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PubMed1991

New isomeric classes of topically active ocular hypotensive carbonic anhydrase inhibitors: 5-substituted thieno[2,3-b]thiophene-2-sulfonamides and 5-substituted thieno[3,2-b]thiophene-2-sulfonamides.

A series of 5-substituted thieno[2,3-b]- and thieno[3,2-b)- and thieno[3,2-b)thiophene-2-sulfonamides was prepared and evaluated for topical ocular hypotensive activity in glaucoma models. The 5-substituents were varied to maximize both inhibitory potency against carbonic anhydrase and water solubility. At the same time, these substituents were varied in order to obtain compounds with the appropriate pKa to minimize pigment binding in the iris. All of these variables were optimized in the best compound, 5-[[(methoxyethyl)[(methoxyethyl)ethyl] amino]methyl]thieno[2,3-b]thiophene-2-sulfonamide hydrochloride (55).

Animals↗
PubMed1996

Unexpected binding mode of the sulfonamide fluorophore 5-dimethylamino-1-naphthalene sulfonamide to human carbonic anhydrase II. Implications for the development of a zinc biosensor.

The three-dimensional structure of human carbonic anhydrase II (CAII) complexed with the sulfonamide fluorophore 5-dimethylamino-1-naphthalene sulfonamide (dansylamide) has been determined to 2.1-A resolution by x-ray crystallographic methods. Unlike other arylsulfonamide inhibitors of CAII, the naphthyl ring of dansylamide binds in a hydrophobic pocket in the active site, making van der Waals contacts with Val-121, Phe-131, Val-143, Leu-198, and Trp-209. Interestingly, a conformational change of Leu-198 is required to accommodate dansylamide binding, which rationalizes the enhanced dansylamide affinity measured for certain Leu-198 variants (Nair, S. K., Krebs, J.F., Christianson, D. W., and Fierke, C. A. (1995) Biochemistry 34, 3981-3989). Modeling studies indicate that a second binding mode, in which the fused aromatic ring is rotated out of the hydrophobic pocket, is sterically feasible. Both experimentally observed and modeled binding modes have implications for new leads in the design of avid CAII inhibitors. Finally, the structure of the CAII-dansylamide complex has implications for its exploitation in zinc biosensor applications, and possible routes toward the optimization of fluorophore design are considered on the basis on this structure.

Carbonic Anhydrases↗
PubMed2005

QSAR studies on benzene sulfonamide carbonic anhydrase inhibitors: need of hydrophobic parameter for topological modeling of binding constants of sulfonamides to human CA-II.

The binding constants (logK) of benzene sulfonamides to human CA-II have been modeled using a large series of distance-based topological indices. The need or otherwise of the hydrophobic parameter (logP) for such topological modeling of logK has been examined critically. In both the cases excellent results have been obtained. In multiparametric models involving indicator parameters we observed that introduction of hydrophobic parameter (logP) yields much improved statistics. The results are discussed on the basis of statistical parameters and also by using cross-validation method.

Benzene Derivatives↗
PubMed2004

Trace determination of macrolide and sulfonamide antimicrobials, a human sulfonamide metabolite, and trimethoprim in wastewater using liquid chromatography coupled to electrospray tandem mass spectrometry.

An analytical method has been developed and validated for the simultaneous trace determination of four macrolide antibiotics, six sulfonamides, the human metabolite N4-acetylsulfamethoxazole, and trimethoprim in wastewater. The method was validated for tertiary, secondary, and-unlike in previously published methods-also for primary effluents of municipal wastewater treatment plants. This wide range of application is necessary to thoroughly investigate the occurrence and fate of chemicals in wastewater treatment. Wastewater samples were enriched by solid-phase extraction, followed by reversed-phase liquid chromatography coupled to tandem mass spectrometry using positive electrospray ionization. Recoveries from all sample matrixes were generally above 80%, and the combined measurement uncertainty varied between 2 and 18%. Concentrations measured in tertiary effluents ranged between 10 ng/L for roxithromycin and 423 ng/L for sulfamethoxazole. Corresponding levels in primary effluents varied from 22 to 1450 ng/L, respectively. Trace amounts of these emerging contaminants reach ambient waters, since all analytes were not fully eliminated during conventional activated sludge treatment followed by sand filtration. In the case of sulfamethoxazole, the amount present as human metabolite N4-acetylsulfamethoxazole had to be taken into account in order to correctly assess the fate of sulfamethoxazole in wastewater treatment.

Macrolides↗
PubMed2006

Design and synthesis of novel sulfonamide-containing bradykinin hB2 receptor antagonists. 1. Synthesis and SAR of alpha,alpha-dimethylglycine sulfonamides.

We recently published the extensive in vivo pharmacological characterization of MEN 16132 (J. Pharmacol. Exp. Ther. 2005, 616-623; Eur. J. Pharmacol. 2005, 528, 7), a member of the sulfonamide-containing human B(2) receptor (hB(2)R) antagonists. Here we report, in detail, how this family of compounds was designed, synthesized, and optimized to provide a group of products with subnanomolar affinity for the hB(2)R and high in vivo potency after topical administration to the respiratory tract. The series was designed on the basis of indications from the X-ray structures of the key structural motifs A and B present in known antagonists and is characterized by the presence of an alpha,alpha-dialkyl amino acid. The first lead (17) of the series was submitted to extensive chemical work to elucidate the structural requirements to increase hB(2) receptor affinity and antagonist potency in bioassays expressing the human B(2) receptor (hB(2)R). The following structural features were selected: a 2,4-dimethylquinoline moiety and a piperazine linker acylated with a basic amino acid. The representative lead compound 68 inhibited the specific binding of [(3)H]BK to hB(2)R with a pKi of 9.4 and antagonized the BK-induced inositolphosphate (IP) accumulation in recombinant cell systems expressing the hB(2)R with a pA(2) of 9.1. Moreover, compound 68 when administered (300 nmol/kg) intratracheally in the anesthetized guinea pig, was able to significantly inhibit BK-induced bronchoconstriction for up to 120 min after its administration, while having a lower and shorter lasting effect on hypotension.

Animals↗
PubMed2005

Electrochemical synthesis and structural characterization of silver(I) complexes of N-2-pyridyl sulfonamide ligands with different nuclearity: influence of the steric hindrance at the pyridine ring and the sulfonamide group on the structure of the complexes.

A new series of silver complexes, [AgL], of the anionic forms of potentially bidentate N-2-pyridyl sulfonamide ligands [N-(3-methyl-2-pyridyl)-p-toluenenesulfonamide (HTs3mepy), N-(3-methyl-2-pyridyl)mesitylenesulfonamide (HMs3mepy), N-(4-methyl-2-pyridyl)-p-toluenesulfonamide (HTs4mepy), and N-(6-methyl-2-pyridyl)mesitylenesulfonamide (HMs6mepy)] have been prepared by an electrochemical procedure. In addition, heteroleptic complexes of composition [AgLL'] (L' = 1,10-phenanthroline and 2,2'-bipyridine) were obtained when the coligand L' was added to the electrolytic phase. The complexes were characterized by microanalysis, IR and (1)H NMR spectroscopy, and LSI mass spectrometry. In the cases of the compounds [Ag(Ts3mepy)](n)() (1), [Ag(4)(Ms3mepy)(4)] (2a), [Ag(Ms3mepy)](n)() (2b), [Ag(4)(Ms6mepy)(4)] (3a), [Ag(2)(Ms6mepy)(2)](n)() (3b), [Ag(2)(Ms3mepy)(2)(phen)(2)] (5), [Ag(2)(Ms6mepy)(2)phen] (7), and [Ag(2)(Ts4mepy)(2)(bipy)(2)] (8), characterization was also carried out by single-crystal X-ray diffraction. Compounds 1 and 2b present a polymer structure formed by an {AgN(2)} digonal core. Compounds 2a and 3a are tetranuclear and also have a distorted {AgN(2)} digonal core. Compound 3b is based on binuclear distorted {AgN(2)} digonal units joined by an intermolecular sulfonyl oxygen atom to produce a stairlike polymer structure. The heteroleptic complexes 5 and 8 are dimeric with a distorted {AgN(4)} tetrahedral geometry, while compound 7 shows two different geometries around the metal, distorted {AgN(2)} digonal and {AgN(4)} tetrahedral. The supramolecular structures of all species are organized by pi,pi-stacking, C-H...pi, or C-H...O interactions.

Journal Article↗
PubMed1977

Studies on the in vitro development of drug resistance of Proteeae to sulfonamides, trimethoprim and combinations of a sulfonamide and trimethoprim.

A strain of Proteus mirabilis repeatedly subcultured in the presence of a combination of sulfisoxazole and 0.4 microgram/ml of trimethoprim and a strain of P. vulgaris subcultured in the presence of sulfamethoxazole and trimethoprim combined in a 5:1 ratio gradually developed resistance to the combinations. However, the level of resistance developed by the organisms exposed to the combination was always appreciably lower than the level of resistance developed by the same strains exposed to either the sulfonamide or trimethoprim alone.

Drug Combinations↗
PubMed1986

Significance of the sulfonamide component for the clinical efficacy of trimethoprim-sulfonamide combinations.

The reasons for combining trimethoprim (TMP) with sulfonamides (SUL) are still mainly theoretical but are supported by results from experimental infections and treatment of specific pathogens in humans, such as Branhamella catarrhalis, Neisseria gonorrhoeae, Brucella, Nocardia asteroides and perhaps Bordetella pertussis and Chlamydia trachomatis. Addition of SUL to TMP confers a therapeutic advantage also in patients with complicated urinary tract infection but probably not in young women with acute cystitis. Conditions that may enable TMP-SUL synergy in vivo can be expected to occur only in occasional cases of infection due to staphylococci, streptococci, Haemophilus or enteric bacteria. This fact together with ethical problems and availability of alternative therapies make further evaluations of the clinical significance of the SUL component of TMP-SUL very difficult. Although the use of TMP alone has shown promise in exacerbations of chronic bronchitis the role of the SUL component in TMP-SUL treatment of infections outside the urinary tract remains to be defined in comparative clinical trials.

Aged↗