Contribution to the Synthesis, Characterization, Separation and Quantification of New <i>N</i>-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant Potential
The present study aimed to synthesize, characterize, and validate a separation and quantification method of new <i>N</i>-acyl thiourea derivatives (<b>1a</b>–<b>1o</b>), incorporating thiazole or pyridine nucleus in the same molecule and showing antimicrobial pote...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-10-01
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| Series: | Pharmaceutics |
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| Online Access: | https://www.mdpi.com/1999-4923/15/10/2501 |
| _version_ | 1797572585017311232 |
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| author | Roxana Roman Lucia Pintilie Diana Camelia Nuță Miron Teodor Căproiu Florea Dumitrașcu Irina Zarafu Petre Ioniță Ioana Cristina Marinaș Luminița Măruțescu Eleonora Kapronczai Simona Ardelean Carmen Limban |
| author_facet | Roxana Roman Lucia Pintilie Diana Camelia Nuță Miron Teodor Căproiu Florea Dumitrașcu Irina Zarafu Petre Ioniță Ioana Cristina Marinaș Luminița Măruțescu Eleonora Kapronczai Simona Ardelean Carmen Limban |
| author_sort | Roxana Roman |
| collection | DOAJ |
| description | The present study aimed to synthesize, characterize, and validate a separation and quantification method of new <i>N</i>-acyl thiourea derivatives (<b>1a</b>–<b>1o</b>), incorporating thiazole or pyridine nucleus in the same molecule and showing antimicrobial potential previously predicted in silico. The compounds have been physiochemically characterized by their melting points, IR, NMR and MS spectra. Among the tested compounds, <b>1a</b>, <b>1g</b>, <b>1h</b>, and <b>1o</b> were the most active against planktonic <i>Staphylococcus aureus</i> and <i>Pseudomonas aeruginosa</i>, as revealed by the minimal inhibitory concentration values, while <b>1e</b> exhibited the best anti-biofilm activity against <i>Escherichia coli</i> (showing the lowest value of minimal inhibitory concentration of biofilm development). The total antioxidant activity (TAC) assessed by the DPPH method, evidenced the highest values for the compound <b>1i,</b> followed by <b>1a</b>. A routine quality control method for the separation of highly related compounds bearing a chlorine atom on the molecular backbone (<b>1g</b>, <b>1h</b>, <b>1i</b>, <b>1j</b>, <b>1m</b>, <b>1n</b>) has been developed and validated by reversed-phase high-performance liquid chromatography (RP—HPLC), the results being satisfactory for all validation parameters recommended by the ICH guidelines (i.e., system suitability, specificity, the limits of detection and quantification, linearity, precision, accuracy and robustness) and recommending it for routine separation of these highly similar compounds. |
| first_indexed | 2024-03-10T20:57:53Z |
| format | Article |
| id | doaj.art-af1c63a5a4c0470b85a722cbd034c57c |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-03-10T20:57:53Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj.art-af1c63a5a4c0470b85a722cbd034c57c2023-11-19T17:45:25ZengMDPI AGPharmaceutics1999-49232023-10-011510250110.3390/pharmaceutics15102501Contribution to the Synthesis, Characterization, Separation and Quantification of New <i>N</i>-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant PotentialRoxana Roman0Lucia Pintilie1Diana Camelia Nuță2Miron Teodor Căproiu3Florea Dumitrașcu4Irina Zarafu5Petre Ioniță6Ioana Cristina Marinaș7Luminița Măruțescu8Eleonora Kapronczai9Simona Ardelean10Carmen Limban11Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, RomaniaNational Institute of Chemical-Pharmaceutical Research & Development, 112 Vitan Av., 031299 Bucharest, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, Romania“C. D. Nenitzescu” Institute of Organic and Supramolecular Chemistry, 202B Splaiul Independenței, 060023 Bucharest, Romania“C. D. Nenitzescu” Institute of Organic and Supramolecular Chemistry, 202B Splaiul Independenței, 060023 Bucharest, RomaniaDepartment of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta, 030018 Bucharest, RomaniaDepartment of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta, 030018 Bucharest, RomaniaResearch Institute of the University of Bucharest, University of Bucharest, 90 Panduri Road, 030018 Bucharest, RomaniaSanimed International Impex S.R.L., 087040 Calugareni, RomaniaSupramolecular Organic and Organometallic Chemistry Centre, Department of Chemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany János, 400028 Cluj-Napoca, RomaniaDepartment of Pharmaceutical Technology, Faculty of Pharmacy, “Vasile Goldiș” Western University, 86 Liviu Rebreanu, 310045 Arad, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, RomaniaThe present study aimed to synthesize, characterize, and validate a separation and quantification method of new <i>N</i>-acyl thiourea derivatives (<b>1a</b>–<b>1o</b>), incorporating thiazole or pyridine nucleus in the same molecule and showing antimicrobial potential previously predicted in silico. The compounds have been physiochemically characterized by their melting points, IR, NMR and MS spectra. Among the tested compounds, <b>1a</b>, <b>1g</b>, <b>1h</b>, and <b>1o</b> were the most active against planktonic <i>Staphylococcus aureus</i> and <i>Pseudomonas aeruginosa</i>, as revealed by the minimal inhibitory concentration values, while <b>1e</b> exhibited the best anti-biofilm activity against <i>Escherichia coli</i> (showing the lowest value of minimal inhibitory concentration of biofilm development). The total antioxidant activity (TAC) assessed by the DPPH method, evidenced the highest values for the compound <b>1i,</b> followed by <b>1a</b>. A routine quality control method for the separation of highly related compounds bearing a chlorine atom on the molecular backbone (<b>1g</b>, <b>1h</b>, <b>1i</b>, <b>1j</b>, <b>1m</b>, <b>1n</b>) has been developed and validated by reversed-phase high-performance liquid chromatography (RP—HPLC), the results being satisfactory for all validation parameters recommended by the ICH guidelines (i.e., system suitability, specificity, the limits of detection and quantification, linearity, precision, accuracy and robustness) and recommending it for routine separation of these highly similar compounds.https://www.mdpi.com/1999-4923/15/10/2501<i>N</i>-acyl thiourea derivativesantimicrobialantibiofilmantioxidant activityvalidationHPLC |
| spellingShingle | Roxana Roman Lucia Pintilie Diana Camelia Nuță Miron Teodor Căproiu Florea Dumitrașcu Irina Zarafu Petre Ioniță Ioana Cristina Marinaș Luminița Măruțescu Eleonora Kapronczai Simona Ardelean Carmen Limban Contribution to the Synthesis, Characterization, Separation and Quantification of New <i>N</i>-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant Potential Pharmaceutics <i>N</i>-acyl thiourea derivatives antimicrobial antibiofilm antioxidant activity validation HPLC |
| title | Contribution to the Synthesis, Characterization, Separation and Quantification of New <i>N</i>-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant Potential |
| title_full | Contribution to the Synthesis, Characterization, Separation and Quantification of New <i>N</i>-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant Potential |
| title_fullStr | Contribution to the Synthesis, Characterization, Separation and Quantification of New <i>N</i>-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant Potential |
| title_full_unstemmed | Contribution to the Synthesis, Characterization, Separation and Quantification of New <i>N</i>-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant Potential |
| title_short | Contribution to the Synthesis, Characterization, Separation and Quantification of New <i>N</i>-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant Potential |
| title_sort | contribution to the synthesis characterization separation and quantification of new i n i acyl thiourea derivatives with antimicrobial and antioxidant potential |
| topic | <i>N</i>-acyl thiourea derivatives antimicrobial antibiofilm antioxidant activity validation HPLC |
| url | https://www.mdpi.com/1999-4923/15/10/2501 |
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