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1.
ACS Appl Bio Mater ; 7(5): 2752-2761, 2024 May 20.
Artigo em Inglês | MEDLINE | ID: mdl-38662509

RESUMO

Carbon dots (CDs) were synthesized hydrothermally by mixing citric acid (CA) and an antifolic agent, sulfanilamide (SNM), employed for pH sensing and bacterial growth inactivation. Sulfanilamide is a prodrug; aromatic hetero cyclization of the amine moiety along with other chemical modifications produces an active pharmacological compound (chloromycetin and miconazole), mostly administered for the treatment of various microbial infections. On the other hand, the efficacy of the sulfanilamide molecule as a drug for antimicrobial activity was very low. We anticipated that the binding of the sulfanilamide molecule on the carbon dot (CD) surface may form antibacterial CDs. Citric acid was hybridized with sulfanilamide during the hydrothermal preparation of the CDs. The molecular fragments of bioactivated sulfanilamide molecule play a crucial role in bacterial growth inactivation for Gram-positive and Gram-negative bacteria. The functional groups of citric acid and sulfanilamide were conserved during the CD formation, facilitating the zwitterionic behavior of CDs associated with its photophysical activity. At low concentrations of CDs, the antibacterial activity was apparent for Gram-positive bacteria only. This Gram-positive bacteria selectivity was also rationalized by zeta potential measurement.


Assuntos
Antibacterianos , Materiais Biocompatíveis , Carbono , Teste de Materiais , Testes de Sensibilidade Microbiana , Tamanho da Partícula , Sulfanilamida , Carbono/química , Carbono/farmacologia , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/síntese química , Concentração de Íons de Hidrogênio , Sulfanilamida/química , Sulfanilamida/farmacologia , Materiais Biocompatíveis/química , Materiais Biocompatíveis/farmacologia , Materiais Biocompatíveis/síntese química , Pontos Quânticos/química , Sulfanilamidas/química , Sulfanilamidas/farmacologia , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Negativas/efeitos dos fármacos
2.
Talanta ; 257: 124383, 2023 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-36863298

RESUMO

A possibility of the use of a common monitor calibrator as a portable and inexpensive tool for the fluorometric determination of sulfonamide drugs after their reaction with fluorescamine was examined. The luminescence measurements with a calibrator are based on irradiation of a test sample by the device lamp with a broadband spectrum in the visible and near UV regions and simultaneous registration of the secondary radiation by the device detector. Two types of cuvettes with black light absorbing sides eliminating the reflected self-radiation were tested. The commercially available Eppendorf-type black plastic microtubes ("LightSafe") were suggested as a good option for such measurements. It was shown that a monitor calibrator can be applied for optimization of the determination conditions. By the example of sulfanilamide and sulfamethazine, it was shown that the procedure should be carried out at pH 4-6 and fluorescamine concentration of 200 µmol L-1, and 40 min of the interaction. The limit of detection of sulfanilamide and sulfamethazine using a monitor calibrator is 0.9 µmol L-1 and 0.8 µmol L-1, respectively, which is comparable with their spectrophotometric determination.


Assuntos
Fluorescamina , Sulfametazina , Sulfonamidas/química , Sulfametazina/química , Fluorescamina/química , Sulfanilamida/análise , Sulfanilamida/química
3.
Acta Chim Slov ; 69(4): 772-778, 2022 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-36562158

RESUMO

The current study reports synthesis, structure establishment, anti-glycation, and anti-oxidant activities of ligand 4-[(2-hydroxynaphthalene-1-ylmethylene)-amino]-benzenesulfonamide (L) and its coordination compounds with Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) metal ions. The analytical techniques used (UV-Vis, FT-IR, CHN/S) confirmed the bidentate nature of the ligand, coordinating via O and N atoms in 2:1 ligand-to-metal ratio. The TG/DTA anylsis displayed that these compounds are thermally stable. Furthermore, the synthesized compounds were evaluated for their anti-glycation and antioxidant potential and showed significant activities with IC50 values range 184.11-386.34 µM and 37.05-126.27 µM, respectively. The Mn (IC50 = 184.11 ± 2.11 µM), Ni (IC50 = 211.26 ± 1.46 µM), Cu (IC50 = 254.56 ± 1.16 µM), and Zn (IC50 = 276.43 ± 2.14 µM) metal complexes exhibited substantial anti-glycation activity and comparatively better activity than the standard rutin (IC50 = 294.4 ± 1.50 µM), whereas Zn complex (IC50 = 37.05 ± 1.53 µM) also showed better DPPH radical scavenging activity than the standard tert-butyl-4-hydroxyanisole (IC50 = 44.7 ± 1.21 µM).


Assuntos
Antioxidantes , Complexos de Coordenação , Bases de Schiff , Sulfanilamida , Ligantes , Espectroscopia de Ressonância Magnética , Metais , Testes de Sensibilidade Microbiana , Bases de Schiff/síntese química , Bases de Schiff/química , Espectroscopia de Infravermelho com Transformada de Fourier , Sulfanilamida/análogos & derivados , Sulfanilamida/síntese química , Sulfanilamida/química
4.
Eur J Med Chem ; 228: 114021, 2022 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-34871841

RESUMO

Fluoroquinolones are a class of antibacterial agents used clinically to treat a wide array of bacterial infections. Although being potent, susceptibility to CNS side effects limits their use. It was observed that improvements in absorption, activity and side effects were achieved via modifications at the N atom of the C7 of the side chain. To meet the increasing demand for development of new antibacterial agents, nineteen novel ciprofloxacin-sulfonamide hybrid molecules were designed, synthesized and characterized by IR, 1H NMR and 13C NMR as potential antibacterial agents with dual DNA gyrase/topoisomerase IV inhibitory activity. Most of the synthesized compounds showed significant antibacterial activity that was revealed by testing their inhibitory activity against DNA gyrase, DNA topoisomerase IV as well as their minimum inhibitory concentration against Staphylococcus aureus. Six ciprofloxacin-sulfonamide hybrids (3f, 5d, 7a, 7d, 7e and 9b) showed potent inhibitory activity against DNA topoisomerase IV, compared to ciprofloxacin (IC50: 0.55 µM), with IC50 range: 0.23-0.44 µM. DNA gyrase was also efficiently inhibited by five ciprofloxacin-sulfonamide hybrids (3f, 5d, 5e, 7a and 7d) with IC50 range: 0.43-1.1 µM (IC50 of ciprofloxacin: 0.83 µM). Compounds 3a and 3b showed a marked improvement in the antibacterial activity over ciprofloxacin against both Gram-positive and Gram-negative pathogens, namely, Staphylococcus aureus Newman and Escherichia coli ATCC8739, with MIC = 0.324 and 0.422 µM, respectively, that is 4.2-fold and 3.2-fold lower than ciprofloxacin (MIC = 1.359 µM) against the Gram-positive Staphylococcus aureus, and MIC = 0.025 and 0.013 µM, respectively, that is 10.2-fold and 19.6-fold lower than ciprofloxacin (MIC = 0.255 µM) against the Gram-negative Escherichia coli ATCC8739. Also, the most active compounds showed lower CNS and convulsive side effects compared to ciprofloxacin with a concomitant decrease in GABA expression.


Assuntos
Antibacterianos/farmacologia , Ciprofloxacina/farmacologia , DNA Topoisomerase IV/antagonistas & inibidores , Desenho de Fármacos , Sulfanilamida/farmacologia , Inibidores da Topoisomerase/farmacologia , Animais , Antibacterianos/síntese química , Antibacterianos/química , Ciprofloxacina/química , DNA Topoisomerase IV/metabolismo , Relação Dose-Resposta a Droga , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Masculino , Camundongos , Testes de Sensibilidade Microbiana , Simulação de Acoplamento Molecular , Estrutura Molecular , Relação Estrutura-Atividade , Sulfanilamida/química , Inibidores da Topoisomerase/síntese química , Inibidores da Topoisomerase/química
5.
J Mol Model ; 27(10): 283, 2021 Sep 13.
Artigo em Inglês | MEDLINE | ID: mdl-34515848

RESUMO

The adsorption and interaction of sulfanilamide (SA) with a pristine magnesium oxide (MgO) nano-cage was scrutinized through density functional theory (DFT) calculations. All geometries were optimized at M06-2X/6-311G(d,p) level, and the single-point energy calculation was also carried out at the same level of theory. Also, natural bond orbital (NBO) analysis was carried out and the values related to Wiberg bond index (WBI), donor-acceptor interactions, and partial natural charges were inspected. The MgO nano-cage can adsorb SA more strongly with the adsorption energy (Eads) of - 41.74 kcal/mol, corresponding to the stable configurations. In addition, NBO analysis showed that the donor-acceptor interactions with SA and the MgO nano-cage are stronger. Based on our computations, the HOMO-LUMO gap of the MgO nano-cage changed to a great extent following the adsorption of the SA molecule, which corresponds to the most stable configuration that leads to improved electrical conductivity of the MgO nano-cage. The change in the gap determines the sensing mechanism, which is associated with the change in the electrical conductivity. To calculate the recovery time, transition-state theory (TST) was employed. Based on our calculation, Mg12O12-SA complex composites possess a short recovery time for the desorption of SA. The results show that the MgO nano-cage is an ideal candidate to be employed for developing SA sensors with high efficiency.


Assuntos
Óxido de Magnésio/química , Nanoestruturas/química , Sulfanilamida/química , Adsorção , Teoria da Densidade Funcional , Condutividade Elétrica , Modelos Moleculares , Teoria Quântica , Fatores de Tempo
6.
Bioorg Chem ; 113: 105039, 2021 08.
Artigo em Inglês | MEDLINE | ID: mdl-34091291

RESUMO

A series of 2-aminothiazole sulfanilamide oximes were developed as new membrane active antibacterial agents to conquer the microbial infection. Benzoyl derivative 10c was preponderant for the treatment of drug-resistant A. baumannii infection in contrast to norfloxacin and exerted excellent biocompatibility against mammalian cells including erythrocyte and LO2 cell line. Meanwhile, it had ability to eradicate established biofilm to alleviate the resistance burden. Mechanism investigation elucidated that compound 10c was able to disturb the membrane effectively and inhibit lactic dehydrogenase, which led to cytoplasmic content leakage. The cellular redox homeostasis was interfered via the production of reactive oxygen and nitrogen species (RONS), which further contributed to respiratory pathway inactivation and reduction of GSH activity. This work indicated that 2-aminothiazole sulfanilamide oximes could be a promising start for the exploitation of novel antibacterial agents against pathogens.


Assuntos
Acinetobacter baumannii/efeitos dos fármacos , Antibacterianos/farmacologia , Desenho de Fármacos , Farmacorresistência Bacteriana Múltipla/efeitos dos fármacos , Oximas/química , Acinetobacter baumannii/fisiologia , Animais , Antibacterianos/química , Biofilmes/efeitos dos fármacos , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Eritrócitos/citologia , Eritrócitos/efeitos dos fármacos , Eritrócitos/metabolismo , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Hemólise/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Conformação Molecular , Estresse Oxidativo/efeitos dos fármacos , Oximas/farmacologia , Relação Estrutura-Atividade , Sulfanilamida/química , Tiazóis/química
7.
J Enzyme Inhib Med Chem ; 35(1): 1422-1432, 2020 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-32602377

RESUMO

Many studies have been conducted on the selective inhibition of human monoamine oxidase B (hMAO-B) enzyme using benzylamine-sulphonamide derivatives. Using various chemical modifications on BB-4h, which was reported previously by our team and showed a significant level of MAO-B inhibition, novel benzylamine-sulphonamide derivatives were designed, synthesised, and their MAO inhibition potentials were evaluated. Among the tested derivatives, compounds 4i and 4t achieved IC50 values of 0.041 ± 0.001 µM and 0.065 ± 0.002 µM, respectively. The mechanism of hMAO-B inhibition by compounds 4i and 4t was studied using Lineweaver-Burk plot. The nature of inhibition was also determined to be non-competitive. Cytotoxicity tests were conducted and compounds 4i and 4t were found to be non-toxic. Molecular docking studies were also carried out for compound 4i, which was found as the most potent agent, within hMAO-B catalytic site.


Assuntos
Benzilaminas/farmacologia , Simulação de Acoplamento Molecular , Inibidores da Monoaminoxidase/farmacologia , Monoaminoxidase/metabolismo , Sulfanilamida/farmacologia , Animais , Benzilaminas/química , Relação Dose-Resposta a Droga , Humanos , Camundongos , Estrutura Molecular , Inibidores da Monoaminoxidase/síntese química , Inibidores da Monoaminoxidase/química , Células NIH 3T3 , Relação Estrutura-Atividade , Sulfanilamida/química
8.
Int J Biol Macromol ; 157: 522-529, 2020 Aug 15.
Artigo em Inglês | MEDLINE | ID: mdl-32353503

RESUMO

In this work, alginate hydrogel fibers loading sulfanilamide were proposed using a combination of Ca2+ ions and glutaraldehyde crosslinking to develop an efficient wound dressing. The structure, mechanical properties, absorbency, in vitro drug release and cytotoxicity of the proposed alginate hydrogel fibers were investigated systematically. The results indicated that crosslinking with glutaraldehyde can efficiently enhance the mechanical properties of the alginate hydrogel fibers, and reduce their swelling degree which is beneficial for hydrogel fibers to obtain adjustable fluid adsorption capacity, sustained drug release feature over hydrogel fibers crosslinked only by Ca2+ ions. Antibacterial activity assay demonstrated the bactericidal ability of the alginate hydrogel fibers towards S. aureus and E. coli with the highest antibacterial rate of 99.9%. Furthermore, a preliminary trial of papermaking process for producing alginate hydrogel mats showed the workability and the applicability of the mechanically tough hydrogel fibers. Cytotoxicity assay indicated the enhancement of cell adhesion and proliferation, revealing the non-cytotoxicity and biocompatibility of the alginate hydrogel mats. Based on the excellent mechanical strength, adjustable fluid adsorption capacity, sustained drug release, and biocompatibility, the bi-crosslinked alginate hydrogel fibers had a promising application as ideal wound dressings in clinic.


Assuntos
Alginatos/química , Antibacterianos/química , Bandagens , Reagentes de Ligações Cruzadas/química , Hidrogéis/química , Íons/química , Sulfanilamida/química , Antibacterianos/administração & dosagem , Fenômenos Químicos , Liberação Controlada de Fármacos , Concentração de Íons de Hidrogênio , Fenômenos Mecânicos , Análise Espectral , Sulfanilamida/administração & dosagem , Cicatrização
9.
Arch Pharm (Weinheim) ; 353(7): e2000074, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32390214

RESUMO

Novel Val-Val dipeptide-benzenesulfonamide conjugates were reported in this study. These were achieved by a condensation reaction of p-substituted benzenesulfonamoyl alkanamides with 2-amino-4-methyl-N-substituted phenyl butanamide using classical peptide-coupling reagents. The compounds were characterized using Fourier transform infrared, 1 H-nuclear magnetic resonance (NMR), 13 C-NMR, and electrospray ionization-high-resolution mass spectrometry spectroscopic techniques. As predicted from in silico studies, the Val-Val dipeptide-benzenesulfonamide conjugates exhibited antimalarial and antioxidant properties that were analogous to the standard drug. The synthesized compounds were evaluated for in vivo antimalarial activity against Plasmodium berghei. The hematological analysis was also conducted on the synthesized compounds. At 50 mg/kg body weight, compounds 8a, 8d, and 8g-i inhibited the multiplication of the parasite by 48-54% on Day 7 of posttreatment exposure, compared with the 67% reduction with artemisinin. All the synthesized dipeptides had a good antioxidant property, but it was less when compared with vitamin C. The dipeptides reported herein showed the ability to reduce oxidative stress arising from the malaria parasite.


Assuntos
Antimaláricos/farmacologia , Dipeptídeos/farmacologia , Plasmodium falciparum/efeitos dos fármacos , Sulfanilamida/farmacologia , Antimaláricos/síntese química , Antimaláricos/química , Dipeptídeos/química , Relação Dose-Resposta a Droga , Estrutura Molecular , Estresse Oxidativo/efeitos dos fármacos , Testes de Sensibilidade Parasitária , Relação Estrutura-Atividade , Sulfanilamida/química
10.
Bioorg Med Chem Lett ; 30(11): 127110, 2020 06 01.
Artigo em Inglês | MEDLINE | ID: mdl-32229060

RESUMO

A series of substituted sulfonamide bioisosteres of 8-hydroxyquinoline were evaluated for their antibacterial activity against the common mastitis causative pathogens Streptococcus uberis, Staphylococcus aureus and Escherichia coli, both in the presence and absence of supplementary zinc. Compounds 9a-e, 10a-c, 11a-e, 12 and 13 were demonstrated to have MICs of 0.0625 µg/mL against S. uberis in the presence of 50 µM ZnSO4. Against S. aureus compounds 9g (MIC 4 µg/mL) and 11d (MIC 8 µg/mL) showed the greatest activity, whereas all compounds were found to be inactive against E. coli (MIC > 256 µg/mL); again in the presence of 50 µM ZnSO4. All compounds were demonstrated to be significantly less active in the absence of supplementary zinc. Compound 9g was subsequently confirmed to be bactericidal, with an MBC (≥3log10 cfu/mL reduction) of 0.125 µg/mL against S. uberis in the presence of 50 µM ZnSO4. To validate the sanitising activity of compound 9g in the presence of supplementary zinc, a quantitative suspension disinfection (sanitizer) test was performed. In this preliminary test, sanitizing activity (>5log10 reduction of CFU/mL in 5 min) was observed against S. uberis for compound 9g at concentrations as low as 1 mg/mL, validating the potential of this compound to function as a topical sanitizer against the major environmental mastitis-causing microorganism S. uberis.


Assuntos
Antibacterianos/química , Oxiquinolina/química , Sulfanilamida/química , Zinco/química , Antibacterianos/farmacologia , Escherichia coli/efeitos dos fármacos , Interações Hidrofóbicas e Hidrofílicas , Testes de Sensibilidade Microbiana , Oxiquinolina/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Streptococcus/efeitos dos fármacos , Relação Estrutura-Atividade
11.
Molecules ; 25(5)2020 Feb 25.
Artigo em Inglês | MEDLINE | ID: mdl-32106611

RESUMO

A new ß-class carbonic anhydrase was cloned and purified from the filamentous ascomycete Sordaria macrospora, CAS3. This enzyme has a higher catalytic activity compared to the other two such enzymes from this fungus, CAS1 and CAS2, which were reported earlier, with the following kinetic parameters: kcat of (7.9 ± 0.2) × 105 s-1, and kcat/Km of (9.5 ± 0.12) × 107 M-1∙s-1. An inhibition study with a panel of sulfonamides and one sulfamate was also performed. The most effective CAS3 inhibitors were benzolamide, brinzolamide, dichlorophnamide, methazolamide, acetazolamide, ethoxzolamide, sulfanilamide, methanilamide, and benzene-1,3-disulfonamide, with KIs in the range of 54-95 nM. CAS3 generally shows a higher affinity for this class of inhibitors compared to CAS1 and CAS2. As S. macrospora is a model organism for the study of fruiting body development in fungi, these data may be useful for developing antifungal compounds based on CA inhibition.


Assuntos
Inibidores da Anidrase Carbônica/química , Anidrases Carbônicas/química , Sordariales/enzimologia , Relação Estrutura-Atividade , Acetazolamida/química , Sequência de Aminoácidos/genética , Benzolamida/química , Inibidores da Anidrase Carbônica/classificação , Inibidores da Anidrase Carbônica/farmacologia , Anidrases Carbônicas/genética , Anidrases Carbônicas/isolamento & purificação , Etoxzolamida/química , Humanos , Cinética , Metazolamida/química , Sulfanilamida/química , Sulfonamidas/química , Tiazinas/química
12.
Bioorg Med Chem Lett ; 30(6): 126982, 2020 03 15.
Artigo em Inglês | MEDLINE | ID: mdl-32001137

RESUMO

This work explored a novel type of potential multi-targeting antimicrobial three-component sulfanilamide hybrids in combination of pyrimidine and azoles. The hybridized target molecules were characterized by 1H NMR, 13C NMR and HRMS spectra. Some of the developed target compounds exerted promising antimicrobial activity in comparison with the reference drugs norfloxacin and fluconazole. Noticeably, sulfanilamide hybrid 5c with pyrimidine and indole could effectively inhibit the growth of E. faecalis with MIC value of 1 µg/mL. The active molecule 5c showed low cell toxicity and did not obviously trigger the development of resistance towards the tested bacteria strains. Mechanism exploration indicated that compound 5c could not only exert efficient membrane permeability, but also intercalate into DNA of resistant E. faecalis to form 5c-DNA supramolecular complex, which might be responsible for its antimicrobial action. The further investigation showed that this molecule could be effectively transported by human serum albumins through hydrogen bonds and van der Waals force.


Assuntos
Anti-Infecciosos/química , Azóis/farmacologia , Substâncias Intercalantes/química , Pirimidinas/farmacologia , Sulfanilamida/química , Células A549 , Anti-Infecciosos/farmacologia , Permeabilidade da Membrana Celular , Proliferação de Células/efeitos dos fármacos , DNA/química , DNA Girase/química , Quimioterapia Combinada , Enterococcus faecalis/efeitos dos fármacos , Fluconazol/farmacologia , Fluconazol/normas , Humanos , Substâncias Intercalantes/farmacologia , Simulação de Acoplamento Molecular , Norfloxacino/farmacologia , Norfloxacino/normas , Albumina Sérica Humana/química , Relação Estrutura-Atividade , Sulfanilamida/farmacologia
13.
J Hazard Mater ; 390: 122157, 2020 05 15.
Artigo em Inglês | MEDLINE | ID: mdl-31999959

RESUMO

Fast and efficient tracking of micropollutants in aquatic environment by developing novel electrode materials is of great significance. Herein, a polyvinylpyrrolidone (PVP) assisted strategy is applied for synthesis of nitrogen doped Cu MOFs (N-Cu-MOF) for micropollutants electrochemical detection. The designed N-Cu-MOFs possess uniform octahedral shape with large surface area (1184 m2 g-1) and an average size of roughly 450 nm, exhibiting the excellent electroanalytical capability for the detection of multipollutants. In the case of dopamine (DA) and sulfonamides (SA) as typical microcontaminants, the designed N-Cu-MOFs exhibited wide linear ranges of 0.50 nM-1.78 mM and low detection limit (LOD, 0.15 nM, S/N = 3) for the determination of DA, as well as a linear range of 0.01-58.3 µM and LOD (0.003 µM, S/N = 3) for monitoring SA. The improved performance is attributed to the heteroatom introduction and good dispersion stability of N-Cu-MOF with PVP-decorated. The good electroanalytical ability of N-Cu-MOF for detection of DA and SA can provide a guide to efficient and rapid monitor other micropollutants and construct novel electrochemical sensors.


Assuntos
Cobre/química , Dopamina/análise , Estruturas Metalorgânicas/química , Nitrogênio/química , Sulfanilamida/análise , Poluentes Químicos da Água/análise , Dopamina/química , Técnicas Eletroquímicas , Sulfanilamida/química , Poluentes Químicos da Água/química
14.
Acta Chim Slov ; 67(1): 23-35, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33558919

RESUMO

A rapid, simple and sensitive spectrophotometric method for the determination of amoxicillin (AM) is described. The method is based on the previous sulphanilamide (SA) and sulphathiazole (STZ) diazotization in the medium of 0.6-0.7 M hydrochloric acid and their subsequent interaction with amoxicillin at pH = 10.5 with formation of yellow-colored azo compouds. Effective molar absorptivities at the absorbance maxima at 445 nm (SA) and 448 nm (STZ) for azo compounds were (1.74 ± 0,06)∆104 L×mol-1×cm-1 and (1.97 ± 0,05)∆104 L×mol-1×cm-1, respectively. Stoichiometric ratios of the components of azo compounds were determined using continuous variations method. Based on the optimum reaction conditions, new methods were developed. These methods allow to determine the amoxicillin in concentration range 1.3-32.9 mg×mL-1 with sulphanilamide and 0.7-27.4 mg×mL-1 with sulphathiazole. The methods were successfully validated for amoxicillin determination in tablets "Amoxil".


Assuntos
Amoxicilina/análise , Sulfanilamida/química , Comprimidos/análise , Amoxicilina/química , Compostos Azo/análise , Compostos Azo/síntese química , Indicadores e Reagentes/química , Limite de Detecção , Espectrofotometria/métodos , Sulfatiazol/química
15.
J Liposome Res ; 30(3): 255-262, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31185766

RESUMO

Nonionic surfactants have an extraordinary fascination for the researchers in the field of drug delivery for enhancing drug bioavailability and therapeutic efficacy. Here, we are reporting the synthesis, characterization, drug entrapment efficiency (EE), critical micellar concentration, and biocompatibility evaluation of sulphanilamide based new nonionic surfactants. The surfactants were synthesized in single step reactions and characterized through 1H NMR, FT-IR, and mass spectrometric analysis. The surfactants abilities for niosomal vesicles formation were investigated utilizing Ciprofloxacin as a model drug. The drug loaded niosomal suspension of the synthesized surfactants was screened for shape; size, polydispersity index, and drug EE utilizing AFM, Zetasizer, and UV, respectively. The compatibility of the drug in drug loaded vesicles with excipients was assessed utilizing FT-IR spectroscopy. The biocompatibility of the synthesized surfactants was assessed through blood haemolysis and cell cytotoxicity assays. Results of this study showed that the synthesized surfactants were quite haemocompatible and nontoxic in nature and were able to form spherical vesicles. The size and drug EE of the vesicles were dependant on the length of surfactant aliphatic chain. Surfactant with long aliphatic chain was more efficient in entrapping the drug and could be used as a potential vesicular drug delivery vehicle for improving the lipophilic drug's bioavailability.


Assuntos
Hemólise/efeitos dos fármacos , Sulfanilamida/farmacologia , Tensoativos/síntese química , Tensoativos/farmacologia , Animais , Disponibilidade Biológica , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Camundongos , Estrutura Molecular , Células NIH 3T3 , Tamanho da Partícula , Sulfanilamida/síntese química , Sulfanilamida/química , Propriedades de Superfície , Tensoativos/química
16.
Inorg Chem ; 58(14): 9404-9413, 2019 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-31246015

RESUMO

A simple "click-chemistry" approach was employed in order to functionalize the known antibiotic fragment sulfanilamide with a bidentate pyridyl-triazole pocket, which allowed for the synthesis of ruthenium(II) and rhenium(I) carbonyl chloride complexes. Six new complexes were prepared and comprehensively characterized, including five single crystal X-ray structures, photophysical characterization, and testing for antimicrobial activity. Interestingly, functionalization of the pyridine ring with an ortho-hydroxymethyl group resulted in a greater than 100-fold increase in the rate of ligand release in a dimethylsulfoxide solution. Subsequent studies indicated this process could be further accelerated by irradiation with 265 nm light. Structural characterization of four of the complexes indicates that this is the result of a lengthening and weakening of the Re-NPyridine bond (average (Ltri) = 2.19 Å vs LtriOH = 2.25 Å) due to the steric influence of the hydroxymethyl group. The organometallic rhenium(I) pyridyl-triazole functionality maintains its characteristic fluorescent properties despite the presence of the sulfonamide moiety. Two of the compounds showed modest antimicrobial activity against methicillin-resistant Staphylococcus aureus, whereas the structurally similar sulfamethoxazole alone showed no activity under the same conditions.


Assuntos
Cobre/química , Metais/química , Sulfanilamida/análogos & derivados , Sulfanilamida/química , Catálise , Química Click , Cristalografia por Raios X , Modelos Moleculares , Estrutura Molecular
17.
Anal Chem ; 91(15): 10110-10115, 2019 08 06.
Artigo em Inglês | MEDLINE | ID: mdl-31251032

RESUMO

The parameters characterizing the formation of complexes with albumin (in particular, human serum albumin (HSA)) are fundamental for the characterization of a drug for commercialization purposes and for the determination of common pharmacokinetic parameters. Electrochemical methods appear particularly attractive for the determination of the complexation constant, complex stoichiometry, and percentage of free/bound drug, due to the ease of operation and the wide availability. In this article, we propose an electrochemical method based on differential pulse voltammetry for the determination of albumin-drug interaction parameters, including the replacement of the drug-albumin adduct by a competitive compound, sulfanilamide. The formation of either single or multiple complexes between the considered drug and albumin has been considered. Typically, the method operates with a glassy carbon electrode in NaCl 0.9% as the supporting electrolyte.


Assuntos
Albuminas/metabolismo , Eletroquímica , Eletrodos , Sulfanilamida/metabolismo , Albuminas/química , Animais , Bovinos , Humanos , Concentração de Íons de Hidrogênio , Ligação Proteica , Ovinos , Sulfanilamida/química
18.
J Hazard Mater ; 375: 161-173, 2019 08 05.
Artigo em Inglês | MEDLINE | ID: mdl-31055193

RESUMO

A novel Z-scheme system, Ag/ZnFe2O4/Ag/BiTa1-xVxO4 with enhanced electron transfer capacity was constructed for degrading sulfanilamide (SAM) using solar light. The photocatalytic activity of Ag/ZnFe2O4/Ag/BiTa1-xVxO4 was investigated. The effects of the mass ratio (ZnFe2O4:BiTaO4), doped V dose, Ag wt.% content, and irradiation time on the catalytic performance were evaluated. The reasonable mechanism of Ag/ZnFe2O4/Ag/BiTa1-xVxO4 solar photocatalytic degradation was also presented. These results reveal Ag/ZnFe2O4/Ag/BiTa1-xVxO4 possesses enhanced photocatalytic performance. The loaded Ag as electron mediator increases the electron transfer rate. Particularly, the doped V and the Fe ions from ZnFe2O4 form a powerful electron driving force, which enhances the electron transfer capacity. Ag/ZnFe2O4/Ag/BiTa1-xVxO4 shows optimal photocatalytic performance at 2.0 wt.% Ag and 0.5% doped V dose (ZnFe2O4:BiTaO4 = 1.0:0.5). Also, Ag/ZnFe2O4/Ag/BiTa1-xVxO4 exhibits high stability and repeatability in photocatalytic degradation. Several active species (•OH, •O2-, and h+) are produced in the Z-scheme photodegradation of SAM. These results on the enhanced photocatalytic activity of Ag/ZnFe2O4/Ag/BiTa1-xVxO4 are ascribed to synergistic photocatalytic effects of ZnFe2O4 and BiTa1-xVxO4 mediated through Ag and driven by doped V and Fe ions. Therefore, the Z-scheme Ag/ZnFe2O4/Ag/BiTa1-xVxO4 photocatalytic technology proves to be promising for the solar photocatalytic treatment of antibiotics under solar light.


Assuntos
Antibacterianos/química , Compostos Férricos , Metais Pesados , Nanocompostos , Óxidos , Sulfanilamida/química , Compostos de Zinco , Catálise , Compostos Férricos/química , Compostos Férricos/efeitos da radiação , Metais Pesados/química , Metais Pesados/efeitos da radiação , Nanocompostos/química , Nanocompostos/efeitos da radiação , Oxirredução , Óxidos/química , Óxidos/efeitos da radiação , Fotólise , Luz Solar , Compostos de Zinco/química , Compostos de Zinco/efeitos da radiação
19.
J Pharm Sci ; 108(9): 2865-2870, 2019 09.
Artigo em Inglês | MEDLINE | ID: mdl-31128123

RESUMO

To demonstrate the selectivity of 14N nuclear quadrupole resonance (14N NQR) spectroscopy in chemistry and pharmacy, a study of sulfanilamide polymorphism was undertaken. We studied 3 known polymorphs of sulfanilamide by 14N NQR. We found at room temperature 2 sets of 3 14N NQR transition frequencies, corresponding to 2 different nitrogen sites in the crystal structure for each of 3 polymorphs. We measured the temperature dependence of all quadrupole frequencies ν+, ν-. In each set, only 1 of the 3 14N NQR frequencies is enough to characterize the polymorph. Spin-lattice relaxation time (T1) measurement is supplemental information. We also measured the transition temperature between polymorphs and estimated the ratio of polymorphs after thermal treatment of sample.


Assuntos
Sulfanilamida/química , Química Farmacêutica , Cristalização , Espectroscopia de Ressonância Magnética , Nitrogênio/química , Temperatura
20.
Drug Dev Ind Pharm ; 45(7): 1120-1129, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30883240

RESUMO

Objective: The aim of this study was to explore the possibility of using natural deep eutectic solvents (NADES) as solvation media for enhancement of solubility of sulfonamides, as well as gaining some thermodynamic characteristics of the analyzed systems. Significance: Low solubility of many active pharmaceutical ingredients is a well-recognized difficulty in pharmaceutical industry, hence the need for different strategies addressing this problem. Among such strategies, those that are environmentally and economically beneficial are of particular interest. Methods: The solubility of sulfanilamide and sulfacetamide in 21 different NADES compositions comprising choline chloride with sugars or sugar alcohols was measured spectrophotometrically. Thermodynamic parameters describing the studied systems were determined using the COSMO-RS computational protocol. Results: All of the considered NADES compositions gave an increase in solubility of the studied sulfonamides, with the highest solubilities obtained for the system comprising choline chloride and glycerol in unimolar proportions, which gave a solubility advantage of 83.7 and 73.8 for sulfanilamide and sulfacetamide, respectively. Theoretical studies indicated that the dissolution of both considered sulfonamides has a low endothermic character, with the lowest enthalpy values obtained for the most optimal, i.e. unimolar, proportions. The non-monotonous trend of enthalpy of dissolution was also discussed in terms of intermolecular interactions. Conclusions: The obtained results show the feasibility of using NADES as solubility enhancers for sulfonamides and encourage for further exploration in this field.


Assuntos
Sulfacetamida/química , Sulfanilamida/química , Colina/química , Glicerol/química , Solubilidade , Solventes/química
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