Discovery of benzochromene derivatives first example with dual cytotoxic activity against the resistant cancer cell MCF-7/ADR and inhibitory effect of the P-glycoprotein expression levels
A series of 1H-benzo[f]chromene moieties (4a-z) were synthesised under Ultrasonic irradiation and confirmed with spectral analyses. Derivative 4i solely possessed an X-ray single crystal. The anti-proliferative efficacy of the desired molecules has been explored against three cancer cells: MCF-7, HC...
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| creator | Al-Harbi, Laila M. Al-Harbi, Eman A. Okasha, Rawda M. El-Eisawy, R. A. El-Nassag, Mohammed A. A. Mohamed, Hany M. Fouda, Ahmed M. Elhenawy, Ahmed A. Mora, Ahmed El-Agrody, Ahmed M. El-Mawgoud, Heba K. A. |
| description | A series of 1H-benzo[f]chromene moieties (4a-z) were synthesised under Ultrasonic irradiation and confirmed with spectral analyses. Derivative 4i solely possessed an X-ray single crystal. The anti-proliferative efficacy of the desired molecules has been explored against three cancer cells: MCF-7, HCT-116, and HepG-2 with the cytotoxically active derivatives screened against MCF-7/ADR and normal cells HFL-1 and WI-38. Furthermore, compounds 4b-d, 4k, 4n, 4q, and 4w, which possessed good potency against MCF-7/ADR, were tested as permeability glycoprotein (P-glycoprotein [P-gp]) expression inhibitors. The attained data confirmed that 4b-d, 4q, and 4w exhibited strong expression inhibition against the P-gp alongside its cytotoxic effect on MCF-7/ADR. The western blot results and Rho123 accumulation assays showed that compounds 4b-d, 4q, and 4w effectively inhibited the P-gp expression and efflux function. Meanwhile, 4b-d, 4q, and 4w induced apoptosis and accumulation of the treated MCF-7/ADR cells in the G1 phase and 4k and 4n in the S phase of the cell cycle. |
| doi_str_mv | 10.1080/14756366.2022.2155814 |
| format | Article |
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A. ; El-Nassag, Mohammed A. A. ; Mohamed, Hany M. ; Fouda, Ahmed M. ; Elhenawy, Ahmed A. ; Mora, Ahmed ; El-Agrody, Ahmed M. ; El-Mawgoud, Heba K. A.</creator><creatorcontrib>Al-Harbi, Laila M. ; Al-Harbi, Eman A. ; Okasha, Rawda M. ; El-Eisawy, R. A. ; El-Nassag, Mohammed A. A. ; Mohamed, Hany M. ; Fouda, Ahmed M. ; Elhenawy, Ahmed A. ; Mora, Ahmed ; El-Agrody, Ahmed M. ; El-Mawgoud, Heba K. A.</creatorcontrib><description>A series of 1H-benzo[f]chromene moieties (4a-z) were synthesised under Ultrasonic irradiation and confirmed with spectral analyses. Derivative 4i solely possessed an X-ray single crystal. The anti-proliferative efficacy of the desired molecules has been explored against three cancer cells: MCF-7, HCT-116, and HepG-2 with the cytotoxically active derivatives screened against MCF-7/ADR and normal cells HFL-1 and WI-38. Furthermore, compounds 4b-d, 4k, 4n, 4q, and 4w, which possessed good potency against MCF-7/ADR, were tested as permeability glycoprotein (P-glycoprotein [P-gp]) expression inhibitors. The attained data confirmed that 4b-d, 4q, and 4w exhibited strong expression inhibition against the P-gp alongside its cytotoxic effect on MCF-7/ADR. The western blot results and Rho123 accumulation assays showed that compounds 4b-d, 4q, and 4w effectively inhibited the P-gp expression and efflux function. Meanwhile, 4b-d, 4q, and 4w induced apoptosis and accumulation of the treated MCF-7/ADR cells in the G1 phase and 4k and 4n in the S phase of the cell cycle.</description><identifier>ISSN: 1475-6366</identifier><identifier>EISSN: 1475-6374</identifier><identifier>DOI: 10.1080/14756366.2022.2155814</identifier><identifier>PMID: 36662632</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject>1H-Benzo[f]chromenes ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; antitumor activity ; Apoptosis ; ATP Binding Cassette Transporter, Subfamily B - pharmacology ; ATP Binding Cassette Transporter, Subfamily B, Member 1 - metabolism ; Benzopyrans - pharmacology ; Cell cycle ; cell cycle arrest ; Cytotoxicity ; Doxorubicin - pharmacology ; Drug Resistance, Neoplasm ; G1 phase ; Glycoproteins ; Humans ; MCF-7 Cells ; MCF-7/ADR ; Neoplasms ; P-Glycoprotein ; Permeability ; Research Paper ; S phase ; SAR ; Ultrasound synthesis ; western blot</subject><ispartof>Journal of enzyme inhibition and medicinal chemistry, 2023-12, Vol.38 (1), p.2155814-2155814</ispartof><rights>2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. 2023</rights><rights>2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. This work is licensed under the Creative Commons Attribution License http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. 2023 The Author(s)</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c562t-6e162c9c836cbc001908956f19c76e89d5cf7682cb80e657a03f6c93837a666c3</citedby><cites>FETCH-LOGICAL-c562t-6e162c9c836cbc001908956f19c76e89d5cf7682cb80e657a03f6c93837a666c3</cites><orcidid>0000-0001-9453-8132 ; 0000-0003-2893-0376 ; 0000-0001-7019-411X</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/PMC9869995/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9869995/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,2096,27479,27901,27902,53766,53768,59116,59117</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36662632$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Al-Harbi, Laila M.</creatorcontrib><creatorcontrib>Al-Harbi, Eman A.</creatorcontrib><creatorcontrib>Okasha, Rawda M.</creatorcontrib><creatorcontrib>El-Eisawy, R. A.</creatorcontrib><creatorcontrib>El-Nassag, Mohammed A. A.</creatorcontrib><creatorcontrib>Mohamed, Hany M.</creatorcontrib><creatorcontrib>Fouda, Ahmed M.</creatorcontrib><creatorcontrib>Elhenawy, Ahmed A.</creatorcontrib><creatorcontrib>Mora, Ahmed</creatorcontrib><creatorcontrib>El-Agrody, Ahmed M.</creatorcontrib><creatorcontrib>El-Mawgoud, Heba K. A.</creatorcontrib><title>Discovery of benzochromene derivatives first example with dual cytotoxic activity against the resistant cancer cell MCF-7/ADR and inhibitory effect of the P-glycoprotein expression levels</title><title>Journal of enzyme inhibition and medicinal chemistry</title><addtitle>J Enzyme Inhib Med Chem</addtitle><description>A series of 1H-benzo[f]chromene moieties (4a-z) were synthesised under Ultrasonic irradiation and confirmed with spectral analyses. Derivative 4i solely possessed an X-ray single crystal. The anti-proliferative efficacy of the desired molecules has been explored against three cancer cells: MCF-7, HCT-116, and HepG-2 with the cytotoxically active derivatives screened against MCF-7/ADR and normal cells HFL-1 and WI-38. Furthermore, compounds 4b-d, 4k, 4n, 4q, and 4w, which possessed good potency against MCF-7/ADR, were tested as permeability glycoprotein (P-glycoprotein [P-gp]) expression inhibitors. The attained data confirmed that 4b-d, 4q, and 4w exhibited strong expression inhibition against the P-gp alongside its cytotoxic effect on MCF-7/ADR. The western blot results and Rho123 accumulation assays showed that compounds 4b-d, 4q, and 4w effectively inhibited the P-gp expression and efflux function. Meanwhile, 4b-d, 4q, and 4w induced apoptosis and accumulation of the treated MCF-7/ADR cells in the G1 phase and 4k and 4n in the S phase of the cell cycle.</description><subject>1H-Benzo[f]chromenes</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>antitumor activity</subject><subject>Apoptosis</subject><subject>ATP Binding Cassette Transporter, Subfamily B - pharmacology</subject><subject>ATP Binding Cassette Transporter, Subfamily B, Member 1 - metabolism</subject><subject>Benzopyrans - pharmacology</subject><subject>Cell cycle</subject><subject>cell cycle arrest</subject><subject>Cytotoxicity</subject><subject>Doxorubicin - pharmacology</subject><subject>Drug Resistance, Neoplasm</subject><subject>G1 phase</subject><subject>Glycoproteins</subject><subject>Humans</subject><subject>MCF-7 Cells</subject><subject>MCF-7/ADR</subject><subject>Neoplasms</subject><subject>P-Glycoprotein</subject><subject>Permeability</subject><subject>Research Paper</subject><subject>S phase</subject><subject>SAR</subject><subject>Ultrasound synthesis</subject><subject>western blot</subject><issn>1475-6366</issn><issn>1475-6374</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>0YH</sourceid><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><sourceid>DOA</sourceid><recordid>eNp9kstu1DAUhiMEoqXwCCBLbLrJ1JfYiTeIakqhUhEIwdryOCczrhJ7sD3Thlfj5XA60xFlwcrW8X--c_FfFK8JnhHc4DNS1VwwIWYUUzqjhPOGVE-K4yleClZXTw93IY6KFzHeYEwJJdXz4iiHBBWMHhe_L2w0fgthRL5DC3C_vFkFP4AD1EKwW53sFiLqbIgJwZ0e1j2gW5tWqN3oHpkx-eTvrEHaZKVNI9JLbV0WpxWgANHGpF1CRjsDARnoe_R5flnWZ-cX35B2LbJuZRc2-dwCdB2YNHUyJX8tl_1o_Dr4BNbl4uuMi9Y71MMW-viyeNbpPsKr_XlS_Lj88H3-qbz-8vFqfn5dGi5oKgUQQY00DRNmYTAmEjeSi45IUwtoZMtNV4uGmkWDQfBaY9YJI1nDap33ZNhJcbXjtl7fqHWwgw6j8tqq-4APS6VDsqYH1QophZaZimklKdFNxTQmGDOODaF1Zr3bsdabxQCtAZeC7h9BH784u1JLv1WyyWjJM-B0Dwj-5wZiUkP-wbxV7cBvoqLTKIxTJrP07T_SG78JLq9KUUlqXklyr-I7lQk-xgDdoRmC1WQ19WA1NVlN7a2W8978Pckh68FbWfB-J7Cu82HQtz70rUp67H3oQraDjYr9v8YfZaPl-w</recordid><startdate>202312</startdate><enddate>202312</enddate><creator>Al-Harbi, Laila M.</creator><creator>Al-Harbi, Eman A.</creator><creator>Okasha, Rawda M.</creator><creator>El-Eisawy, R. 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A. ; El-Nassag, Mohammed A. A. ; Mohamed, Hany M. ; Fouda, Ahmed M. ; Elhenawy, Ahmed A. ; Mora, Ahmed ; El-Agrody, Ahmed M. ; El-Mawgoud, Heba K. 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A.</au><au>El-Nassag, Mohammed A. A.</au><au>Mohamed, Hany M.</au><au>Fouda, Ahmed M.</au><au>Elhenawy, Ahmed A.</au><au>Mora, Ahmed</au><au>El-Agrody, Ahmed M.</au><au>El-Mawgoud, Heba K. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of benzochromene derivatives first example with dual cytotoxic activity against the resistant cancer cell MCF-7/ADR and inhibitory effect of the P-glycoprotein expression levels</atitle><jtitle>Journal of enzyme inhibition and medicinal chemistry</jtitle><addtitle>J Enzyme Inhib Med Chem</addtitle><date>2023-12</date><risdate>2023</risdate><volume>38</volume><issue>1</issue><spage>2155814</spage><epage>2155814</epage><pages>2155814-2155814</pages><issn>1475-6366</issn><eissn>1475-6374</eissn><abstract>A series of 1H-benzo[f]chromene moieties (4a-z) were synthesised under Ultrasonic irradiation and confirmed with spectral analyses. Derivative 4i solely possessed an X-ray single crystal. The anti-proliferative efficacy of the desired molecules has been explored against three cancer cells: MCF-7, HCT-116, and HepG-2 with the cytotoxically active derivatives screened against MCF-7/ADR and normal cells HFL-1 and WI-38. Furthermore, compounds 4b-d, 4k, 4n, 4q, and 4w, which possessed good potency against MCF-7/ADR, were tested as permeability glycoprotein (P-glycoprotein [P-gp]) expression inhibitors. The attained data confirmed that 4b-d, 4q, and 4w exhibited strong expression inhibition against the P-gp alongside its cytotoxic effect on MCF-7/ADR. The western blot results and Rho123 accumulation assays showed that compounds 4b-d, 4q, and 4w effectively inhibited the P-gp expression and efflux function. 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| source | Taylor & Francis Open Access; MEDLINE; DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central |
| subjects | 1H-Benzo[f]chromenes Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology antitumor activity Apoptosis ATP Binding Cassette Transporter, Subfamily B - pharmacology ATP Binding Cassette Transporter, Subfamily B, Member 1 - metabolism Benzopyrans - pharmacology Cell cycle cell cycle arrest Cytotoxicity Doxorubicin - pharmacology Drug Resistance, Neoplasm G1 phase Glycoproteins Humans MCF-7 Cells MCF-7/ADR Neoplasms P-Glycoprotein Permeability Research Paper S phase SAR Ultrasound synthesis western blot |
| title | Discovery of benzochromene derivatives first example with dual cytotoxic activity against the resistant cancer cell MCF-7/ADR and inhibitory effect of the P-glycoprotein expression levels |
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