Voltamperometry of 1,4-dihydropyridine derivatives

Stradyn, Ya. P.; Dubur, G. Ya.; Beilis, Yu. I.; Uldrikis, Ya. R.; Sausin, A. E.; Chekavichus, B. S.

doi:10.1007/bf00474459

Cited by 3 publications

(3 citation statements)

References 1 publication

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“…It should be noted that the parent compounds—1,4-DHP derivatives without cationic moieties—demonstrated lower electrooxidation potentials. Thus, 4-phenyl-substituted Hantzsch 1,4-dihydropyridine has a 1.08 V potential on a glassy carbon electrode [ 50 ] and the other 4-aryl-substituted 1,4-DHPs have 1.11 V potentials [ 51 ], but 4-monoalkyl-substituted 1,4-dihydropyridines at the same conditions have 1.01–1.03 V oxidation potentials [ 47 ].…”

Section: Resultsmentioning

confidence: 99%

Pleiotropic Properties of Amphiphilic Dihydropyridines, Dihydropyridones, and Aminovinylcarbonyl Compounds

Ruciņš

Smits

Sipola

et al. 2020

Oxidative Medicine and Cellular Longevity

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Three groups of synthetic lipids are chosen for studies: (1) 1,4-dihydropyridines (1,4-DHPs) containing two cationic moieties and their analogues; (2) 3,4-dihydro-2(1H)-pyridones containing a cationic moiety; and (3) acyclic, open-chain analogues, i.e., 2-amino-3-alkoxycarbonylalkylammonium derivatives. 1,4-DHPs possessing dodecyl alkyl chains in the ester groups in positions 3 and 5 and cationic nitrogen-containing groups in positions 2 and 6 have high cytotoxicity in cancer cells HT-1080 (human lung fibrosarcoma) and MH-22A (mouse hepatoma), but low cytotoxicity in the noncancerous NIH3T3 cells (mouse embryonic fibroblast). On the contrary, similar compounds having short (methyl, ethyl, or propoxyethyl) chains in the ester groups in positions 3 and 5 lack cytotoxicity in the cancer cells HT-1080 and MH-22A even at high doses. Inclusion of fluorine atoms in the alkyl chains in positions 3 and 5 of the DHP cycle decreases the cytotoxicity of the mentioned compounds. Structurally related dihydropyridones with a polar head group are substantially more toxic to normal and cancerous cells than the DHP analogues. Open-chain analogues of DHP lipids comprise the same conjugated aminovinylcarbonyl moiety and possess anticancer activity, but they also have high basal cytotoxicity. Electrochemical oxidation data demonstrate that oxidation potentials of selected compounds are in the range of 1.6–1.7 V for cationic 1,4-DHP, 2.0–2.4 V for cationic 3,4-dihydropyridones, and 1.2–1.5 V for 2-amino-3-alkoxycarbonylalkylammonium derivatives. Furthermore, the tested cationic 1,4-DHP amphiphiles possess antiradical activity. Molecular topological polar surface area values for the tested compounds were defined in accordance with the main fragments of compound structures. The determined log P values were highest for dodecyl ester groups in positions 3 and 5 of the 1,4-DHP and lowest for short alkyl chain-containing amphiphiles.

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Section: Resultsmentioning

confidence: 99%

Pleiotropic Properties of Amphiphilic Dihydropyridines, Dihydropyridones, and Aminovinylcarbonyl Compounds

Ruciņš

Smits

Sipola

et al. 2020

Oxidative Medicine and Cellular Longevity

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“…In order to avoid degradation on silica gel we investigated electron deficient 3,5-diethoxycarbonyl-DHP derivatives which have higher oxidation potentials. 35,36 For this reason, an electron deficient 4-phenyl DHP amide was prepared and this proved stable towards purification by silica gel chromatography (Fig. 1B).…”

Section: Resultsmentioning

confidence: 99%

Oxidative activation of dihydropyridine amides to reactive acyl donors

2015

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Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields.

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“…The possibility to characterize DHP as electron-donating compounds, including interaction with ROS, was studied by determining their electrooxidation potentials [27]. Electrochemistry as a tool for studying antioxidant properties was proposed [28].…”

Section: Introductionmentioning

confidence: 99%

4-Pyridinio-1,4-Dihydropyridines as Calcium Ion Transport Modulators: Antagonist, Agonist, and Dual Action

Домрачева

Kanepe

Vilšķe̅rsts

et al. 2020

Oxidative Medicine and Cellular Longevity

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A set of six new 4-pyridinio-1,4-dihydropyridine (1,4-DHP) compounds has been synthesized. The calcium channel modulating activity of these compounds was evaluated in an aorta vascular smooth muscle cell line (A7R5), in an isolated rat aortic ring model, and in human neuroblastoma cell lines (SH-SY5Y). The antagonistic effect of these 1,4-DHP was tested by modulating the impact of carbachol-dependent mobilization of intracellular Ca 2+ in SH-SY5Y cells. The intracellular free Ca 2+ concentration was measured in confluent monolayers of SH-SY5Y cells and A7R5 cells with the Ca 2+ -sensitive fluorescent indicator Fluo-4 NW. Only four compounds showed calcium channel blocking activity in SH-SY5Y and A7R5 cells as well as in the aortic ring model. Among them, compound 3 was the most active calcium channel antagonist, which had 3 times higher activity on carbachol-activated SH-SY5Y cells than amlodipine. Two of the compounds were inactive. Compound 4 had 9 times higher calcium agonist activity than the classic DHP calcium agonist Bay K8644. The intracellular mechanism for the action of compound 4 using inhibitor analysis was elucidated. Nicotinic as well as muscarinic receptors were not involved. Sarcoplasmic reticulum (ER) Ca 2+ (SERCA) stores were not affected. Ryanodine receptors (RyRs), another class of intracellular Ca 2+ releasing channels, participated in the agonist response evoked by compound 4. The electrooxidation data suggest that the studied compounds could serve as antioxidants in OS.

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Voltamperometry of 1,4-dihydropyridine derivatives

Cited by 3 publications

References 1 publication

Pleiotropic Properties of Amphiphilic Dihydropyridines, Dihydropyridones, and Aminovinylcarbonyl Compounds

Pleiotropic Properties of Amphiphilic Dihydropyridines, Dihydropyridones, and Aminovinylcarbonyl Compounds

Oxidative activation of dihydropyridine amides to reactive acyl donors

4-Pyridinio-1,4-Dihydropyridines as Calcium Ion Transport Modulators: Antagonist, Agonist, and Dual Action

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