Biomaterial Database

Structure-activity relationship for the inotropic effect of aromatic methyl-p-quinones. 1990

M Itoigawa, and K Takeya, and H Furukawa

Department of Pharmacology, Aichi Medical University, Aichi-ken, Japan.

The structure-activity relationship of a novel natural substance murrayaquinone-A and related compounds, was studied by evaluating their positive inotropic potencies on guinea-pig papillary muscle in Krebs-Henseleit solution. Among the selected eight compounds, menadione and plumbagin (aromatic methyl-p-quinone) induced a potent triphasic inotropic response, as reported previously for murrayaquinone-A. The order of potency of these active compounds was: plumbagin (pD2 = 6.40) greater menadione (pD2 = 5.70) greater than murrayaquinone-A (pD2 = 5.27). Demethyl derivatives of aromatic methyl-p-quinones (carbazolequinone, 1,4-naphthoquinone and 2-hydroxy-1,4-naphthoquinone) and methyl-benzoquinones (co-enzyme Q10 and 2-methyl-1,4-benzoquinone) did not produce any positive inotropic effect. It is concluded that the presence of the aromatic methyl-p-quinone skeleton is essential for the development of an inotropic response. A common mechanism for this positive inotropic effect is suggested by the fact that in all cases it was triphasic in nature and inhibited in anoxic conditions or by 2,4-dinitrophenol and dicumarol.

UI	MeSH Term	Description	Entries
D008297	Male		Males
D009200	Myocardial Contraction	Contractile activity of the MYOCARDIUM.	Heart Contractility,Inotropism, Cardiac,Cardiac Inotropism,Cardiac Inotropisms,Contractilities, Heart,Contractility, Heart,Contraction, Myocardial,Contractions, Myocardial,Heart Contractilities,Inotropisms, Cardiac,Myocardial Contractions
D010210	Papillary Muscles	Conical muscular projections from the walls of the cardiac ventricles, attached to the cusps of the atrioventricular valves by the chordae tendineae.	Muscle, Papillary,Muscles, Papillary,Papillary Muscle
D002227	Carbazoles	Benzo-indoles similar to CARBOLINES which are pyrido-indoles. In plants, carbazoles are derived from indole and form some of the INDOLE ALKALOIDS.
D005260	Female		Females
D006168	Guinea Pigs	A common name used for the genus Cavia. The most common species is Cavia porcellus which is the domesticated guinea pig used for pets and biomedical research.	Cavia,Cavia porcellus,Guinea Pig,Pig, Guinea,Pigs, Guinea
D000470	Alkaloids	Organic nitrogenous bases. Many alkaloids of medical importance occur in the animal and vegetable kingdoms, and some have been synthesized. (Grant & Hackh's Chemical Dictionary, 5th ed)	Alkaloid,Plant Alkaloid,Plant Alkaloids,Alkaloid, Plant,Alkaloids, Plant
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D016227	Benzoquinones	Benzene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	1,2-Benzoquinones,1,4-Benzoquinones,Benzodiones,2,5-Cyclohexadiene-1,4-Diones,o-Benzoquinones,p-Benzoquinones