Synthesis of Ergosterol Peroxide Conjugates as Mitochondria Targeting Probes for Enhanced Anticancer Activity

Bu, Ming; Li, Hongling; Wang, Haijun; Wang, Jing; Lin, Yu; Ma, Yueming

doi:10.3390/molecules24183307

Cited by 23 publications

(17 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The live cell studies indicate these EP probes accumulate in the mitochondria, enhancing its ROS generating potential. 68 …”

Section: Triterpenoid Chemical Probesmentioning

confidence: 99%

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

Ling¹,

Boyd²,

Rivas³

2022

Chem. Res. Toxicol.

View full text Add to dashboard Cite

The triterpenoid natural products have played an important role in understanding mechanistic models of human diseases. These natural products are diverse, but many have been characterized as reactive oxygen species (ROS) modulators. ROS can regulate cell survival and function, which ultimately affects biological processes leading to disease. The triterpenoids offer an untapped source of creativity to generate tool compounds with high selectivity to regulate ROS. This brief Review highlights the diverse complexity by which these secondary metabolites induce many cell death modalities (apoptosis, autophagy, ferroptosis, etc.) that can affect various complex cell signaling pathways through ROS and ultimately lead to evading or accelerating cell death.

show abstract

“…The live cell studies indicate these EP probes accumulate in the mitochondria, enhancing its ROS generating potential. 68 …”

Section: Triterpenoid Chemical Probesmentioning

confidence: 99%

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

Ling¹,

Boyd²,

Rivas³

2022

Chem. Res. Toxicol.

View full text Add to dashboard Cite

show abstract

“…Then we synthesized several series of steroidal 5α,8α-endoperoxide derivatives with 17-(O-carboxymethyl)oxime side-chain and hydrazone hybrid side-chain. The MTT assay indicated that some derivatives possessing the 5α,8α-peroxy group and different side chains displayed distinct cytotoxic activity against some cancer cell lines [23][24][25][26][27]. Based on the above results, we speculate that the difference between side chains at C-17 position and 5α,8α-peroxy group would provide a synergistic effect for the bioactivity.…”

Section: Introductionmentioning

confidence: 68%

Novel Steroidal 5α,8α-Endoperoxide Derivatives with Semicarbazone/Thiosemicarbazone Side-chain as Apoptotic Inducers through an Intrinsic Apoptosis Pathway: Design, Synthesis and Biological Studies

Wang

et al. 2020

Molecules

Self Cite

View full text Add to dashboard Cite

A series of novel steroidal 5α,8α-endoperoxide derivatives bearing semicarbazone (7a–g) or thiosemicarbazone (7h–k) side chain were designed, synthesized and evaluated for their cytotoxicities in four human cancer cell lines (HepG2, HCT-116, MCF-7, and A549) using the MTT assay in vitro. The results showed that compound 7j exhibited significant cytotoxic activity against HepG2 cells (IC50 = 3.52 μM), being more potent than ergosterol peroxide. Further cellular mechanism studies in HepG2 cells indicated that compound 7j triggered the mitochondrial-mediated apoptosis by decreasing mitochondrial membrane potential (MMP), which was associated with up-regulation of Bax, down-regulation of Bcl-2, activation levels of the caspase cascade, and formation of reactive oxygen species (ROS). The above findings indicated that compound 7j may be used as a promising skeleton for antitumor agents with improved efficacy.

show abstract

“…Several adducts of EP with 7- N , N -diethylaminocoumarins have been obtained by Bu et al [ 145 ]. Analogues 21c and 21d exhibited increased cytotoxicity compared to 21a , which was explained by their localization mainly in mitochondria, as followed from fluorescence imaging.…”

Section: Endoperoxidesmentioning

confidence: 99%

Structure and Biological Activity of Ergostane-Type Steroids from Fungi

2022

View full text Add to dashboard Cite

Mushrooms are known not only for their taste but also for beneficial effects on health attributed to plethora of constituents. All mushrooms belong to the kingdom of fungi, which also includes yeasts and molds. Each year, hundreds of new metabolites of the main fungal sterol, ergosterol, are isolated from fungal sources. As a rule, further testing is carried out for their biological effects, and many of the isolated compounds exhibit one or another activity. This study aims to review recent literature (mainly over the past 10 years, selected older works are discussed for consistency purposes) on the structures and bioactivities of fungal metabolites of ergosterol. The review is not exhaustive in its coverage of structures found in fungi. Rather, it focuses solely on discussing compounds that have shown some biological activity with potential pharmacological utility.

show abstract

Synthesis of Ergosterol Peroxide Conjugates as Mitochondria Targeting Probes for Enhanced Anticancer Activity

Cited by 23 publications

References 43 publications

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

Novel Steroidal 5α,8α-Endoperoxide Derivatives with Semicarbazone/Thiosemicarbazone Side-chain as Apoptotic Inducers through an Intrinsic Apoptosis Pathway: Design, Synthesis and Biological Studies

Structure and Biological Activity of Ergostane-Type Steroids from Fungi

Contact Info

Product

Resources

About