Structure-property and structure–activity relationships of phenylferrocene derivatives as androgen receptor antagonists

Ochiai, Kotaro; Fujii, Shinya

doi:10.1016/j.bmcl.2021.128141

Cited by 8 publications

(5 citation statements)

References 34 publications

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“…The synthetic ferrocene derivatives demonstrated AR-antagonistic action, and 3-nitrophenylferrocene 24a was the most effective of these, with an IC 50 value of 0.28 M. As AR antagonists, the discovered compounds might be suitable for further structural development. These results confirm the usefulness of organometallic substances as structural options for drug discovery [38].…”

Section: Synthesis Of Ferrocenyl Etherssupporting

confidence: 75%

Contemporary Developments in Ferrocene Chemistry: Physical, Chemical, Biological and Industrial Aspects

Rauf,

Shabir,

Bukhari

et al. 2023

Molecules

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Ferrocenyl-based compounds have many applications in diverse scientific disciplines, including in polymer chemistry as redox dynamic polymers and dendrimers, in materials science as bioreceptors, and in pharmacology, biochemistry, electrochemistry, and nonlinear optics. Considering the horizon of ferrocene chemistry, we attempted to condense the neoteric advancements in the synthesis and applications of ferrocene derivatives reported in the literature from 2016 to date. This paper presents data on the progression of the synthesis of diverse classes of organic compounds having ferrocene scaffolds and recent developments in applications of ferrocene-based organometallic compounds, with a special focus on their biological, medicinal, bio-sensing, chemosensing, asymmetric catalysis, material, and industrial applications.

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Section: Synthesis Of Ferrocenyl Etherssupporting

confidence: 75%

Contemporary Developments in Ferrocene Chemistry: Physical, Chemical, Biological and Industrial Aspects

Rauf,

Shabir,

Bukhari

et al. 2023

Molecules

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“…Generally, the sensor is prepared by immobilizing MEA on a gold microelectrode vis Au–S bonding under acidic conditions, resulting in a positively charged sensor surface. − During the detection process, negatively charged NPs (Figure S3 in the Supporting Information) can be selectively captured by the sensor through electrostatic interactions. Then, Fc serves as an electrochemical beacon, , attached to the NPs via hydrophobic interactions, and measured by DPV. At a certain concentration, the peak current obtained at 0.18 V is related to the size of the NPs.…”

Section: Resultsmentioning

confidence: 99%

“…Information) can be selectively captured by the sensor through electrostatic interactions. Then, Fc serves as an electrochemical beacon, 34,35 attached to the NPs via hydrophobic interactions, and measured by DPV. At a certain concentration, the peak current obtained at 0.18 V is related to the size of the NPs.…”

mentioning

confidence: 99%

Convenient Size Analysis of Nanoplastics on a Microelectrode

He,

Xie,

Xiang

et al. 2024

Anal. Chem.

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Chemical recycling is a promising approach to reduce plastic pollution. Timely and accurate size analysis of produced nanoplastics is necessary to monitor the process and assess the quality of chemical recycling. In this work, a sandwich-type microelectrode sensor was developed for the size assessment of nanoplastics. β-Mercaptoethylamine was modified on the microelectrode to enhance its surface positive charge density. Polystyrene (PS) nanoplastics were captured on the sensor through electrostatic interactions. Ferrocene was used as an electrochemical beacon and attached to PS via hydrophobic interactions. The results show a nonlinear dependence of the sensor's current response on the PS particle size. The size resolving ability of the microelectrode is mainly attributed to the small size of the electrode and the resulting attenuation of the electric field strength. For mixed samples with different particle sizes, this method can provide accurate average particle sizes. Through an effective pretreatment process, the method can be applied to PS nanoplastics with different surface properties, ensuring its application in evaluating different chemical recycling methods.

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“…[15] Furthermore, we recently found that simple phenylferrocene derivatives such as 13-18 exhibit significant AR antagonistic activity (Figure 2). [16] These results indicated that the phenylferrocene structures in these compounds could function as steroid surrogates, serving as a hydrophobic pharmacophore. Here, in order to obtain data for structural optimization of these AR antagonists, we explored the structure-activity relationship (SAR) at the phenyl group of these derivatives.…”

Section: Introductionmentioning

confidence: 92%

Structural Development of Androgen Receptor Antagonists Using Phenylferrocene Framework as a Hydrophobic Pharmacophore

Ochiai,

Yonezawa,

Fujii

2024

ChemMedChem

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We previously identified nitrophenylferrocenes and cyanophenylferrocenes as promising lead structures of novel androgen receptor (AR) antagonists, based on the structural similarity between ferrocene and the steroidal skeleton. In the present research, we explored the structure‐activity relationship (SAR) of phenylferrocene derivatives. Introduction of a hydrophobic substituent such as a chlorine atom at the 2‐position or 3‐position of phenylferrocene derivatives significantly increased the antagonistic activity toward wild‐type AR, and among the synthesized compounds, 3‐chloro‐4‐cyanophenylferrocene (29) exhibited the most potent anti‐proliferative activity toward the androgen‐dependent growth of SC‐3 cells expressing wild‐type AR (IC50 14 nM). Like conventional antiandrogens such as hydroxyflutamide, the major active metabolite of flutamide, compound 29 exhibited agonistic activity toward T877A‐AR, a mutant AR expressed in human prostate cancer cell line LNCaP. Notably, however, the 2‐chloro isomer 27 showed potent antagonistic activity toward wild‐type AR (IC50 49 nM) and also exhibited antagonistic activity toward T877A‐AR. Our SAR data should prove helpful for the development of new‐generation AR antagonists based on phenylferrocene as candidate agents to treat drug‐resistant prostate cancer.

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Structure-property and structure–activity relationships of phenylferrocene derivatives as androgen receptor antagonists

Cited by 8 publications

References 34 publications

Contemporary Developments in Ferrocene Chemistry: Physical, Chemical, Biological and Industrial Aspects

Contemporary Developments in Ferrocene Chemistry: Physical, Chemical, Biological and Industrial Aspects

Convenient Size Analysis of Nanoplastics on a Microelectrode

Structural Development of Androgen Receptor Antagonists Using Phenylferrocene Framework as a Hydrophobic Pharmacophore

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