Structural, spectroscopic and computational studies of the 2:1 complex of nipecotic acid with squaric acid

Bartoszak-Adamska, Elżbieta; Dega‐Szafran, Z.; Komasa, Anna; Szafran, M.

doi:10.1016/j.chemphys.2014.09.004

Cited by 9 publications

(2 citation statements)

References 59 publications

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“…The specific rotation

of 3 is +5 (C 1, water). The results of compound 3 were in good concordance with the data in the literature for nipecotic acid ( Figure 1 ) [ 27 , 28 ].…”

Section: Resultssupporting

confidence: 88%

In Vitro Characterization of Inhibitors for Lung A549 and Leukemia K562 Cell Lines from Fungal Transformation of Arecoline Supported by In Silico Docking to M3-mAChR and ADME Prediction

et al. 2022

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The search for anticancer drugs is of continuous interest. Arecoline is an alkaloid with anticancer activity. Herein, the metabolism of arecoline through fungal transformation was investigated for the discovery of potential anticancer drugs with higher activity and selectivity. Compounds 1–5 were isolated, and their structures were fully elucidated using various spectroscopic analyses, including 1D and 2D NMR, ESIMS, and HRESIMS. This is the first report for the isolation of compounds 1 and 2. An MTT assay was performed to determine the cytotoxic activity of arecoline and its metabolites in vitro using non-small-cell lung cancer A549 and leukemia K562 cell lines compared to staurosporine and doxorubicin as positive controls. For the non-small-cell lung A549 cell line, arecoline hydrobromide, staurosporine, and doxorubicin resulted in IC50 values of 11.73 ± 0.71 µM, 10.47 ± 0.64 µM, and 5.05 ± 0.13 µM, respectively, while compounds 1, 3, and 5 exhibited IC50 values of 3.08 ± 0.19 µM, 7.33 ± 0.45 µM, and 3.29 ± 0.20 µM, respectively. For the leukemia K562 cell line, the IC50 values of arecoline hydrobromide, staurosporine, and doxorubicin were 15.3 ± 1.08 µM, 5.07 ± 0.36 µM, and 6.94 ± 0.21 µM, respectively, while the IC50 values of compounds 1, 3 and 5 were 1.56 ± 0.11 µM, 3.33 ± 0.24 µM, and 2.15 ± 0.15 µM, respectively. The selectivity index value of these compounds was higher than 3. These results indicated that compounds 1, 3, and 5 are very strong cytotoxic agents with higher activity than the positive controls and good selectivity toward the tested cancer cell lines. Cell cycle arrest was then studied by flow cytometry to investigate the apoptotic mechanism. Docking simulation revealed that most compounds possessed good binding poses and favorable protein-ligand interactions with muscarinic acetylcholine receptor M3-mAChR protein. In silico study of pharmacokinetics using SwissADME predicted compounds 1–5 to be drug-like with a high probability of good oral bioavailability.

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“…The specific rotation

of 3 is +5 (C 1, water). The results of compound 3 were in good concordance with the data in the literature for nipecotic acid ( Figure 1 ) [ 27 , 28 ].…”

Section: Resultssupporting

confidence: 88%

In Vitro Characterization of Inhibitors for Lung A549 and Leukemia K562 Cell Lines from Fungal Transformation of Arecoline Supported by In Silico Docking to M3-mAChR and ADME Prediction

et al. 2022

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“…[11][12][13] Squaric acid (H 2 SQ, 3,4-dihydroxycyclobut-3-ene-1,2-dione) and its salts show promising pharmacological properties. 14 Recently, complexes of squaric acid with isomeric piperidine carboxylic acids, [15][16][17] trigonelline 18 and vitamin B 6 (pyridoxine) 19 have also been studied.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural characteristic of pyridine carboxylic acid adducts with squaric acid

et al. 2022

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Tunable Self‐Assembled Micro/Nanostructures of Carboxyl‐Functionalized Squarylium Cyanine for Ammonia Sensing

Yan

et al. 2015

Adv Funct Materials

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Orderly molecular self‐assembly for tunable micro/nanostructures is an effective way to prepare novel functional materials with desired properties. Squarylium cyanine (SCy) dyes have received great attention in the fields of laser, imaging, and optoelectronic device. However, the detailed self‐assembly behavior of SCy has rarely been investigated. In the present work, two SCy derivatives, D1 and D2, respectively, bearing four and two carboxylic acid groups at different positions are prepared and used as a model system to investigate the molecular self‐assembly, morphology, and optical properties of SCy dyes. The hydrogen‐bonding interactions between the carboxylic acid groups in D1 and D2 are determined with X‐ray diffraction, 2D nuclear magnetic resonance, and Fourier transformation infrared spectroscopy. The two types of hydrogen bonds in D1 cooperating with inherent π–π stacking interaction result in tunable molecular aggregations, which further leads to the transformation between J‐aggregation and H‐aggregation of D1 in the solid state in response to ammonia gas. In all, this work provides a feasible and effective way to study the self‐assembled aggregates of SCy dyes at both molecular and supramolecular levels, and has developed a reversible sensor for ammonia gas detection.

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Structural, spectroscopic and computational studies of the 2:1 complex of nipecotic acid with squaric acid

Cited by 9 publications

References 59 publications

In Vitro Characterization of Inhibitors for Lung A549 and Leukemia K562 Cell Lines from Fungal Transformation of Arecoline Supported by In Silico Docking to M3-mAChR and ADME Prediction

In Vitro Characterization of Inhibitors for Lung A549 and Leukemia K562 Cell Lines from Fungal Transformation of Arecoline Supported by In Silico Docking to M3-mAChR and ADME Prediction

Synthesis and structural characteristic of pyridine carboxylic acid adducts with squaric acid

Tunable Self‐Assembled Micro/Nanostructures of Carboxyl‐Functionalized Squarylium Cyanine for Ammonia Sensing

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