Synthesis of trimethoxy-benzylidene-hydrazine-carboxamide compounds: antioxidant, antimicrobial and antiparasitic agent, evaluation of the interaction with BSA and ADMET parameters
The search for new compounds that present low toxicity and high efficiency in the treatment of different diseases is a challenge. Therefore, this study brings as a novelty the synthesis, biological evaluation and a study of the mechanism of action in serum albumin of trimethoxy-benzylidene-hydrazine...
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| Veröffentlicht in: | Chemical papers 2024-02, Vol.78 (3), p.1897-1913 |
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| creator | da Silva, Maria José Cristiane Marques, Diego Santa Clara do Bomfim Nascimento, Pedro Henrique Mendes, Raudiney Frankilin Vasconcelos Buonafina-Paz, Maria Daniela Silva Machado, Dijanah Cota dos Santos, Fábio André Brayner Alves, Luiz Carlos Ximenes, Rafael Matos Neves, Rejane Pereira da Cruz Filho, Iranildo José de Lima, Maria do Carmo Alves |
| description | The search for new compounds that present low toxicity and high efficiency in the treatment of different diseases is a challenge. Therefore, this study brings as a novelty the synthesis, biological evaluation and a study of the mechanism of action in serum albumin of trimethoxy-benzylidene-hydrazine-carbothioamide compounds. The in silico results received that all compounds showed good oral availability and could be accepted as potential drug candidates. In cytotoxicity assays, the compounds promoted moderate to low toxicity against macrophage cells (82.90 ± 1.19 to 231.49 ± 1.96 µM) and Hepg2 (91.19 ± 1.09 to 254.64 ± 3.96 µM). In addition to not being hemolytic ( |
| doi_str_mv | 10.1007/s11696-023-03214-3 |
| format | Article |
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L. amazonensis
in different promastigote (27.84–40.52 µM) and amastigote (29–49.71 µM) forms. Furthermore, they inhibited the growth of
T.cruzi
trypomastigotes (28.90–45.24 µM). Assays with albumin generally pleased that the compounds can be transported by these proteins without changes in the macromolecules. In this context, we can conclude that the compounds considered can promote different activities and can contribute to the arsenal of new drug candidate compounds that can act as new antifungal and antiparasitic agents.</description><identifier>ISSN: 0366-6352</identifier><identifier>EISSN: 1336-9075</identifier><identifier>EISSN: 2585-7290</identifier><identifier>DOI: 10.1007/s11696-023-03214-3</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Antioxidants ; Assaying ; Biochemistry ; Biocompatibility ; Biotechnology ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Fungicides ; Hydrazines ; Industrial Chemistry/Chemical Engineering ; Macromolecules ; Materials Science ; Medicinal Chemistry ; Original Paper ; Serum albumin ; Synthesis ; Toxicity</subject><ispartof>Chemical papers, 2024-02, Vol.78 (3), p.1897-1913</ispartof><rights>The Author(s), under exclusive licence to the Institute of Chemistry, Slovak Academy of Sciences 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c270t-76a891c580fc64615ad2df556dd169f158531634bc3cb67a5217f5c346a0f7f3</cites><orcidid>0000-0002-5466-6567</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11696-023-03214-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11696-023-03214-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>da Silva, Maria José Cristiane</creatorcontrib><creatorcontrib>Marques, Diego Santa Clara</creatorcontrib><creatorcontrib>do Bomfim Nascimento, Pedro Henrique</creatorcontrib><creatorcontrib>Mendes, Raudiney Frankilin Vasconcelos</creatorcontrib><creatorcontrib>Buonafina-Paz, Maria Daniela Silva</creatorcontrib><creatorcontrib>Machado, Dijanah Cota</creatorcontrib><creatorcontrib>dos Santos, Fábio André Brayner</creatorcontrib><creatorcontrib>Alves, Luiz Carlos</creatorcontrib><creatorcontrib>Ximenes, Rafael Matos</creatorcontrib><creatorcontrib>Neves, Rejane Pereira</creatorcontrib><creatorcontrib>da Cruz Filho, Iranildo José</creatorcontrib><creatorcontrib>de Lima, Maria do Carmo Alves</creatorcontrib><title>Synthesis of trimethoxy-benzylidene-hydrazine-carboxamide compounds: antioxidant, antimicrobial and antiparasitic agent, evaluation of the interaction with BSA and ADMET parameters</title><title>Chemical papers</title><addtitle>Chem. Pap</addtitle><description>The search for new compounds that present low toxicity and high efficiency in the treatment of different diseases is a challenge. Therefore, this study brings as a novelty the synthesis, biological evaluation and a study of the mechanism of action in serum albumin of trimethoxy-benzylidene-hydrazine-carbothioamide compounds. The in silico results received that all compounds showed good oral availability and could be accepted as potential drug candidates. In cytotoxicity assays, the compounds promoted moderate to low toxicity against macrophage cells (82.90 ± 1.19 to 231.49 ± 1.96 µM) and Hepg2 (91.19 ± 1.09 to 254.64 ± 3.96 µM). In addition to not being hemolytic (< 10%). Regarding in vivo toxicity, they were not toxic in mice at a concentration of 2000 mg/kg (gavage). In in vitro biological assays, the compounds showed low antioxidant activity. The antifungal activity assays showed that the compounds were capable of inhibiting the growth of different strains of yeast. The compounds were also able to inhibit the growth of the parasite
L. amazonensis
in different promastigote (27.84–40.52 µM) and amastigote (29–49.71 µM) forms. Furthermore, they inhibited the growth of
T.cruzi
trypomastigotes (28.90–45.24 µM). Assays with albumin generally pleased that the compounds can be transported by these proteins without changes in the macromolecules. In this context, we can conclude that the compounds considered can promote different activities and can contribute to the arsenal of new drug candidate compounds that can act as new antifungal and antiparasitic agents.</description><subject>Antioxidants</subject><subject>Assaying</subject><subject>Biochemistry</subject><subject>Biocompatibility</subject><subject>Biotechnology</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Fungicides</subject><subject>Hydrazines</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Macromolecules</subject><subject>Materials Science</subject><subject>Medicinal Chemistry</subject><subject>Original Paper</subject><subject>Serum albumin</subject><subject>Synthesis</subject><subject>Toxicity</subject><issn>0366-6352</issn><issn>1336-9075</issn><issn>2585-7290</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9UU1vEzEQtRBIhMIf4LQSVwz-WNsJt1BKQSri0NytWX90XSV2sJ2S7e_iB9bZIHHjNJ6n996M5yH0lpIPlBD1sVAqVxITxjHhjPaYP0MLyrnEK6LEc7QgXEosuWAv0atS7gnpeyLIAv25nWIdXQmlS76rOexcHdNxwoOLj9M2WBcdHieb4TG0l4E8pCPsGt6ZtNunQ7TlUwexhnQMttX3c7MLJqchwLZ1dkb2kKGEGkwHd-5Ecw-wPUDTxXny6LoQq8tgZuh3qGP3-XY969dfflxtupND287l8hq98LAt7s3feoE2X682l9_wzc_r75frG2yYIhUrCcsVNWJJvJG9pAIss14IaW27lqdiKTiVvB8MN4NUIBhVXhjeSyBeeX6B3p1t9zn9OrhS9X065NgmarYSkhGl-r6x2JnVflxKdl7v2xUhT5oSfQpHn8PRLRw9h6N5E_GzqDRyvHP5n_V_VE9RtZZ8</recordid><startdate>20240201</startdate><enddate>20240201</enddate><creator>da Silva, Maria José Cristiane</creator><creator>Marques, Diego Santa Clara</creator><creator>do Bomfim Nascimento, Pedro Henrique</creator><creator>Mendes, Raudiney Frankilin Vasconcelos</creator><creator>Buonafina-Paz, Maria Daniela Silva</creator><creator>Machado, Dijanah Cota</creator><creator>dos Santos, Fábio André Brayner</creator><creator>Alves, Luiz Carlos</creator><creator>Ximenes, Rafael Matos</creator><creator>Neves, Rejane Pereira</creator><creator>da Cruz Filho, Iranildo José</creator><creator>de Lima, Maria do Carmo Alves</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-5466-6567</orcidid></search><sort><creationdate>20240201</creationdate><title>Synthesis of trimethoxy-benzylidene-hydrazine-carboxamide compounds: antioxidant, antimicrobial and antiparasitic agent, evaluation of the interaction with BSA and ADMET parameters</title><author>da Silva, Maria José Cristiane ; Marques, Diego Santa Clara ; do Bomfim Nascimento, Pedro Henrique ; Mendes, Raudiney Frankilin Vasconcelos ; Buonafina-Paz, Maria Daniela Silva ; Machado, Dijanah Cota ; dos Santos, Fábio André Brayner ; Alves, Luiz Carlos ; Ximenes, Rafael Matos ; Neves, Rejane Pereira ; da Cruz Filho, Iranildo José ; de Lima, Maria do Carmo Alves</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c270t-76a891c580fc64615ad2df556dd169f158531634bc3cb67a5217f5c346a0f7f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Antioxidants</topic><topic>Assaying</topic><topic>Biochemistry</topic><topic>Biocompatibility</topic><topic>Biotechnology</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Fungicides</topic><topic>Hydrazines</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Macromolecules</topic><topic>Materials Science</topic><topic>Medicinal Chemistry</topic><topic>Original Paper</topic><topic>Serum albumin</topic><topic>Synthesis</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>da Silva, Maria José Cristiane</creatorcontrib><creatorcontrib>Marques, Diego Santa Clara</creatorcontrib><creatorcontrib>do Bomfim Nascimento, Pedro Henrique</creatorcontrib><creatorcontrib>Mendes, Raudiney Frankilin Vasconcelos</creatorcontrib><creatorcontrib>Buonafina-Paz, Maria Daniela Silva</creatorcontrib><creatorcontrib>Machado, Dijanah Cota</creatorcontrib><creatorcontrib>dos Santos, Fábio André Brayner</creatorcontrib><creatorcontrib>Alves, Luiz Carlos</creatorcontrib><creatorcontrib>Ximenes, Rafael Matos</creatorcontrib><creatorcontrib>Neves, Rejane Pereira</creatorcontrib><creatorcontrib>da Cruz Filho, Iranildo José</creatorcontrib><creatorcontrib>de Lima, Maria do Carmo Alves</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical papers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>da Silva, Maria José Cristiane</au><au>Marques, Diego Santa Clara</au><au>do Bomfim Nascimento, Pedro Henrique</au><au>Mendes, Raudiney Frankilin Vasconcelos</au><au>Buonafina-Paz, Maria Daniela Silva</au><au>Machado, Dijanah Cota</au><au>dos Santos, Fábio André Brayner</au><au>Alves, Luiz Carlos</au><au>Ximenes, Rafael Matos</au><au>Neves, Rejane Pereira</au><au>da Cruz Filho, Iranildo José</au><au>de Lima, Maria do Carmo Alves</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of trimethoxy-benzylidene-hydrazine-carboxamide compounds: antioxidant, antimicrobial and antiparasitic agent, evaluation of the interaction with BSA and ADMET parameters</atitle><jtitle>Chemical papers</jtitle><stitle>Chem. Pap</stitle><date>2024-02-01</date><risdate>2024</risdate><volume>78</volume><issue>3</issue><spage>1897</spage><epage>1913</epage><pages>1897-1913</pages><issn>0366-6352</issn><eissn>1336-9075</eissn><eissn>2585-7290</eissn><abstract>The search for new compounds that present low toxicity and high efficiency in the treatment of different diseases is a challenge. Therefore, this study brings as a novelty the synthesis, biological evaluation and a study of the mechanism of action in serum albumin of trimethoxy-benzylidene-hydrazine-carbothioamide compounds. The in silico results received that all compounds showed good oral availability and could be accepted as potential drug candidates. In cytotoxicity assays, the compounds promoted moderate to low toxicity against macrophage cells (82.90 ± 1.19 to 231.49 ± 1.96 µM) and Hepg2 (91.19 ± 1.09 to 254.64 ± 3.96 µM). In addition to not being hemolytic (< 10%). Regarding in vivo toxicity, they were not toxic in mice at a concentration of 2000 mg/kg (gavage). In in vitro biological assays, the compounds showed low antioxidant activity. The antifungal activity assays showed that the compounds were capable of inhibiting the growth of different strains of yeast. The compounds were also able to inhibit the growth of the parasite
L. amazonensis
in different promastigote (27.84–40.52 µM) and amastigote (29–49.71 µM) forms. Furthermore, they inhibited the growth of
T.cruzi
trypomastigotes (28.90–45.24 µM). Assays with albumin generally pleased that the compounds can be transported by these proteins without changes in the macromolecules. In this context, we can conclude that the compounds considered can promote different activities and can contribute to the arsenal of new drug candidate compounds that can act as new antifungal and antiparasitic agents.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><doi>10.1007/s11696-023-03214-3</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0002-5466-6567</orcidid></addata></record> |
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| subjects | Antioxidants Assaying Biochemistry Biocompatibility Biotechnology Chemistry Chemistry and Materials Science Chemistry/Food Science Fungicides Hydrazines Industrial Chemistry/Chemical Engineering Macromolecules Materials Science Medicinal Chemistry Original Paper Serum albumin Synthesis Toxicity |
| title | Synthesis of trimethoxy-benzylidene-hydrazine-carboxamide compounds: antioxidant, antimicrobial and antiparasitic agent, evaluation of the interaction with BSA and ADMET parameters |
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