Biomaterial Database

Inhibition of dihydropteroate synthetase from Escherichia coli by sulfones and sulfonamides. 1973

J L McCullough, and T H Maren

The inhibitory action of various diphenylsulfones and sulfonamides on dihydropteroate synthetase partially purified from Escherichia coli was examined. 4,4'-Diaminodiphenylsulfone (DDS; I(50) = 2 x 10(-5) M) and the monosubstituted derivatives 4-amino-4'-formamidodiphenylsulfone (I(50) = 5.8 x 10(-5) M) and 4-amino-4'-acetamidodiphenylsulfone (I(50) = 5.2 x 10(-5) M) were effective inhibitors of dihydropteroate synthetase activity. Disubstitution of the arylamine groups of DDS (4,4'-diformamidodiphenylsulfone and 4,4'-diacetamidodiphenylsulfone) resulted in complete loss of inhibitory activity. Both DDS (K(I) = 5.9 x 10(-6) M) and sulfadiazine (K(I) = 2.5 x 10(-6) M) were found to be competitive inhibitors of dihydropteroate synthetase. These findings are discussed in regard to the Bell and Roblin theory of structure-activity relationships for p-aminobenzoic acid antagonists.

UI	MeSH Term	Description	Entries
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D011621	Pteridines	Compounds based on pyrazino[2,3-d]pyrimidine which is a pyrimidine fused to a pyrazine, containing four NITROGEN atoms.	1,3,5,8-Tetraazanaphthalene,Pteridine,Pteridinone,Pyrazino(2,3-d)pyrimidine,Pyrazinopyrimidine,Pyrazinopyrimidines,Pyrimido(4,5-b)pyrazine,Pteridinones
D003622	Dapsone	A sulfone active against a wide range of bacteria but mainly employed for its actions against MYCOBACTERIUM LEPRAE. Its mechanism of action is probably similar to that of the SULFONAMIDES which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with PYRIMETHAMINE in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8)	Diaminodiphenylsulfone,Sulfonyldianiline,4,4'-Diaminophenyl Sulfone,Avlosulfone,DADPS,Dapsoderm-X,Dapson-Fatol,Diaphenylsulfone,Disulone,Sulfona,4,4' Diaminophenyl Sulfone,Sulfone, 4,4'-Diaminophenyl
D004926	Escherichia coli	A species of gram-negative, facultatively anaerobic, rod-shaped bacteria (GRAM-NEGATIVE FACULTATIVELY ANAEROBIC RODS) commonly found in the lower part of the intestine of warm-blooded animals. It is usually nonpathogenic, but some strains are known to produce DIARRHEA and pyogenic infections. Pathogenic strains (virotypes) are classified by their specific pathogenic mechanisms such as toxins (ENTEROTOXIGENIC ESCHERICHIA COLI), etc.	Alkalescens-Dispar Group,Bacillus coli,Bacterium coli,Bacterium coli commune,Diffusely Adherent Escherichia coli,E coli,EAggEC,Enteroaggregative Escherichia coli,Enterococcus coli,Diffusely Adherent E. coli,Enteroaggregative E. coli,Enteroinvasive E. coli,Enteroinvasive Escherichia coli
D013449	Sulfonamides	A group of compounds that contain the structure SO2NH2.	Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide
D013450	Sulfones		Sulfone
D014166	Transferases	Transferases are enzymes transferring a group, for example, the methyl group or a glycosyl group, from one compound (generally regarded as donor) to another compound (generally regarded as acceptor). The classification is based on the scheme "donor:acceptor group transferase". (Enzyme Nomenclature, 1992) EC 2.	Transferase
D062365	Aminobenzoates	Derivatives of BENZOIC ACID that contain one or more amino groups attached to the benzene ring structure. Included under this heading are a broad variety of acid forms, salts, esters, and amides that include the aminobenzoate structure.	Aminobenzoic Acids,Acids, Aminobenzoic