Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones
A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per- -acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antim...
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| Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2020-08, Vol.25 (16), p.3577 |
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| creator | Sabutski, Yuri E Menchinskaya, Ekaterina S Shevchenko, Ludmila S Chingizova, Ekaterina A Chingizov, Artur R Popov, Roman S Denisenko, Vladimir A Mikhailov, Valery V Aminin, Dmitry L Polonik, Sergey G |
| description | A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-
-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC
values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (
,
), Gram-negative bacteria (
and
), and fungus
by the agar diffusion method. The most effective juglone conjugates with d-xylose or l-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown. |
| doi_str_mv | 10.3390/molecules25163577 |
| format | Article |
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-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC
values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (
,
), Gram-negative bacteria (
and
), and fungus
by the agar diffusion method. The most effective juglone conjugates with d-xylose or l-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules25163577</identifier><identifier>PMID: 32781642</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>1,4-naphthoquinones ; Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; antibiotic activity ; Antibiotics ; Antiinfectives and antibacterials ; Antimicrobial activity ; Antimicrobial agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Arabinose ; Ascites ; Bacteria ; Biofilms ; Biological activity ; Carbohydrates ; Chemistry Techniques, Synthetic ; Coliforms ; Conjugates ; cytotoxic activity ; Cytotoxicity ; D-Galactose ; Fungi ; Galactose ; Gentamicin ; Glucose ; Gram-negative bacteria ; Gram-positive bacteria ; HeLa Cells ; Humans ; Hydroxyl groups ; Juglone ; Microorganisms ; Minimum inhibitory concentration ; Naphthoquinones - chemistry ; Oxathiins - chemistry ; Pseudomonas aeruginosa ; quinoid compounds ; quinone-sugar conjugates ; Quinones ; Quinones - chemistry ; Thioglucosides - chemical synthesis ; Thioglucosides - chemistry ; Thioglucosides - pharmacology ; thioglycosides ; Xylose</subject><ispartof>Molecules (Basel, Switzerland), 2020-08, Vol.25 (16), p.3577</ispartof><rights>2020. This work is licensed under http://creativecommons.org/licenses/by/3.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2020 by the authors. 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c493t-57d61c6ffb680d7ea1f050c9eb86b62266f367208fbe24eebc5967c357543e7c3</citedby><cites>FETCH-LOGICAL-c493t-57d61c6ffb680d7ea1f050c9eb86b62266f367208fbe24eebc5967c357543e7c3</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/PMC7463537/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7463537/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,724,777,781,861,882,2096,27905,27906,53772,53774</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32781642$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sabutski, Yuri E</creatorcontrib><creatorcontrib>Menchinskaya, Ekaterina S</creatorcontrib><creatorcontrib>Shevchenko, Ludmila S</creatorcontrib><creatorcontrib>Chingizova, Ekaterina A</creatorcontrib><creatorcontrib>Chingizov, Artur R</creatorcontrib><creatorcontrib>Popov, Roman S</creatorcontrib><creatorcontrib>Denisenko, Vladimir A</creatorcontrib><creatorcontrib>Mikhailov, Valery V</creatorcontrib><creatorcontrib>Aminin, Dmitry L</creatorcontrib><creatorcontrib>Polonik, Sergey G</creatorcontrib><title>Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-
-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC
values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (
,
), Gram-negative bacteria (
and
), and fungus
by the agar diffusion method. The most effective juglone conjugates with d-xylose or l-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown.</description><subject>1,4-naphthoquinones</subject><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antibiotic activity</subject><subject>Antibiotics</subject><subject>Antiinfectives and antibacterials</subject><subject>Antimicrobial activity</subject><subject>Antimicrobial agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Arabinose</subject><subject>Ascites</subject><subject>Bacteria</subject><subject>Biofilms</subject><subject>Biological activity</subject><subject>Carbohydrates</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Coliforms</subject><subject>Conjugates</subject><subject>cytotoxic activity</subject><subject>Cytotoxicity</subject><subject>D-Galactose</subject><subject>Fungi</subject><subject>Galactose</subject><subject>Gentamicin</subject><subject>Glucose</subject><subject>Gram-negative bacteria</subject><subject>Gram-positive bacteria</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Hydroxyl groups</subject><subject>Juglone</subject><subject>Microorganisms</subject><subject>Minimum inhibitory concentration</subject><subject>Naphthoquinones - chemistry</subject><subject>Oxathiins - chemistry</subject><subject>Pseudomonas aeruginosa</subject><subject>quinoid compounds</subject><subject>quinone-sugar conjugates</subject><subject>Quinones</subject><subject>Quinones - chemistry</subject><subject>Thioglucosides - chemical synthesis</subject><subject>Thioglucosides - chemistry</subject><subject>Thioglucosides - pharmacology</subject><subject>thioglycosides</subject><subject>Xylose</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>DOA</sourceid><recordid>eNplUk1v1DAQjRCIfsAP4IIiceFAwF-xkwvSatWWShUVajlbjjPZeOW1l9hedX8JfxenW6oWTh573nszfjNF8Q6jz5S26MvGW9DJQiA15rQW4kVxjBlBFUWsffkkPipOQlgjRDDD9eviiBLRYM7IcfH7Zu_iCMGEUrm-PNspm1Q03pV-KBcumo3Rk--Msvf55T766O-MLhc6mp2J-xl3fafiaIyD6jwF6MsfyTifb7ej8SubtA-mh3Lp3TqtVIQwc25SF6KJKWY8_sSq72o7xtH_OlDDm-LVoGyAtw_nafHz_Ox2-a26ur64XC6uKs1aGqta9BxrPgwdb1AvQOEB1Ui30DW844RwPlAuCGqGDggD6HTdcqGzVzWjkIPT4vKg23u1ltvJbNS0l14Zef_gp5VUUzTagmR9MyikCB1oLi7arkW8Y4pz1FNOeJ21vh60tqnbQK_BxUnZZ6LPM86McuV3UrA8PSqywMcHgSkbASHKjQkarFUOfAqSMEoJw6JpM_TDP9C1T5PLVs0owpumxXNH-IDKMwxhguGxGYzkvELyvxXKnPdPf_HI-Lsz9A8pwsfN</recordid><startdate>20200806</startdate><enddate>20200806</enddate><creator>Sabutski, Yuri E</creator><creator>Menchinskaya, Ekaterina S</creator><creator>Shevchenko, Ludmila S</creator><creator>Chingizova, Ekaterina A</creator><creator>Chingizov, Artur R</creator><creator>Popov, Roman S</creator><creator>Denisenko, Vladimir A</creator><creator>Mikhailov, Valery V</creator><creator>Aminin, Dmitry L</creator><creator>Polonik, Sergey G</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></search><sort><creationdate>20200806</creationdate><title>Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones</title><author>Sabutski, Yuri E ; Menchinskaya, Ekaterina S ; Shevchenko, Ludmila S ; Chingizova, Ekaterina A ; Chingizov, Artur R ; Popov, Roman S ; Denisenko, Vladimir A ; Mikhailov, Valery V ; Aminin, Dmitry L ; Polonik, Sergey G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c493t-57d61c6ffb680d7ea1f050c9eb86b62266f367208fbe24eebc5967c357543e7c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>1,4-naphthoquinones</topic><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antibiotic activity</topic><topic>Antibiotics</topic><topic>Antiinfectives and antibacterials</topic><topic>Antimicrobial activity</topic><topic>Antimicrobial agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Arabinose</topic><topic>Ascites</topic><topic>Bacteria</topic><topic>Biofilms</topic><topic>Biological activity</topic><topic>Carbohydrates</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Coliforms</topic><topic>Conjugates</topic><topic>cytotoxic activity</topic><topic>Cytotoxicity</topic><topic>D-Galactose</topic><topic>Fungi</topic><topic>Galactose</topic><topic>Gentamicin</topic><topic>Glucose</topic><topic>Gram-negative bacteria</topic><topic>Gram-positive bacteria</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Hydroxyl groups</topic><topic>Juglone</topic><topic>Microorganisms</topic><topic>Minimum inhibitory concentration</topic><topic>Naphthoquinones - chemistry</topic><topic>Oxathiins - chemistry</topic><topic>Pseudomonas aeruginosa</topic><topic>quinoid compounds</topic><topic>quinone-sugar conjugates</topic><topic>Quinones</topic><topic>Quinones - chemistry</topic><topic>Thioglucosides - chemical synthesis</topic><topic>Thioglucosides - chemistry</topic><topic>Thioglucosides - pharmacology</topic><topic>thioglycosides</topic><topic>Xylose</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sabutski, Yuri E</creatorcontrib><creatorcontrib>Menchinskaya, Ekaterina S</creatorcontrib><creatorcontrib>Shevchenko, Ludmila S</creatorcontrib><creatorcontrib>Chingizova, Ekaterina A</creatorcontrib><creatorcontrib>Chingizov, Artur R</creatorcontrib><creatorcontrib>Popov, Roman S</creatorcontrib><creatorcontrib>Denisenko, Vladimir A</creatorcontrib><creatorcontrib>Mikhailov, Valery V</creatorcontrib><creatorcontrib>Aminin, Dmitry L</creatorcontrib><creatorcontrib>Polonik, Sergey G</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>Health & Medical Collection</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 Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</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>Medical Database</collection><collection>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>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sabutski, Yuri E</au><au>Menchinskaya, Ekaterina S</au><au>Shevchenko, Ludmila S</au><au>Chingizova, Ekaterina A</au><au>Chingizov, Artur R</au><au>Popov, Roman S</au><au>Denisenko, Vladimir A</au><au>Mikhailov, Valery V</au><au>Aminin, Dmitry L</au><au>Polonik, Sergey G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2020-08-06</date><risdate>2020</risdate><volume>25</volume><issue>16</issue><spage>3577</spage><pages>3577-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-
-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC
values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (
,
), Gram-negative bacteria (
and
), and fungus
by the agar diffusion method. The most effective juglone conjugates with d-xylose or l-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>32781642</pmid><doi>10.3390/molecules25163577</doi><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; DOAJ Directory of Open Access Journals; MDPI - Multidisciplinary Digital Publishing Institute; EZB-FREE-00999 freely available EZB journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | 1,4-naphthoquinones Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology antibiotic activity Antibiotics Antiinfectives and antibacterials Antimicrobial activity Antimicrobial agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Arabinose Ascites Bacteria Biofilms Biological activity Carbohydrates Chemistry Techniques, Synthetic Coliforms Conjugates cytotoxic activity Cytotoxicity D-Galactose Fungi Galactose Gentamicin Glucose Gram-negative bacteria Gram-positive bacteria HeLa Cells Humans Hydroxyl groups Juglone Microorganisms Minimum inhibitory concentration Naphthoquinones - chemistry Oxathiins - chemistry Pseudomonas aeruginosa quinoid compounds quinone-sugar conjugates Quinones Quinones - chemistry Thioglucosides - chemical synthesis Thioglucosides - chemistry Thioglucosides - pharmacology thioglycosides Xylose |
| title | Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones |
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