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Allylpolyalkoxybenzene Inhibitors of Galactonolactone Oxidase from Trypanosoma cruzi
Inhibition of biosynthetic pathways of compounds essential for Trypanosoma cruzi is considered as one of the possible action mechanisms of drugs against Chagas disease. Here, we investigated the inhibition of galactonolactone oxidase from T. cruzi (TcGAL), which catalyzes the final step in the synth...
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| Published in: | Biochemistry (Moscow) 2023, Vol.88 (1), p.131-141 |
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| Main Authors: | , , , , |
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| cites | cdi_FETCH-LOGICAL-c439t-4e485e5fce6454ff921104ae955ac03362602822d4de8bce4e8f81fbd4f06d983 |
| container_end_page | 141 |
| container_issue | 1 |
| container_start_page | 131 |
| container_title | Biochemistry (Moscow) |
| container_volume | 88 |
| creator | Chudin, Andrey A. Zlotnikov, Igor D. Krylov, Sergey S. Semenov, Victor V. Kudryashova, Elena V. |
| description | Inhibition of biosynthetic pathways of compounds essential for
Trypanosoma cruzi
is considered as one of the possible action mechanisms of drugs against Chagas disease. Here, we investigated the inhibition of galactonolactone oxidase from
T. cruzi
(TcGAL), which catalyzes the final step in the synthesis of vitamin C, an antioxidant that
T. cruzi
is unable to assimilate from outside and must synthesize itself, and identified allylbenzenes from plant sources as a new class of TcGAL inhibitors. Natural APABs (apiol, dillapiol, etc.) inhibited TcGAL with IC
50
= 20-130 µM. The non-competitive mechanism of TcGAL inhibition by apiol was established. Conjugation of APABs with triphenylphosphonium, which ensures selective delivery of biologically active substances to the mitochondria, increased the efficiency and/or the maximum percentage of TcGAL inhibition compared to nonmodified APABs. |
| doi_str_mv | 10.1134/S000629792301011X |
| format | article |
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Trypanosoma cruzi
is considered as one of the possible action mechanisms of drugs against Chagas disease. Here, we investigated the inhibition of galactonolactone oxidase from
T. cruzi
(TcGAL), which catalyzes the final step in the synthesis of vitamin C, an antioxidant that
T. cruzi
is unable to assimilate from outside and must synthesize itself, and identified allylbenzenes from plant sources as a new class of TcGAL inhibitors. Natural APABs (apiol, dillapiol, etc.) inhibited TcGAL with IC
50
= 20-130 µM. The non-competitive mechanism of TcGAL inhibition by apiol was established. Conjugation of APABs with triphenylphosphonium, which ensures selective delivery of biologically active substances to the mitochondria, increased the efficiency and/or the maximum percentage of TcGAL inhibition compared to nonmodified APABs.</description><identifier>ISSN: 0006-2979</identifier><identifier>EISSN: 1608-3040</identifier><identifier>DOI: 10.1134/S000629792301011X</identifier><identifier>PMID: 37068875</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Analysis ; Ascorbic acid ; Biochemistry ; Biological activity ; Biomedical and Life Sciences ; Biomedicine ; Bioorganic Chemistry ; Biosynthesis ; Care and treatment ; Chagas Disease ; Conjugation ; Enzymes ; Humans ; Identification and classification ; Inhibitors ; Life Sciences ; Metabolites ; Microbiology ; Mitochondria ; Organic chemistry ; Oxidase ; Oxidases ; Oxidoreductases - metabolism ; Parasites ; Properties ; Protozoa ; Sodium ; Sterols ; Sugar Acids - metabolism ; Trypanosoma cruzi ; Trypanosoma cruzi - metabolism ; Vector-borne diseases</subject><ispartof>Biochemistry (Moscow), 2023, Vol.88 (1), p.131-141</ispartof><rights>Pleiades Publishing, Ltd. 2023</rights><rights>COPYRIGHT 2023 Springer</rights><rights>Pleiades Publishing, Ltd. 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c439t-4e485e5fce6454ff921104ae955ac03362602822d4de8bce4e8f81fbd4f06d983</citedby><cites>FETCH-LOGICAL-c439t-4e485e5fce6454ff921104ae955ac03362602822d4de8bce4e8f81fbd4f06d983</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37068875$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chudin, Andrey A.</creatorcontrib><creatorcontrib>Zlotnikov, Igor D.</creatorcontrib><creatorcontrib>Krylov, Sergey S.</creatorcontrib><creatorcontrib>Semenov, Victor V.</creatorcontrib><creatorcontrib>Kudryashova, Elena V.</creatorcontrib><title>Allylpolyalkoxybenzene Inhibitors of Galactonolactone Oxidase from Trypanosoma cruzi</title><title>Biochemistry (Moscow)</title><addtitle>Biochemistry Moscow</addtitle><addtitle>Biochemistry (Mosc)</addtitle><description>Inhibition of biosynthetic pathways of compounds essential for
Trypanosoma cruzi
is considered as one of the possible action mechanisms of drugs against Chagas disease. Here, we investigated the inhibition of galactonolactone oxidase from
T. cruzi
(TcGAL), which catalyzes the final step in the synthesis of vitamin C, an antioxidant that
T. cruzi
is unable to assimilate from outside and must synthesize itself, and identified allylbenzenes from plant sources as a new class of TcGAL inhibitors. Natural APABs (apiol, dillapiol, etc.) inhibited TcGAL with IC
50
= 20-130 µM. The non-competitive mechanism of TcGAL inhibition by apiol was established. Conjugation of APABs with triphenylphosphonium, which ensures selective delivery of biologically active substances to the mitochondria, increased the efficiency and/or the maximum percentage of TcGAL inhibition compared to nonmodified APABs.</description><subject>Analysis</subject><subject>Ascorbic acid</subject><subject>Biochemistry</subject><subject>Biological activity</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Bioorganic Chemistry</subject><subject>Biosynthesis</subject><subject>Care and treatment</subject><subject>Chagas Disease</subject><subject>Conjugation</subject><subject>Enzymes</subject><subject>Humans</subject><subject>Identification and classification</subject><subject>Inhibitors</subject><subject>Life Sciences</subject><subject>Metabolites</subject><subject>Microbiology</subject><subject>Mitochondria</subject><subject>Organic chemistry</subject><subject>Oxidase</subject><subject>Oxidases</subject><subject>Oxidoreductases - metabolism</subject><subject>Parasites</subject><subject>Properties</subject><subject>Protozoa</subject><subject>Sodium</subject><subject>Sterols</subject><subject>Sugar Acids - metabolism</subject><subject>Trypanosoma cruzi</subject><subject>Trypanosoma cruzi - metabolism</subject><subject>Vector-borne diseases</subject><issn>0006-2979</issn><issn>1608-3040</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kUtr3DAUhUVpaKbT_oBuiqGbbpzoZUteDiFNA4EsOoHuhCxfpUplaSrZEOfXV8OkDX0ELS7S-c7h6l6E3hF8Qgjjp18wxi3tREcZJpiQry_QirRY1gxz_BKt9nK914_R65zvypXijr1Cx0zgVkrRrNB24_3id9Ev2n-P90sP4QECVJfhm-vdFFOuoq0utNdmiiEeClTX927QGSqb4lht07LTIeY46sqk-cG9QUdW-wxvH-sa3Xw63559rq-uLy7PNle14aybag5cNtBYAy1vuLUdJQRzDV3TaIMZa2mLqaR04API3gAHaSWx_cAtbodOsjX6eMjdpfhjhjyp0WUD3usAcc6KyuKXLWGioB_-Qu_inELpTlEhREMpofyJutUelAs2TkmbfajaCFYwIcus1-jkP1Q5A4zOlPFYV97_MJCDwaSYcwKrdsmNOi2KYLXfpPpnk8Xz_rHhuR9h-O34tboC0AOQixRuIT396PnUn2z1pu0</recordid><startdate>2023</startdate><enddate>2023</enddate><creator>Chudin, Andrey A.</creator><creator>Zlotnikov, Igor D.</creator><creator>Krylov, Sergey S.</creator><creator>Semenov, Victor V.</creator><creator>Kudryashova, Elena V.</creator><general>Pleiades Publishing</general><general>Springer</general><general>Springer Nature B.V</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>7QL</scope><scope>7TM</scope><scope>7U9</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8C1</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope></search><sort><creationdate>2023</creationdate><title>Allylpolyalkoxybenzene Inhibitors of Galactonolactone Oxidase from Trypanosoma cruzi</title><author>Chudin, Andrey A. ; Zlotnikov, Igor D. ; Krylov, Sergey S. ; Semenov, Victor V. ; Kudryashova, Elena V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c439t-4e485e5fce6454ff921104ae955ac03362602822d4de8bce4e8f81fbd4f06d983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Analysis</topic><topic>Ascorbic acid</topic><topic>Biochemistry</topic><topic>Biological activity</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Bioorganic Chemistry</topic><topic>Biosynthesis</topic><topic>Care and treatment</topic><topic>Chagas Disease</topic><topic>Conjugation</topic><topic>Enzymes</topic><topic>Humans</topic><topic>Identification and classification</topic><topic>Inhibitors</topic><topic>Life Sciences</topic><topic>Metabolites</topic><topic>Microbiology</topic><topic>Mitochondria</topic><topic>Organic chemistry</topic><topic>Oxidase</topic><topic>Oxidases</topic><topic>Oxidoreductases - metabolism</topic><topic>Parasites</topic><topic>Properties</topic><topic>Protozoa</topic><topic>Sodium</topic><topic>Sterols</topic><topic>Sugar Acids - metabolism</topic><topic>Trypanosoma cruzi</topic><topic>Trypanosoma cruzi - metabolism</topic><topic>Vector-borne diseases</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chudin, Andrey A.</creatorcontrib><creatorcontrib>Zlotnikov, Igor D.</creatorcontrib><creatorcontrib>Krylov, Sergey S.</creatorcontrib><creatorcontrib>Semenov, Victor V.</creatorcontrib><creatorcontrib>Kudryashova, Elena V.</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>Bacteriology Abstracts (Microbiology B)</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Health & Medical Collection (Proquest)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest Public Health Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</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)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>ProQuest Natural Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Biological Sciences</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Science Database (ProQuest)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science 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>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><jtitle>Biochemistry (Moscow)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chudin, Andrey A.</au><au>Zlotnikov, Igor D.</au><au>Krylov, Sergey S.</au><au>Semenov, Victor V.</au><au>Kudryashova, Elena V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Allylpolyalkoxybenzene Inhibitors of Galactonolactone Oxidase from Trypanosoma cruzi</atitle><jtitle>Biochemistry (Moscow)</jtitle><stitle>Biochemistry Moscow</stitle><addtitle>Biochemistry (Mosc)</addtitle><date>2023</date><risdate>2023</risdate><volume>88</volume><issue>1</issue><spage>131</spage><epage>141</epage><pages>131-141</pages><issn>0006-2979</issn><eissn>1608-3040</eissn><abstract>Inhibition of biosynthetic pathways of compounds essential for
Trypanosoma cruzi
is considered as one of the possible action mechanisms of drugs against Chagas disease. Here, we investigated the inhibition of galactonolactone oxidase from
T. cruzi
(TcGAL), which catalyzes the final step in the synthesis of vitamin C, an antioxidant that
T. cruzi
is unable to assimilate from outside and must synthesize itself, and identified allylbenzenes from plant sources as a new class of TcGAL inhibitors. Natural APABs (apiol, dillapiol, etc.) inhibited TcGAL with IC
50
= 20-130 µM. The non-competitive mechanism of TcGAL inhibition by apiol was established. Conjugation of APABs with triphenylphosphonium, which ensures selective delivery of biologically active substances to the mitochondria, increased the efficiency and/or the maximum percentage of TcGAL inhibition compared to nonmodified APABs.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><pmid>37068875</pmid><doi>10.1134/S000629792301011X</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Biochemistry (Moscow), 2023, Vol.88 (1), p.131-141 |
| issn | 0006-2979 1608-3040 |
| language | eng |
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| source | Springer Nature |
| subjects | Analysis Ascorbic acid Biochemistry Biological activity Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Biosynthesis Care and treatment Chagas Disease Conjugation Enzymes Humans Identification and classification Inhibitors Life Sciences Metabolites Microbiology Mitochondria Organic chemistry Oxidase Oxidases Oxidoreductases - metabolism Parasites Properties Protozoa Sodium Sterols Sugar Acids - metabolism Trypanosoma cruzi Trypanosoma cruzi - metabolism Vector-borne diseases |
| title | Allylpolyalkoxybenzene Inhibitors of Galactonolactone Oxidase from Trypanosoma cruzi |
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