Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives

Mayer, Szabolcs; Keglevich, Péter; Ábrányi‐Balogh, Péter; Szigetvári, Áron; Dékány, Miklós; Szántay, Csaba; Hazai, László

doi:10.3390/molecules25040888

Cited by 17 publications

(15 citation statements)

References 25 publications

(68 reference statements)

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“…In the present review, we provided a mechanistic review of chrysin and its underlying mechanisms for anti-tumor activity [ 323 , 324 , 325 ]. Noteworthy, chrysin derivatives have also shown potential anti-tumor activity [ 326 , 327 , 328 , 329 ], showing that future studies can focus on chemical modification of chrysin structure in improving its bioavailability, anti-tumor activity, etc. Although chemical modification is a promising strategy in promoting the anti-tumor activity of chrysin, it seems that nanoscale delivery systems, such as polymeric nanoparticles, liposomes, solid lipid nanoparticles, etc., can also be considered in promoting cellular uptake of chrysin and enhancing its anti-tumor activity.…”

Section: Conclusion and Remarksmentioning

confidence: 99%

Broad-Spectrum Preclinical Antitumor Activity of Chrysin: Current Trends and Future Perspectives

et al. 2020

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Pharmacological profile of phytochemicals has attracted much attention to their use in disease therapy. Since cancer is a major problem for public health with high mortality and morbidity worldwide, experiments have focused on revealing the anti-tumor activity of natural products. Flavonoids comprise a large family of natural products with different categories. Chrysin is a hydroxylated flavonoid belonging to the flavone category. Chrysin has demonstrated great potential in treating different disorders, due to possessing biological and therapeutic activities, such as antioxidant, anti-inflammatory, hepatoprotective, neuroprotective, etc. Over recent years, the anti-tumor activity of chrysin has been investigated, and in the present review, we provide a mechanistic discussion of the inhibitory effect of chrysin on proliferation and invasion of different cancer cells. Molecular pathways, such as Notch1, microRNAs, signal transducer and activator of transcription 3 (STAT3), nuclear factor-kappaB (NF-κB), PI3K/Akt, MAPK, etc., as targets of chrysin are discussed. The efficiency of chrysin in promoting anti-tumor activity of chemotherapeutic agents and suppressing drug resistance is described. Moreover, poor bioavailability, as one of the drawbacks of chrysin, is improved using various nanocarriers, such as micelles, polymeric nanoparticles, etc. This updated review will provide a direction for further studies in evaluating the anti-tumor activity of chrysin.

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Section: Conclusion and Remarksmentioning

confidence: 99%

Broad-Spectrum Preclinical Antitumor Activity of Chrysin: Current Trends and Future Perspectives

et al. 2020

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“…Moreover, the anticancer activity of the amino acid chrysin derivatives obtained by chemical synthesis has been proven [53]. Thus, the development of new chrysin derivatives with potentially better antitumor properties is reasonable [54][55][56].…”

Section: Biological Activity 41 Anticancer Activity Of Chrysin and Its Derivativesmentioning

confidence: 99%

Chrysin: Perspectives on Contemporary Status and Future Possibilities as Pro-Health Agent

2021

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Chrysin belongs to the group of natural polyphenols. It can be found, among others, in honey, propolis and fruits and has a wide range of biological activities, including the prevention of oxidative stress, inflammation, neurodegeneration and carcinogenesis. Being a part of the human diet, chrysin is considered to be a promising compound to be used in the prevention of many diseases, including cancers, diabetes and neurodegenerative diseases such as Alzheimer’s or Parkinson’s. Nevertheless, due to the low solubility of chrysin in water and under physiological conditions, its bioavailability is low. For this reason, attempts at its functionalization have been undertaken, aiming to increase its absorption and thus augment its in vivo therapeutic efficacy. The aim of this review is to summarize the most recent research on chrysin, including its sources, metabolism, pro-health effects and the effects of its functionalization on biological activity and pharmacological efficacy, evaluated both in vitro and in vivo.

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“…Therefore, we synthesized several new aryloxy acetamide derivatives (45)(46)(47)(48) (Figure 13). These products were rearranged to a biphenyl amine structure via Smiles rearrangement and hydrolysis to obtain a new series of 7-aminoflavone derivatives (49-52) ( Figure 14) [49].…”

Section: -Oh and 7-nh Modified Flavonoid Derivativesmentioning

confidence: 99%

“…Therefore, we synthesized several new aryloxy acetamide derivatives (45-48) ( Figure 13). These products were rearranged to a biphenyl amine structure via Smiles rearrangement and hydrolysis to obtain a new series of 7-aminoflavone derivatives (49-52) ( Figure 14) [49]. The products (45-52) were tested on 60 different human tumor cell lines in vitro (NIH, MD, USA) and three of the hydrolyzed Smiles products (50-52) showed prominent antitumor effect on several cell lines [49].…”

Section: -Oh and 7-nh Modified Flavonoid Derivativesmentioning

confidence: 99%

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Results in Chemistry of Natural Organic Compounds. Synthesis of New Anticancer Vinca Alkaloids and Flavone Alkaloids

et al. 2020

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The antitumor indole–indoline alkaloids of the evergreen Catharanthus roseus—namely vinblastine and vincristine—are widely used in chemotherapy of cancer. Many efforts were made to synthesize more efficient derivatives with less side-effect. The 14,15-cyclopropane derivative of vinblastine was synthesized successfully by a five-step procedure starting from vindoline. Vincristine, vinorelbine and several derivatives condensed with a cyclopropane ring were synthesized. Various hybrid molecules were prepared by the coupling reaction of vindoline and methyl ester of tryptophan, which were conjugated by carrier peptides of octaarginine. Studying the halogenation reactions of vindoline and catharanthine some fluorine derivatives were obtained which showed promising antitumor activity on various tumor types. The synthesis of the Aspidospermane alkaloid bannucine and 5′-epibannucine were carried out using N-acyliminium intermediates. The same intermediate was also applied in the first synthesis of sessiline. The research group have synthesized of flavonoid alkaloids: dracocephins A and B. Further three flavonoid alkaloids, namely 8-(2”-pyrrolidinon-5′′-yl)quercetin, 6-(2′′-pyrrolidinon-5′′-yl)-(−)- and 8-(2′′-pyrrolidinon-5′′-yl)-(−)-epicatechin were prepared by acid-catalyzed regioselective Mannich reaction starting from the corresponding flavonoid precursor. Vindoline was also coupled to synthetic pharmacophores, such as triphenylphosphine and various N-heterocycles. Some of these hybrid molecules showed significant antitumor activity. Furthermore, 7-OH and 7-NH modified flavonoid derivatives were synthesized by a regioselective alkylation followed by Smiles rearrangement and hydrolysis.

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Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives

Cited by 17 publications

References 25 publications

Broad-Spectrum Preclinical Antitumor Activity of Chrysin: Current Trends and Future Perspectives

Broad-Spectrum Preclinical Antitumor Activity of Chrysin: Current Trends and Future Perspectives

Chrysin: Perspectives on Contemporary Status and Future Possibilities as Pro-Health Agent

Results in Chemistry of Natural Organic Compounds. Synthesis of New Anticancer Vinca Alkaloids and Flavone Alkaloids

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