Identification of Spiro-Fused Pyrrolo[3,4- a ]pyrrolizines and Tryptanthrines as Potential Antitumor Agents: Synthesis and In Vitro Evaluation
A series of heterocyclic compounds containing a spiro-fused pyrrolo[3,4- ]pyrrolizine and tryptanthrin framework have been synthesized and studied as potential antitumor agents. Cytotoxicity of products was screened against human erythroleukemia (K562) and human cervical carcinoma (HeLa) cell lines....
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| Veröffentlicht in: | International journal of molecular sciences 2021-11, Vol.22 (21), p.11997 |
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| container_issue | 21 |
| container_start_page | 11997 |
| container_title | International journal of molecular sciences |
| container_volume | 22 |
| creator | Latypova, Diana K Shmakov, Stanislav V Pechkovskaya, Sofya A Filatov, Alexander S Stepakov, Alexander V Knyazev, Nickolay A Boitsov, Vitali M |
| description | A series of heterocyclic compounds containing a spiro-fused pyrrolo[3,4-
]pyrrolizine and tryptanthrin framework have been synthesized and studied as potential antitumor agents. Cytotoxicity of products was screened against human erythroleukemia (K562) and human cervical carcinoma (HeLa) cell lines. Among the screened compounds.
,
and
were active against human erythroleukemia (K562) cell line, while
and
were active against cervical carcinoma (HeLa) cell line. In agreement with the DNA cytometry studies, the tested compounds have achieved significant cell-cycle perturbation with higher accumulation of cells in G2/M phase and induced apoptosis. Using confocal microscopy, we found that with
and
treatment of HeLa cells, actin filaments disappeared, and granular actin was distributed diffusely in the cytoplasm in 76-91% of cells. We discovered that HeLa cells after treatment with compounds
and
significantly reduced the number of cells with filopodium-like membrane protrusions (from 63 % in control cells to 29% after treatment) and a decrease in cell motility. |
| doi_str_mv | 10.3390/ijms222111997 |
| format | Article |
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]pyrrolizine and tryptanthrin framework have been synthesized and studied as potential antitumor agents. Cytotoxicity of products was screened against human erythroleukemia (K562) and human cervical carcinoma (HeLa) cell lines. Among the screened compounds.
,
and
were active against human erythroleukemia (K562) cell line, while
and
were active against cervical carcinoma (HeLa) cell line. In agreement with the DNA cytometry studies, the tested compounds have achieved significant cell-cycle perturbation with higher accumulation of cells in G2/M phase and induced apoptosis. Using confocal microscopy, we found that with
and
treatment of HeLa cells, actin filaments disappeared, and granular actin was distributed diffusely in the cytoplasm in 76-91% of cells. We discovered that HeLa cells after treatment with compounds
and
significantly reduced the number of cells with filopodium-like membrane protrusions (from 63 % in control cells to 29% after treatment) and a decrease in cell motility.</description><identifier>ISSN: 1422-0067</identifier><identifier>ISSN: 1661-6596</identifier><identifier>EISSN: 1422-0067</identifier><identifier>DOI: 10.3390/ijms222111997</identifier><identifier>PMID: 34769424</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Actin ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Apoptosis ; Apoptosis - drug effects ; Cancer ; Cell cycle ; Cell Cycle - drug effects ; Cell death ; Cell Line, Tumor ; Cell Movement - drug effects ; Cell Proliferation - drug effects ; Cervical cancer ; Cervical carcinoma ; Cervix ; Chromatography ; Confocal microscopy ; Cystic fibrosis ; Cytometry ; Cytoplasm ; Cytotoxicity ; Drug resistance ; Drug Screening Assays, Antitumor ; Erythroleukemia ; Female ; Filaments ; Heterocyclic compounds ; Humans ; Leukemia, Erythroblastic, Acute - drug therapy ; Leukemia, Erythroblastic, Acute - metabolism ; Leukemia, Erythroblastic, Acute - pathology ; Morphology ; Natural products ; Pyrrolidines - chemical synthesis ; Pyrrolidines - pharmacology ; Quinazolines - chemical synthesis ; Quinazolines - pharmacology ; Spiro Compounds - chemical synthesis ; Spiro Compounds - pharmacology ; Tumor cell lines ; Uterine Cervical Neoplasms - drug therapy ; Uterine Cervical Neoplasms - metabolism ; Uterine Cervical Neoplasms - pathology</subject><ispartof>International journal of molecular sciences, 2021-11, Vol.22 (21), p.11997</ispartof><rights>2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2021 by the authors. 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c481t-2dfacfb8a5c8b9f7e863df66644e399eddc50f3ee64e733de360b97594935be13</citedby><cites>FETCH-LOGICAL-c481t-2dfacfb8a5c8b9f7e863df66644e399eddc50f3ee64e733de360b97594935be13</cites><orcidid>0000-0002-4857-2046</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8584944/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8584944/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,725,778,782,883,27913,27914,53780,53782</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34769424$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Latypova, Diana K</creatorcontrib><creatorcontrib>Shmakov, Stanislav V</creatorcontrib><creatorcontrib>Pechkovskaya, Sofya A</creatorcontrib><creatorcontrib>Filatov, Alexander S</creatorcontrib><creatorcontrib>Stepakov, Alexander V</creatorcontrib><creatorcontrib>Knyazev, Nickolay A</creatorcontrib><creatorcontrib>Boitsov, Vitali M</creatorcontrib><title>Identification of Spiro-Fused Pyrrolo[3,4- a ]pyrrolizines and Tryptanthrines as Potential Antitumor Agents: Synthesis and In Vitro Evaluation</title><title>International journal of molecular sciences</title><addtitle>Int J Mol Sci</addtitle><description>A series of heterocyclic compounds containing a spiro-fused pyrrolo[3,4-
]pyrrolizine and tryptanthrin framework have been synthesized and studied as potential antitumor agents. Cytotoxicity of products was screened against human erythroleukemia (K562) and human cervical carcinoma (HeLa) cell lines. Among the screened compounds.
,
and
were active against human erythroleukemia (K562) cell line, while
and
were active against cervical carcinoma (HeLa) cell line. In agreement with the DNA cytometry studies, the tested compounds have achieved significant cell-cycle perturbation with higher accumulation of cells in G2/M phase and induced apoptosis. Using confocal microscopy, we found that with
and
treatment of HeLa cells, actin filaments disappeared, and granular actin was distributed diffusely in the cytoplasm in 76-91% of cells. We discovered that HeLa cells after treatment with compounds
and
significantly reduced the number of cells with filopodium-like membrane protrusions (from 63 % in control cells to 29% after treatment) and a decrease in cell motility.</description><subject>Actin</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis</subject><subject>Apoptosis - drug effects</subject><subject>Cancer</subject><subject>Cell cycle</subject><subject>Cell Cycle - drug effects</subject><subject>Cell death</subject><subject>Cell Line, Tumor</subject><subject>Cell Movement - drug effects</subject><subject>Cell Proliferation - drug effects</subject><subject>Cervical cancer</subject><subject>Cervical carcinoma</subject><subject>Cervix</subject><subject>Chromatography</subject><subject>Confocal microscopy</subject><subject>Cystic fibrosis</subject><subject>Cytometry</subject><subject>Cytoplasm</subject><subject>Cytotoxicity</subject><subject>Drug resistance</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Erythroleukemia</subject><subject>Female</subject><subject>Filaments</subject><subject>Heterocyclic compounds</subject><subject>Humans</subject><subject>Leukemia, Erythroblastic, Acute - 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chemical synthesis</topic><topic>Pyrrolidines - pharmacology</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - pharmacology</topic><topic>Spiro Compounds - chemical synthesis</topic><topic>Spiro Compounds - pharmacology</topic><topic>Tumor cell lines</topic><topic>Uterine Cervical Neoplasms - drug therapy</topic><topic>Uterine Cervical Neoplasms - metabolism</topic><topic>Uterine Cervical Neoplasms - pathology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Latypova, Diana K</creatorcontrib><creatorcontrib>Shmakov, Stanislav V</creatorcontrib><creatorcontrib>Pechkovskaya, Sofya A</creatorcontrib><creatorcontrib>Filatov, Alexander S</creatorcontrib><creatorcontrib>Stepakov, Alexander V</creatorcontrib><creatorcontrib>Knyazev, Nickolay A</creatorcontrib><creatorcontrib>Boitsov, Vitali M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Research Library</collection><collection>Research Library (Corporate)</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>International journal of molecular sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Latypova, Diana K</au><au>Shmakov, Stanislav V</au><au>Pechkovskaya, Sofya A</au><au>Filatov, Alexander S</au><au>Stepakov, Alexander V</au><au>Knyazev, Nickolay A</au><au>Boitsov, Vitali M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of Spiro-Fused Pyrrolo[3,4- a ]pyrrolizines and Tryptanthrines as Potential Antitumor Agents: Synthesis and In Vitro Evaluation</atitle><jtitle>International journal of molecular sciences</jtitle><addtitle>Int J Mol Sci</addtitle><date>2021-11-05</date><risdate>2021</risdate><volume>22</volume><issue>21</issue><spage>11997</spage><pages>11997-</pages><issn>1422-0067</issn><issn>1661-6596</issn><eissn>1422-0067</eissn><abstract>A series of heterocyclic compounds containing a spiro-fused pyrrolo[3,4-
]pyrrolizine and tryptanthrin framework have been synthesized and studied as potential antitumor agents. Cytotoxicity of products was screened against human erythroleukemia (K562) and human cervical carcinoma (HeLa) cell lines. Among the screened compounds.
,
and
were active against human erythroleukemia (K562) cell line, while
and
were active against cervical carcinoma (HeLa) cell line. In agreement with the DNA cytometry studies, the tested compounds have achieved significant cell-cycle perturbation with higher accumulation of cells in G2/M phase and induced apoptosis. Using confocal microscopy, we found that with
and
treatment of HeLa cells, actin filaments disappeared, and granular actin was distributed diffusely in the cytoplasm in 76-91% of cells. We discovered that HeLa cells after treatment with compounds
and
significantly reduced the number of cells with filopodium-like membrane protrusions (from 63 % in control cells to 29% after treatment) and a decrease in cell motility.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>34769424</pmid><doi>10.3390/ijms222111997</doi><orcidid>https://orcid.org/0000-0002-4857-2046</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; MDPI - Multidisciplinary Digital Publishing Institute; PubMed Central |
| subjects | Actin Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Apoptosis Apoptosis - drug effects Cancer Cell cycle Cell Cycle - drug effects Cell death Cell Line, Tumor Cell Movement - drug effects Cell Proliferation - drug effects Cervical cancer Cervical carcinoma Cervix Chromatography Confocal microscopy Cystic fibrosis Cytometry Cytoplasm Cytotoxicity Drug resistance Drug Screening Assays, Antitumor Erythroleukemia Female Filaments Heterocyclic compounds Humans Leukemia, Erythroblastic, Acute - drug therapy Leukemia, Erythroblastic, Acute - metabolism Leukemia, Erythroblastic, Acute - pathology Morphology Natural products Pyrrolidines - chemical synthesis Pyrrolidines - pharmacology Quinazolines - chemical synthesis Quinazolines - pharmacology Spiro Compounds - chemical synthesis Spiro Compounds - pharmacology Tumor cell lines Uterine Cervical Neoplasms - drug therapy Uterine Cervical Neoplasms - metabolism Uterine Cervical Neoplasms - pathology |
| title | Identification of Spiro-Fused Pyrrolo[3,4- a ]pyrrolizines and Tryptanthrines as Potential Antitumor Agents: Synthesis and In Vitro Evaluation |
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