Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics
A series of new chiral benzisoselenazol-3(2 )-ones and their corresponding diselenides bearing an -amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to tho...
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| Veröffentlicht in: | Materials 2022-03, Vol.15 (6), p.2068 |
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| creator | Laskowska, Anna Pacuła-Miszewska, Agata Joanna Długosz-Pokorska, Angelika Janecka, Anna Wojtczak, Andrzej Ścianowski, Jacek |
| description | A series of new chiral benzisoselenazol-3(2
)-ones and their corresponding diselenides bearing an
-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to thoroughly evaluate the three-dimensional structure-activity correlation. First, bensisoselenazol-3(2
)-ones were synthesized by reacting 2-(chloroseleno)benzoyl chloride with an appropriate enantiomerically pure amine. Then, the Se-N bond was cleaved by a reduction-oxidation procedure using sodium borohydride and then air oxidation to obtain the corresponding diselenides. All derivatives were tested as antioxidants and anticancer agents. In general, the diselenides were more reactive peroxide scavengers, with the highest activity observed for 2,2'-diselenobis[
-(1
,2
)-(-)-
-2-hydroksy-1-indanylbezamide]. The most cytotoxic derivative towards human promyelocytic leukemia HL-60 and breast cancer MCF-7 cell lines was
-[(1
,2
)-(-)-
-2-hydroksy-1-indanyl]-1,2-benzizoselenazol-3(2
)-one. The structure-activity relationship of the obtained organoselenium derivatives was discussed. |
| doi_str_mv | 10.3390/ma15062068 |
| format | Article |
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)-ones and their corresponding diselenides bearing an
-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to thoroughly evaluate the three-dimensional structure-activity correlation. First, bensisoselenazol-3(2
)-ones were synthesized by reacting 2-(chloroseleno)benzoyl chloride with an appropriate enantiomerically pure amine. Then, the Se-N bond was cleaved by a reduction-oxidation procedure using sodium borohydride and then air oxidation to obtain the corresponding diselenides. All derivatives were tested as antioxidants and anticancer agents. In general, the diselenides were more reactive peroxide scavengers, with the highest activity observed for 2,2'-diselenobis[
-(1
,2
)-(-)-
-2-hydroksy-1-indanylbezamide]. The most cytotoxic derivative towards human promyelocytic leukemia HL-60 and breast cancer MCF-7 cell lines was
-[(1
,2
)-(-)-
-2-hydroksy-1-indanyl]-1,2-benzizoselenazol-3(2
)-one. The structure-activity relationship of the obtained organoselenium derivatives was discussed.</description><identifier>ISSN: 1996-1944</identifier><identifier>EISSN: 1996-1944</identifier><identifier>DOI: 10.3390/ma15062068</identifier><identifier>PMID: 35329523</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Amino acids ; Anticancer properties ; Antioxidants ; Biological activity ; Carbon ; Enantiomers ; Enzymes ; Functional groups ; Leukemia ; Nitrogen ; Oxidation ; Selenides ; Synthesis</subject><ispartof>Materials, 2022-03, Vol.15 (6), p.2068</ispartof><rights>2022 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>2022 by the authors. 2022</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c336t-bf614f7f945c63565bdde3399bc9fea3108a8a5902e3326c92761edd49b3cb33</citedby><cites>FETCH-LOGICAL-c336t-bf614f7f945c63565bdde3399bc9fea3108a8a5902e3326c92761edd49b3cb33</cites><orcidid>0000-0002-3868-2022 ; 0000-0001-8801-7728</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/PMC8950439/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8950439/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27923,27924,53790,53792</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35329523$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Laskowska, Anna</creatorcontrib><creatorcontrib>Pacuła-Miszewska, Agata Joanna</creatorcontrib><creatorcontrib>Długosz-Pokorska, Angelika</creatorcontrib><creatorcontrib>Janecka, Anna</creatorcontrib><creatorcontrib>Wojtczak, Andrzej</creatorcontrib><creatorcontrib>Ścianowski, Jacek</creatorcontrib><title>Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics</title><title>Materials</title><addtitle>Materials (Basel)</addtitle><description>A series of new chiral benzisoselenazol-3(2
)-ones and their corresponding diselenides bearing an
-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to thoroughly evaluate the three-dimensional structure-activity correlation. First, bensisoselenazol-3(2
)-ones were synthesized by reacting 2-(chloroseleno)benzoyl chloride with an appropriate enantiomerically pure amine. Then, the Se-N bond was cleaved by a reduction-oxidation procedure using sodium borohydride and then air oxidation to obtain the corresponding diselenides. All derivatives were tested as antioxidants and anticancer agents. In general, the diselenides were more reactive peroxide scavengers, with the highest activity observed for 2,2'-diselenobis[
-(1
,2
)-(-)-
-2-hydroksy-1-indanylbezamide]. The most cytotoxic derivative towards human promyelocytic leukemia HL-60 and breast cancer MCF-7 cell lines was
-[(1
,2
)-(-)-
-2-hydroksy-1-indanyl]-1,2-benzizoselenazol-3(2
)-one. The structure-activity relationship of the obtained organoselenium derivatives was discussed.</description><subject>Amino acids</subject><subject>Anticancer properties</subject><subject>Antioxidants</subject><subject>Biological activity</subject><subject>Carbon</subject><subject>Enantiomers</subject><subject>Enzymes</subject><subject>Functional groups</subject><subject>Leukemia</subject><subject>Nitrogen</subject><subject>Oxidation</subject><subject>Selenides</subject><subject>Synthesis</subject><issn>1996-1944</issn><issn>1996-1944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNpdkdtKAzEQhoMoKuqNDyABb0SoJplNurkRStEqeITeh2w2a1O6m7rJVvv2ph7qITcZZr78808GoUNKzgAkOa815UQwIvINtEulFD0qs2zzV7yDDkKYknQAaM7kNtoBDkxyBrvoaRCjNpPaNhH7Cg8nrtUzfNU1JjrfpHDU-m4ecPT4zpeuWuI4sXiQqgsXl6sn9_YVjx7f8J2rbXQm7KOtSs-CPfi699D46nI8vO7dPoxuhoPbngEQsVdUgmZVv5IZNwK44EVZ2jSRLIysrAZKcp1rLglLWSaMZH1BbVlmsgBTAOyhi0_ZeVfUtjRpgORczVtX63apvHbqb6VxE_XsFyqXnGQgk8DJl0DrXzoboqpdMHY20431XVBMZBmhqfeq1_E_dOq7Nv3OB8V4DoyyRJ1-Uqb1IbS2WpuhRK12pX52leCj3_bX6Pdm4B3rnY4s</recordid><startdate>20220311</startdate><enddate>20220311</enddate><creator>Laskowska, Anna</creator><creator>Pacuła-Miszewska, Agata Joanna</creator><creator>Długosz-Pokorska, Angelika</creator><creator>Janecka, Anna</creator><creator>Wojtczak, Andrzej</creator><creator>Ścianowski, Jacek</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</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>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-3868-2022</orcidid><orcidid>https://orcid.org/0000-0001-8801-7728</orcidid></search><sort><creationdate>20220311</creationdate><title>Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics</title><author>Laskowska, Anna ; Pacuła-Miszewska, Agata Joanna ; Długosz-Pokorska, Angelika ; Janecka, Anna ; Wojtczak, Andrzej ; Ścianowski, Jacek</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c336t-bf614f7f945c63565bdde3399bc9fea3108a8a5902e3326c92761edd49b3cb33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Amino acids</topic><topic>Anticancer properties</topic><topic>Antioxidants</topic><topic>Biological activity</topic><topic>Carbon</topic><topic>Enantiomers</topic><topic>Enzymes</topic><topic>Functional groups</topic><topic>Leukemia</topic><topic>Nitrogen</topic><topic>Oxidation</topic><topic>Selenides</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Laskowska, Anna</creatorcontrib><creatorcontrib>Pacuła-Miszewska, Agata Joanna</creatorcontrib><creatorcontrib>Długosz-Pokorska, Angelika</creatorcontrib><creatorcontrib>Janecka, Anna</creatorcontrib><creatorcontrib>Wojtczak, Andrzej</creatorcontrib><creatorcontrib>Ścianowski, Jacek</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection (ProQuest)</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</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>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Laskowska, Anna</au><au>Pacuła-Miszewska, Agata Joanna</au><au>Długosz-Pokorska, Angelika</au><au>Janecka, Anna</au><au>Wojtczak, Andrzej</au><au>Ścianowski, Jacek</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics</atitle><jtitle>Materials</jtitle><addtitle>Materials (Basel)</addtitle><date>2022-03-11</date><risdate>2022</risdate><volume>15</volume><issue>6</issue><spage>2068</spage><pages>2068-</pages><issn>1996-1944</issn><eissn>1996-1944</eissn><abstract>A series of new chiral benzisoselenazol-3(2
)-ones and their corresponding diselenides bearing an
-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to thoroughly evaluate the three-dimensional structure-activity correlation. First, bensisoselenazol-3(2
)-ones were synthesized by reacting 2-(chloroseleno)benzoyl chloride with an appropriate enantiomerically pure amine. Then, the Se-N bond was cleaved by a reduction-oxidation procedure using sodium borohydride and then air oxidation to obtain the corresponding diselenides. All derivatives were tested as antioxidants and anticancer agents. In general, the diselenides were more reactive peroxide scavengers, with the highest activity observed for 2,2'-diselenobis[
-(1
,2
)-(-)-
-2-hydroksy-1-indanylbezamide]. The most cytotoxic derivative towards human promyelocytic leukemia HL-60 and breast cancer MCF-7 cell lines was
-[(1
,2
)-(-)-
-2-hydroksy-1-indanyl]-1,2-benzizoselenazol-3(2
)-one. The structure-activity relationship of the obtained organoselenium derivatives was discussed.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>35329523</pmid><doi>10.3390/ma15062068</doi><orcidid>https://orcid.org/0000-0002-3868-2022</orcidid><orcidid>https://orcid.org/0000-0001-8801-7728</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1996-1944 |
| ispartof | Materials, 2022-03, Vol.15 (6), p.2068 |
| issn | 1996-1944 1996-1944 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8950439 |
| source | PubMed Central Open Access; MDPI - Multidisciplinary Digital Publishing Institute; EZB-FREE-00999 freely available EZB journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Amino acids Anticancer properties Antioxidants Biological activity Carbon Enantiomers Enzymes Functional groups Leukemia Nitrogen Oxidation Selenides Synthesis |
| title | Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics |
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