Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity

Peroković, Vesna Petrović; Car, Željka; Usenik, Andrea; Opačak-Bernardi, Teuta; Jurić, Andrea; Tomić, Srđanka

doi:10.1007/s11030-019-09948-1

Cited by 14 publications

(6 citation statements)

References 28 publications

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“…[53] Also, esters of adamantan-1-yl-acetic acid with kojic or chlorokojic acids demonstrated antiproliferative effects on colorectal adenocarcinoma (Caco-2 cells), bronchioalveolar carcinoma (NCI-H358 cells), cervical cancer (HeLa cells) or chronic myelogenous leukemia (K562 cells). [54] Over the past decades, the skin has been frequently reported as one of the routes in drug delivery. The nanocarrier system based on kojic acid has shown effective deliveries of antitumor preparations which markedly reduce tumor growth.…”

Section: Antiproliferative Activities Of Kojic Acid Derivativesmentioning

confidence: 99%

Biological functions of kojic acid and its derivatives in medicine, cosmetics, and food industry: Insights into health aspects

Brtko

2022

Archiv der Pharmazie

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This review traces the road leading to the demonstration of a variety of kojic acid chemical and biological properties. It illustrates the biological effects of several synthetic kojic acid derivatives. Besides the main capability of kojic acid to inhibit the activity of tyrosinase in melanin synthesis, the focus is also on antibacterial, antifungal, antiproliferative, anti-inflammatory, and other biological activities of kojic acid derivatives, which may be applicable in medicine. Kojic acid derivatives manifest antiparasitic effects and its metal complexes may serve as potential radioprotective agents. Several kojic acid derivatives exert antidiabetic therapeutic potential as nuclear peroxisome proliferator-activated receptor alpha/gamma dual agonists. Kojic acid derivatives show pancreatic lipase inhibitor properties and some of its derivatives are cognate ligands for the histamine H 3 receptor. Recently, "KojoTacrines" were reported as novel perspective preparations for the therapy of Alzheimer's disease. Kojic acid derivatives possess insecticidal or pesticidal activity, and they are powerful chelators, able to form iron(III) containing nanocomposites, as well. Toxicology and health aspects of products containing kojic acid produced by the cosmetic, health care, or food industry are summarized. Kojic acid thus represents a highly attractive molecule containing a skeleton that allows the synthesis of new kojic acid derivatives to create a novel class of effective and specific pharmaceutical preparations.

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Section: Antiproliferative Activities Of Kojic Acid Derivativesmentioning

confidence: 99%

Biological functions of kojic acid and its derivatives in medicine, cosmetics, and food industry: Insights into health aspects

Brtko

2022

Archiv der Pharmazie

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“…Compounds III and IV act as antioxidants and inhibit growth of gram‐positive and gram negative bacteria [6] . Double esters V produced from kojic acid and adamantyl acetic acid exhibit antiproliferative activity in vitro [7] . Surprisingly, in spite of obvious attractiveness of the kojic acid framework for the medicinal chemistry, insufficient attention has been paid so far to asymmetric synthesis of chiral molecules of this type.…”

Section: Introductionmentioning

confidence: 99%

“…, 32.0, 30.8,19.6, 19.5, 19.4 ppm. HPLC data: Chiralpak ADÀ H, nhexane : i-PrOH = 70 : 30; 220 nm, flow rate: 1.0 mL/min, t R1(major) = 13.0 min, t R2(minor) = 15.9 min, t R1(minor) = 21.2 min, t R2(major) = 25 7. min, 97 % ee for 7 af, 76 % ee for epi-7 af.…”

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confidence: 99%

Organocatalytic Asymmetric Double Addition of Kojic Acids to 2‐Nitroallylic Carbonates

et al. 2022

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2-Nitroallylic carbonates were first applied as promising biselectrophilic C3 synthons for bifunctional squaramide catalyzed asymmetric domino reaction with kojic acid derivatives to afford so far inaccessible nitro compounds bearing two hydroxypyranone units. The reaction products undergo noncatalytic epimerization at the carbon atom next to the nitro group. Plausible mechanism of the epimerization based on reversible formation of intermediate aci-nitro compound is proposed. The double addition products were transformed to configurationally stable acetates and to chiral nitro glutarates, promising precursors to chiral amino glutaric acid derivatives.

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“…Herein, we pursue the development of new molecules, with the selenourea functioning as cytotoxic agents decorated in the nitrogen atoms with a small set of fragment hits. Therefore, we select nucleus as coumarin [ 25 ], furan [ 26 ], thiazole [ 27 ], and adamantine [ 28 ], all of them with reported antitumoral and/or antioxidant activity. In the opposing nitrogen, we enclose the phenyl ring, functionalized with different electron-donating and electron-withdrawing substituents in order to cover a relatively broad range of electronic effects.…”

Section: Introductionmentioning

confidence: 99%

Novel N,N′-Disubstituted Selenoureas as Potential Antioxidant and Cytotoxic Agents

et al. 2021

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A series of 30 novel N,N disubstituted selenoureas were synthesized, characterized, and their antioxidant ability was tested using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid (ABTS) assays. Additionally, their cytotoxic activity was tested in vitro in a panel of three different cancer (breast, lung and colon) and two normal cell lines. Each selenourea entity contains a para-substituted phenyl ring with different electron-withdrawing and electron-donating groups, and different aliphatic and aromatic nuclei. All of the synthesized selenoureas present antioxidant capacity at high concentrations in the DPPH assay, and three of them (2b, 2c and 2d) showed greater radical scavenging capacity than ascorbic acid at lower concentrations. These results were confirmed by the ABTS assay, where these novel selenoureas present even higher antioxidant capacity than the reference compound Trolox. On the other hand, 10 selenoureas present IC50 values below 10 µM in at least one cancer cell line, resulting in the adamantyl nucleus (6a–6e), the most interesting in terms of activity and selectivity. Outstanding results were found for selenourea 6c, tested in the NCI60 cell line panel and showing an average GI50 of 1.49 µM for the 60 cell lines, and LC50 values ranging from 9.33 µM to 4.27 µM against 10 of these cancer cell lines. To gain insight into its anticancer activity mechanism, we investigated the cell cycle progression of the promising compound 6c, as well as the type of programmed-cell death in a colon cancer cell line it provokes (HT-29). Compound 6c provoked S phase cell cycle arrest and the induction of cell death was independent of caspase activation, suggesting autophagy, though this assertion requires additional studies. Overall, we envision that this compound can be further developed for the potential treatment of colon cancer.

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Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity

Cited by 14 publications

References 28 publications

Biological functions of kojic acid and its derivatives in medicine, cosmetics, and food industry: Insights into health aspects

Biological functions of kojic acid and its derivatives in medicine, cosmetics, and food industry: Insights into health aspects

Organocatalytic Asymmetric Double Addition of Kojic Acids to 2‐Nitroallylic Carbonates

Novel N,N′-Disubstituted Selenoureas as Potential Antioxidant and Cytotoxic Agents

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