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Article ; Online: Glucose starvation greatly enhances antiproliferative and antiestrogenic potency of oligomycin A in MCF-7 breast cancer cells.

Scherbakov, Alexander M / Sorokin, Danila V / Omelchuk, Olga A / Shchekotikhin, Andrey E / Krasil'nikov, Mikhail A

2021 Volume 186, Page(s) 51–58

Abstract: Energy imbalance is one of the key properties of tumour cells, which in certain cases supports fast cancer progression and resistance to therapy. The simultaneous blocking of glycolytic processes and oxidative phosphorylation pathways seems to be a ... ...

Abstract	Energy imbalance is one of the key properties of tumour cells, which in certain cases supports fast cancer progression and resistance to therapy. The simultaneous blocking of glycolytic processes and oxidative phosphorylation pathways seems to be a promising strategy for antitumor therapies. The study aimed to evaluate the effect of glucose starvation on the antiproliferative and antiestrogenic potency of oligomycin A against hormone-dependent breast cancer cells. Cell viability was assessed by the MTT test. Estrogen receptor alpha (ERα) activity was evaluated by reporter assay. mTOR, AMPK, Akt, and S6 kinase expression was assessed by immunoblotting. Glucose starvation caused multiple increases in the antiproliferative potency of oligomycin A in the hormone-dependent breast cancer MCF-7 cells, while its effect on the sensitivity of the second hormone-dependent cancer cell line, named T47D, was weak and limited. Glycolytic inhibitors, 3-bromopyruvate and 2-deoxyglucose, greatly enhanced the antiproliferative potency of oligomycin A in MCF-7 cells. Glucose starvation leads to remarkable activation of Akt in MCF-7 cells, whereas oligomycin A enhances its effect. The mTOR, S6 kinase, and AMPK signalling pathways are significantly modulated by oligomycin A under glucose starvation. Oligomycin A demonstrates more pronounced antiestrogenic effects under glucose starvation. Thus, glucose starvation and pharmacological inhibition of glycolysis are of interest for revealing the antitumor potential of macrolide oligomycin A against hormone-dependent breast cancers.
MeSH term(s)	Breast Neoplasms/drug therapy ; Breast Neoplasms/metabolism ; Breast Neoplasms/pathology ; Cell Proliferation/drug effects ; Estrogen Receptor Modulators/pharmacology ; Female ; Glucose/deficiency ; Humans ; MCF-7 Cells ; Oligomycins/pharmacology
Chemical Substances	Estrogen Receptor Modulators ; Oligomycins ; oligomycin A (05HQS4AI99) ; Glucose (IY9XDZ35W2)
Language	English
Publishing date	2021-04-16
Publishing country	France
Document type	Journal Article
ZDB-ID	120345-9
ISSN	1638-6183 ; 0300-9084
ISSN (online)	1638-6183
ISSN	0300-9084
DOI	10.1016/j.biochi.2021.04.003
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Article: Glucose starvation greatly enhances antiproliferative and antiestrogenic potency of oligomycin A in MCF-7 breast cancer cells

Scherbakov, Alexander M / Sorokin, Danila V / Omelchuk, Olga A / Shchekotikhin, Andrey E / Krasil’nikov, Mikhail A

Biochimie. 2021 July, v. 186

2021

Abstract: Energy imbalance is one of the key properties of tumour cells, which in certain cases supports fast cancer progression and resistance to therapy.The simultaneous blocking of glycolytic processes and oxidative phosphorylation pathways seems to be a ... ...

Abstract	Energy imbalance is one of the key properties of tumour cells, which in certain cases supports fast cancer progression and resistance to therapy.The simultaneous blocking of glycolytic processes and oxidative phosphorylation pathways seems to be a promising strategy for antitumor therapies. The study aimed to evaluate the effect of glucose starvation on the antiproliferative and antiestrogenic potency of oligomycin A against hormone-dependent breast cancer cells.Cell viability was assessed by the MTT test. Estrogen receptor alpha (ERα) activity was evaluated by reporter assay. mTOR, AMPK, Akt, and S6 kinase expression was assessed by immunoblotting.Glucose starvation caused multiple increases in the antiproliferative potency of oligomycin A in the hormone-dependent breast cancer MCF-7 cells, while its effect on the sensitivity of the second hormone-dependent cancer cell line, named T47D, was weak and limited. Glycolytic inhibitors, 3-bromopyruvate and 2-deoxyglucose, greatly enhanced the antiproliferative potency of oligomycin A in MCF-7 cells. Glucose starvation leads to remarkable activation of Akt in MCF-7 cells, whereas oligomycin A enhances its effect. The mTOR, S6 kinase, and AMPK signalling pathways are significantly modulated by oligomycin A under glucose starvation. Oligomycin A demonstrates more pronounced antiestrogenic effects under glucose starvation. Thus, glucose starvation and pharmacological inhibition of glycolysis are of interest for revealing the antitumor potential of macrolide oligomycin A against hormone-dependent breast cancers.
Keywords	2-deoxyglucose ; antineoplastic activity ; breast neoplasms ; breasts ; energy ; estrogen receptors ; glucose ; glycolysis ; neoplasm cells ; neoplasm progression ; oligomycin ; oxidative phosphorylation ; starvation ; viability
Language	English
Dates of publication	2021-07
Size	p. 51-58.
Publishing place	Elsevier B.V.
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	120345-9
ISSN	0300-9084
ISSN	0300-9084
DOI	10.1016/j.biochi.2021.04.003
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Article: Semisynthetic Amides of Amphotericin B and Nystatin A

Tevyashova, Anna / Efimova, Svetlana / Alexandrov, Alexander / Omelchuk, Olga / Ghazy, Eslam / Bychkova, Elena / Zatonsky, Georgy / Grammatikova, Natalia / Dezhenkova, Lyubov / Solovieva, Svetlana / Ostroumova, Olga / Shchekotikhin, Andrey

Antibiotics (Basel, Switzerland)

2023 Volume 12, Issue 1

Abstract: Polyene antifungal amphotericin B (AmB) has been used for over 60 years, and remains a valuable clinical treatment for systemic mycoses, due to its broad antifungal activity and low rate of emerging resistance. There is no consensus on how exactly it ... ...

Abstract	Polyene antifungal amphotericin B (AmB) has been used for over 60 years, and remains a valuable clinical treatment for systemic mycoses, due to its broad antifungal activity and low rate of emerging resistance. There is no consensus on how exactly it kills fungal cells but it is certain that AmB and the closely-related nystatin (Nys) can form pores in membranes and have a higher affinity towards ergosterol than cholesterol. Notably, the high nephro- and hemolytic toxicity of polyenes and their low solubility in water have led to efforts to improve their properties. We present the synthesis of new amphotericin and nystatin amides and a comparative study of the effects of identical modifications of AmB and Nys on the relationship between their structure and properties. Generally, increases in the activity/toxicity ratio were in good agreement with increasing ratios of selective permeabilization of ergosterol- vs. cholesterol-containing membranes. We also show that the introduced modifications had an effect on the sensitivity of mutant yeast strains with alterations in ergosterol biosynthesis to the studied polyenes, suggesting a varying affinity towards intermediate ergosterol precursors. Three new water-soluble nystatin derivatives showed a prominent improvement in safety and were selected as promising candidates for drug development.
Language	English
Publishing date	2023-01-11
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2681345-2
ISSN	2079-6382
ISSN	2079-6382
DOI	10.3390/antibiotics12010151
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Article: Stereochemistries and Biological Properties of Oligomycin A Diels–Alder Adducts

Omelchuk, Olga A. / Malyshev, Vadim I. / Medvedev, Michael G. / Lysenkova, Lyudmila N. / Belov, Nikita M. / Dezhenkova, Lyubov G. / Grammatikova, Natalia E. / Scherbakov, Alexander M. / Shchekotikhin, Andrey E.

Journal of organic chemistry. 2021 May 27, v. 86, no. 12

2021

Abstract: Oligomycin A is a potent antibiotic and antitumor agent. However, its applications are restricted by its high toxicity and low bioavailability. In this study, we obtained Oligomycin A Diels–Alder adducts with benzoquinone and N-benzylmaleimide and ... ...

Abstract	Oligomycin A is a potent antibiotic and antitumor agent. However, its applications are restricted by its high toxicity and low bioavailability. In this study, we obtained Oligomycin A Diels–Alder adducts with benzoquinone and N-benzylmaleimide and determined their absolute configurations by combining ¹H and ROESY NMR data with molecular mechanics conformational analysis and quantum chemical reaction modeling. The latter showed that adduct stereochemistry is controlled by hydrogen bonding of the Oligomycin A side-chain isopropanol moiety with the carbonyl group of the dienophile. Biological studies showed that the Diels–Alder modification of the Oligomycin A diene system resulted in a complex antiproliferative potential pattern. The synthesized adducts were determined to be more active against the triple-negative (ERα, PR, and HER2 negative) breast cancer cell line MDA-MB-231 and lung carcinoma cell line A-549 compared to Oligomycin A. Meanwhile, Oligomycin A was more potent against myeloid leukemia cell line K-562 and breast carcinoma cell line MCF-7 than its derivatives. Thus, modification of the diene moiety of Oligomycin A is a promising strategy for developing novel antitumor agents based on its scaffold.
Keywords	antineoplastic agents ; benzoquinones ; bioavailability ; breast neoplasms ; cell lines ; cycloaddition reactions ; hydrogen ; isopropyl alcohol ; lung neoplasms ; moieties ; molecular conformation ; myeloid leukemia ; neoplasm cells ; oligomycin ; organic chemistry ; quantum mechanics ; stereochemistry ; toxicity
Language	English
Dates of publication	2021-0527
Size	p. 7975-7986.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.1c00296
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Article ; Online: Stereochemistries and Biological Properties of Oligomycin A Diels-Alder Adducts.

Omelchuk, Olga A / Malyshev, Vadim I / Medvedev, Michael G / Lysenkova, Lyudmila N / Belov, Nikita M / Dezhenkova, Lyubov G / Grammatikova, Natalia E / Scherbakov, Alexander M / Shchekotikhin, Andrey E

The Journal of organic chemistry

2021 Volume 86, Issue 12, Page(s) 7975–7986

Abstract	Oligomycin A is a potent antibiotic and antitumor agent. However, its applications are restricted by its high toxicity and low bioavailability. In this study, we obtained Oligomycin A Diels-Alder adducts with benzoquinone and
MeSH term(s)	Humans ; MCF-7 Cells ; Models, Molecular ; Molecular Conformation ; Oligomycins/pharmacology
Chemical Substances	Oligomycins ; oligomycin A (05HQS4AI99)
Language	English
Publishing date	2021-05-27
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.1c00296
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Article: Synthesis, antimicrobial and antiproliferative properties of epi-oligomycin A, the (33S)-diastereomer of oligomycin A

Lysenkova, Lyudmila N / Saveljev, Oleg Y / Omelchuk, Olga A / Zatonsky, George V / Korolev, Alexander M / Grammatikova, Natalya E / Bekker, Olga B / Danilenko, Valery N / Dezhenkova, Lyubov G / Mavletova, Dilara A / Scherbakov, Alexander M / Shchekotikhin, Andrey E

Natural product research. 2020 Nov. 1, v. 34, no. 21

2020

Abstract: We describe the synthesis of epi-oligomycin A, a (33S)-diastereomer of the antibiotic oligomycin A. The structure of (33S)-oligomycin A was determined by elemental analysis, spectroscopic studies, including 1D and 2D NMR spectroscopy, and mass ... ...

Abstract	We describe the synthesis of epi-oligomycin A, a (33S)-diastereomer of the antibiotic oligomycin A. The structure of (33S)-oligomycin A was determined by elemental analysis, spectroscopic studies, including 1D and 2D NMR spectroscopy, and mass spectrometry. Isomerization of C33 hydroxyl group led to minor changes in the potency against Aspergillus niger, Candida spp., and filamentous fungi whereas the activity against Streptomyces fradiae decreased by approximately 20-fold compared to oligomycin A. We observed that 33-epi-oligomycin A had the same activity on the human leukemia cell line K562 as oligomycin A but was more potent for the multidrug resistant subline K562/4. Non-malignant cells were less sensitive to both oligomycin isomers. Finally, our results pointed at the dependence of the cytotoxicity of oligomycins on oxygen supply.
Keywords	Aspergillus niger ; Candida ; Streptomyces fradiae ; cell lines ; cytotoxicity ; fungi ; humans ; isomerization ; isomers ; mass spectrometry ; multiple drug resistance ; neoplasm cells ; nuclear magnetic resonance spectroscopy ; oligomycin ; oxygen ; research ; spectral analysis ; supply ; synthesis
Language	English
Dates of publication	2020-1101
Size	p. 3073-3081.
Publishing place	Taylor & Francis
Document type	Article
Note	NAL-light
ZDB-ID	2185747-7
ISSN	1478-6427 ; 1478-6419
ISSN (online)	1478-6427
ISSN	1478-6419
DOI	10.1080/14786419.2019.1608540
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Semisynthetic Amides of Polyene Antibiotic Natamycin.

Tevyashova, Anna N / Efimova, Svetlana S / Alexandrov, Alexander I / Ghazy, Eslam S M O / Bychkova, Elena N / Solovieva, Svetlana E / Zatonsky, Georgy B / Grammatikova, Natalia E / Dezhenkova, Lyubov G / Pereverzeva, Eleonora R / Isakova, Elena B / Ostroumova, Olga S / Omelchuk, Olga A / Muravieva, Vera V / Krotova, Marina M / Priputnevich, Tatiana V / Shchekotikhin, Andrey E

ACS infectious diseases

2022 Volume 9, Issue 1, Page(s) 42–55

Abstract: Natamycin is a macrolide polyene antibiotic, characterized by a potent broad spectrum antifungal activity and low toxicity. However, it is not used for the treatment of systemic mycoses due to its low bioavailability and low solubility in aqueous ... ...

Abstract	Natamycin is a macrolide polyene antibiotic, characterized by a potent broad spectrum antifungal activity and low toxicity. However, it is not used for the treatment of systemic mycoses due to its low bioavailability and low solubility in aqueous solutions. In order to create new semisynthetic antifungal agents for treatment of mycoses, a series of water-soluble amides of natamycin were synthesized. Antifungal activities of natamycin derivatives were investigated against
MeSH term(s)	Animals ; Mice ; Humans ; Natamycin/pharmacology ; Antifungal Agents/pharmacology ; Antifungal Agents/therapeutic use ; Anti-Bacterial Agents/pharmacology ; Anti-Bacterial Agents/therapeutic use ; HEK293 Cells ; Polyenes/pharmacology ; Mycoses/drug therapy ; Candida ; Saccharomyces cerevisiae ; Mammals
Chemical Substances	Natamycin (8O0C852CPO) ; Antifungal Agents ; Anti-Bacterial Agents ; Polyenes
Language	English
Publishing date	2022-12-23
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	2373-8227
ISSN (online)	2373-8227
DOI	10.1021/acsinfecdis.2c00237
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Article ; Online: Synthesis, antimicrobial and antiproliferative properties of epi-oligomycin A, the (33

Natural product research

2019 Volume 34, Issue 21, Page(s) 3073–3081

Abstract: We describe the synthesis of epi-oligomycin A, a ( ... ...

Abstract	We describe the synthesis of epi-oligomycin A, a (33
MeSH term(s)	Animals ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Antibiotics, Antineoplastic/chemistry ; Antibiotics, Antineoplastic/pharmacology ; Aspergillus niger/drug effects ; Candida/drug effects ; Cell Proliferation/drug effects ; Dogs ; Drug Resistance, Neoplasm ; Humans ; K562 Cells ; MCF-7 Cells ; Madin Darby Canine Kidney Cells ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Microbial Sensitivity Tests ; Oligomycins/chemical synthesis ; Oligomycins/pharmacology ; Stereoisomerism ; Streptomyces/drug effects ; Structure-Activity Relationship
Chemical Substances	Anti-Bacterial Agents ; Antibiotics, Antineoplastic ; Oligomycins ; oligomycin A (05HQS4AI99)
Language	English
Publishing date	2019-05-10
Publishing country	England
Document type	Journal Article
ZDB-ID	2185747-7
ISSN	1478-6427 ; 1478-6419
ISSN (online)	1478-6427
ISSN	1478-6419
DOI	10.1080/14786419.2019.1608540
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Article: Verification of oligomycin A structure: synthesis and biological evaluation of 33-dehydrooligomycin A.

Lysenkova, Lyudmila N / Saveljev, Oleg Y / Grammatikova, Natalya E / Tsvetkov, Vladimir B / Bekker, Olga B / Danilenko, Valery N / Dezhenkova, Lyubov G / Bykov, Eugene E / Omelchuk, Olga A / Korolev, Alexander M / Shchekotikhin, Andrey E

The Journal of antibiotics

2017 Volume 70, Issue 8, Page(s) 871–877

Abstract: Although, the structure of oligomycin A (1) was confirmed by spectroscopic and chemical evaluations, some crystallographic data cast doubt on the originally adopted structure of the side 2-hydroxypropyl moiety of this antibiotic. It was suggested that ... ...

Abstract	Although, the structure of oligomycin A (1) was confirmed by spectroscopic and chemical evaluations, some crystallographic data cast doubt on the originally adopted structure of the side 2-hydroxypropyl moiety of this antibiotic. It was suggested that the side chain of the oligomycin is enol-related (2-hydroxy-1-propenyl). To clarify this matter we synthesized and evaluated 33-dehydrooligomycin A (2) prepared by the Kornblum oxidation of 33-O-mesyloligomycin A (3) by dimethyl sulfoxide. NMR data for 33-dehydrooligomycin (2) and results of quantum chemical calculations have shown that this derivative exists in the keto rather than in the enol tautomer 2a. The in vitro antimicrobial activity of 2 was approximately two times weaker in comparison with oligomycin A against Streptomyces fradiae ATCC-19609 and reference Candida spp. strains and similar activity against certain filamentous fungi. The docking binding estimate of 2 with F
MeSH term(s)	Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Antifungal Agents/chemistry ; Antifungal Agents/pharmacology ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Candida/drug effects ; Cell Line, Tumor ; Humans ; Magnetic Resonance Spectroscopy ; Oligomycins/chemistry ; Oligomycins/pharmacology ; Streptomyces/drug effects
Chemical Substances	33-dehydrooligomycin A ; Anti-Bacterial Agents ; Antifungal Agents ; Antineoplastic Agents ; Oligomycins ; oligomycin A (05HQS4AI99)
Language	English
Publishing date	2017-07
Publishing country	Japan
Document type	Comparative Study ; Journal Article
ZDB-ID	390800-8
ISSN	1881-1469 ; 0021-8820 ; 0368-3532
ISSN (online)	1881-1469
ISSN	0021-8820 ; 0368-3532
DOI	10.1038/ja.2017.48
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