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Design, Synthesis, and Antitumor Activity of Isoliquiritigenin Amino Acid Ester Derivatives
Isoliquiritigenin (ISL) is a chalcone that has shown great potential in the treatment of cancer. However, its relatively weak activity and low water solubility limit its clinical application. In this study, we designed and synthesized 21 amino acid ester derivatives of ISL and characterized the comp...
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| Published in: | Molecules (Basel, Switzerland) Switzerland), 2024-06, Vol.29 (11), p.2641 |
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| creator | Liu, Chi Liu, Xinyue Ma, Qing Su, Fengyan Cai, Enbo |
| description | Isoliquiritigenin (ISL) is a chalcone that has shown great potential in the treatment of cancer. However, its relatively weak activity and low water solubility limit its clinical application. In this study, we designed and synthesized 21 amino acid ester derivatives of ISL and characterized the compounds using
H NMR and
C NMR. Among them, compound
(IC
= 14.36 μM) had a better inhibitory effect on human cervical cancer (Hela) than ISL (IC
= 126.5 μM), and it was superior to the positive drug 5-FU (IC
= 33.59 μM). The mechanism of the action experiment showed that compound
could induce Hela cell apoptosis and autophagy through the PI3K/Akt/mTOR pathway. |
| doi_str_mv | 10.3390/molecules29112641 |
| format | article |
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H NMR and
C NMR. Among them, compound
(IC
= 14.36 μM) had a better inhibitory effect on human cervical cancer (Hela) than ISL (IC
= 126.5 μM), and it was superior to the positive drug 5-FU (IC
= 33.59 μM). The mechanism of the action experiment showed that compound
could induce Hela cell apoptosis and autophagy through the PI3K/Akt/mTOR pathway.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules29112641</identifier><identifier>PMID: 38893517</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Amino acids ; Amino Acids - chemistry ; Amino Acids - pharmacology ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; antitumor ; Apoptosis ; Apoptosis - drug effects ; Autophagy - drug effects ; Cancer therapies ; Cell adhesion & migration ; Cell cycle ; Cell growth ; Cell Proliferation - drug effects ; Cervical cancer ; Chalcones - chemical synthesis ; Chalcones - chemistry ; Chalcones - pharmacology ; Chemotherapy ; Chinese medicine ; Cloning ; Cytotoxicity ; Drug Design ; Esters - chemical synthesis ; Esters - chemistry ; Esters - pharmacology ; Ethylenediaminetetraacetic acid ; Health aspects ; HeLa Cells ; Humans ; isoliquiritigenin derivatives ; Molecular Structure ; Phosphatidylinositol 3-Kinases - metabolism ; PI3K/Akt/mTOR signaling pathway ; Proto-Oncogene Proteins c-akt - metabolism ; Radiation ; Signal Transduction - drug effects ; Structure-Activity Relationship ; TOR Serine-Threonine Kinases - metabolism ; Toxicity</subject><ispartof>Molecules (Basel, Switzerland), 2024-06, Vol.29 (11), p.2641</ispartof><rights>COPYRIGHT 2024 MDPI AG</rights><rights>2024 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>2024 by the authors. 2024</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c443t-9de63dfdc706c93f4df6239f691e6106aa5088ab698b355c47817e12cafa6f163</cites><orcidid>0000-0002-6355-7071</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/3067453719/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/3067453719?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38893517$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Chi</creatorcontrib><creatorcontrib>Liu, Xinyue</creatorcontrib><creatorcontrib>Ma, Qing</creatorcontrib><creatorcontrib>Su, Fengyan</creatorcontrib><creatorcontrib>Cai, Enbo</creatorcontrib><title>Design, Synthesis, and Antitumor Activity of Isoliquiritigenin Amino Acid Ester Derivatives</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>Isoliquiritigenin (ISL) is a chalcone that has shown great potential in the treatment of cancer. However, its relatively weak activity and low water solubility limit its clinical application. In this study, we designed and synthesized 21 amino acid ester derivatives of ISL and characterized the compounds using
H NMR and
C NMR. Among them, compound
(IC
= 14.36 μM) had a better inhibitory effect on human cervical cancer (Hela) than ISL (IC
= 126.5 μM), and it was superior to the positive drug 5-FU (IC
= 33.59 μM). The mechanism of the action experiment showed that compound
could induce Hela cell apoptosis and autophagy through the PI3K/Akt/mTOR pathway.</description><subject>Amino acids</subject><subject>Amino Acids - chemistry</subject><subject>Amino Acids - pharmacology</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>antitumor</subject><subject>Apoptosis</subject><subject>Apoptosis - drug effects</subject><subject>Autophagy - drug effects</subject><subject>Cancer therapies</subject><subject>Cell adhesion & migration</subject><subject>Cell cycle</subject><subject>Cell growth</subject><subject>Cell Proliferation - drug effects</subject><subject>Cervical cancer</subject><subject>Chalcones - chemical synthesis</subject><subject>Chalcones - chemistry</subject><subject>Chalcones - pharmacology</subject><subject>Chemotherapy</subject><subject>Chinese medicine</subject><subject>Cloning</subject><subject>Cytotoxicity</subject><subject>Drug Design</subject><subject>Esters - chemical synthesis</subject><subject>Esters - chemistry</subject><subject>Esters - pharmacology</subject><subject>Ethylenediaminetetraacetic acid</subject><subject>Health aspects</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>isoliquiritigenin derivatives</subject><subject>Molecular Structure</subject><subject>Phosphatidylinositol 3-Kinases - metabolism</subject><subject>PI3K/Akt/mTOR signaling pathway</subject><subject>Proto-Oncogene Proteins c-akt - metabolism</subject><subject>Radiation</subject><subject>Signal Transduction - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>TOR Serine-Threonine Kinases - metabolism</subject><subject>Toxicity</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNptksFvFCEUxidGY2v1D_BiJvHSQ7fCwMBwMpO26iZNPKgnD4SFx5TNDLTAbLL_vaxbm101HHh5fN-PfC-vqt5idEmIQB-mMIKeR0iNwLhhFD-rTjFt0IIgKp4f1CfVq5TWCDWY4vZldUK6TpAW89Pq5zUkN_iL-tvW57tSp4taeVP3Prs8TyHWvc5u4_K2DrZepjC6h9lFl90A3vm6n5wPReNMfZMyxPoaotuoYoH0unph1ZjgzeN9Vv34dPP96svi9uvn5VV_u9CUkrwQBhgx1miOmBbEUmNZQ4RlAgPDiCnVoq5TKya6FWlbTXmHOeBGK6uYxYycVcs91wS1lvfRTSpuZVBO_m6EOEgVs9MjSApCq1axrhGUwqrtNO9aBdYYCq1mqrA-7ln382oCo8HnqMYj6PGLd3dyCBuJMeYUN00hnD8SYniYIWU5uaRhHJWHMCdJEEcdwiVhkb7_S7oOc_RlVkXFOG0JxweqQZUEzttQPtY7qOy54ALtxlNUl_9RlWNgcjp4sK70jwx4b9AxpBTBPoXESO7WS_6zXsXz7nA6T44_-0R-ARbLzRk</recordid><startdate>20240603</startdate><enddate>20240603</enddate><creator>Liu, Chi</creator><creator>Liu, Xinyue</creator><creator>Ma, Qing</creator><creator>Su, Fengyan</creator><creator>Cai, Enbo</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-6355-7071</orcidid></search><sort><creationdate>20240603</creationdate><title>Design, Synthesis, and Antitumor Activity of Isoliquiritigenin Amino Acid Ester Derivatives</title><author>Liu, Chi ; Liu, Xinyue ; Ma, Qing ; Su, Fengyan ; Cai, Enbo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c443t-9de63dfdc706c93f4df6239f691e6106aa5088ab698b355c47817e12cafa6f163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Amino acids</topic><topic>Amino Acids - chemistry</topic><topic>Amino Acids - pharmacology</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>antitumor</topic><topic>Apoptosis</topic><topic>Apoptosis - drug effects</topic><topic>Autophagy - drug effects</topic><topic>Cancer therapies</topic><topic>Cell adhesion & migration</topic><topic>Cell cycle</topic><topic>Cell growth</topic><topic>Cell Proliferation - drug effects</topic><topic>Cervical cancer</topic><topic>Chalcones - chemical synthesis</topic><topic>Chalcones - chemistry</topic><topic>Chalcones - pharmacology</topic><topic>Chemotherapy</topic><topic>Chinese medicine</topic><topic>Cloning</topic><topic>Cytotoxicity</topic><topic>Drug Design</topic><topic>Esters - chemical synthesis</topic><topic>Esters - chemistry</topic><topic>Esters - pharmacology</topic><topic>Ethylenediaminetetraacetic acid</topic><topic>Health aspects</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>isoliquiritigenin derivatives</topic><topic>Molecular Structure</topic><topic>Phosphatidylinositol 3-Kinases - metabolism</topic><topic>PI3K/Akt/mTOR signaling pathway</topic><topic>Proto-Oncogene Proteins c-akt - metabolism</topic><topic>Radiation</topic><topic>Signal Transduction - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>TOR Serine-Threonine Kinases - metabolism</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Chi</creatorcontrib><creatorcontrib>Liu, Xinyue</creatorcontrib><creatorcontrib>Ma, Qing</creatorcontrib><creatorcontrib>Su, Fengyan</creatorcontrib><creatorcontrib>Cai, Enbo</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>ProQuest - Health & Medical Complete保健、医学与药学数据库</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>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Publicly Available Content Database (ProQuest Open Access資料庫)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Chi</au><au>Liu, Xinyue</au><au>Ma, Qing</au><au>Su, Fengyan</au><au>Cai, Enbo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis, and Antitumor Activity of Isoliquiritigenin Amino Acid Ester Derivatives</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2024-06-03</date><risdate>2024</risdate><volume>29</volume><issue>11</issue><spage>2641</spage><pages>2641-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>Isoliquiritigenin (ISL) is a chalcone that has shown great potential in the treatment of cancer. However, its relatively weak activity and low water solubility limit its clinical application. In this study, we designed and synthesized 21 amino acid ester derivatives of ISL and characterized the compounds using
H NMR and
C NMR. Among them, compound
(IC
= 14.36 μM) had a better inhibitory effect on human cervical cancer (Hela) than ISL (IC
= 126.5 μM), and it was superior to the positive drug 5-FU (IC
= 33.59 μM). The mechanism of the action experiment showed that compound
could induce Hela cell apoptosis and autophagy through the PI3K/Akt/mTOR pathway.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>38893517</pmid><doi>10.3390/molecules29112641</doi><orcidid>https://orcid.org/0000-0002-6355-7071</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Amino acids Amino Acids - chemistry Amino Acids - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology antitumor Apoptosis Apoptosis - drug effects Autophagy - drug effects Cancer therapies Cell adhesion & migration Cell cycle Cell growth Cell Proliferation - drug effects Cervical cancer Chalcones - chemical synthesis Chalcones - chemistry Chalcones - pharmacology Chemotherapy Chinese medicine Cloning Cytotoxicity Drug Design Esters - chemical synthesis Esters - chemistry Esters - pharmacology Ethylenediaminetetraacetic acid Health aspects HeLa Cells Humans isoliquiritigenin derivatives Molecular Structure Phosphatidylinositol 3-Kinases - metabolism PI3K/Akt/mTOR signaling pathway Proto-Oncogene Proteins c-akt - metabolism Radiation Signal Transduction - drug effects Structure-Activity Relationship TOR Serine-Threonine Kinases - metabolism Toxicity |
| title | Design, Synthesis, and Antitumor Activity of Isoliquiritigenin Amino Acid Ester Derivatives |
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