5112-36-7Relevant academic research and scientific papers
2,6-Pyridinedicarbohydrazide-Salicylal hydrazone-base derivative with High detection limit and binding Constant for emissive ion chemosensing in aqueous solution
Amini, Abbas,Behmadi, Hossein,Benson, Veronika,Cheng, Chun,Nazari, Marziyeh,Rahimi, Marjan,Samali, Bijan
, (2020)
A new tridentate luminescent molecule, N2,N6-bis(salicylidene)pyridine-2,6-dicarbohydrazide (BSPDH), was introduced and facilely eco-synthesized with high yield. It was then characterized through Fourier transform infrared, Hydrogen-
Novel 2,6-disubstituted pyridine hydrazones: Synthesis, anticancer activity, docking studies and effects on caspase-3-mediated apoptosis
?evik, ?zge,?enkarde?, Sevil,Abbak, Mürüvvet,Durak, As?m Tu?rul,Ekrek, Sedanur,Güniz Kü?ükgüzel, ?.,Kü?ükgüzel, ?lkay,Ka?katepe, Banu,Türe, Asl?
, (2021)
Novel pyridine-based dihydrazones (3a-l) were synthesized by the condensation of appropriate aldehydes and pyridine-2,6-dicarbohydrazide (2) which was obtained by the treatment of dimethyl pyridine-2,6-dicarboxylate (1) with hydrazine hydrate. Structures of all the synthesized compounds were supported by their FTIR, 1H NMR, 13C NMR and microanalytical data. The compounds were screened primarily for their antibacterial activities as well as anticancer activities. None of the synthesized compounds had important antibacterial activity. Among the compounds which were tested against human colon cancer cell line (HT-29), compounds 3f and 3k showed significant activity (IC50=6.78 μM for compound 3f, IC50=8.88 μM for compound 3k). In addition, compound 3g exhibited promising activity against Ishikawa human endometrial cancer cell line (ISH) with an IC50 value of 8.26 μM. At 10 μM, compounds 3f, 3k and 3g caused morphological changes of HT-29 and ISH cells and caspase-3 activation. In addition, these compounds were evaluated against NIH 3T3 mouse embriyonic fibroblast cell line and all synthesized compounds (3a-l) were found to be less toxic than paclitaxel. Moreover, possible inhibition mechanism of compound 3g was evaluated in silico against BRAF kinase enzyme.
Synthesis and characterization of bis[N′-(4-carboxybenzylidene)]- pyridine-2,6-dicarbohydrazide: Colorimetric and fluorometric modulation in presence of F- ions
Sinha, Priti,Srivastava, Ashish Kumar,Mishra, Lallan
, p. 286 - 294 (2013)
(Graph Presented) A novel organic compound bis[N′-(4- carboxybenzylidene)]-pyridine-2,6-dicarbohydrazide (L) was synthesized and characterized using spectroscopic and X-ray diffraction techniques. Tetrabutyl ammonium halides [(Bu)4N+X-] X = F, Cl, Br and I were allowed to react separately with a solution of L in DMSO (1 × 10-5 M). The solution of L turned to shining yellow colour in the presence of F- ion only. The binding properties have been studied using absorption, emission and 1H NMR titrations. Theoretical studies on compound L and compound L + X- (X = F, Cl and Br) in DMSO medium were carried out using density functional theory (DFT) at the B3LYP/6-31G(d,p)/6-31G+(d,p) level. The theoretical calculations agreed to the experimental results.
Colorimetric sensing of anions in aqueous solution using a charge neutral, cleft-like, amidothiourea receptor: Tilting the balance between hydrogen bonding and deprotonation in anion recognition
Duke, Rebecca M.,O'Brien, John E.,McCabe, Thomas,Gunnlaugsson, Thorfinnur
, p. 4089 - 4092 (2008)
The design, synthesis and physical evaluation of 1, a visible colorimetric 'naked eye' pyridyl based bis-amidothiourea sensor for anions, is described. This charge neutral sensor gives rise to significant changes in the absorption spectra upon interactions with several important biological anions such as AMP and ADP in 4: 1 DMSO-H2O solution, while ATP was not detected. These colorimetric changes are due to the formation, or the combination of hydrogen bonding complexes and/or deprotonation between these anions and 1.
2,6-Bis[(2-hydr-oxy-3-methoxy-benzyl-idene)hydrazinocarbon-yl]pyridine monohydrate
Li, Zhi-Feng,Wang, Ping,Zhang, Qian,Chen, Zao-Ming,Wang, Chun-Xiang
, p. o369-o370 (2007)
In the title compound, C23H19N5O6·H2O, the two components are linked into complex chains by a combination of two independent O - H...O and two independent N - H...O hydrogen bonds. The complex chains are linked into a two-dimensional sheet network via π-π
Synthesis, density functional theory calculations and luminescence of lanthanide complexes with 2,6-bis[(3-methoxybenzylidene)hydrazinocarbonyl] pyridine Schiff base ligand
Taha, Ziyad A.,Ababneh, Taher S.,Hijazi, Ahmed K.,Abu-Salem, Qutaiba,Ajlouni, Abdulaziz M.,Ebwany, Shroq
, p. 79 - 88 (2018)
A pyridine-diacylhydrazone Schiff base ligand, L?=?2,6-bis[(3-methoxy benzylidene)hydrazinocarbonyl]pyridine was prepared and characterized by single crystal X-ray diffraction. Lanthanide complexes, Ln–L, {[LnL(NO3)2]NO3.xH2O (Ln?=?La, Pr, Nd, Sm, Eu, Gd, Tb, Dy and Er)} were prepared and characterized by elemental analysis, molar conductance, thermal analysis (TGA/DTGA), mass spectrometry (MS), Fourier transform infra-red (FT-IR) and nuclear magnetic resonance (NMR) spectroscopy. Ln–L complexes are isostructural with four binding sites provided by two nitro groups along with four coordination sites for L. Density functional theory (DFT) calculations on L and its cationic [LnL(NO3)2]+ complexes were carried out at the B3LYP/6–31G(d) level of theory. The FT-IR vibrational wavenumbers were computed and compared with the experimentally values. The luminescence investigations of L and Ln–L indicated that Tb–L and Eu–L complexes showed the characteristic luminescence of Tb(III) and Eu(III) ions. Ln–L complexes show higher antioxidant activity than the parent L ligand.
Dicarbohydrazide based chemosensors for copper and cyanide ions: Via a displacement approach
Yadav, Neetu,Singh, Ashok Kumar
, p. 6023 - 6033 (2018)
Ligands attached to pyridine dicarbohydrazide were synthesized and characterized by NMR, FT-IR, elemental analysis, UV-visible spectroscopy, mass spectrophotometry, emission spectra and single crystal X-ray diffraction. These ligands were found to recognize copper ions over other metal ions and cyanide ions by a copper complex performing an in situ experiment with turn on-off-on behaviour over different anions in a CH3OH:H2O (9:1, v/v solution) medium. These ligands displayed a red shift in their absorption spectra and quenching in their emission spectra when exposed to copper ions via a PET mechanism and a further copper complex was applied for cyanide detection among the other anions. The 1:2, 1:3, 1:2 and 1:2 stoichiometric ratios of the ligands (L1-L4, respectively) with copper ions were calculated from a Job plot based on the UV-visible spectra. The S-V plot represents the linearity of the ligands with copper ions. The limits of detection (LOD) of copper ions along with the ligands (L1-L4) were calculated to be 0.12, 0.10, 0.097 and 0.098 μM using emission spectra, respectively. The binding affinities of the ligands with copper ions were determined by various characterization techniques such as FTIR, mass spectrophotometry and electrochemical and optical studies. Furthermore, an in situ experiment was performed for cyanide detection via a metal displacement approach. L1 and L4 with Cu2+ ions showed an affinity towards cyanide ions, with detection limits of 0.31 and 0.53 μM.
Fluorescent sensing of anions using a bis-quinoxaline amidothiourea based supramolecular cleft; an example of an anion-induced deprotonation event
Duke, Rebecca M.,Gunnlaugsson, Thorfinnur
, p. 5402 - 5405 (2010)
The quinoxaline 1, possessing a 2,6-pyridyl-based amidothiourea moiety, with the view of forming a pre-organised molecular cleft, was developed as a fluorescent anion sensor. The sensing ability of 1 was evaluated in organic solution where both the ground and the excited state of 1 was affected upon recognition of anions such as acetate [as tetrabutylammonium salt (TBAAc) solution] at the amiodothiourea moieties in MeCN. The fluorescence of 1, with λmax at 477 nm, was, on all occasions quenched, upon anion recognition. Using TBAOH, we also show that the same anion-induced changes occurred; demonstrating that for this particular sensor, the anion-sensing takes place via a deprotonation mechanism. This anion-induced deprotonation event was further investigated by carrying out 1H NMR titrations on 1, using both AcO- and OH- in DMSO-d6.
Hydrazones in anion transporters: The detrimental effect of a second binding site
Félix, Vítor,Halgreen, Lau,Marques, Igor,Martínez-Crespo, Luis,Soares, Márcio,Valkenier, Hennie
supporting information, p. 8324 - 8337 (2021/10/12)
Synthetic anion transporters can be developed using anion receptors that are able to bind the anion and stabilize it in the lipophilic interior of a bilayer membrane, and they usually contain functional groups with acidic NHs, such as ureas, thioureas and squaramides. To assess the suitability of acylhydrazones as a new functional group for the preparation of anion transporters, we have studied a family of thioureas functionalized with these and related functional groups.1H NMR titrations and DFT calculations indicate that the thioureas bearing acylhydrazone groups behave as chloride receptors with two separate binding sites, of which the acylhydrazone binds weaker than the thiourea. Chloride transport studies show that the additional binding site has a detrimental effect on thiourea-based transporters, and this phenomenon is also observed for bis(thio)ureas with two separate binding sites. We propose that the presence of a second anion binding unit hinders the transport activity of the thiourea due to additional interactions with the phospholipids of the membrane. In agreement with this hypothesis, extensive molecular dynamics simulations suggest that the molecules will tend to be positioned in the water/lipid interface, driven by the interaction of the NHs of the thiourea and of the acylhydrazone groups with the POPC polar head groups and water molecules. Moreover, the interaction energies show that the poorest transporters have indeed the strongest interactions with the membrane phospholipids, inhibiting chloride transport. This detrimental effect of additional functional groups on transport activity should be considered when designing new ion transporters, unless these groups cooperatively promote anion recognition and transmembrane transport.
Chromogenic and fluorogenic "off-on-off" chemosensor for selective and sensitive detection of aluminum (Al3+) and bifluoride (HF2-) ions in solution and in living Hep G2 cells: Synthesis, experimental and theoretical studies
Manna, Saikat Kumar,Mondal, Debasish,Mukhopadhyay, Subrata,Pal, Kunal,Pathak, Sudipta,Pramanik, Samit
, p. 13259 - 13265 (2020/10/07)
A simple pyridine-dicarbohydrazide based colorimetric and fluorometric chemosensor L was designed and synthesized for Al3+ ion sensing in organo aqueous solution. In the presence of Al3+ ions, probe L exhibited visible color changes and fluorescence enhancement (20-fold) due to Al3+ induced chelation-enhanced fluorescence (CHEF) effects. Chemosensor L revealed high selectivity toward Al3+ ions by "turn-on"fluorescence among the other competitive metal ions examined with a detection limit of 0.8 μM. Probe L was found to bind with Al3+ ions in a 1 : 2 (probe : metal) stoichiometric fashion, with an association constant (Ka) of 4.26 × 104 M-2. In addition, DFT and TDDFT calculations were carried out to recognize the binding nature and electronic properties of probe L and its Al-complex. Furthermore, the in situ prepared [L-Al] complex was able to detect HF2- anions via a metal displacement strategy. The bioimaging application of Al3+ and HF2- was implemented in living human liver cancer cells (Hep G2). This journal is
