Synthesis and Antiproliferative Activity of Daunorubicin Conjugates with Sesquiterpene Lactones

Аникина, Л. В.; Semakov, A. V.; Afanas’eva, S. V.; Pukhov, S. A.; Клочков, С. Г.

doi:10.1007/s11094-018-1812-7

Cited by 4 publications

(3 citation statements)

References 6 publications

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“…Table 2 shows a comparison, using the example of a conjugate with isotelekin 3 a , of the changes in chemical shifts near the new bond in comparison with the chemical shifts of the starting substances. Similar conjugates of DAU with elecampane lactones and their epoxy derivatives were described by us earlier, including the synthesis of the conjugate with epoxyisoalantolactone 3 g [14] .…”

Section: Resultsmentioning

confidence: 75%

New Conjugates of Daunorubicin with Sesquiterpene Lactones and Their Biological Activity

et al. 2021

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New conjugates of daunorubicin with sesquiterpene lactones at the 3′‐amino group of anthracycline were synthesized and their effect on the viability of cell lines (HL60, Jurkat, K562, and A549) was assessed using a resazurin test. The effect on the cell cycle and apoptosis by flow cytometry was studied. The following natural lactones were used for modification: telekin, isotelekin, reynosin, costunolide, dehydrocostuslactone, santamarine and epoxyisoalantolactone. The synthesized conjugates are characterized by a general high toxicity (8…0.14 μM) in relation to tumor cell lines (in some cases, higher than the toxicity of the initial antibiotic), as well as a comparable effect on the cell cycle (arrest in the G2/M‐phase) with a relatively low the effect on the initiation of apoptosis at concentrations close to the IC50.

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Section: Resultsmentioning

confidence: 75%

New Conjugates of Daunorubicin with Sesquiterpene Lactones and Their Biological Activity

et al. 2021

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“…Anthracycline antibiotics conjugates ( 1a ), ( 2a ), ( 4a) , ( 5a ), ( 6a ), ( 1b ), ( 3b ), ( 4b ), ( 5b ), ( 6b ) were obtained as described earlier; the spectral characteristics corresponded to the literature data [ 20 , 21 , 22 ].…”

Section: Methodsmentioning

confidence: 99%

“…The anthracycline antibiotics doxorubicin ( a ) and daunorubicin ( b ) were modified with sesquiterpene lactones—isoalantholactone ( 1 ), alantolactone ( 2 ), alloalantholactone ( 3 ), epoxy-isoalantholactone ( 4 ), epoxyalantholactolactone ( 5 ), epoxyalloalantholactone ( 6 ), 6-hydroxyxanthanodiene ( 7 ), alanthodiene ( 8 ). Conjugates 1-6a-b were obtained in our previous works [ 20 , 21 , 22 ]; compounds 7a , b and 8a , b were first obtained and studied. Their cytotoxic and antiproliferative properties in relation to tumor cell lines were evaluated and their influence on key aspects of formation of cytotoxicity—mitochondrial functional characteristics (mitochondrial swelling, membrane potential, and mitochondrial respiratory chain complexes) as well as the glycolytic function parameters of HeLa tumor cells— was studied.…”

Section: Introductionmentioning

confidence: 99%

N-Alkylation of Anthracycline Antibiotics by Natural Sesquiterpene Lactones as a Way to Obtain Antitumor Agents with Reduced Side Effects

et al. 2021

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Anthracycline antitumor antibiotics are one of the promising classes of chemotherapeutic agents for cancer treatment. The main deterrent to their use is high toxicity to a healthy environment, including cumulative cardiotoxicity. In our work, bipharmacophore molecules containing in their structure a fragment of the known anthracycline antibiotics daunorubicin and doxorubicin and natural sesquiterpene lactones were obtained for the first time. When studying the biological activity of the synthesized compounds, it was found that with equal and, in some cases, higher cytotoxicity and glycolysis inhibition by anthracycline antibiotics conjugates with sesquiterpene lactones in comparison with doxo- and daunorubicin, a reduced damaging effect on the functioning of rat heart mitochondria was observed. The results obtained allow us to confirm the assumption that the chemical modification of the anthracycline antibiotics molecules doxo- and daunorubicin by natural sesquiterpene lactones can be a promising strategy for creating potential antitumor chemotherapeutic drugs with a pronounced cytotoxic effect on tumor cells and a reduced damaging effect on healthy cells of the human organism.

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N-Phosphorylation of daunorubicin—synthetic approaches and antiproliferative properties of the products

et al. 2022

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Synthesis and Antiproliferative Activity of Daunorubicin Conjugates with Sesquiterpene Lactones

Cited by 4 publications

References 6 publications

New Conjugates of Daunorubicin with Sesquiterpene Lactones and Their Biological Activity

New Conjugates of Daunorubicin with Sesquiterpene Lactones and Their Biological Activity

N-Alkylation of Anthracycline Antibiotics by Natural Sesquiterpene Lactones as a Way to Obtain Antitumor Agents with Reduced Side Effects

N-Phosphorylation of daunorubicin—synthetic approaches and antiproliferative properties of the products

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