of nicotine. Noradrenaline methochloride has no effect. In the sciatic nerve-tibialis preparation of the cat, the quaternary derivatives of tyramine and dopamine are approximately equipotent in producing neuromuscular paralysis, having about three times the activity of nicotine and one-fifth that of suxamethonium. These effects are not antagonized either by neostigmine or by edrophonium. Noradrenaline methochloride has no neuromuscular blocking effect.The nicotine-like properties of these quaternized sympathomimetic amines are discussed. It is of interest that the presence of an hydroxyl group attached to the /-carbon atom of the side-chain greatly reduces nicotine-like activity. By comparison, choline had about one forty-fifth the pressor activity of ethyltrimethylammonium.The elucidation of the chemical structure of adrenaline, at the end of the last century, stimulated the synthesis of a number of related compounds. Dakin (1905), in examining the activity of a series of these compounds, noted that the quaternary compound (1) HO HO O. -CH2N(CH3)3 aC

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“…This has been found to be true for directly acting agents (Patil, LaPidus & Tye, 1970). The absolute configuration of many catecholamines and related compounds has been determined by chemical methods (Pratesi, 1963). The stereoselective preference of adrenergic receptors for optical isomers of both catecholamines and directly acting analogues having the R configuration is well established (Table 3).…”

Section: (D) Stereoselectivitymentioning

confidence: 94%

The molecular structure of adrenergic and dopaminergic substances

Giesecke

Hebert

1979

Quart. Rev. Biophys.

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At the end of the last century it was established that the different nerve cells along a neuronal path do not come into direct physical contact with one another, but that there are narrow gaps between them, called synapses (Sherrington, 1897; Ramón y Cajal, 1906). Elliot (1905) made the basic experimental observation that the propagation of nerve impulses across a synapse might be mediated by specific chemical agents (see Fig. i). Such substances are now called neurotransmitters, and some 20 different compounds putatively responsible for synaptic transmission in different parts of the nervous system are known at present, e.g. a few recently isolated polypeptides. The most extensively studied transmitters are acetylcholine and the catecholamine group, consisting of dopamine (a), noradrenaline (b), and adrenaline (c).

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Chemical structure and biological activity of catecholamines

Cited by 12 publications

References 5 publications

Interactions Between the Argininyl Moieties of Neurotensin and the Catechol Protons of Dopamine

Interactions Between the Argininyl Moieties of Neurotensin and the Catechol Protons of Dopamine

Relative Actions of Quaternary Methyl Derivatives of Tyramine, Dopamine and Noradrenaline

The molecular structure of adrenergic and dopaminergic substances

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