Potential anti-amoebic effects of synthetic 1,4-benzothiazine derivatives against Acanthamoeba castellanii

A rare but lethal central nervous system disease known as granulomatous amoebic encephalitis (GAE) and potentially blinding Acanthamoeba keratitis are diseases caused by free-living Acanthamoeba. Currently, no therapeutic agent can completely eradicate or prevent GAE. Synthetic compounds are a likel...

Full description

Saved in:
Bibliographic Details
Published in:Heliyon 2024-01, Vol.10 (1), p.e23258-e23258, Article e23258
Main Authors: Alishba, Ahmed, Usman, Taha, Muhammad, Khan, Naveed Ahmed, Salar, Uzma, Khan, Khalid Mohammed, Anwar, Ayaz, Siddiqui, Ruqaiyyah
Format: Article
Language:English
Subjects:
Acanthamoeba
Amoebicidal
Benzothiazine
One-pot synthesis
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites cdi_FETCH-LOGICAL-c482t-4c473b46ce403bc20052eda8813b75a528c793daca8ac0b14572185354123623
container_end_page e23258
container_issue 1
container_start_page e23258
container_title Heliyon
container_volume 10
creator Alishba
Ahmed, Usman
Taha, Muhammad
Khan, Naveed Ahmed
Salar, Uzma
Khan, Khalid Mohammed
Anwar, Ayaz
Siddiqui, Ruqaiyyah
description A rare but lethal central nervous system disease known as granulomatous amoebic encephalitis (GAE) and potentially blinding Acanthamoeba keratitis are diseases caused by free-living Acanthamoeba. Currently, no therapeutic agent can completely eradicate or prevent GAE. Synthetic compounds are a likely source of bioactive compounds for developing new drugs. This study synthesized seventeen 1,4-benzothiazine derivatives (I –XVII) by a base-catalyzed one-pot reaction of 2-amino thiophenol with substituted bromo acetophenones. Different spectroscopic techniques, such as EI-MS, 1H-, and 13C NMR (only for the new compounds), were used for the structural characterization and conformation of compounds. These compounds were assessed for the first time against Acanthamoeba castellanii. All compounds showed anti-amoebic potential in vitro against A. castellanii, reducing its ability to encyst and excyst at 100 μM. Compounds IX, X, and XVI showed the most potent activities among all derivatives and significantly reduced the viability to 5.3 × 104 (p 
doi_str_mv 10.1016/j.heliyon.2023.e23258
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_89b62601f2ec41b89647b81fd1a240ac</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S240584402310466X</els_id><doaj_id>oai_doaj_org_article_89b62601f2ec41b89647b81fd1a240ac</doaj_id><sourcerecordid>2913451506</sourcerecordid><originalsourceid>FETCH-LOGICAL-c482t-4c473b46ce403bc20052eda8813b75a528c793daca8ac0b14572185354123623</originalsourceid><addsrcrecordid>eNqFkU1v1DAQhiMEolXpTwDlyIEs_o5zQlXFR6VKcOjdGjuTjaNsXGzvSttfj7u7lPbEaazxzDMz71tV7ylZUULV52k14uz3YVkxwvgKGWdSv6rOmSCy0UKQ18_eZ9VlShMhhEqtupa_rc64ZkQyLc-r6VfIuGQPcw0lNLAJaL2rcRjQ5VSHoU77JY-YS5J-Eo3F5SHk0cODX7DuMfodZL_DVMMa_JJyfeUKaTyAoHaQMs4zLN6_q94MMCe8PMWL6u7b17vrH83tz-8311e3jROa5UY40XIrlENBuHWMlE2xB60pt62EsrZrO96DAw2OWCpky6iWXArKuGL8oro5YvsAk7mPfgNxbwJ4c0iEuDYQyzUzGt1ZxRShA0MnqNWdEq3VdOgpFPXAFdaXI-t-azfYu6JUhPkF9OXP4kezDjtDSduqTtJC-HgixPB7iymbjU_uoAiGbTKso1xIKokqpfJY6mJIKeLwNIcS82i7mczJdvNouznaXvo-PF_yqeuvyf-uwKL6zmM0yXlcHPY-FpOLLv4_I_4AcTDCiA</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2913451506</pqid></control><display><type>article</type><title>Potential anti-amoebic effects of synthetic 1,4-benzothiazine derivatives against Acanthamoeba castellanii</title><source>Open Access: PubMed Central</source><source>ScienceDirect®</source><creator>Alishba ; Ahmed, Usman ; Taha, Muhammad ; Khan, Naveed Ahmed ; Salar, Uzma ; Khan, Khalid Mohammed ; Anwar, Ayaz ; Siddiqui, Ruqaiyyah</creator><creatorcontrib>Alishba ; Ahmed, Usman ; Taha, Muhammad ; Khan, Naveed Ahmed ; Salar, Uzma ; Khan, Khalid Mohammed ; Anwar, Ayaz ; Siddiqui, Ruqaiyyah</creatorcontrib><description>A rare but lethal central nervous system disease known as granulomatous amoebic encephalitis (GAE) and potentially blinding Acanthamoeba keratitis are diseases caused by free-living Acanthamoeba. Currently, no therapeutic agent can completely eradicate or prevent GAE. Synthetic compounds are a likely source of bioactive compounds for developing new drugs. This study synthesized seventeen 1,4-benzothiazine derivatives (I –XVII) by a base-catalyzed one-pot reaction of 2-amino thiophenol with substituted bromo acetophenones. Different spectroscopic techniques, such as EI-MS, 1H-, and 13C NMR (only for the new compounds), were used for the structural characterization and conformation of compounds. These compounds were assessed for the first time against Acanthamoeba castellanii. All compounds showed anti-amoebic potential in vitro against A. castellanii, reducing its ability to encyst and excyst at 100 μM. Compounds IX, X, and XVI showed the most potent activities among all derivatives and significantly reduced the viability to 5.3 × 104 (p &lt; 0.0003), 2 × 105 (p &lt; 0.006), and 2.4 × 105 (p &lt; 0.002) cells/mL, respectively. The cytotoxicity profile revealed that these molecules showed lower to moderate cytotoxicity, i.e., 36 %, 2 %, and 21 %, respectively, against human keratinocytes in vitro. These results indicate that 1,4-benzothiazines showed potent in vitro activity against trophozoites and cysts of A. castellanii. Hence, these 1,4-benzothiazine derivatives should be considered to develop new potential therapeutic agents against Acanthamoeba infections.</description><identifier>ISSN: 2405-8440</identifier><identifier>EISSN: 2405-8440</identifier><identifier>DOI: 10.1016/j.heliyon.2023.e23258</identifier><identifier>PMID: 38205285</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Acanthamoeba ; Amoebicidal ; Benzothiazine ; One-pot synthesis</subject><ispartof>Heliyon, 2024-01, Vol.10 (1), p.e23258-e23258, Article e23258</ispartof><rights>2023 The Authors</rights><rights>2023 The Authors.</rights><rights>2023 The Authors 2023</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c482t-4c473b46ce403bc20052eda8813b75a528c793daca8ac0b14572185354123623</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10776951/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S240584402310466X$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,3548,27923,27924,45779,53790,53792</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38205285$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Alishba</creatorcontrib><creatorcontrib>Ahmed, Usman</creatorcontrib><creatorcontrib>Taha, Muhammad</creatorcontrib><creatorcontrib>Khan, Naveed Ahmed</creatorcontrib><creatorcontrib>Salar, Uzma</creatorcontrib><creatorcontrib>Khan, Khalid Mohammed</creatorcontrib><creatorcontrib>Anwar, Ayaz</creatorcontrib><creatorcontrib>Siddiqui, Ruqaiyyah</creatorcontrib><title>Potential anti-amoebic effects of synthetic 1,4-benzothiazine derivatives against Acanthamoeba castellanii</title><title>Heliyon</title><addtitle>Heliyon</addtitle><description>A rare but lethal central nervous system disease known as granulomatous amoebic encephalitis (GAE) and potentially blinding Acanthamoeba keratitis are diseases caused by free-living Acanthamoeba. Currently, no therapeutic agent can completely eradicate or prevent GAE. Synthetic compounds are a likely source of bioactive compounds for developing new drugs. This study synthesized seventeen 1,4-benzothiazine derivatives (I –XVII) by a base-catalyzed one-pot reaction of 2-amino thiophenol with substituted bromo acetophenones. Different spectroscopic techniques, such as EI-MS, 1H-, and 13C NMR (only for the new compounds), were used for the structural characterization and conformation of compounds. These compounds were assessed for the first time against Acanthamoeba castellanii. All compounds showed anti-amoebic potential in vitro against A. castellanii, reducing its ability to encyst and excyst at 100 μM. Compounds IX, X, and XVI showed the most potent activities among all derivatives and significantly reduced the viability to 5.3 × 104 (p &lt; 0.0003), 2 × 105 (p &lt; 0.006), and 2.4 × 105 (p &lt; 0.002) cells/mL, respectively. The cytotoxicity profile revealed that these molecules showed lower to moderate cytotoxicity, i.e., 36 %, 2 %, and 21 %, respectively, against human keratinocytes in vitro. These results indicate that 1,4-benzothiazines showed potent in vitro activity against trophozoites and cysts of A. castellanii. Hence, these 1,4-benzothiazine derivatives should be considered to develop new potential therapeutic agents against Acanthamoeba infections.</description><subject>Acanthamoeba</subject><subject>Amoebicidal</subject><subject>Benzothiazine</subject><subject>One-pot synthesis</subject><issn>2405-8440</issn><issn>2405-8440</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>DOA</sourceid><recordid>eNqFkU1v1DAQhiMEolXpTwDlyIEs_o5zQlXFR6VKcOjdGjuTjaNsXGzvSttfj7u7lPbEaazxzDMz71tV7ylZUULV52k14uz3YVkxwvgKGWdSv6rOmSCy0UKQ18_eZ9VlShMhhEqtupa_rc64ZkQyLc-r6VfIuGQPcw0lNLAJaL2rcRjQ5VSHoU77JY-YS5J-Eo3F5SHk0cODX7DuMfodZL_DVMMa_JJyfeUKaTyAoHaQMs4zLN6_q94MMCe8PMWL6u7b17vrH83tz-8311e3jROa5UY40XIrlENBuHWMlE2xB60pt62EsrZrO96DAw2OWCpky6iWXArKuGL8oro5YvsAk7mPfgNxbwJ4c0iEuDYQyzUzGt1ZxRShA0MnqNWdEq3VdOgpFPXAFdaXI-t-azfYu6JUhPkF9OXP4kezDjtDSduqTtJC-HgixPB7iymbjU_uoAiGbTKso1xIKokqpfJY6mJIKeLwNIcS82i7mczJdvNouznaXvo-PF_yqeuvyf-uwKL6zmM0yXlcHPY-FpOLLv4_I_4AcTDCiA</recordid><startdate>20240115</startdate><enddate>20240115</enddate><creator>Alishba</creator><creator>Ahmed, Usman</creator><creator>Taha, Muhammad</creator><creator>Khan, Naveed Ahmed</creator><creator>Salar, Uzma</creator><creator>Khan, Khalid Mohammed</creator><creator>Anwar, Ayaz</creator><creator>Siddiqui, Ruqaiyyah</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>6I.</scope><scope>AAFTH</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20240115</creationdate><title>Potential anti-amoebic effects of synthetic 1,4-benzothiazine derivatives against Acanthamoeba castellanii</title><author>Alishba ; Ahmed, Usman ; Taha, Muhammad ; Khan, Naveed Ahmed ; Salar, Uzma ; Khan, Khalid Mohammed ; Anwar, Ayaz ; Siddiqui, Ruqaiyyah</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c482t-4c473b46ce403bc20052eda8813b75a528c793daca8ac0b14572185354123623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Acanthamoeba</topic><topic>Amoebicidal</topic><topic>Benzothiazine</topic><topic>One-pot synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alishba</creatorcontrib><creatorcontrib>Ahmed, Usman</creatorcontrib><creatorcontrib>Taha, Muhammad</creatorcontrib><creatorcontrib>Khan, Naveed Ahmed</creatorcontrib><creatorcontrib>Salar, Uzma</creatorcontrib><creatorcontrib>Khan, Khalid Mohammed</creatorcontrib><creatorcontrib>Anwar, Ayaz</creatorcontrib><creatorcontrib>Siddiqui, Ruqaiyyah</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Open Access: DOAJ - Directory of Open Access Journals</collection><jtitle>Heliyon</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alishba</au><au>Ahmed, Usman</au><au>Taha, Muhammad</au><au>Khan, Naveed Ahmed</au><au>Salar, Uzma</au><au>Khan, Khalid Mohammed</au><au>Anwar, Ayaz</au><au>Siddiqui, Ruqaiyyah</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Potential anti-amoebic effects of synthetic 1,4-benzothiazine derivatives against Acanthamoeba castellanii</atitle><jtitle>Heliyon</jtitle><addtitle>Heliyon</addtitle><date>2024-01-15</date><risdate>2024</risdate><volume>10</volume><issue>1</issue><spage>e23258</spage><epage>e23258</epage><pages>e23258-e23258</pages><artnum>e23258</artnum><issn>2405-8440</issn><eissn>2405-8440</eissn><abstract>A rare but lethal central nervous system disease known as granulomatous amoebic encephalitis (GAE) and potentially blinding Acanthamoeba keratitis are diseases caused by free-living Acanthamoeba. Currently, no therapeutic agent can completely eradicate or prevent GAE. Synthetic compounds are a likely source of bioactive compounds for developing new drugs. This study synthesized seventeen 1,4-benzothiazine derivatives (I –XVII) by a base-catalyzed one-pot reaction of 2-amino thiophenol with substituted bromo acetophenones. Different spectroscopic techniques, such as EI-MS, 1H-, and 13C NMR (only for the new compounds), were used for the structural characterization and conformation of compounds. These compounds were assessed for the first time against Acanthamoeba castellanii. All compounds showed anti-amoebic potential in vitro against A. castellanii, reducing its ability to encyst and excyst at 100 μM. Compounds IX, X, and XVI showed the most potent activities among all derivatives and significantly reduced the viability to 5.3 × 104 (p &lt; 0.0003), 2 × 105 (p &lt; 0.006), and 2.4 × 105 (p &lt; 0.002) cells/mL, respectively. The cytotoxicity profile revealed that these molecules showed lower to moderate cytotoxicity, i.e., 36 %, 2 %, and 21 %, respectively, against human keratinocytes in vitro. These results indicate that 1,4-benzothiazines showed potent in vitro activity against trophozoites and cysts of A. castellanii. Hence, these 1,4-benzothiazine derivatives should be considered to develop new potential therapeutic agents against Acanthamoeba infections.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>38205285</pmid><doi>10.1016/j.heliyon.2023.e23258</doi><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2405-8440
ispartof Heliyon, 2024-01, Vol.10 (1), p.e23258-e23258, Article e23258
issn 2405-8440
2405-8440
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_89b62601f2ec41b89647b81fd1a240ac
source Open Access: PubMed Central; ScienceDirect®
subjects Acanthamoeba
Amoebicidal
Benzothiazine
One-pot synthesis
title Potential anti-amoebic effects of synthetic 1,4-benzothiazine derivatives against Acanthamoeba castellanii
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-08T12%3A21%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Potential%20anti-amoebic%20effects%20of%20synthetic%201,4-benzothiazine%20derivatives%20against%20Acanthamoeba%20castellanii&rft.jtitle=Heliyon&rft.au=Alishba&rft.date=2024-01-15&rft.volume=10&rft.issue=1&rft.spage=e23258&rft.epage=e23258&rft.pages=e23258-e23258&rft.artnum=e23258&rft.issn=2405-8440&rft.eissn=2405-8440&rft_id=info:doi/10.1016/j.heliyon.2023.e23258&rft_dat=%3Cproquest_doaj_%3E2913451506%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c482t-4c473b46ce403bc20052eda8813b75a528c793daca8ac0b14572185354123623%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2913451506&rft_id=info:pmid/38205285&rfr_iscdi=true