Saligenin analogs of sympathomimetic catechol amines

Collin, D. T.; Hartley, David J.; Jack, David; Lunts, L. H. C.; Press, Jeffrey; Ritchie, Alexander C.; Toon, P.

doi:10.1021/jm00298a022

Cited by 56 publications

(22 citation statements)

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“…2 Electrically stimulated inotropic response (Lands et al, 1967a,b). Our results provided strong support for this supposition and our conclusion was that Pl-and P2-adrenoceptor proteins are chemically different and, since at that time we assumed that P-adrenoceptor agonists interact directly with adenylate cyclase, that the enzyme might exist in isoenzymic forms with minor differences in their amino acid sequences (Collin et al, 1970). Pl-and P32-adrenoceptor proteins were recently found to vary in much this way.…”

Section: Determinants Of the Potency Of -Adrenoceptor Agonistssupporting

confidence: 76%

The 1990 Lilly Prize Lecture. A way of looking at agonism and antagonism: lessons from salbutamol, salmeterol and other beta‐ adrenoceptor agonists.

Jack¹

1991

Brit J Clinical Pharma

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Section: Determinants Of the Potency Of -Adrenoceptor Agonistssupporting

confidence: 76%

The 1990 Lilly Prize Lecture. A way of looking at agonism and antagonism: lessons from salbutamol, salmeterol and other beta‐ adrenoceptor agonists.

Jack¹

1991

Brit J Clinical Pharma

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“…Previous reports have demonstrated local anaesthetic and adrenergic activity of saligenin and its derivatives [18][19][20]. A search for DNA sequences orthologous to the mouse and rat adrenoceptors in WormBase showed sequences with significant similarity to those encoding multiple receptors in C. elegans such as Dop-1, Ser-5, Ser-7 and Tyra-3.…”

Section: (D) Mechanism Of Saligenin Toxicitymentioning

confidence: 99%

Hydrolysis of aromatic β-glucosides by non-pathogenic bacteria confers a chemical weapon against predators

et al. 2013

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Bacteria present in natural environments such as soil have evolved multiple strategies to escape predation. We report that natural isolates of Enterobacteriaceae that actively hydrolyze plant-derived aromatic b-glucosides such as salicin, arbutin and esculin, are able to avoid predation by the bacteriovorous amoeba Dictyostelium discoideum and nematodes of multiple genera belonging to the family Rhabditidae. This advantage can be observed under laboratory culture conditions as well as in the soil environment. The aglycone moiety released by the hydrolysis of b-glucosides is toxic to predators and acts via the dopaminergic receptor Dop-1 in the case of Caenorhabditis elegans. While soil isolates of nematodes belonging to the family Rhabditidae are repelled by the aglycone, laboratory strains and natural isolates of Caenorhabditis sp. are attracted to the compound, mediated by receptors that are independent of Dop-1, leading to their death. The b-glucosides-positive (Bgl þ ) bacteria that are otherwise non-pathogenic can obtain additional nutrients from the dead predators, thereby switching their role from prey to predator. This study also offers an evolutionary explanation for the retention by bacteria of 'cryptic' or 'silent' genetic systems such as the bgl operon.

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“…As a general rule, isoproterenol analogs in which the meta-OH is retained and the para-OH is replaced by a "OH-simulating" group are $-adrenoreceptor antagonists or they are only very weak agonists (26,27 of an ordered water crust that interacts with adenylate cyclase to induce a specific and highly favored conformational perturba tion of this enzyme that may be involved in 3-adrenergic receptor actions (76,77,78). In fact, structure-activity relationships based on measurement of the ability of catecholamines to bind to the 3-receptor 'and activate or inhibit adenylate cyclase in mem branes of turkey erythrocytes corresponds closely with those derived using guinea pig tissue (79,80).…”

Section: Modification Of the Catechol Systemmentioning

confidence: 99%

“…The salicylic acid derivative, i.e. a congener bearing a meta-COOH group, is described as "inactive" (27). Clearly, a methylene bridge between the ring and sulfonyl group affords maximum 3-adrenergic agonist potency.…”

Section: -Adrenergic Antagonistmentioning

confidence: 99%

New Aspects of β-Adrenergic Bronchodilator Drugs

Kaiser¹

1980

ACS Symposium Series

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Although bronchoconstriction caused by contraction of bron chiolar muscles is only one of several factors involved in asthma, drugs that induce relaxation of these muscles are frequently used in therapy. Agents that cause bronchiolar muscle relaxation may act by several different modes as suggested by the biochemical mechanism of smooth muscle relaxation (1). Such agents include a group of adrenergic receptor agonists. In mild and occasional episodic asthma, bronchoconstriction and its resultant symptoms are easily reversed by administration of effective β-adrenorecep tor activators. Such agents also find some utility in alleviation of respiratory distress in emphysema and bronchitis. Some more recent aspects of such adrenergic bronchodilators, i.e., compounds that are structurally related to the natural hormones and neuro transmitters norepinephrine (1a) and epinephrine (1b), are the subject of this review.Classification of adrenergic receptors into α and β subtypes (2) is now generally accepted. On the basis of differences in response to selective agonists (3, 4, 5) and antagonists (6, 7), Lands and his associates (3, 4, 5, 8) further subdivided the β receptors into two groups, i.e., β 1 and β 2 -drenoreceptors. Acti vation of β 2 -drenoreceptors causes relaxation of smooth muscle in bronchi, uterus and vasculature, decreases tension in some skele tal muscle, and mediates glycolysis and glycogenolysis.Responses mediated by interaction with 3i~adrenoreceptors are increased force and rate of contraction of cardiac muscle, dilation of coro nary blood vessels (9, 10), relaxation of smooth muscle in the alimentary tract, and lipolysis.Epinephrine, administered either by injection or inhalation, is still employed to relieve bronchoconstriction in bronchial asthma. Isoproterenol (lc), the prototype of 3-adrenergic recep tor agonists, because of its greater potency and selectivity has largely replaced epinephrine as an inhaled bronchodilator. This synthetic analog of epinephrine also lacks selectivity.It is almost equally effective in activating both βχ and $2~a c * rener gi c receptors. Thus, it not only produces a powerful bronchodilating 0-8412-0536-l/80/47-118-251$08.25/0

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Saligenin analogs of sympathomimetic catechol amines

Cited by 56 publications

References 0 publications

The 1990 Lilly Prize Lecture. A way of looking at agonism and antagonism: lessons from salbutamol, salmeterol and other beta‐ adrenoceptor agonists.

The 1990 Lilly Prize Lecture. A way of looking at agonism and antagonism: lessons from salbutamol, salmeterol and other beta‐ adrenoceptor agonists.

Hydrolysis of aromatic β-glucosides by non-pathogenic bacteria confers a chemical weapon against predators

New Aspects of β-Adrenergic Bronchodilator Drugs

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