The investigation of structure–activity relationship of polyamine-targeted synthetic compounds from different chemical groups

Syatkin, S. P.; Неборак, Е. В.; Khlebnikov, Аndrei I.; Комарова, М В; Shevkun, Natalia A.; Кравцов, Э. Г.; Благонравов, М. Л.; Agostinelli, Enzo

doi:10.1007/s00726-019-02778-3

Cited by 7 publications

(6 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The products of PA catabolism (mainly reactive oxygen species (ROS), such as hydrogen peroxide and acrolein) are capable of inducing cell death via apoptosis [25,26,32,33]. Apoptosis was the type of cell death in HepG2 cells when 4e was coincubated with Spd/Spm.…”

Section: Discussionmentioning

confidence: 99%

“…The solvent was evaporated, and the residue was distilled in vacuo. A total of 3.05 g (64% of theory) of O-benzoyloxime of 3-(3-methoxypropyl)-7-[3-(imidazol-1-yl)propyl]-3,7-diazabicyclo[3.3.1]nonan-9-one (6c) was obtained in the form of a yellow oil, R f = 0.61 ( The regenerating rat liver was used as the source of the enzymes of PA catabolism [33]. The study was approved by the local Ethics Committee of RUDN University (protocol no.…”

Section: Reagents and Equipmentmentioning

confidence: 99%

“…They are intensively studied as anticancer [29] or antiviral [30] agents as well as suitable ligands for radiopharmaceuticals [31] and theranostic drugs [32]. Our previous study showed that bicyclononane derivatives were among the most potent activators of the PA catabolic pathway [33]. In the present study, a set of previously described diazabicyclononan-9-one derivatives [34][35][36] and novel synthesized diazabicyclononan-9-one derivatives has been tested for their ability to activate the PAdegrading pathway and to induce cancer cell death through such activation.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Anticancer Cytotoxic Activity of Bispidine Derivatives Associated with the Increasing Catabolism of Polyamines

et al. 2022

Self Cite

View full text Add to dashboard Cite

Polyamine (PA) catabolism is often reduced in cancer cells. The activation of this metabolic pathway produces cytotoxic substances that might cause apoptosis in cancer cells. Chemical compounds able to restore the level of PA catabolism in tumors could become potential antineoplastic agents. The search for activators of PA catabolism among bicyclononan-9-ones is a promising strategy for drug development. The aim of the study was to evaluate the biological activity of new 3,7-diazabicyclo[3.3.1]nonan-9-one derivatives that have antiproliferative properties by accelerating PA catabolism. Eight bispidine derivatives were synthetized and demonstrated the ability to activate PA catabolism in regenerating rat liver homogenates. However, only three of them demonstrated a potent ability to decrease the viability of cancer cells in the MTT assay. Compounds 4c and 4e could induce apoptosis more effectively in cancer HepG2 cells rather than in normal WI-38 fibroblasts. The lead compound 4e could significantly enhance cancer cell death, but not the death of normal cells if PAs were added to the cell culture media. Thus, the bispidine derivative 4e 3-(3-methoxypropyl)-7-[3-(1H-piperazin-1-yl)ethyl]-3,7-diazabicyclo[3.3.1]nonane could become a potential anticancer drug substance whose mechanism relies on the induction of PA catabolism in cancer cells.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Reagents and Equipmentmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Anticancer Cytotoxic Activity of Bispidine Derivatives Associated with the Increasing Catabolism of Polyamines

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…A possible role in the regulation of sperm apoptosis may be attributed to these polycationic molecules (35,36). The antiapoptotic and cytoprotective effect of PA upon cells has been well documented (8,(37)(38)(39)(40)(41). The MW irradiation of specific frequencies may induce apoptosis, and this effect is studied as a possible therapeutic tool for the management of cancer (42).…”

Section: Spermatozoa Percentage % -mentioning

confidence: 99%

Assessing the biological effects of microwave irradiation on human semen in vitro and determining the role of seminal plasma polyamines in this process

Плосконос

Zulbalaeva²,

Kurbangalieva³

et al. 2022

Biomed Rep

View full text Add to dashboard Cite

The aim of the present study was to investigate the influence of millimeter-wave electromagnetic (MW) irradiation on normal and pathological human sperm in vitro, and to evaluate a possible role of polyamines (PA) in this process. The stability of sperm membranes, the number of apoptotic gametes, and the content of seminal plasma PA in the ejaculates of fertile and subfertile men were compared before and after short-term MW electromagnetic exposure in vitro. The ejaculate samples were collected from healthy donors [n=25, age 22-38 years old (y.o.), average age 30.6±1.1 y.o. (mean ± SEM)] and from subfertile men (n=78, age 25-48 y.o., average age 34.1±0.8 y.o.) and exposed to MW radiation. The electromagnetic field had a wavelength of 7.1 mm, a frequency of 42.194 GHz and an exposure time of 20 min. The fragility of sperm membranes was evaluated by their resistance to sodium chloride solution (Milovanov test) and to acetic acid (Joel test). Acrosin activity was assayed spectrophotometrically. Apoptosis was determined by the externalization of phosphatidylserine on the outer side of the sperm membrane and propidium iodide staining. The PA levels were determined by agar gel electrophoretic fractionation. An increase in the resistance of sperm membranes, a decrease in acrosin activity, a decrease in the number of apoptotic gametes and a decrease in the seminal plasma PA concentrations were found after exposure of the native human sperm to low-intensity MW irradiation. Two types of reactions were revealed for the subfertile samples. The results revealed positive bio-effects of specific microwaves on the human semen and the participation of PA in the realization of these effects.

show abstract

“…Several compounds are known to induce PA catabolic enzymes (Di Paolo et al 2019). Syatkin et al (2020) report the investigation of structure-activity relationship of polyamine-targeted synthetic compounds from different chemical groups. The aim of this work was to explore if low molecular compounds could activate them directly and how their structure determines their action using docking simulations.…”

Section: Editorialmentioning

confidence: 99%

Biochemical and pathophysiological properties of polyamines

Agostinelli

2020

Amino Acids

Self Cite

View full text Add to dashboard Cite

The investigation of structure–activity relationship of polyamine-targeted synthetic compounds from different chemical groups

Cited by 7 publications

References 35 publications

Anticancer Cytotoxic Activity of Bispidine Derivatives Associated with the Increasing Catabolism of Polyamines

Anticancer Cytotoxic Activity of Bispidine Derivatives Associated with the Increasing Catabolism of Polyamines

Assessing the biological effects of microwave irradiation on human semen in vitro and determining the role of seminal plasma polyamines in this process

Biochemical and pathophysiological properties of polyamines

Contact Info

Product

Resources

About