Molecular docking studies, biological and toxicity evaluation of dihydroisoquinoline derivatives as potential anticancer agents

Ziemska, Joanna; Guśpiel, Adam; Jarosz, Jerzy; Nasulewicz‐Goldeman, Anna; Wietrzyk, Joanna; Kawęcki, R.; Pypowski, Krzysztof; Jarończyk, Małgorzata; Solecka, Jolanta

doi:10.1016/j.bmc.2016.08.054

Cited by 16 publications

(7 citation statements)

References 35 publications

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“…These include flavone derivatives, cinnamoyl pyrrolidines, cyclic imides, b-amino-a-hydroxyphenylbutanoic acids, indoline-2,3-diones, and 1,2,3,4-tetrahydroisoquinoline-3carboxylic acids (for details about these compounds, see Mucha et al 2010;Amin et al 2018). Dihydroisoquinoline 282 (Figure 22) inhibits APN and shows antiproliferative effects in several cell lines (Ziemska et al 2016).…”

Section: Substrates Apn Catalyzes the Hydrolysis Of N-ter-mentioning

confidence: 99%

The mercapturic acid pathway

Hanna

Anders

2019

Critical Reviews in Toxicology

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The mercapturic acid pathway is a major route for the biotransformation of xenobiotic and endobiotic electrophilic compounds and their metabolites. Mercapturic acids (N-acetyl-L-cysteine S-conjugates) are formed by the sequential action of the glutathione transferases, c-glutamyltransferases, dipeptidases, and cysteine S-conjugate N-acetyltransferase to yield glutathione S-conjugates, L-cysteinylglycine S-conjugates, L-cysteine S-conjugates, and mercapturic acids; these metabolites constitute a "mercapturomic" profile. Aminoacylases catalyze the hydrolysis of mercapturic acids to form cysteine S-conjugates. Several renal transport systems facilitate the urinary elimination of mercapturic acids; urinary mercapturic acids may serve as biomarkers for exposure to chemicals. Although mercapturic acid formation and elimination is a detoxication reaction, L-cysteine S-conjugates may undergo bioactivation by cysteine Sconjugate b-lyase. Moreover, some L-cysteine S-conjugates, particularly L-cysteinyl-leukotrienes, exert significant pathophysiological effects. Finally, some enzymes of the mercapturic acid pathway are described as the so-called "moonlighting proteins," catalytic proteins that exert multiple biochemical or biophysical functions apart from catalysis.

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Section: Substrates Apn Catalyzes the Hydrolysis Of N-ter-mentioning

confidence: 99%

The mercapturic acid pathway

Hanna

Anders

2019

Critical Reviews in Toxicology

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“…[30][31][32][33][34] Recently, Zhang group employed Ni 2 P or NiO as the electrocatalyst to achieve the aqueous semi-dehydrogenation of tetrahydroisoquinolines (THIQs) by coupling with effective HER or nitrate reduction reaction, which made a breakthrough in achieving value-added product dihydroisoquinolines (DHIQs). [27,35] Considering the positive function of DHIQ in pharmaceutical chemistry, [36][37] it is highly desirable to develop more readily available electrocatalysts especially based on other earth-abundant metal elements, which could integrate the selective oxidation from THIQs to DHIQs with HER in water.…”

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confidence: 99%

Accelerating H₂ Evolution by Anodic Semi‐dehydrogenation of Tetrahydroisoquinolines in Water over Co₃O₄ Nanoribbon Arrays Decorated Nickel Foam

Xiang

Wang

et al. 2021

Chemistry A European J

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Coupling the H 2 evolution reaction in water with thermodynamically favorable organic oxidation reactions is highly desirable, because it can enhance the energy conversion efficiency compared with electrocatalytic water splitting, and produce value-added chemicals instead of O 2 in the anodic reaction. Herein, Co 3 O 4 nanoribbon arrays in situ grown on nickel foam (Co 3 O 4 @NF) was employed as an effective electrocatalyst for the selective oxidation of tetrahydroisoquinolines (THIQs). Various value-added semidehydrogenation products including dihydroisoquinolines with electro-deficient or -rich groups could be obtained with moderate yields and faradaic efficiencies. Benefitting from the rich surface active sites of Co 3 O 4 @NF, a twoelectrode (Co 3 O 4 @NF j j Pt) electrolytic system drove a benchmark current density of 10 mA cm À 2 at a cell voltage as low as 1.446 V in 1.0 M KOH aqueous solution containing 0.02 M THIQ, which was reduced by 174 mV in comparison with that of overall water splitting.

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“…Compounds from Spark were also docked into the LAP active site, and the top 100 compounds with the best score in the range of −22.33 to −38.66 were then selected for 3D-QSAR using Forge software. The docking analysis indicated that the compound with the best docking score (−38.66) ({[6,8-(dibenzyloxy)-3-(ethoxycarbonyl)-3,4-dihydroisoquinolin-3-yl]oxy}acetic acid), shown in Figure 4, is placed in a similar way in the binding pocket of 1LAN as the starter ligand was docked in our previous studies [14,18].…”

Section: Molecular Dockingmentioning

confidence: 85%

“…In the previous studies, we discovered that a group of 3,4-dihydroisoquinoline ( Figure 1b) derivatives exhibit LAP inhibitory activity [14]. We also proved that one of the studied compounds, diethyl 6,8-dibenzyloxy-3,4,-dihydroisoquinoline-3,3-dicarboxylate ( Figure 1a), exhibited significant activity against microsomal LAP (IC 50 = 16.5 µM) and promising antiproliferative activity on human cancer cell lines, including human promyelocytic leukemia cell line HL-60, human breast cancer cell line MCF-7, Burkitt's lymphoma cell line Raji, camptothecin resistant CEM/C2 human T-cell leukemia cell line with mutated catalytic site of topoisomerase 1 and its parental cell line CCRF/CEM, LoVo colon cancer cell line, LoVo/Dx-variant cell line resistant to doxorubicin with multidrug cross-resistance, prostate cancer cell lines LNCaP and PC3, and urinary bladder cancer cell line HCV29T.…”

Section: Introductionmentioning

confidence: 97%

In Silico Screening for Novel Leucine Aminopeptidase Inhibitors with 3,4-Dihydroisoquinoline Scaffold

2020

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Cancers are the leading cause of deaths worldwide. In 2018, an estimated 18.1 million new cancer cases and 9.6 million cancer-related deaths occurred globally. Several previous studies have shown that the enzyme, leucine aminopeptidase is involved in pathological conditions such as cancer. On the basis of the knowledge that isoquinoline alkaloids have antiproliferative activity and inhibitory activity towards leucine aminopeptidase, the present study was conducted a study which involved database search, virtual screening, and design of new potential leucine aminopeptidase inhibitors with a scaffold based on 3,4-dihydroisoquinoline. These compounds were then filtered through Lipinski’s “rule of five,” and 25 081 of them were then subjected to molecular docking. Next, three-dimensional quantitative structure-activity relationship (3D-QSAR) study was performed for the selected group of compounds with the best binding score results. The developed model, calculated by leave-one-out method, showed acceptable predictive and descriptive capability as represented by standard statistical parameters r2 (0.997) and q2 (0.717). Further, 35 compounds were identified to have an excellent predictive reliability. Finally, nine selected compounds were evaluated for drug-likeness and different pharmacokinetics parameters such as absorption, distribution, metabolism, excretion, and toxicity. Our methodology suggested that compounds with 3,4-dihydroisoquinoline moiety were potentially active in inhibiting leucine aminopeptidase and could be used for further in-depth in vitro and in vivo studies.

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Molecular docking studies, biological and toxicity evaluation of dihydroisoquinoline derivatives as potential anticancer agents

Cited by 16 publications

References 35 publications

The mercapturic acid pathway

The mercapturic acid pathway

Accelerating H₂ Evolution by Anodic Semi‐dehydrogenation of Tetrahydroisoquinolines in Water over Co₃O₄ Nanoribbon Arrays Decorated Nickel Foam

In Silico Screening for Novel Leucine Aminopeptidase Inhibitors with 3,4-Dihydroisoquinoline Scaffold

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Molecular docking studies, biological and toxicity evaluation of dihydroisoquinoline derivatives as potential anticancer agents

Cited by 16 publications

References 35 publications

The mercapturic acid pathway

The mercapturic acid pathway

Accelerating H2 Evolution by Anodic Semi‐dehydrogenation of Tetrahydroisoquinolines in Water over Co3O4 Nanoribbon Arrays Decorated Nickel Foam

In Silico Screening for Novel Leucine Aminopeptidase Inhibitors with 3,4-Dihydroisoquinoline Scaffold

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Accelerating H₂ Evolution by Anodic Semi‐dehydrogenation of Tetrahydroisoquinolines in Water over Co₃O₄ Nanoribbon Arrays Decorated Nickel Foam