A new class of hybrid anticancer agents inspired by the synergistic effects of curcumin and genistein: Design, synthesis, and anti-proliferative evaluation

Bioorganic & Medicinal Chemistry Letters
Qiao-Hong ChenLiva Harinantenaina Rakotondraibe

Abstract

Inspired by the synergistic effects of dietary natural products with different scaffolds on the inhibition of cancer cell proliferation, incorporation of central (1E,4E)-1,4-penta-dien-3-one linker (an optimal substitute for the central metabolically unstable diketone linker of curcumin), 1-alkyl-1H-imidazol-2-yl (a promising bioisostere of terminal aryl group in curcumin), and chromone (the common pharmacophore in genistein and quercetin) into one chemical entity resulted in ten new hybrid molecules, 3-((1E,4E)-5-(1-alkyl-1H-imidazol-2-yl)-3-oxopenta-1,4-dien-1-yl)-4H-chromen-4-ones. They were synthesized through a three-step transformation using acid-catalyzed aldol condensation as key step. The WST-1 cell proliferation assay showed that they have greater anti-proliferative potency than curcumin, quercetin, and genistein on both androgen-dependent and androgen-independent human prostate cancer cells.

Citations

Dec 31, 2016·European Journal of Medicinal Chemistry·P V Sri RamyaAhmed Kamal
Dec 21, 2016·Chemistry Central Journal·Reem Ibrahim Al-WabliWafaa Abdou Zaghary
Jul 22, 2018·Current Medicinal Chemistry·Aysegul HanikogluTomris Ozben
Aug 19, 2020·International Journal of Molecular Sciences·Karan ModiAshakumary Lakshmikuttyamma
Jul 8, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Cuili ChenHong Dai
Aug 25, 2020·Pharmaceutical Chemistry Journal·Noor Ul Amin MohsinUsman Saleem
Sep 4, 2019·European Journal of Medicinal Chemistry·Sawsan A NoureddinKhalid O Al-Footy
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Cristian HernándezWilson Cardona-G
Aug 8, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nicola MicaleAntonio Speciale
Apr 20, 2018·ACS Medicinal Chemistry Letters·Ángela P HernándezMa Ángeles Castro
Jan 4, 2018·The Journal of Organic Chemistry·Tanner L MetzLevi M Stanley
Mar 26, 2019·Journal of Agricultural and Food Chemistry·Christopher S ChambersKateřina Valentová

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.