Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers
Bacterial resistance remains a significant threat and a leading cause of death worldwide, despite massive attempts to control infections. In an effort to develop biologically active antibacterial and antifungal agents, six novel aryl-substituted-1,2,3-triazoles linked to carbohydrate units were synt...
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| Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2020-02, Vol.25 (4), p.790 |
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| creator | El Malah, Tamer Nour, Hany F Satti, Amira A E Hemdan, Bahaa A El-Sayed, Wael A |
| description | Bacterial resistance remains a significant threat and a leading cause of death worldwide, despite massive attempts to control infections. In an effort to develop biologically active antibacterial and antifungal agents, six novel aryl-substituted-1,2,3-triazoles linked to carbohydrate units were synthesized through the Cu(I)-catalyzed azide-alkyne cycloaddition CuAAC of substituted-arylazides with a selection of alkyne-functionalized sugars. The chemical structures of the new derivatives were verified using different spectroscopic techniques. The novel clicked 1,2,3-triazoles were evaluated for in vitro antibacterial activity against Gram-positive
and Gram-negative
and the obtained results were compared with the activity of the reference antibiotic "Ampicillin". Likewise, in vitro antifungal activity of the new 1,2,3-triazoles was investigated against
and
using "Nystatin" as a reference drug. The results of the biological evaluation pointed out that
was more susceptible to all of the tested compounds than other examined microbes. In addition, some tested compounds exhibited promising antifungal activity. |
| doi_str_mv | 10.3390/molecules25040790 |
| format | Article |
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and Gram-negative
and the obtained results were compared with the activity of the reference antibiotic "Ampicillin". Likewise, in vitro antifungal activity of the new 1,2,3-triazoles was investigated against
and
using "Nystatin" as a reference drug. The results of the biological evaluation pointed out that
was more susceptible to all of the tested compounds than other examined microbes. In addition, some tested compounds exhibited promising antifungal activity.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules25040790</identifier><identifier>PMID: 32059480</identifier><language>eng</language><publisher>Switzerland: MDPI</publisher><subject>1,2,3-triazole ; Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; antibacterial ; antifungal ; Aspergillus niger - drug effects ; Aspergillus niger - pathogenicity ; Candida albicans - drug effects ; Candida albicans - pathogenicity ; Click Chemistry ; glycoside ; Glycosides - chemical synthesis ; Glycosides - chemistry ; Glycosides - pharmacology ; Humans ; Pseudomonas aeruginosa - drug effects ; Pseudomonas aeruginosa - pathogenicity ; Staphylococcus aureus - drug effects ; Staphylococcus aureus - pathogenicity ; Structure-Activity Relationship ; Triazoles - chemical synthesis ; Triazoles - chemistry ; Triazoles - pharmacology</subject><ispartof>Molecules (Basel, Switzerland), 2020-02, Vol.25 (4), p.790</ispartof><rights>2020 by the authors. 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c531t-3e5d5201cd82ed2fd266e9623894a8585b575172ac7269e8ab2b7a4f5365a1953</citedby><cites>FETCH-LOGICAL-c531t-3e5d5201cd82ed2fd266e9623894a8585b575172ac7269e8ab2b7a4f5365a1953</cites><orcidid>0000-0002-1138-9571 ; 0000-0002-2868-3857 ; 0000-0002-8232-1830 ; 0000-0002-0261-1572 ; 0000-0003-4560-7204</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/PMC7071105/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7071105/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,2102,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32059480$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>El Malah, Tamer</creatorcontrib><creatorcontrib>Nour, Hany F</creatorcontrib><creatorcontrib>Satti, Amira A E</creatorcontrib><creatorcontrib>Hemdan, Bahaa A</creatorcontrib><creatorcontrib>El-Sayed, Wael A</creatorcontrib><title>Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>Bacterial resistance remains a significant threat and a leading cause of death worldwide, despite massive attempts to control infections. In an effort to develop biologically active antibacterial and antifungal agents, six novel aryl-substituted-1,2,3-triazoles linked to carbohydrate units were synthesized through the Cu(I)-catalyzed azide-alkyne cycloaddition CuAAC of substituted-arylazides with a selection of alkyne-functionalized sugars. The chemical structures of the new derivatives were verified using different spectroscopic techniques. The novel clicked 1,2,3-triazoles were evaluated for in vitro antibacterial activity against Gram-positive
and Gram-negative
and the obtained results were compared with the activity of the reference antibiotic "Ampicillin". Likewise, in vitro antifungal activity of the new 1,2,3-triazoles was investigated against
and
using "Nystatin" as a reference drug. The results of the biological evaluation pointed out that
was more susceptible to all of the tested compounds than other examined microbes. In addition, some tested compounds exhibited promising antifungal activity.</description><subject>1,2,3-triazole</subject><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antibacterial</subject><subject>antifungal</subject><subject>Aspergillus niger - drug effects</subject><subject>Aspergillus niger - pathogenicity</subject><subject>Candida albicans - drug effects</subject><subject>Candida albicans - pathogenicity</subject><subject>Click Chemistry</subject><subject>glycoside</subject><subject>Glycosides - chemical synthesis</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - pharmacology</subject><subject>Humans</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Pseudomonas aeruginosa - pathogenicity</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Staphylococcus aureus - pathogenicity</subject><subject>Structure-Activity Relationship</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - chemistry</subject><subject>Triazoles - pharmacology</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>DOA</sourceid><recordid>eNplkd1O20AQhVdVqxJoH6A3lR8ghtk_23tTKQotICFxUejtarw7Dkv9g3adSOnT1yGAiLia0YzON0dzGPvG4VRKA2fd0JJbt5SEBgWlgQ9sxpWAXIIyH9_0R-w4pQcAwRXXn9mRFKCNqmDG_pxTCqt-nv3e9uP91Kd5hr3PFv0YuuDiUAdss4UbwyaMgVI2NBmfi7nMb2PAf5OB7KLduiEFT9myDe4vdhTTF_apwTbR1-d6wu5-_bxdXubXNxdXy8V17rTkYy5Jey2AO18J8qLxoijIFEJWRmGlK13rUvNSoCtFYajCWtQlqkbLQiM3Wp6wqz3XD_hgH2PoMG7tgME-DYa4shjH4FqyhagdNQXWumiUriTWFfnpGihdNgZwYv3Ysx7XdUfeUT9GbA-gh5s-3NvVsLEllJzDzgzfA6a3pRSpedVysLvA7LvAJs33t0dfFS8Jyf_0rZQX</recordid><startdate>20200212</startdate><enddate>20200212</enddate><creator>El Malah, Tamer</creator><creator>Nour, Hany F</creator><creator>Satti, Amira A E</creator><creator>Hemdan, Bahaa A</creator><creator>El-Sayed, Wael A</creator><general>MDPI</general><general>MDPI AG</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>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-1138-9571</orcidid><orcidid>https://orcid.org/0000-0002-2868-3857</orcidid><orcidid>https://orcid.org/0000-0002-8232-1830</orcidid><orcidid>https://orcid.org/0000-0002-0261-1572</orcidid><orcidid>https://orcid.org/0000-0003-4560-7204</orcidid></search><sort><creationdate>20200212</creationdate><title>Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers</title><author>El Malah, Tamer ; 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In an effort to develop biologically active antibacterial and antifungal agents, six novel aryl-substituted-1,2,3-triazoles linked to carbohydrate units were synthesized through the Cu(I)-catalyzed azide-alkyne cycloaddition CuAAC of substituted-arylazides with a selection of alkyne-functionalized sugars. The chemical structures of the new derivatives were verified using different spectroscopic techniques. The novel clicked 1,2,3-triazoles were evaluated for in vitro antibacterial activity against Gram-positive
and Gram-negative
and the obtained results were compared with the activity of the reference antibiotic "Ampicillin". Likewise, in vitro antifungal activity of the new 1,2,3-triazoles was investigated against
and
using "Nystatin" as a reference drug. The results of the biological evaluation pointed out that
was more susceptible to all of the tested compounds than other examined microbes. In addition, some tested compounds exhibited promising antifungal activity.</abstract><cop>Switzerland</cop><pub>MDPI</pub><pmid>32059480</pmid><doi>10.3390/molecules25040790</doi><orcidid>https://orcid.org/0000-0002-1138-9571</orcidid><orcidid>https://orcid.org/0000-0002-2868-3857</orcidid><orcidid>https://orcid.org/0000-0002-8232-1830</orcidid><orcidid>https://orcid.org/0000-0002-0261-1572</orcidid><orcidid>https://orcid.org/0000-0003-4560-7204</orcidid><oa>free_for_read</oa></addata></record> |
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| source | MDPI - Multidisciplinary Digital Publishing Institute; MEDLINE; Full-Text Journals in Chemistry (Open access); DOAJ Directory of Open Access Journals; PubMed Central; EZB Electronic Journals Library |
| subjects | 1,2,3-triazole Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology antibacterial antifungal Aspergillus niger - drug effects Aspergillus niger - pathogenicity Candida albicans - drug effects Candida albicans - pathogenicity Click Chemistry glycoside Glycosides - chemical synthesis Glycosides - chemistry Glycosides - pharmacology Humans Pseudomonas aeruginosa - drug effects Pseudomonas aeruginosa - pathogenicity Staphylococcus aureus - drug effects Staphylococcus aureus - pathogenicity Structure-Activity Relationship Triazoles - chemical synthesis Triazoles - chemistry Triazoles - pharmacology |
| title | Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers |
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