Synthesis and Cytostatic Activity of New Mepregenol 17-Acetate Derivatives with Respect to Hela Cancer Cell Culture

Федотчева, Т. А.; Sveshnikova, E. D.; Sheina, N. I.; Sokolov, Mikhail N.; Kudryavtsev, Konstantin V.; Федотчева, Н. И.; Шимановский, Н. Л.

doi:10.1007/s11094-020-02167-1

Cited by 9 publications

(6 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Solutions of agrimoniin in DMEM medium were added to final concentrations of 10 −9 -10 −3 M and incubated for 48 and 72 h with the cells in 96-well plates. At the end of incubation, the viability of the culture was assessed using the standard MTT test [35]. Color development was determined by measuring the optical density at a wavelength of 530 nm on a microplate reader (enzyme-linked immunosorbent assay "UNIPLAN" AIFR-01 (Pikon, Moscow, Russia).…”

Section: Methodsmentioning

confidence: 99%

New Properties and Mitochondrial Targets of Polyphenol Agrimoniin as a Natural Anticancer and Preventive Agent

2021

View full text Add to dashboard Cite

Agrimoniin is a polyphenol from the group of tannins with antioxidant and anticancer activities. It is assumed that the anticancer action of agrimoniin is associated with the activation of mitochondria-dependent apoptosis, but its mitochondrial targets have not been estimated. We examined the direct influence of agrimoniin on different mitochondrial functions, including the induction of the mitochondrial permeability transition pore (MPTP) as the primary mechanism of mitochondria-dependent apoptosis. Agrimoniin was isolated from Agrimonia pilosa Ledeb by multistep purification. The content of agrimoniin in the resulting substance reached 80%, as determined by NMR spectroscopy. The cytotoxic effect of purified agrimoniin was confirmed on the cultures of K562 and HeLa cancer cells by the MTT assay. When tested on isolated rat liver mitochondria, agrimoniin at a low concentration (10 µM) induced the low-amplitude swelling, which was inhibited by the MPTP inhibitors ADP and cyclosporine A, activated the opening of MPTP by calcium ions and stimulated the respiration supported by succinate oxidation. Also, agrimoniin reduced the electron acceptor DCPIP in a concentration-dependent manner and chelated iron ions. Owing to all these properties, agrimoniin can stimulate apoptosis or activate mitochondrial functions, which can be helpful in the prevention and elimination of stagnant pathological states.

show abstract

Section: Methodsmentioning

confidence: 99%

New Properties and Mitochondrial Targets of Polyphenol Agrimoniin as a Natural Anticancer and Preventive Agent

2021

View full text Add to dashboard Cite

show abstract

“…Progesterone inhibits TRPM7 expression, thereby switching acidotoxic necrosis of tumor cells to apoptosis [ 66 ]. A number of studies on HeLa cells have demonstrated the cytotoxic effect not only of progesterone, but also of its synthetic derivatives, the cytotoxic effect being observed both upon stimulation with estradiol and without stimulation [ 67 , 68 ].…”

Section: Clinical Use Of Gestagensmentioning

confidence: 99%

Clinical Use of Progestins and Their Mechanisms of Action: Present and Future (Review)

Федотчева

2021

Sovrem Tehnol Med

View full text Add to dashboard Cite

This review summarizes the current opinions on the mechanisms of action of nuclear, mitochondrial, and membrane progesterone receptors. The main aspects of the pharmacological action of progestins have been studied. Data on the clinical use of gestagens by nosological groups are presented. Particular attention is paid to progesterone, megestrol acetate, medroxyprogesterone acetate due to broadening of their spectrum of action. The possibilities of using gestagens as neuroprotectors, immunomodulators, and chemosensitizers are considered.

show abstract

“…We succeeded in green modification of the discussed reductive procedure and performed it in aqueous tetrahydrofuran (THF) for the first time with the almost quantitive yield . Subsequent acryloylation of C‐3β alcohol 4 afforded chiral ester 5 with seven stereogenic centers (Scheme ) . Spatial structure and stereogenic centers’ absolute configuration including C‐3β position for the novel pregnane acrylate 5 was confirmed by us with X‐ray analysis …”

Section: Figurementioning

confidence: 99%

“…Subsequent acryloylation of C‐3β alcohol 4 afforded chiral ester 5 with seven stereogenic centers (Scheme ) . Spatial structure and stereogenic centers’ absolute configuration including C‐3β position for the novel pregnane acrylate 5 was confirmed by us with X‐ray analysis …”

Section: Figurementioning

confidence: 99%

“…[11] Subsequent acryloylation of C-3β alcohol 4 afforded chiral ester 5 with seven stereogenic centers (Scheme 1). [11] Spatial structure and stereogenic centers' absolute configuration including C-3β position for the novel pregnane acrylate 5 was confirmed by us with X-ray analysis. [11] Having a deep expertise in utilizing of different chiral dipolarophiles in 1,3-cycloaddition of azomethine ylides [12][13][14] we introduced pregnane acrylate 5 in interaction with corresponding iminoglycinates and obtained chiral 5-arylpyrrolidine-2,4-dicarboxylates 6 a-c (a: R=H; b: R=CF 3 ; c: R=Br) with pregnane fragment at 4-carboxylic group of pyrrolidine cycle (Scheme 1).…”

mentioning

confidence: 99%

See 1 more Smart Citation

A Pregnane Steroid as the Chiral Auxiliary in 1,3‐Dipolar Azomethine Ylide's Cycloaddition: Asymmetric Synthesis and Anticancer Activity of Novel Hybrid Compounds

et al. 2020

View full text Add to dashboard Cite

Hybrid chiral molecules containing frameworks of a pregnane steroid and 5‐arylpyrrolidine‐2,4‐dicarboxylate have been synthesized for the first time in a diastereomerically pure form. Chiral pregnane‐based acrylate induced stereoselective formation of all‐cis trisubstituted pyrrolidine moiety under cycloaddition with stabilized N‐metalated azomethine ylides. β‐Dipeptidic fragment was built up at C‐3 pregnane position using consequent acryloylation and stereoselective cycloaddition with stabilized N‐metalated azomethine ylide. All novel hybrid molecules demonstrated micromolar cytotoxic activity against human cervical epithelioid cancer HeLa cell culture in native and estradiol‐stimulated forms and breast carcinoma MCF‐7 cell culture. The most of hybrid compounds are less toxic towards human skin fibroblasts HSF as compared with studied hormonal tumor cells.

show abstract

Synthesis and Cytostatic Activity of New Mepregenol 17-Acetate Derivatives with Respect to Hela Cancer Cell Culture

Cited by 9 publications

References 12 publications

New Properties and Mitochondrial Targets of Polyphenol Agrimoniin as a Natural Anticancer and Preventive Agent

New Properties and Mitochondrial Targets of Polyphenol Agrimoniin as a Natural Anticancer and Preventive Agent

Clinical Use of Progestins and Their Mechanisms of Action: Present and Future (Review)

A Pregnane Steroid as the Chiral Auxiliary in 1,3‐Dipolar Azomethine Ylide's Cycloaddition: Asymmetric Synthesis and Anticancer Activity of Novel Hybrid Compounds

Contact Info

Product

Resources

About