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PubMed2003

Investigation of structural and dynamic features of the radicals produced in gamma irradiated sulfanilamide: an ESR study.

Characteristic features of the radiolytical intermediates produced in gamma irradiated solid sulfanilamide (SA) were investigated in the present work using ESR spectroscopy. SO(2), which is the most sensitive group to radiation of SA molecule, was found to be at the origin of radiation produced ionic radical species. The latters give rise to an axially symmetric and an isotropic ESR spectra so that their sum appears as a three line antisymmetric ESR spectrum. Heights of these lines measured with respect to the base line were used to monitor microwave, temperature, time-dependent and kinetic features of the radical species contributing to ESR spectrum. Based on the experimental results derived from this study, it was concluded that as in the case of other solid sulfonamides radiation, yield of solid SA is very low (G=0.5) compared with those obtained for sulfonamide aqueous solutions (G=3.5-5.1), so that SA and SA-containing drugs could be safely sterilized by radiation.

Computer Simulation↗
PubMed2006

Vibrational spectroscopic studies and ab initio calculations of sulfanilamide.

FT-Raman and FT-IR spectra of sulfanilamide were recorded and analyzed. The vibrational frequencies of the compound have been computed using the Hartree-Fock/6-21G(*) basis and compared with the experimental values. The assignments of the observed bands were made on the basis of available literature.

Molecular Structure↗
PubMed2001

Molecular and crystal structures of N-arylglycopyranosylamines formed by reaction between sulfanilamide and D-ribose, D-arabinose and D-mannose.

The X-ray crystal structures of three monosaccharide derivatives prepared by the reaction of sulfanilamide with D-ribose, D-arabinose, and D-mannose have been determined. The derivatives are N-(p-sulfamoylphenyl)-alpha-D-ribopyranosylamine (1), N-(p-sulfamoylphenyl)-alpha-D-arabinopyranosylamine (2), and N-(p-sulfamoylphenyl)-beta-D-mannopyranosylamine monohydrate (3). The monosaccharide ring of 1 and 2 has the 1C4 conformation, stabilized in 1 by an intramolecular hydrogen bond from 0-2 to 0-4. Compound 3 has the 4C1 conformation at the monosaccharide ring and the gt conformation at the C-6-O-6 side chain. Occupancy of the water molecule in the crystal of 3 actually examined was 22%. The degree of interaction between sulfamoyl groups and monosaccharide moieties varies from structure to structure. The packing arrangement of 2 involves hydrogen bonding between sulfamoyl groups and monosaccharide hydroxyl groups, but interactions of this type are fewer in 1, and in 3 the hydrogen bonds are either strictly between monosaccharide hydroxyl groups or strictly between sulfamoyl groups. Pairs of hydrogen bonds (two-point contacts) link neighboring molecules in all three structures, between screw-axially related molecules in 1 and 2 and between translationally related molecules in 3. The contact in 3 defined by the O-3-H...O-5 and O-6-H...O-4 hydrogen bonds is found in several other N-aryl-beta-D-mannopyranosylamine crystal structures and is apparently an especially favorable mode of intermolecular interaction in these compounds.

Amino Sugars↗
PubMed1992

Influence of paracetamol, sulfanilamide and ascorbic acid on the electrocatalytic glucose sensor.

An electrocatalytic glucose sensor for in vivo application has been developed. The principle of measurement is based on the direct electrochemical oxidation of glucose at a platinum electrode without an enzymatic reaction. In an in vivo experiment with sheep the glucose sensor was tested with respect to its cross-sensitivity towards ascorbic acid, paracetamol and sulfanilamide. The influence of these substances could be reduced by an adapted calibration to such an extent, that the sensor performance could be ensured.

Acetaminophen↗
PubMed1998

Effects of sulfanilamide and methotrexate on 13C fluxes through the glycine decarboxylase/serine hydroxymethyltransferase enzyme system in arabidopsis.

In C3 plants large amounts of photorespiratory glycine (Gly) are converted to serine by the tetrahydrofolate (THF)-dependent activities of the Gly decarboxylase complex (GDC) and serine hydroxymethyltransferase (SHMT). Using 13C nuclear magnetic resonance, we monitored the flux of carbon through the GDC/SHMT enzyme system in Arabidopsis thaliana (L.) Heynh. Columbia exposed to inhibitors of THF-synthesizing enzymes. Plants exposed for 96 h to sulfanilamide, a dihydropteroate synthase inhibitor, showed little reduction in flux through GDC/SHMT. Two other sulfonamide analogs were tested with similar results, although all three analogs competitively inhibited the partially purified enzyme. However, methotrexate or aminopterin, which are confirmed inhibitors of Arabidopsis dihydrofolate reductase, decreased the flux through the GDC/SHMT system by 60% after 48 h and by 100% in 96 h. The uptake of [alpha-13C]Gly was not inhibited by either drug class. The specificity of methotrexate action was shown by the ability of 5-formyl-THF to restore flux through the GDC/SHMT pathway in methotrexate-inhibited plants. The experiments with sulfonamides strongly suggest that the mitochondrial THF pool has a long half-life. The studies with methotrexate support the additional, critical role of dihydrofolate reductase in recycling THF oxidized in thymidylate synthesis.

Amino Acid Oxidoreductases↗
PubMed1987

Characterization and mobilization of nonconjugative plasmids encoding resistance to streptomycin and sulfanilamide.

Most of nonconjugative streptomycin (Sm)- and sulfanilamide (Su)- resistance of clinical isolates belonging to various species of Enterobacteriaceae and Pseudomonas were encoded by an Inc Q plasmid, molecular size of which was 5.5 Md. The SmSu plasmids were efficiently mobilized by Inc P plasmids between E. coli strains. Inc I group and Inc F group plasmids could mobilize the Inc Q plasmids at lower efficiencies. The Inc Q plasmid was also mobilized to various species of Enterobacteriaceae at high frequencies without accompanying the conjugative Inc P plasmid; as a result, most of the SmSu-resistant transconjugants were nontransferable. The above results may explain the wide distribution of nonconjugative SmSu strains among clinical isolates.

Conjugation, Genetic↗
PubMed1975

Drug-biomolecule interactions: topographical study of active site of erythrocyte carbonic anhydrase using spin-labeled sulfanilamide drugs.

The topography of the active sites of human erythrocyte carbonic anhydrases B and C and bovine erythrocyte carbonic anhydrase B was studied using a series of spin-labeled sulfanilamide analogs. Results show that the active site of human carbonic anhydrase C is a narrow cleft approximately 14 A in depth. This observation is in good agreement with previously published X-ray diffraction data. While the active sites of human carbonic anhydrase B and bovine carbonic anhydrase B have the same general shape as the active site of human carbonic anhydrase C, they are slightly deeper.

Benzyl Compounds↗
PubMed1984

Remarks on the structure-activity relationship of silver sulfanilamides.

The biological activity of a series of 10 silver sulfanilamides is studied in relation to the physical parameters pK alpha, log K, and the aqueous solubility. None of the parameters demonstrate a simple relationship with the activity. A discussion of the significance of log K and the solubility in relation to the activity is given.

Ointments↗
PubMed1983

Novel techniques for determination of antibacterial activity of silver sulfanilamides.

By means of suspension techniques, MIC's of ten silver sulfanilamides against fifty-six different strains of bacteria were determined. The only two bacteria which were sensitive were Streptococcus pyogenes and Escherichia coli. The local application of these drugs in burn patients only reduces colonization. The cream base is probably also involved in the anticolonization effect.

Anti-Bacterial Agents↗
PubMed2003

Quantitative structure-activity relationship study on sulfanilamide schiff's bases: carbonic anhydrase (CA) inhibitors.

The paper deals with quantitative structure-activity studies on a group of sulfanilamide Schiff's base inhibitors of carbonic anhydrase (CA) using distance-based topological indices. The regression analysis of the data has shown that the activities of the compounds used in inhibiting Carbonic AnhydraseII (CAII) activity can be modeled excellently in multi-parametric model in that some indicator parameters are also involved. The results are discussed critically.

Carbonic Anhydrase II↗
PubMed2006

Pre-systemic metabolism prevents in vivo antikinetoplastid activity of N1,N4-substituted 3,5-dinitro sulfanilamide, GB-II-150.

We previously showed that N1-phenyl-3,5-dinitro-N4,N4-di-n-butylsulfanilamide (denoted GB-II-150) possesses selective antimicrotubule activity against Leishmania donovani and Trypanosoma brucei in vitro [Bhattacharya, G., Herman, J., Delfin, D., Salem, M.M., Barszcz, T., Mollet, M., Riccio, G., Brun, R., Werbovetz, K.A., 2004. Synthesis and antitubulin activity of N(1)- and N(4)-substituted 3,5-dinitro sulfanilamides against African trypanosomes and Leishmania. Journal of Medicinal Chemistry 47, 1823-1832]. When GB-II-150 was administered orally to male Sprague-Dawley rats, extensive first-pass metabolism of the compound was observed and the oral bioavailability was zero. GB-II-150 displayed a half-life of 170 min and a clearance of 31.5 mL/min/kg in rats when administered intravenously. In vitro metabolism studies indicated that less than 5% of GB-II-150 remained intact after a 60-min incubation with rat liver S9 fraction. As expected, the compound was extensively metabolized, with the major products resulting from N1-ring oxidation, N4-alkane oxidation, N4-oxidation, and nitro reduction. These data indicate that GB-II-150 undergoes rapid and extensive first-pass metabolism, precluding the attainment of effective systemic drug concentrations and explaining the lack of in vivo antitrypanosomal activity of this compound.

Administration, Oral↗
PubMed1981

Structure-activity relationships in dihydropteroate synthase inhibition by sulfanilamides. Comparison with the antibacterial activity.

A set of 12 acidic, 5 imidic, and 5 amidic sulfanilamides (SA) were tested for their inhibitory activity on dihydropteroate synthase of Escherichia coli. The enzyme inhibition indexes (EII50) were compared with the growth inhibition indexes (GII50), and electronic structures of SA and cell permeability effects were discussed as possible determinant factors of the observed variation of the activity in the SA set. The results strongly support the following conclusion: (a) permeability factors are highly effective in depressing the activity of SA in growth inhibition with respect to enzyme inhibition, but they do not appear to contribute significantly to the activity variation; (b) the activities of the different SA, both in growth and enzyme inhibition experiments, are well accounted for by the electronic features of these compounds.

Bacteria↗
PubMed1978

Electronic aspects of the antibacterial action of sulfanilamides.

Intramolecular interactions in N1-substituted sulfanilamides (SA) can rationalize the trend of their antibacterial powers with the use of a resonance scheme, derived from d orbital symmetry and tested with an extensive spectroscopic investigation on amidic, imidic, and anionic SA. On quantitative grounds, a good relationship is presented between the antibacterial power and the proton chemical shift of the p-amino group. The electronic features for high activity are described.

Bacteria↗
PubMed2001

Carbonic anhydrase inhibitors: metal complexes of a sulfanilamide derived Schiff base and their interaction with isozymes I, II and IV.

Metal complexes of aromatic/heterocyclic sulfonamides act as stronger inhibitors of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1) as compared to the uncomplexed sulfonamides from which they are derived. Here we report the synthesis and inhibition studies against the physiologically relevant isozymes CA I, CA II and CA IV, of a series of metal complexes (Co(II), Ni(II) and Cu(II) derivatives) of a Schiff-base ligand, obtained from sulfanilamide and salicylaldehyde. The best activity was observed for the Cu(II) and Co(II) complexes, against CA II and CA IV, for which inhibition constants in the range of 15-39 and 72-108nM, respectively, were seen. The enhanced efficacy in inhibiting the enzyme may be due to a dual mechanism of action of the metal complexes, which interact with CA both by means of the sulfonamide moieties as well as the metal ions present in their molecule.

Carbonic Anhydrase Inhibitors↗
PubMed1978

Plasmid-mediated sulfanilamide resistance.

Dihydropteroate synthetase (DHPS) is specified by a substrain of Escherichia coli K12, ML1410. This enzyme activity is inhibited by sulfanilamides (Sa) and is known to be heat-stable, i.e., an Sa-sensitive normal enzyme. Another DHPS activity specified by E. coli ML1410 carrying drug resistance plasmids is Sa-resistant but heat-sensitive, i.e., an Sa-resistant enzyme. Most plasmids encoding single Sa or double (Sa. Tc or Sa. Sm) (Tc, tetracycline; Sm, streptomycin) resistance mediate the formation of this type of DHPS. Therefore, E. coli carrying these plasmids becomes diploid for DHPS, i.e., an Sa-resistant and an Sa-sensitive normal enzyme. The biochemical mechanism of Sa resistance mediated by plasmids encoding triple (Cm.Sm.Sa; Tc.Sm.Sa) and quadruple (Cm.Tc.Sm.Sa) resistance is not due to the formation of an altered DHPS but probably due to the decrease in permeation of the drug into the cell. The evolutionary process of the formation of Sa-resistance determinants on plasmids is discussed based on the presence of two types of Sa resistance mechanism.

Bacteria↗
PubMed1973

Chemotherapeutic activity of combination doses of chloroquine, pyrimethamine, and sulfamethoxy-diazine, a long-acting sulfanilamide, against Plasmodium berghei infections in mice.

During the course of antimalarial screening, it was discovered that sulfamethoxydiazine, a long-acting sulfanilamide extensively used in genitourinary tract infections, not only was effective against Plasmodium berghei infections in mice when administered alone but also was active when used in combination with chloroquine, in effect making it possible to use half as much of the latter drug as normally required to achieve the same results. The triple combination of chloroquine, sulfamethoxydiazine, and pyrimethamine, when administered in a ratio of 30:10:1, was found to be potentiating against both blood-induced and sporozoite-induced P. berghei NK(65) infections. Mean effective dose values were calculated for chloroquine, sulfamethoxydiazine, and pyrimethamine against blood-induced P. berghei infection, and when a combination of the three drugs was administered therapeutically in the ratio given above, only one-tenth as much chloroquine, one-thirtieth as much sulfamethoxydiazine, and one-sixtieth as much pyrimethamine were needed to cure 50% of murine infections as was needed for each drug alone. The triple combination also showed enhanced activity against lethal sporozoite-induced P. berghei NK(65) infection in A/J strain mice.

Animals↗
PubMed1968

Drug resistance of staphylococci. VII. Genetic determinants responsible for the resistance to tetracycline, streptomycin, sulfanilamide, and penicillin.

A genetic analysis of resistance to tetracycline (TC), streptomycin (SM), sulfanilamide (SA), and penicillin G was carried out through transduction with phage lysates obtained from a multiply resistant strain of Staphylococcus aureus by ultraviolet irradiation. All transductants acquired resistance to both TC and SA, even when singly selected for either SA or TC resistance. The locus responsible for TC resistance could not be separated genetically from that for SA resistance. On the other hand, in transduction of SM resistance, about 30% of the transductants jointly acquired resistance to both TC and SA. These observations suggest that the loci governing resistance to TC, SA, and SM exist close together on a single genetic unit, this probably being the chromosome.

Chromosome Mapping↗