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(a) DTA–TGA graphics of TBZA; (b) DSC–TGA graphics of Co(II) complex; (c) DSC–TGA graphics of Cu(II) complex; (d) DSC–TGA graphics of Zn(II) complex.
Source publication
A sulfonamide 1-tosyl-1-H-benzo(d)imidazol-2-amine (TBZA) and three new complexes of Co(II), Cu(II), and Zn(II) have been synthesized. The compounds have been characterized by elemental analyses, FTIR, (1)H, and (13)C-NMR spectroscopy. The structure of the TBZA, and its Co(II) and Cu(II) complexes, was determined by X-ray diffraction methods. TBZA...
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... achieve this assignment, the 1 H, HSQC, and HMBC calculations were performed (see figures in Supplementary Material). Figure 4(a) shows the sulfonamide thermal diagrams (DTA - TGA). The compound is stable up to 190 C. ...
Citations
... Compared with the CsPb 0.4 Sn 0.6 I 3 sample, the Fourier transform infrared (FTIR) spectrum of the PTSH sample exhibits distinctive peaks corresponding to the NH stretching vibration peak at 3384 and 3251 cm −1 , the asymmetric and symmetric stretching peaks of the sulfonamide sulfonyl group at 1301 and 1155 cm -1 , and the S-N stretching peak at 955 cm −1 (Supplementary Fig. 17) 31,32 . We simulated the heating process of the CsPb 0.4 Sn 0.6 I 3 :GLE sample and monitored the peak changes using in-situ TG-FTIR measurement to con rm the interaction (Fig. 3C) Fig. 18,19). ...
Inorganic perovskite tandem solar cells (IPTSCs) are promising candidates to break the efficiency bottleneck and address the stability issue. However, challenges remain in fabricating 2-terminal (2T) IPTSCs due to the inferior film formation and deep trap states induced by tin cations. Herein, a green ligand evolution (GLE) strategy with p-toluenesulfonyl hydrazide is employed to regulate film formation and eliminate deep traps in inorganic narrow bandgap perovskite, enabling the successful development of 2T IPTSCs. Accordingly, the 1.31 eV CsPb0.4Sn0.6I3:GLE device delivers a record efficiency of 17.41%. Combined with the 1.92 eV CsPbI2Br top-cell, 2T-IPTSCs exhibit a champion efficiency of 22.57% (certified 21.92%). Additionally, IPTSCs are engineered to deliver remarkable operation durability under maximum power point tracking, maintaining 80% of the initial efficiency at 65 ℃ for 1510 h and 85℃ for 800 h, respectively.
... Metal ions are vital for many biological function and cell process in microorganisms, usually serving as the co-factor for different enzymes [32,33]. Also, the literature describes quinolione -sulfonamide complexes with antimicrobial activity [34][35][36][37][38]. Hence, using molecular hybridization approach it appear logical to combine the quinolione and sulfonamide pharmacophores with a metal, in order to obtain newly hybrid quinolinebenzenesulfonamide -metal (HQBSM) derivatives with antimicrobial activity. ...
We present in this paper a direct and efficient study regarding synthesis and spectral characterization of three series of hybrid quinoline anchored with 4-R-benzenesulfonamide moiety, with potential antimicrobial activity, by using ultrasound (US) irradiation and conventional methods (CV). The synthesis pathway is efficient and direct, in two steps: an initial N-acylation of 8-aminoquinoline followed by metal complexation with variously M²⁺ metals (Cd²⁺, Co²⁺, Cu²⁺, Ni²⁺, Pd²⁺, Zn²⁺). For both type of reactions, N-acylation and complexation, under US irradiations the synthesis have some undeniable advantages: the most relevant being the higher yields, a dramatically decrease for reaction time (with about 150 (one hundred fifty) folds for complexation) comparative with conventional methods (CV) (therefore the spent energy decrease in the same way), a decrease of the amount of used solvents. Taking into account the above considerations these reactions setup could be appreciated as eco-friendly. The structures of the obtained hybrid quinoline – sulfonamide complexes (HQBSM) were determined by elemental analysis and by using spectral investigations: FT-IR, NMR experiments, and X-ray diffraction (in three cases). The FT-IR and NMR spectra of complexes show a similar spectroscopic pattern for all complexes and fully confirm the proposed structures. The X-ray spectra analyses prove without doubts the structure of metal complexes, indicating that their structure depends essentially by two factors: the nature of metal and the nature of sulfonamide-quinoline moieties. Complexes containing 4-methoxy-benzoyl moiety and Zn²⁺ (e.g. 6a) are tetra-coordinated while in the Ni²⁺ complex (e.g. 6e) the metallic ion forms a distorted square-based bi-pyramid. In the complexes containing 4-nitro-benzoyl moiety and Cd²⁺ (e.g. 5d) the metallic ion forms a triangular bipyramid. The antibacterial and antifungal assay reveal that only hybrid HQBSM complex (4e) (with 4-chlorophenyl moiety and Ni²⁺ in molecule) have a significant antibacterial activity.
... The QSCM derivatives pay a particularly attention on scientific community during the last few years, especially for their fotoluminiscent [9][10][11][12] and biological properties. As far for biological properties, these compounds were found to have several activities, these including antiprotozoals and antimalarial and also antibacterial and antifungal activity [13][14][15]. ...
... Zinc(II) and copper(II) are endogenous, essential, and non-expensive metals. However, a few numbers of zinc(II) and copper(II) complexes were investigated as effective chemotherapeutic agents against fungi [16][17][18][19][20]. In order to change this scenario, herein we report the synthesis and characterization of Zn(II) and Cu(II) complexes containing ketoconazole (KTZ) or clotrimazole (CTZ) (Fig. 1), and evaluation of their in vitro antifungal activity against some fungi of medical relevance: Candida albicans, Cryptococcus neoformans, and Sporothrix brasiliensis. ...
... [Zn(CTZ) 2 13 C NMR (500 MHz, CDCl 3 ), δ (ppm): 122.37 (C 6 ), 127.14 (C 4 ), 130.77-127.36 (C 5 , C 7 , C 8 , C 9, C 10 , C 11, C 12 , C 13, C 14 , C 15, C 16 ...
A series of new metal complexes, [Zn(KTZ)2(Ac)2]·H2O (1), [Zn(KTZ)2Cl2]·0.4CH3OH (2), [Zn(KTZ)2(H2O)(NO3)](NO3) (3), [Cu(KTZ)2(Ac)2]·H2O (4), [Cu(KTZ)2Cl2]·3.2H2O (5), [Cu(KTZ)2(H2O)(NO3)](NO3)·H2O (6), were synthesized by a reaction of ketoconazole (KTZ) with their respective zinc or copper salts under mild conditions. Similarly, six corresponding metal-CTZ (clotrimazole) complexes [Zn(CTZ)2(Ac)2]·4H2O (7), [Zn(CTZ)2Cl2] (8), [Zn(CTZ)2(H2O)(NO3)](NO3)·4H2O (9), [Cu(CTZ)2(Ac)2]·H2O (10), [Cu(CTZ)2Cl2]·2H2O (11), [Cu(CTZ)2(H2O)(NO3)](NO3)·2H2O (12), were obtained. These metal complexes were characterized by elemental analyses, molar conductivity, 1H and 13C{1H} nuclear magnetic resonance, UV/Vis, and infrared spectroscopies. Further, the crystal structure for complexes 7 and 10 was determined by single-crystal X-ray diffraction. The antifungal activity of these metal complexes was evaluated against three fungal species of medical relevance: Candida albicans, Cryptococcus neoformans, and Sporothrix brasiliensis. Complexes 1 and 3 exhibited the greatest antifungal activity with a broad spectrum of action at low concentrations and high selectivity. Some morphological changes induced by these metal complexes in S. brasiliensis cells included yeast-hyphae conversion, an increase in cell size and cell wall damage. The strategy of coordination of clinic drugs (KTZ and CTZ) to zinc and copper was successful, since the corresponding metal complexes were more effective than the parent drug. Particularly, the promising antifungal activities displayed by Zn-KTZ complexes make them potential candidates for the development of an alternative drug to treat mycoses.
... Fortunately, many CA inhibitors (CAIs) exist and belong to many chemical classes, such as substituted benzene-sulfonamides, inorganic metalcomplexing anions, dithiocarbamates, and carboxylic acids [99][100][101]. Among them, the sulfonamides shown in Figure 2 are the most potent investigated CA inhibitors (CAIs) (simple derivatives 1-24 and clinically used drugs or agents in clinical development) [87,98,[102][103][104][105][106][107][108][109][110][111][112][113][114][115][116][117][118][119]. All of them were shown to also act as CAI primary sulfonamides as these inhibit CAs by binding to the Zn 2+ ion from the enzyme active site, in a tetrahedral geometry of the metal, whereas the sulfonamide is deprotonated at the SO 2 NH 2 moiety. ...
The involvement of the human microbiome is crucial for different host functions such as protection, metabolism, reproduction, and especially immunity. However, both endogenous and exogenous factors can affect the balance of the microbiota, creating a state of dysbiosis, which can start various gastrointestinal or systemic diseases. The challenge of future medicine is to remodel the intestinal microbiota to bring it back to healthy equilibrium (eubiosis) and, thus, counteract its negative role in the diseases’ onset. The shaping of the microbiota is currently practiced in different ways ranging from diet (or use of prebiotics, probiotics, and synbiotics) to phage therapy and antibiotics, including microbiota fecal transplantation. Furthermore, because microbiota modulation is a capillary process, and because many microbiota bacteria (both beneficial and pathogenic) have carbonic anhydrases (specifically the four classes α, β, γ, and ι), we believe that the use of CA inhibitors and activators can open up new therapeutic strategies for many diseases associated with microbial dysbiosis, such as the various gastrointestinal disorders and the same colorectal cancer.
... The aromatic/heterocyclic part of the inhibitor interacts with the hydrophilic and hydrophobic residues of the catalytic cavity [32,61]. Compounds containing -SO 2 NH 2 group, including clinically licensed drugs, are generally considered CAIs [27,[63][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78]. Some examples include: AAZ, MZA, EZA, and DCP, which are systemically acting antiglaucoma CAIs; DZA and BRZ are antiglaucoma agents; BZA belongs to the same pharmacological class; ZNS, SLT, and TPM are antiepileptic drugs; and SLP and IND, with COX2 selective inhibitors CLX and VLX. ...
Carbon dioxide (CO2), a vital molecule of the carbon cycle, is a critical component in living organisms’ metabolism, performing functions that lead to the building of compounds fundamental for the life cycle. In all living organisms, the CO2/bicarbonate (HCO3−) balancing is governed by a superfamily of enzymes, known as carbonic anhydrases (CAs, EC 4.2.1.1). CAs catalyze the pivotal physiological reaction, consisting of the reversible hydration of the CO2 to HCO3− and protons. Opportunistic and pathogenic fungi can sense the environmental CO2 levels, which influence their virulence or environmental subsistence traits. The fungal CO2-sensing is directly stimulated by HCO3− produced in a CA-dependent manner, which directly activates adenylyl cyclase (AC) involved in the fungal spore formation. The interference with CA activity may impair fungal growth and virulence, making this approach interesting for designing antifungal drugs with a novel mechanism of action: the inhibition of CAs linked to the CO2/HCO3−/pH chemosensing and signaling. This review reports that sulfonamides and their bioisosteres as well as inorganic anions can inhibit in vitro the β- and α-CAs from the fungi, suggesting how CAs may be considered as a novel “pathogen protein” target of many opportunistic, pathogenic fungi.
... Sulfa drugs are derived from sulfonamides, and the presence of primary sulfonamide moieties in sulfanilamide characterizes most of the investigated CA inhibitors (CAIs) (Supuran, 2016a(Supuran, ,b, 2017a. Sulfonamides and their structurally related derivatives, such as sulfamates and sulfamides, have the general formula A-SO 2 NH-R, where A can be an aromatic, heterocyclic, aliphatic, or sugar scaffold, while R may be hydrogen (primary sulfonamides/sulfamates/sulfamides), or a multiplicity of moieties incorporating heteroatoms (-OH, -NH 2 , etc.), as well as organic scaffolds like those said for A. Thus, a range of compounds containing the -SO 2 NH 2 group were investigated as CAIs against bacterial CAs or CAs from other organisms (Supuran, 2017b). of these sulfonamide inhibitors (simple derivatives 1-24 and clinically used drugs or agents in clinical development) (Carta et al., 2009;Nishimori et al., 2010Nishimori et al., , 2014Vullo et al., 2013Vullo et al., , 2015aAlafeefy et al., 2015a,b;Dedeoglu et al., 2015;Abdel Gawad et al., 2016;Del Prete et al., 2016b,c,d;Diaz et al., 2016;Supuran, 2016d). Acetazolamide (AAZ), methazolamide (MZA), ethoxzolamide (EZA) and dichlorophenamide (DCP) are systemically acting antiglaucoma CAIs. ...
Our understanding of the function of bacterial carbonic anhydrases (CAs, EC 4.2.1.1) has increased significantly in the last years. CAs are metalloenzymes able to modulate CO 2 , HCO 3 – and H ⁺ concentration through their crucial role in catalysis of reversible CO 2 hydration (CO 2 + H 2 O ⇄ HCO 3 – + H ⁺ ). In all living organisms, CA activity is linked to physiological processes, such as those related to the transport and supply of CO 2 or HCO 3 – , pH homeostasis, secretion of electrolytes, biosynthetic processes and photosynthesis. These important processes cannot be ensured by the very low rate of the non-catalyzed reaction of CO 2 hydration. It has been recently shown that CAs are important biomolecules for many bacteria involved in human infections, such as Vibrio cholerae , Brucella suis , Salmonella enterica , Pseudomonas aeruginosa , and Helicobacter pylori . In these species, CA activity promotes microorganism growth and adaptation in the host, or modulates bacterial toxin production and virulence. In this review, recent literature in this research field and some of the above-mentioned issues are discussed, namely: ( i ) the implication of CAs from bacterial pathogens in determining the microorganism growth and virulence; ( ii ) the druggability of these enzymes using classical CA inhibitors (CAIs) of the sulfonamide-type as examples; ( iii ) the role played by Helicobacter pylori CAs in the acid tolerance/adaptation of the microbe within the human abdomen; ( iv ) the role of CAs played in the outer membrane vesicles spawned by H. pylori in its planktonic and biofilm phenotypes; ( v ) the possibility of using H. pylori CAIs in combination with probiotic strains as a novel anti-ulcer treatment approach. The latter approach may represent an innovative and successful strategy to fight gastric infections in the era of increasing resistance of pathogenic bacteria to classical antibiotics.
... After sulfanilamide was demonstrated to be an effective antibacterial agent, a range of molecular analogs constituting the so-called sulfa drugs entered in clinical use [30]. The presence of primary sulfonamide moieties in sulfanilamide characterizes most investigated CA inhibitors (CAIs) [8,[34][35][36][37]. Figure 3 shows some of these sulfonamide inhibitors (simple derivatives 1-24 and clinically used drugs) [3,[38][39][40][41][42][43][44][45][46][47][48][49][50][51][52]. Acetazolamide (AAZ), methazolamide (MZA), ethoxzolamide (EZA) and dichlorphenamide (DCP) are systemically acting antiglaucoma CAIs. ...
Carbonic anhydrases (CAs) are essential metalloenzymes in nature, catalyzing the carbon dioxide reversible hydration into bicarbonate and proton. In humans, breathing and many other critical physiological processes depend on this enzymatic activity. The CA superfamily function and inhibition in pathogenic bacteria has recently been the object of significant advances, being demonstrated to affect microbial survival/virulence. Targeting bacterial CAs may thus be a valid alternative to expand the pharmacological arsenal against the emergence of widespread antibiotic resistance. Here, we report an extensive study on the inhibition profile of the recently discovered ι-CA class present in some bacteria, including Burkholderia territorii, namely BteCAι, using substituted benzene-sulfonamides and clinically licensed sulfonamide-, sulfamate- and sulfamide-type drugs. The BteCAι inhibition profile showed: (i) several benzene-sulfonamides with an inhibition constant lower than 100 nM; (ii) a different behavior with respect to other α, β and γ-CAs; (iii) clinically used drugs having a micromolar affinity. This prototype study contributes to the initial recognition of compounds which efficiently and selectively inhibit a bacterial member of the ι-CA class, for which such a selective inhibition with respect to other protein isoforms present in the host is highly desired and may contribute to the development of novel antimicrobials.
... After 24 hours and 45 o C temperature of stirring 1 to 2 mL of HCl was added gradually to the mixture drop by drop finally, we filter the sample with filter paper (dark brown ppt). 29,30 ...
... For 24 hours, the sample's behavior was determined by the establishment of a Zone of Inhibition. Table 3 below shows the size of inhibition zone of graphene oxide derivative measured by (mm) with hole dimeter size 6 mm. the result of inhibition zones for compound 2 in gram/positive gram/negative and fungi (30,22,28,22,30, and 14 mm), respectively, the values for compound 3 shows ( 29, 19, 27, 19, 29 and 14 mm), also compound 4 shows resistance fore bacteria an fungi (19, 29,16, 22, 19, and 17 mm). However, compound 5 shows these values (20, 29, 16, 21, 20, 17 mm). ...
... For 24 hours, the sample's behavior was determined by the establishment of a Zone of Inhibition. Table 3 below shows the size of inhibition zone of graphene oxide derivative measured by (mm) with hole dimeter size 6 mm. the result of inhibition zones for compound 2 in gram/positive gram/negative and fungi (30,22,28,22,30, and 14 mm), respectively, the values for compound 3 shows ( 29, 19, 27, 19, 29 and 14 mm), also compound 4 shows resistance fore bacteria an fungi (19, 29,16, 22, 19, and 17 mm). However, compound 5 shows these values (20, 29, 16, 21, 20, 17 mm). ...
Preparation of graphene oxide and react it with many compounds by forming an amide group because graphene oxide (GO) Its molecular structure is saturated with carboxylic groups, making it an ideal for esterification and amidation.We exploit graphene oxide's capacity to interact with many compounds because of the carbonyl, hydroxyl, and epoxide functional groups in GO to create new products by reacting graphene oxide with those compounds (2-aminopyrmidine, dithiazone, sulfamide, and 1-amino-2-naphthol-4sulfonic acid). Using fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1 H-NMR), field emission scanning electron microscope (FESEM), and X-ray diffraction were used to characterize the derivatives. The X-ray diffraction (XRD) pattern was estimated using two-particle size equations and compared between them. Furthermore, studying the antimicrobial activities of graphene oxide derivatives, inhibition zone illustrates the potency of compound on bacteria and fungi.
... Molecules 2020, 25, 2946 2 of 12 few data was found for their antibacterial and antifungal activity [26]. The antibacterial activity of azaheterocycles sulfonamides is well known [1,2]. ...
... A special class of quinoline derivatives which pay a particularly attention on scientific community, are quinoline-sulfonamide complexes (QSC), studied especially for their fotoluminiscent (mostly fluorescent) properties [17][18][19][20][21][22][23]. As far for biological activity, these compounds were tested mostly as antiprotozoals [24,25] and very antiprotozoals [24,25] and very few data was found for their antibacterial and antifungal activity [26]. The antibacterial activity of azaheterocycles sulfonamides is well known [1,2]. ...
... Molecules 2020, 25, x FOR PEER REVIEW 2 of 13 antiprotozoals [24,25] and very few data was found for their antibacterial and antifungal activity [26]. The antibacterial activity of azaheterocycles sulfonamides is well known [1,2]. ...
Two new series of hybrid quinoline-sulfonamide complexes (M2+: Zn2+, Cu2+, Co2+ and Cd2+) derivatives (QSC) were designed, synthesized and tested for their antimicrobial activity. The synthesis is straightforward and efficient, involving two steps: acylation of aminoquinoline followed by complexation with metal acetate (Cu2+, Co2+ and Cd2+) or chloride (Zn2+). The synthesized QSC compounds were characterized by FTIR and NMR spectroscopy and by X-ray diffraction on single crystal. The QSC compounds were preliminary screened for their antibacterial and antifungal activity and the obtained results are very promising. In this respect, the hybrid N-(quinolin-8-yl)-4-chloro-benzenesulfonamide cadmium (II), considered as leading structure for further studies, has an excellent antibacterial activity against Staphylococcus aureus ATCC25923 (with a diameters of inhibition zones of 21 mm and a minimum inhibitory concentration (MIC) of 19.04 × 10−5 mg/mL), a very good antibacterial activity against Escherichia coli ATCC25922 (with a diameters of inhibition zones of 19 mm and a MIC of 609 × 10−5 mg/mL), and again an excellent antifungal activity against Candida albicans ATCC10231 (with a diameters of inhibition zones of 25 mm and a MIC of 19.04 × 10−5 mg/mL).
