(E)-2-Benzylidenecyclanones: Part XVII. An LC-MS study of microsomal transformation reactions of (E)-2-[(4'-methoxyphenyl)methylene]-benzosuberon-1-one: A cyclic chalcone analog

Kenari, Fatemeh; Molnár, Szilárd; Pintér, Zoltán; Bitaraf, Sobhan; Perjési, Pál

doi:10.25082/jpbr.2022.02.004

Cited by 2 publications

(4 citation statements)

References 48 publications

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“…Chalcones (I) are natural products, the biosynthetic precursors of flavonoids, a large family of plant phenolic secondary metabolites [1,2]. Because of the wide range of beneficial biological actions of the natural chalcones, several analogs have been synthesized and-among others-tested for their antioxidant, antimicrobial, antiprotozoal, antiulcer, antihistaminic, antidiabetic, anti-inflammatory, anticancer and neuroprotective activities [3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

“…Retention times (t R )1 and integrated peak areas (A) of the investigated cyclic chalcone analogs (IIb and IIc) and their GSH adducts 2 .…”

mentioning

confidence: 99%

“…1 Retention times in minutes; 2 data refer to the average of two independent measurements at the 315 min time point; 3 pH value of the aqueous thiol solution; 4 ratios of peak areas measured at 0 and 315 min; 5 not detectable.…”

mentioning

confidence: 99%

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(E)-2-Benzylidenecyclanones: Part XVIII Study the Possible Link between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs

Kenari

Molnár

Borges

et al. 2023

IJMS

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Non-enzymatic thiol addition into the α,β-unsaturated carbonyl system is associated with several biological effects. In vivo, the reactions can form small-molecule thiol (e.g., glutathione) or protein thiol adducts. The reaction of two synthetic (4′-methyl- and 4′-methoxy substituted) cyclic chalcone analogs with reduced glutathione (GSH) and N-acetylcysteine (NAC) was studied by (high-pressure liquid chromatography-ultraviolet spectroscopy) HPLC-UV method. The selected compounds displayed in vitro cancer cell cytotoxicity (IC50) of different orders of magnitude. The structure of the formed adducts was confirmed by (high-pressure liquid chromatography-mass spectrometry) HPLC-MS. The incubations were performed under three different pH conditions (pH 3.2/3.7, 6.3/6.8, and 8.0/7.4). The chalcones intrinsically reacted with both thiols under all incubation conditions. The initial rates and compositions of the final mixtures depended on the substitution and the pH. The frontier molecular orbitals and the Fukui function were carried out to investigate the effects on open-chain and seven-membered cyclic analogs. Furthermore, machine learning protocols were used to provide more insights into physicochemical properties and to support the different thiol-reactivity. HPLC analysis indicated diastereoselectivity of the reactions. The observed reactivities do not directly relate to the different in vitro cancer cell cytotoxicity of the compounds.

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Section: Introductionmentioning

confidence: 99%

“…Retention times (t R )1 and integrated peak areas (A) of the investigated cyclic chalcone analogs (IIb and IIc) and their GSH adducts 2 .…”

mentioning

confidence: 99%

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(E)-2-Benzylidenecyclanones: Part XVIII Study the Possible Link between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs

Kenari

Molnár

Borges

et al. 2023

IJMS

Self Cite

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show abstract

“…Retention times (tR)1 and integrated peak areas (A) of the investigated cyclic chalcone analogs (IIb and IIc) and their GSH adducts 2 .…”

mentioning

confidence: 99%

(E)-2-Benzylidenecyclanones: Part XVIII.[1] Study the Possible Link Between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs. A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs

Perjési¹,

Kenari²,

Molnár³

et al. 2023

Preprint

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Non-enzymatic thiol addition into α,ß-unsaturated carbonyl system is associated with several biological effects. In vivo, the reactions can form small-molecule thiol (e.g., glutathione) or protein thiol adducts. The reaction of two synthetic (4’-methyl- and 4’-methoxy substituted) cyclic chalcone analogs with glutathione and N-acetylcysteine was studied by HPLC-UV method. The selected compounds displayed in vitro cancer cell cytotoxicity (IC50) of different orders of magnitude. The structure of the formed adducts was confirmed by HPLC-MS. The incubations were performed under three different pH conditions (pH 3.5/3.8, 6.3/6.7, and 8.0/7.4). The chalcones intrinsically reacted with both thiols under all incubation conditions. The initial rates and compositions of the final mixtures depended on the substitution and the pH. The frontier molecular orbitals and the Fukui function were carried out to investigate the effects on open-chain and seven-membered cyclic analogs. Furthermore, machine learning protocols were used to provide more insights into physicochemical properties and to support the different thiol-reactivity. HPLC analysis indicated diastereoselectivity of the reactions. The observed reactivities do not directly relate to the different in vitro cancer cell cytotoxicity of the compounds.

show abstract

(E)-2-Benzylidenecyclanones: Part XVII. An LC-MS study of microsomal transformation reactions of (E)-2-[(4'-methoxyphenyl)methylene]-benzosuberon-1-one: A cyclic chalcone analog

Cited by 2 publications

References 48 publications

(E)-2-Benzylidenecyclanones: Part XVIII Study the Possible Link between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs

(E)-2-Benzylidenecyclanones: Part XVIII Study the Possible Link between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs

(E)-2-Benzylidenecyclanones: Part XVIII.[1] Study the Possible Link Between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs. A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs

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