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Journal Articles Journal of Medicinal Chemistry Year : 2024

Deciphering the Diversified Metabolic Behavior of Hydroxyalkyl Ferrocidiphenols as Anticancer Complexes

Ying Xiong
  • Function : Author
Chao Zheng
Yong Wang

Abstract

Ferrocidiphenols possessing appropriate substituents in the aliphatic chain have very promising anticancer properties, but a systematic approach to deciphering their diversified metabolic behavior has so far been lacking. Herein, we show that a series of novel ferrocidiphenols bearing different hydroxyalkyl substituents exhibit strong anticancer activity as revealed in a range of in vitro and in vivo experiments. Moreover, they display diversified oxidative transformation profiles very distinct from those of previous complexes, shown by the use of chemical and enzymatic methods and in cellulo and in vivo metabolism studies. In view of this phenomenon, unprecedented chemo-evolutionary sequences that connect all the ferrocidiphenol-related intermediates and analogues have been established. In addition, a comprehensive density functional theory (DFT) study has been performed to decipher the metabolic diversification profiles of these complexes and demonstrate the delicate modulation of carbenium ions by the ferrocenyl moiety, via either α- or β-positional participation.
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Year Month Jours
Avant la publication
Tuesday, July 2, 2024
Embargoed file
Tuesday, July 2, 2024
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Dates and versions

hal-04369370 , version 1 (02-01-2024)

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Cite

Hui Wang, Xuejing Fan, Pei-Pei Xie, Shuang Yang, Pascal Pigeon, et al.. Deciphering the Diversified Metabolic Behavior of Hydroxyalkyl Ferrocidiphenols as Anticancer Complexes. Journal of Medicinal Chemistry, 2024, 67 (2), pp.1209-1224. ⟨10.1021/acs.jmedchem.3c01709⟩. ⟨hal-04369370⟩
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