New Electroactive Hybridization Indicators 2‐Phthalimido‐<i>N</i>‐Substitutedphenylethanesulfonamide Derivatives for Biosensor Applications: Ring Substituent Effect on Interaction between Compound and DNA

Ozkan-Ariksoysal, Dilsat; Akgül, Özlem; Aydınlık, Şeyma; Topkaya, Seda Nur; Aladağ, Nilay; Ozsoz, Mehmet

doi:10.1002/elan.201000128

Cited by 6 publications

(3 citation statements)

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“…Moreover, in one of our study, title compounds 2, 3, 5, 8, 9, 10 were evaluated for their interaction with DNA and suggested to have different binding affinities which are not consistent with MIC values (32). Therefore, the antibacterial activity may not be suggested as a result of DNA interaction.…”

Section: Antimicrobial Activitymentioning

confidence: 81%

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Akgül¹,

Öztürk²,

Aygül³

et al. 2017

Marmara Pharmaceutical Journal

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In this study, a series of taurinamide derivatives were synthesized and screened for their antimicrobial activity. The structures of the newly synthesized compounds 11-15 were evaluated by 1 H NMR, IR, MS-APCI and elemental analysis. Compounds (1-15) were tested against standard strains of Gram(+), Gram(−) bacteria and fungi by using disc diffusion and broth microdilution methods. Although disc diffusion method did not show any comparable results due to the solubility properties of the compounds; microdilution method results indicated that title compounds showed from poor to good activity against only Enterococcus faecalis. It can be concluded that phtalimido moiety, secondary aryl sulphonamide group and electrondonating group substitution on phenyl ring are essential for the antibacterial activity. Among the tested compounds, para substituted methyl and methoxy derivatives of N-phenyl-2-phthalimidotaurinamide (4, 7), displayed equipotent activity compared to standard drug gentamicin.

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Section: Antimicrobial Activitymentioning

confidence: 81%

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Akgül¹,

Öztürk²,

Aygül³

et al. 2017

Marmara Pharmaceutical Journal

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“…Thus, the ortho-chlorosubstituted isomer N-(2-chlorophenyl)-2-phthalimidoethanesulfonamide, (I), is more active than both the para-isomer N-(4-chlorophenyl)-2-phthalimidoethanesulfonamide, (II), and the meta-isomer N-(3-chlorophenyl)-2-phthalimidoethanesul- (Akgul et al, 2007). Isomer (II) can be used as a disposable electrochemical biosensor and redox indicator; it reduces guanine base oxidation and can cause mutation (Ozkan-Ariksoysal et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Positional isomeric effect on the crystallization of chlorine-substitutedN-phenyl-2-phthalimidoethanesulfonamide derivatives

Koca

Sevinçek

Akgül

et al. 2015

Acta Crystallogr C Struct Chem

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The ortho-, para- and meta-chloro-substituted N-chlorophenyl-2-phthalimidoethanesulfonamide derivatives, C16H13ClN2O4S, have been structurally characterized by single-crystal X-ray crystallography. N-(2-Chlorophenyl)-2-phthalimidoethanesulfonamide, (I), has orthorhombic (P2(1)2(1)2(1)) symmetry, N-(4-chlorophenyl)-2-phthalimidoethanesulfonamide, (II), has triclinic (P1¯) symmetry and N-(3-chlorophenyl)-2-phthalimidoethanesulfonamide, (III), has monoclinic (P2(1)/c) symmetry. The molecules of (I)-(III) are regioisomers which have crystallized in different space groups as a result of the differing intra- and intermolecular hydrogen-bond interactions which are present in each structure. Compounds (I) and (II) are stabilized by N-H···O and C-H···O hydrogen bonds, while (III) is stabilized by N-H···O, C-H···O and C-H···Cl hydrogen-bond interactions. The structure of (II) also displays π-π stacking interactions between the isoindole and benzene rings. All three structures are of interest with respect to their biological activities and have been studied as part of a programme to develop anticonvulsant drugs for the treatment of epilepsy.

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“…21 This event can be performed by DNA-targeting compounds such as metal coordination complexes, antibiotics, or other indicators that interact with single strand (ss) and double strand (ds) DNA differently. 12,[22][23][24][25][26][27][28] Other targeting compounds include metal labels such as gold or silver nanoparticles, 29,30 which are widely used in enhancement of sensor performance (based on amplifying the resulting response).…”

Section: Introductionmentioning

confidence: 99%

A nucleic acid-based electrochemical biosensor for the detection of influenza B virus from PCR samples using gold nanoparticle-adsorbed disposable graphite electrode and Meldola's blue as an intercalator

et al. 2011

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In the presented study, a novel method is introduced that demonstrates the electrochemical detection of influenza B virus based on DNA hybridisation. The detection utilised gold nanoparticles (AuNPs) and Meldola's Blue (MDB), which is utilised as an intercalator label. The developed methodology, combined with a disposable pencil graphite electrode (PGE) and differential pulse voltammetry (DPV), was performed using both synthetic oligonucleotides and polymerase chain reaction (PCR) amplicons. The electrochemical oxidation response of guanine (approximately +0.1 V) and the voltammetric reduction signal of MDB (approximately À0.2 V) were measured before and after hybridisation reactions between a single strand DNA probe and its complementary target strain (synthetic target or denatured PCR samples). Before the immobilisation of the synthetic DNA probe of influenza type B virus, the transducer surface was interacted with AuNPs solution using a simple wet adsorption method. AuNP immobilisation was confirmed with cyclic voltammetry (CV) and electrochemical impedance spectroscopy (EIS) to characterise the recognition surface of the genosensor. After the interaction between the PGE and AuNPs, a thiol-linked DNA probe was immobilised onto the nanoparticle-covered surface. When hybridisation occurred between the probe and its synthetic targets or specific PCR products, the highest MDB signal was observed. The probes were also challenged with equal quantities of non-complementary DNA at the PGE surface for the determination of biosensor selectivity. AuNP-coated electrodes showed high sensitivity and selectivity, specifically in real samples for the detection of the hybridisation reaction. The results obtained in the presented study indicated that the electrode surface area could be enhanced with AuNPs. The detection limit of the genosensor was found to be 54 picomoles for the synthetic target and 3.3 Â 10 7 molecules for the real samples (PCR) in 30 mL of sample volume. Future prospects and analytical performance of the sensor is briefly discussed.

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New Electroactive Hybridization Indicators 2‐Phthalimido‐N‐Substitutedphenylethanesulfonamide Derivatives for Biosensor Applications: Ring Substituent Effect on Interaction between Compound and DNA

Cited by 6 publications

References 50 publications

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Positional isomeric effect on the crystallization of chlorine-substitutedN-phenyl-2-phthalimidoethanesulfonamide derivatives

A nucleic acid-based electrochemical biosensor for the detection of influenza B virus from PCR samples using gold nanoparticle-adsorbed disposable graphite electrode and Meldola's blue as an intercalator

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