Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles

CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2),...

Full description

Saved in:
Bibliographic Details
Published in:Journal of chemistry 2023-09, Vol.2023, p.1-17
Main Authors: Le, Duc Anh, Truong, Ngoc Hung, Vu, Van Dung, Doan, Thanh Huyen, Le, Minh Tri, Nguyen, Thi Huong, Nguyen, Manh Cuong, Do, Huu Nghi, Ninh, Duc Bao, Le, Phong, Nguyen, Thi Phuong Thao, Tran, Khac Vu, Luu, Van Chinh
Format: Article
Language:English
Subjects:
Acids
Adenosine
Alkynes
Biological activity
Cancer
Carbon
Chemistry
Copper
Cycloaddition
Cytotoxicity
Ethylenediaminetetraacetic acid
Hydrazines
Proteases
Severe acute respiratory syndrome coronavirus 2
Triazoles
Zidovudine
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c470t-47a54f4b4d25ba8b584f1b5ea6d41c363b81d37845d6d17c8939df70ef446ff93
cites cdi_FETCH-LOGICAL-c470t-47a54f4b4d25ba8b584f1b5ea6d41c363b81d37845d6d17c8939df70ef446ff93
container_end_page 17
container_issue
container_start_page 1
container_title Journal of chemistry
container_volume 2023
creator Le, Duc Anh
Truong, Ngoc Hung
Vu, Van Dung
Doan, Thanh Huyen
Le, Minh Tri
Nguyen, Thi Huong
Nguyen, Manh Cuong
Do, Huu Nghi
Ninh, Duc Bao
Le, Phong
Nguyen, Thi Phuong Thao
Tran, Khac Vu
Luu, Van Chinh
description CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2), and 3C-like protease (3CLpro) inhibitory activities showed that several triazoles of AZT containing murayafoline A and indirubin-3′-oxime inhibited the growth of HepG2 and LU-1 with the IC50 values ranging from 11.01 to 19.87 μg/mL. Besides that, some triazole derivatives of adenosine exhibited anti-inflammatory activity against RAW264.7 cells with the IC50 values within an interval of 12.00–59.48.00 μg/mL. Especially, two triazoles of adenosine with indirubin-3′-oxime at O- and N1 positions expressed the ACE2 and 3CLpro inhibitory activities in which the triazole of adenosine with indirubin-3′-oxime at N1 inhibited both ACE2 and 3CLpro inhibitory activities with IC50 values of 135.62 and 142.95 μg/mL, respectively.
doi_str_mv 10.1155/2023/1605316
format article
fullrecord <record><control><sourceid>gale_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_5a1b5dd3ea3f450c89580e2d71090dd9</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><galeid>A814824970</galeid><doaj_id>oai_doaj_org_article_5a1b5dd3ea3f450c89580e2d71090dd9</doaj_id><sourcerecordid>A814824970</sourcerecordid><originalsourceid>FETCH-LOGICAL-c470t-47a54f4b4d25ba8b584f1b5ea6d41c363b81d37845d6d17c8939df70ef446ff93</originalsourceid><addsrcrecordid>eNp9kUtPGzEQgFeolYoot_6AlTh2F_xce48p0BYJlUPTSy-W149koo1N7U1Q-uvrEIRAqrAPHo2_-TT2VNUnjM4x5vyCIEIvcIc4xd1RdUxQj9oeCfzuOe7oh-o05xUqS0rKiTiullcuwyI09c9dmJYlzk2tg62_QBzjAowe65mZYAvTrr7e6nGjJ4ihjr7-EbeuXP6eP_Iz60LMEFx75RJsna1xQxrazhPov3F0-WP13usxu9On86T69fV6fvm9vb37dnM5u20NE2hqmdCceTYwS_ig5cAl83jgTneWYUM7OkhsqZCM285iYWRPe-sFcp6xzvuenlQ3B6-NeqXuE6x12qmoQT0mYloonSYwo1NcF7O11GnqGUfFxSVyxApc_svavevs4LpP8c_G5Umt4iaF0r4iUjAkGCUvqIUuUgg-TkmbNWSjZhIzSVgvUKHO_0OVbd0aTAzOQ8m_KmgOBSbFnJPzz4_BSO0nrvYTV08TL_jnA76EYPUDvE3_A-nUpnk</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2874074329</pqid></control><display><type>article</type><title>Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles</title><source>Wiley_OA刊</source><source>ProQuest - Publicly Available Content Database</source><source>Free Full-Text Journals in Chemistry</source><source>Coronavirus Research Database</source><creator>Le, Duc Anh ; Truong, Ngoc Hung ; Vu, Van Dung ; Doan, Thanh Huyen ; Le, Minh Tri ; Nguyen, Thi Huong ; Nguyen, Manh Cuong ; Do, Huu Nghi ; Ninh, Duc Bao ; Le, Phong ; Nguyen, Thi Phuong Thao ; Tran, Khac Vu ; Luu, Van Chinh</creator><contributor>Mitu, Liviu ; Liviu Mitu</contributor><creatorcontrib>Le, Duc Anh ; Truong, Ngoc Hung ; Vu, Van Dung ; Doan, Thanh Huyen ; Le, Minh Tri ; Nguyen, Thi Huong ; Nguyen, Manh Cuong ; Do, Huu Nghi ; Ninh, Duc Bao ; Le, Phong ; Nguyen, Thi Phuong Thao ; Tran, Khac Vu ; Luu, Van Chinh ; Mitu, Liviu ; Liviu Mitu</creatorcontrib><description>CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2), and 3C-like protease (3CLpro) inhibitory activities showed that several triazoles of AZT containing murayafoline A and indirubin-3′-oxime inhibited the growth of HepG2 and LU-1 with the IC50 values ranging from 11.01 to 19.87 μg/mL. Besides that, some triazole derivatives of adenosine exhibited anti-inflammatory activity against RAW264.7 cells with the IC50 values within an interval of 12.00–59.48.00 μg/mL. Especially, two triazoles of adenosine with indirubin-3′-oxime at O- and N1 positions expressed the ACE2 and 3CLpro inhibitory activities in which the triazole of adenosine with indirubin-3′-oxime at N1 inhibited both ACE2 and 3CLpro inhibitory activities with IC50 values of 135.62 and 142.95 μg/mL, respectively.</description><identifier>ISSN: 2090-9063</identifier><identifier>EISSN: 2090-9071</identifier><identifier>DOI: 10.1155/2023/1605316</identifier><language>eng</language><publisher>New York: Hindawi</publisher><subject>Acids ; Adenosine ; Alkynes ; Biological activity ; Cancer ; Carbon ; Chemistry ; Copper ; Cycloaddition ; Cytotoxicity ; Ethylenediaminetetraacetic acid ; Hydrazines ; Proteases ; Severe acute respiratory syndrome coronavirus 2 ; Triazoles ; Zidovudine</subject><ispartof>Journal of chemistry, 2023-09, Vol.2023, p.1-17</ispartof><rights>Copyright © 2023 Duc Anh Le et al.</rights><rights>COPYRIGHT 2023 John Wiley &amp; Sons, Inc.</rights><rights>Copyright © 2023 Duc Anh Le et al. This is an open access article distributed under the Creative Commons Attribution License (the “License”), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. https://creativecommons.org/licenses/by/4.0</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c470t-47a54f4b4d25ba8b584f1b5ea6d41c363b81d37845d6d17c8939df70ef446ff93</citedby><cites>FETCH-LOGICAL-c470t-47a54f4b4d25ba8b584f1b5ea6d41c363b81d37845d6d17c8939df70ef446ff93</cites><orcidid>0000-0001-7904-1785 ; 0000-0002-4773-9596 ; 0000-0003-4954-620X ; 0000-0003-1127-1597 ; 0000-0002-6272-0922 ; 0000-0003-2716-936X ; 0000-0002-9476-0734</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2874074329/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2874074329?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,25753,27924,27925,37012,38516,43895,44590,74412,75126</link.rule.ids></links><search><contributor>Mitu, Liviu</contributor><contributor>Liviu Mitu</contributor><creatorcontrib>Le, Duc Anh</creatorcontrib><creatorcontrib>Truong, Ngoc Hung</creatorcontrib><creatorcontrib>Vu, Van Dung</creatorcontrib><creatorcontrib>Doan, Thanh Huyen</creatorcontrib><creatorcontrib>Le, Minh Tri</creatorcontrib><creatorcontrib>Nguyen, Thi Huong</creatorcontrib><creatorcontrib>Nguyen, Manh Cuong</creatorcontrib><creatorcontrib>Do, Huu Nghi</creatorcontrib><creatorcontrib>Ninh, Duc Bao</creatorcontrib><creatorcontrib>Le, Phong</creatorcontrib><creatorcontrib>Nguyen, Thi Phuong Thao</creatorcontrib><creatorcontrib>Tran, Khac Vu</creatorcontrib><creatorcontrib>Luu, Van Chinh</creatorcontrib><title>Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles</title><title>Journal of chemistry</title><description>CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2), and 3C-like protease (3CLpro) inhibitory activities showed that several triazoles of AZT containing murayafoline A and indirubin-3′-oxime inhibited the growth of HepG2 and LU-1 with the IC50 values ranging from 11.01 to 19.87 μg/mL. Besides that, some triazole derivatives of adenosine exhibited anti-inflammatory activity against RAW264.7 cells with the IC50 values within an interval of 12.00–59.48.00 μg/mL. Especially, two triazoles of adenosine with indirubin-3′-oxime at O- and N1 positions expressed the ACE2 and 3CLpro inhibitory activities in which the triazole of adenosine with indirubin-3′-oxime at N1 inhibited both ACE2 and 3CLpro inhibitory activities with IC50 values of 135.62 and 142.95 μg/mL, respectively.</description><subject>Acids</subject><subject>Adenosine</subject><subject>Alkynes</subject><subject>Biological activity</subject><subject>Cancer</subject><subject>Carbon</subject><subject>Chemistry</subject><subject>Copper</subject><subject>Cycloaddition</subject><subject>Cytotoxicity</subject><subject>Ethylenediaminetetraacetic acid</subject><subject>Hydrazines</subject><subject>Proteases</subject><subject>Severe acute respiratory syndrome coronavirus 2</subject><subject>Triazoles</subject><subject>Zidovudine</subject><issn>2090-9063</issn><issn>2090-9071</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>COVID</sourceid><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNp9kUtPGzEQgFeolYoot_6AlTh2F_xce48p0BYJlUPTSy-W149koo1N7U1Q-uvrEIRAqrAPHo2_-TT2VNUnjM4x5vyCIEIvcIc4xd1RdUxQj9oeCfzuOe7oh-o05xUqS0rKiTiullcuwyI09c9dmJYlzk2tg62_QBzjAowe65mZYAvTrr7e6nGjJ4ihjr7-EbeuXP6eP_Iz60LMEFx75RJsna1xQxrazhPov3F0-WP13usxu9On86T69fV6fvm9vb37dnM5u20NE2hqmdCceTYwS_ig5cAl83jgTneWYUM7OkhsqZCM285iYWRPe-sFcp6xzvuenlQ3B6-NeqXuE6x12qmoQT0mYloonSYwo1NcF7O11GnqGUfFxSVyxApc_svavevs4LpP8c_G5Umt4iaF0r4iUjAkGCUvqIUuUgg-TkmbNWSjZhIzSVgvUKHO_0OVbd0aTAzOQ8m_KmgOBSbFnJPzz4_BSO0nrvYTV08TL_jnA76EYPUDvE3_A-nUpnk</recordid><startdate>20230928</startdate><enddate>20230928</enddate><creator>Le, Duc Anh</creator><creator>Truong, Ngoc Hung</creator><creator>Vu, Van Dung</creator><creator>Doan, Thanh Huyen</creator><creator>Le, Minh Tri</creator><creator>Nguyen, Thi Huong</creator><creator>Nguyen, Manh Cuong</creator><creator>Do, Huu Nghi</creator><creator>Ninh, Duc Bao</creator><creator>Le, Phong</creator><creator>Nguyen, Thi Phuong Thao</creator><creator>Tran, Khac Vu</creator><creator>Luu, Van Chinh</creator><general>Hindawi</general><general>John Wiley &amp; Sons, Inc</general><general>Hindawi Limited</general><scope>RHU</scope><scope>RHW</scope><scope>RHX</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>COVID</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-7904-1785</orcidid><orcidid>https://orcid.org/0000-0002-4773-9596</orcidid><orcidid>https://orcid.org/0000-0003-4954-620X</orcidid><orcidid>https://orcid.org/0000-0003-1127-1597</orcidid><orcidid>https://orcid.org/0000-0002-6272-0922</orcidid><orcidid>https://orcid.org/0000-0003-2716-936X</orcidid><orcidid>https://orcid.org/0000-0002-9476-0734</orcidid></search><sort><creationdate>20230928</creationdate><title>Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles</title><author>Le, Duc Anh ; Truong, Ngoc Hung ; Vu, Van Dung ; Doan, Thanh Huyen ; Le, Minh Tri ; Nguyen, Thi Huong ; Nguyen, Manh Cuong ; Do, Huu Nghi ; Ninh, Duc Bao ; Le, Phong ; Nguyen, Thi Phuong Thao ; Tran, Khac Vu ; Luu, Van Chinh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c470t-47a54f4b4d25ba8b584f1b5ea6d41c363b81d37845d6d17c8939df70ef446ff93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acids</topic><topic>Adenosine</topic><topic>Alkynes</topic><topic>Biological activity</topic><topic>Cancer</topic><topic>Carbon</topic><topic>Chemistry</topic><topic>Copper</topic><topic>Cycloaddition</topic><topic>Cytotoxicity</topic><topic>Ethylenediaminetetraacetic acid</topic><topic>Hydrazines</topic><topic>Proteases</topic><topic>Severe acute respiratory syndrome coronavirus 2</topic><topic>Triazoles</topic><topic>Zidovudine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Le, Duc Anh</creatorcontrib><creatorcontrib>Truong, Ngoc Hung</creatorcontrib><creatorcontrib>Vu, Van Dung</creatorcontrib><creatorcontrib>Doan, Thanh Huyen</creatorcontrib><creatorcontrib>Le, Minh Tri</creatorcontrib><creatorcontrib>Nguyen, Thi Huong</creatorcontrib><creatorcontrib>Nguyen, Manh Cuong</creatorcontrib><creatorcontrib>Do, Huu Nghi</creatorcontrib><creatorcontrib>Ninh, Duc Bao</creatorcontrib><creatorcontrib>Le, Phong</creatorcontrib><creatorcontrib>Nguyen, Thi Phuong Thao</creatorcontrib><creatorcontrib>Tran, Khac Vu</creatorcontrib><creatorcontrib>Luu, Van Chinh</creatorcontrib><collection>Hindawi Publishing Complete</collection><collection>Hindawi Publishing Subscription Journals</collection><collection>Hindawi Publishing Open Access</collection><collection>CrossRef</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science &amp; Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>Coronavirus Research Database</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>SciTech Premium Collection</collection><collection>https://resources.nclive.org/materials</collection><collection>Materials science collection</collection><collection>ProQuest - 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>DOAJ Directory of Open Access Journals</collection><jtitle>Journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Le, Duc Anh</au><au>Truong, Ngoc Hung</au><au>Vu, Van Dung</au><au>Doan, Thanh Huyen</au><au>Le, Minh Tri</au><au>Nguyen, Thi Huong</au><au>Nguyen, Manh Cuong</au><au>Do, Huu Nghi</au><au>Ninh, Duc Bao</au><au>Le, Phong</au><au>Nguyen, Thi Phuong Thao</au><au>Tran, Khac Vu</au><au>Luu, Van Chinh</au><au>Mitu, Liviu</au><au>Liviu Mitu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles</atitle><jtitle>Journal of chemistry</jtitle><date>2023-09-28</date><risdate>2023</risdate><volume>2023</volume><spage>1</spage><epage>17</epage><pages>1-17</pages><issn>2090-9063</issn><eissn>2090-9071</eissn><abstract>CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2), and 3C-like protease (3CLpro) inhibitory activities showed that several triazoles of AZT containing murayafoline A and indirubin-3′-oxime inhibited the growth of HepG2 and LU-1 with the IC50 values ranging from 11.01 to 19.87 μg/mL. Besides that, some triazole derivatives of adenosine exhibited anti-inflammatory activity against RAW264.7 cells with the IC50 values within an interval of 12.00–59.48.00 μg/mL. Especially, two triazoles of adenosine with indirubin-3′-oxime at O- and N1 positions expressed the ACE2 and 3CLpro inhibitory activities in which the triazole of adenosine with indirubin-3′-oxime at N1 inhibited both ACE2 and 3CLpro inhibitory activities with IC50 values of 135.62 and 142.95 μg/mL, respectively.</abstract><cop>New York</cop><pub>Hindawi</pub><doi>10.1155/2023/1605316</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0001-7904-1785</orcidid><orcidid>https://orcid.org/0000-0002-4773-9596</orcidid><orcidid>https://orcid.org/0000-0003-4954-620X</orcidid><orcidid>https://orcid.org/0000-0003-1127-1597</orcidid><orcidid>https://orcid.org/0000-0002-6272-0922</orcidid><orcidid>https://orcid.org/0000-0003-2716-936X</orcidid><orcidid>https://orcid.org/0000-0002-9476-0734</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2090-9063
ispartof Journal of chemistry, 2023-09, Vol.2023, p.1-17
issn 2090-9063
2090-9071
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_5a1b5dd3ea3f450c89580e2d71090dd9
source Wiley_OA刊; ProQuest - Publicly Available Content Database; Free Full-Text Journals in Chemistry; Coronavirus Research Database
subjects Acids
Adenosine
Alkynes
Biological activity
Cancer
Carbon
Chemistry
Copper
Cycloaddition
Cytotoxicity
Ethylenediaminetetraacetic acid
Hydrazines
Proteases
Severe acute respiratory syndrome coronavirus 2
Triazoles
Zidovudine
title Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T13%3A41%3A22IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Design,%20Synthesis,%20and%20Biological%20Activity%20Evaluation%20of%20Novel%20AZT%20and%20Adenosine-Derived%201,2,3-Triazoles&rft.jtitle=Journal%20of%20chemistry&rft.au=Le,%20Duc%20Anh&rft.date=2023-09-28&rft.volume=2023&rft.spage=1&rft.epage=17&rft.pages=1-17&rft.issn=2090-9063&rft.eissn=2090-9071&rft_id=info:doi/10.1155/2023/1605316&rft_dat=%3Cgale_doaj_%3EA814824970%3C/gale_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c470t-47a54f4b4d25ba8b584f1b5ea6d41c363b81d37845d6d17c8939df70ef446ff93%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2874074329&rft_id=info:pmid/&rft_galeid=A814824970&rfr_iscdi=true