Tumor-Specificity, Neurotoxicity, and Possible Involvement of the Nuclear Receptor Response Pathway of 4,6,8-Trimethyl Azulene Amide Derivatives
Very few papers covering the anticancer activity of azulenes have been reported, as compared with those of antibacterial and anti-inflammatory activity. This led us to investigate the antitumor potential of fifteen 4,6,8-trimethyl azulene amide derivatives against oral malignant cells. 4,6,8-Trimeth...
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| Veröffentlicht in: | International journal of molecular sciences 2022-02, Vol.23 (5), p.2601 |
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| creator | Naitoh, Kotone Orihara, Yuta Sakagami, Hiroshi Miura, Takumi Satoh, Keitaro Amano, Shigeru Bandow, Kenjiro Iijima, Yosuke Kurosaki, Kota Uesawa, Yoshihiro Hashimoto, Masashi Wakabayashi, Hidetsugu |
| description | Very few papers covering the anticancer activity of azulenes have been reported, as compared with those of antibacterial and anti-inflammatory activity. This led us to investigate the antitumor potential of fifteen 4,6,8-trimethyl azulene amide derivatives against oral malignant cells.
4,6,8-Trimethyl azulene amide derivatives were newly synthesized. Anticancer activity was evaluated by tumor-specificity against four human oral squamous cell carcinoma (OSCC) cell lines over three normal oral cells. Neurotoxicity was evaluated by cytotoxicity against three neuronal cell lines over normal oral cells. Apoptosis induction was evaluated by Western blot and cell cycle analyses.
Among fifteen derivatives, compounds
,
, and
showed the highest anticancer activity, and relatively lower neurotoxicity than doxorubicin, 5-fluorouracil (5-FU), and melphalan. They induced the accumulation of a comparable amount of a subG
population, but slightly lower extent of caspase activation, as compared with actinomycin D, used as an apoptosis inducer. The quantitative structure-activity relationship analysis suggests the significant correlation of tumor-specificity with a 3D shape of molecules, and possible involvement of inflammation and hormone receptor response pathways.
Compounds
and
can be potential candidates of a lead compound for developing novel anticancer drugs. |
| doi_str_mv | 10.3390/ijms23052601 |
| format | Article |
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4,6,8-Trimethyl azulene amide derivatives were newly synthesized. Anticancer activity was evaluated by tumor-specificity against four human oral squamous cell carcinoma (OSCC) cell lines over three normal oral cells. Neurotoxicity was evaluated by cytotoxicity against three neuronal cell lines over normal oral cells. Apoptosis induction was evaluated by Western blot and cell cycle analyses.
Among fifteen derivatives, compounds
,
, and
showed the highest anticancer activity, and relatively lower neurotoxicity than doxorubicin, 5-fluorouracil (5-FU), and melphalan. They induced the accumulation of a comparable amount of a subG
population, but slightly lower extent of caspase activation, as compared with actinomycin D, used as an apoptosis inducer. The quantitative structure-activity relationship analysis suggests the significant correlation of tumor-specificity with a 3D shape of molecules, and possible involvement of inflammation and hormone receptor response pathways.
Compounds
and
can be potential candidates of a lead compound for developing novel anticancer drugs.</description><identifier>ISSN: 1422-0067</identifier><identifier>ISSN: 1661-6596</identifier><identifier>EISSN: 1422-0067</identifier><identifier>DOI: 10.3390/ijms23052601</identifier><identifier>PMID: 35269748</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>5-Fluorouracil ; Actinomycin ; Amides - pharmacology ; Amides - therapeutic use ; Anti-inflammatory agents ; Antineoplastic Agents - pharmacology ; Antineoplastic Agents - therapeutic use ; Antitumor activity ; Apoptosis ; Azulene ; Azulenes ; Cancer ; Carcinoma, Squamous Cell - pathology ; Caspase ; Cell cycle ; Cell Line, Tumor ; Cell Proliferation ; Cytotoxicity ; Doxorubicin ; Drug development ; Drug dosages ; Drug Screening Assays, Antitumor ; Estrogens ; Experiments ; Fibroblasts ; Humans ; Inflammation ; Lead compounds ; Melphalan ; Molecular Structure ; Mouth Neoplasms - pathology ; Neurotoxicity ; Neurotoxicity Syndromes ; Oral cancer ; Oral carcinoma ; Oral squamous cell carcinoma ; Receptors, Cytoplasmic and Nuclear ; Squamous cell carcinoma ; Thyroid gland ; Tumor cell lines ; Tumors</subject><ispartof>International journal of molecular sciences, 2022-02, Vol.23 (5), p.2601</ispartof><rights>2022 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>2022 by the authors. 2022</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c522t-e77578734dac999da60019e0e48421c6c603b3123cb91c98c975a0e0e3a63a33</citedby><cites>FETCH-LOGICAL-c522t-e77578734dac999da60019e0e48421c6c603b3123cb91c98c975a0e0e3a63a33</cites><orcidid>0000-0002-5773-991X ; 0000-0001-8001-2121 ; 0000-0002-1362-3034</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/PMC8910578/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8910578/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27903,27904,53769,53771</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35269748$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Naitoh, Kotone</creatorcontrib><creatorcontrib>Orihara, Yuta</creatorcontrib><creatorcontrib>Sakagami, Hiroshi</creatorcontrib><creatorcontrib>Miura, Takumi</creatorcontrib><creatorcontrib>Satoh, Keitaro</creatorcontrib><creatorcontrib>Amano, Shigeru</creatorcontrib><creatorcontrib>Bandow, Kenjiro</creatorcontrib><creatorcontrib>Iijima, Yosuke</creatorcontrib><creatorcontrib>Kurosaki, Kota</creatorcontrib><creatorcontrib>Uesawa, Yoshihiro</creatorcontrib><creatorcontrib>Hashimoto, Masashi</creatorcontrib><creatorcontrib>Wakabayashi, Hidetsugu</creatorcontrib><title>Tumor-Specificity, Neurotoxicity, and Possible Involvement of the Nuclear Receptor Response Pathway of 4,6,8-Trimethyl Azulene Amide Derivatives</title><title>International journal of molecular sciences</title><addtitle>Int J Mol Sci</addtitle><description>Very few papers covering the anticancer activity of azulenes have been reported, as compared with those of antibacterial and anti-inflammatory activity. This led us to investigate the antitumor potential of fifteen 4,6,8-trimethyl azulene amide derivatives against oral malignant cells.
4,6,8-Trimethyl azulene amide derivatives were newly synthesized. Anticancer activity was evaluated by tumor-specificity against four human oral squamous cell carcinoma (OSCC) cell lines over three normal oral cells. Neurotoxicity was evaluated by cytotoxicity against three neuronal cell lines over normal oral cells. Apoptosis induction was evaluated by Western blot and cell cycle analyses.
Among fifteen derivatives, compounds
,
, and
showed the highest anticancer activity, and relatively lower neurotoxicity than doxorubicin, 5-fluorouracil (5-FU), and melphalan. They induced the accumulation of a comparable amount of a subG
population, but slightly lower extent of caspase activation, as compared with actinomycin D, used as an apoptosis inducer. The quantitative structure-activity relationship analysis suggests the significant correlation of tumor-specificity with a 3D shape of molecules, and possible involvement of inflammation and hormone receptor response pathways.
Compounds
and
can be potential candidates of a lead compound for developing novel anticancer drugs.</description><subject>5-Fluorouracil</subject><subject>Actinomycin</subject><subject>Amides - pharmacology</subject><subject>Amides - therapeutic use</subject><subject>Anti-inflammatory agents</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antineoplastic Agents - therapeutic use</subject><subject>Antitumor activity</subject><subject>Apoptosis</subject><subject>Azulene</subject><subject>Azulenes</subject><subject>Cancer</subject><subject>Carcinoma, Squamous Cell - pathology</subject><subject>Caspase</subject><subject>Cell cycle</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation</subject><subject>Cytotoxicity</subject><subject>Doxorubicin</subject><subject>Drug development</subject><subject>Drug dosages</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Estrogens</subject><subject>Experiments</subject><subject>Fibroblasts</subject><subject>Humans</subject><subject>Inflammation</subject><subject>Lead compounds</subject><subject>Melphalan</subject><subject>Molecular Structure</subject><subject>Mouth Neoplasms - 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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>Naitoh, Kotone</au><au>Orihara, Yuta</au><au>Sakagami, Hiroshi</au><au>Miura, Takumi</au><au>Satoh, Keitaro</au><au>Amano, Shigeru</au><au>Bandow, Kenjiro</au><au>Iijima, Yosuke</au><au>Kurosaki, Kota</au><au>Uesawa, Yoshihiro</au><au>Hashimoto, Masashi</au><au>Wakabayashi, Hidetsugu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tumor-Specificity, Neurotoxicity, and Possible Involvement of the Nuclear Receptor Response Pathway of 4,6,8-Trimethyl Azulene Amide Derivatives</atitle><jtitle>International journal of molecular sciences</jtitle><addtitle>Int J Mol Sci</addtitle><date>2022-02-26</date><risdate>2022</risdate><volume>23</volume><issue>5</issue><spage>2601</spage><pages>2601-</pages><issn>1422-0067</issn><issn>1661-6596</issn><eissn>1422-0067</eissn><abstract>Very few papers covering the anticancer activity of azulenes have been reported, as compared with those of antibacterial and anti-inflammatory activity. This led us to investigate the antitumor potential of fifteen 4,6,8-trimethyl azulene amide derivatives against oral malignant cells.
4,6,8-Trimethyl azulene amide derivatives were newly synthesized. Anticancer activity was evaluated by tumor-specificity against four human oral squamous cell carcinoma (OSCC) cell lines over three normal oral cells. Neurotoxicity was evaluated by cytotoxicity against three neuronal cell lines over normal oral cells. Apoptosis induction was evaluated by Western blot and cell cycle analyses.
Among fifteen derivatives, compounds
,
, and
showed the highest anticancer activity, and relatively lower neurotoxicity than doxorubicin, 5-fluorouracil (5-FU), and melphalan. They induced the accumulation of a comparable amount of a subG
population, but slightly lower extent of caspase activation, as compared with actinomycin D, used as an apoptosis inducer. The quantitative structure-activity relationship analysis suggests the significant correlation of tumor-specificity with a 3D shape of molecules, and possible involvement of inflammation and hormone receptor response pathways.
Compounds
and
can be potential candidates of a lead compound for developing novel anticancer drugs.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>35269748</pmid><doi>10.3390/ijms23052601</doi><orcidid>https://orcid.org/0000-0002-5773-991X</orcidid><orcidid>https://orcid.org/0000-0001-8001-2121</orcidid><orcidid>https://orcid.org/0000-0002-1362-3034</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | International journal of molecular sciences, 2022-02, Vol.23 (5), p.2601 |
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| source | MDPI - Multidisciplinary Digital Publishing Institute; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central |
| subjects | 5-Fluorouracil Actinomycin Amides - pharmacology Amides - therapeutic use Anti-inflammatory agents Antineoplastic Agents - pharmacology Antineoplastic Agents - therapeutic use Antitumor activity Apoptosis Azulene Azulenes Cancer Carcinoma, Squamous Cell - pathology Caspase Cell cycle Cell Line, Tumor Cell Proliferation Cytotoxicity Doxorubicin Drug development Drug dosages Drug Screening Assays, Antitumor Estrogens Experiments Fibroblasts Humans Inflammation Lead compounds Melphalan Molecular Structure Mouth Neoplasms - pathology Neurotoxicity Neurotoxicity Syndromes Oral cancer Oral carcinoma Oral squamous cell carcinoma Receptors, Cytoplasmic and Nuclear Squamous cell carcinoma Thyroid gland Tumor cell lines Tumors |
| title | Tumor-Specificity, Neurotoxicity, and Possible Involvement of the Nuclear Receptor Response Pathway of 4,6,8-Trimethyl Azulene Amide Derivatives |
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