Synthesis, Characterization, Cytotoxicity Analysis and Evaluation of Novel Heterocyclic Derivatives of Benzamidine against Periodontal Disease Triggering Bacteria
Periodontal disease (PD) is multifactorial oral disease that damages tooth-supporting tissue. PD treatment includes proper oral hygiene, deep cleaning, antibiotics therapy, and surgery. Despite the availability of basic treatments, some of these are rendered undesirable in PD treatment due to side e...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Antibiotics |
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| Online Access: | https://www.mdpi.com/2079-6382/12/2/306 |
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| author | Ramasamy Kavitha Mohammad Auwal Sa’ad Shivkanya Fuloria Neeraj Kumar Fuloria Manickam Ravichandran Pattabhiraman Lalitha |
| author_facet | Ramasamy Kavitha Mohammad Auwal Sa’ad Shivkanya Fuloria Neeraj Kumar Fuloria Manickam Ravichandran Pattabhiraman Lalitha |
| author_sort | Ramasamy Kavitha |
| collection | DOAJ |
| description | Periodontal disease (PD) is multifactorial oral disease that damages tooth-supporting tissue. PD treatment includes proper oral hygiene, deep cleaning, antibiotics therapy, and surgery. Despite the availability of basic treatments, some of these are rendered undesirable in PD treatment due to side effects and expense. Therefore, the aim of the present study is to develop novel molecules to combat the PD triggering pathogens. The study involved the synthesis of 4-((5-(substituted-phenyl)-1,3,4-oxadiazol-2-yl)methoxy)benzamidine (<b>5a-e</b>), by condensation of 2-(4-carbamimidoylphenoxy)acetohydrazide (<b>3</b>) with different aromatic acids; and synthesis of 4-((4-(substituted benzylideneamino)-4H-1,2,4-triazol-3-yl)methoxy)benzamidine <i>(</i><b>6a-b</b>) by treatment of <b>compound 3</b> with CS<sub>2</sub> followed by hydrazination and a Schiff reaction with different aromatic aldehydes. Synthesized <b>compounds</b> were characterized based on the NMR, FTIR, and mass spectrometric data. To assess the effectiveness of the newly synthesized <b>compound</b> in PD, new <b>compounds</b> were subjected to antimicrobial evaluation against <i>P. gingivalis</i> and <i>E. coli</i> using the micro-broth dilution method. Synthesized <b>compounds</b> were also subjected to cytotoxicity evaluation against HEK-293 cells using an MTT assay. The present study revealed the successful synthesis of heterocyclic derivatives of benzamidine with significant inhibitory potential against <i>P. gingivalis</i> and <i>E. coli</i>. Synthesized <b>compounds</b> exhibited minimal to the absence of cytotoxicity. Significant antimicrobial potential and least/no cytotoxicity of new heterocyclic analogs of benzamidine against PD-triggering bacteria supports their potential application in PD treatment. |
| first_indexed | 2024-03-11T09:15:19Z |
| format | Article |
| id | doaj.art-c0e918a6156f423281b2bec16a06a7b3 |
| institution | Directory Open Access Journal |
| issn | 2079-6382 |
| language | English |
| last_indexed | 2024-03-11T09:15:19Z |
| publishDate | 2023-02-01 |
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| series | Antibiotics |
| spelling | doaj.art-c0e918a6156f423281b2bec16a06a7b32023-11-16T18:43:10ZengMDPI AGAntibiotics2079-63822023-02-0112230610.3390/antibiotics12020306Synthesis, Characterization, Cytotoxicity Analysis and Evaluation of Novel Heterocyclic Derivatives of Benzamidine against Periodontal Disease Triggering BacteriaRamasamy Kavitha0Mohammad Auwal Sa’ad1Shivkanya Fuloria2Neeraj Kumar Fuloria3Manickam Ravichandran4Pattabhiraman Lalitha5Department of Biotechnology, Faculty of Applied Science, AIMST University, Bedong 08100, Kedah, MalaysiaDepartment of Biotechnology, Faculty of Applied Science, AIMST University, Bedong 08100, Kedah, MalaysiaCentre of Excellence for Biomaterials Engineering, Faculty of Pharmacy, AIMST University, Bedong 08100, Kedah, MalaysiaCentre of Excellence for Biomaterials Engineering, Faculty of Pharmacy, AIMST University, Bedong 08100, Kedah, MalaysiaDepartment of Biotechnology, Faculty of Applied Science, AIMST University, Bedong 08100, Kedah, MalaysiaDepartment of Biochemistry, Faculty of Medicine, AIMST University, Bedong 08100, Kedah, MalaysiaPeriodontal disease (PD) is multifactorial oral disease that damages tooth-supporting tissue. PD treatment includes proper oral hygiene, deep cleaning, antibiotics therapy, and surgery. Despite the availability of basic treatments, some of these are rendered undesirable in PD treatment due to side effects and expense. Therefore, the aim of the present study is to develop novel molecules to combat the PD triggering pathogens. The study involved the synthesis of 4-((5-(substituted-phenyl)-1,3,4-oxadiazol-2-yl)methoxy)benzamidine (<b>5a-e</b>), by condensation of 2-(4-carbamimidoylphenoxy)acetohydrazide (<b>3</b>) with different aromatic acids; and synthesis of 4-((4-(substituted benzylideneamino)-4H-1,2,4-triazol-3-yl)methoxy)benzamidine <i>(</i><b>6a-b</b>) by treatment of <b>compound 3</b> with CS<sub>2</sub> followed by hydrazination and a Schiff reaction with different aromatic aldehydes. Synthesized <b>compounds</b> were characterized based on the NMR, FTIR, and mass spectrometric data. To assess the effectiveness of the newly synthesized <b>compound</b> in PD, new <b>compounds</b> were subjected to antimicrobial evaluation against <i>P. gingivalis</i> and <i>E. coli</i> using the micro-broth dilution method. Synthesized <b>compounds</b> were also subjected to cytotoxicity evaluation against HEK-293 cells using an MTT assay. The present study revealed the successful synthesis of heterocyclic derivatives of benzamidine with significant inhibitory potential against <i>P. gingivalis</i> and <i>E. coli</i>. Synthesized <b>compounds</b> exhibited minimal to the absence of cytotoxicity. Significant antimicrobial potential and least/no cytotoxicity of new heterocyclic analogs of benzamidine against PD-triggering bacteria supports their potential application in PD treatment.https://www.mdpi.com/2079-6382/12/2/306periodontal diseaseperiodontitisheterocyclicsantibacterialbenzamidine |
| spellingShingle | Ramasamy Kavitha Mohammad Auwal Sa’ad Shivkanya Fuloria Neeraj Kumar Fuloria Manickam Ravichandran Pattabhiraman Lalitha Synthesis, Characterization, Cytotoxicity Analysis and Evaluation of Novel Heterocyclic Derivatives of Benzamidine against Periodontal Disease Triggering Bacteria Antibiotics periodontal disease periodontitis heterocyclics antibacterial benzamidine |
| title | Synthesis, Characterization, Cytotoxicity Analysis and Evaluation of Novel Heterocyclic Derivatives of Benzamidine against Periodontal Disease Triggering Bacteria |
| title_full | Synthesis, Characterization, Cytotoxicity Analysis and Evaluation of Novel Heterocyclic Derivatives of Benzamidine against Periodontal Disease Triggering Bacteria |
| title_fullStr | Synthesis, Characterization, Cytotoxicity Analysis and Evaluation of Novel Heterocyclic Derivatives of Benzamidine against Periodontal Disease Triggering Bacteria |
| title_full_unstemmed | Synthesis, Characterization, Cytotoxicity Analysis and Evaluation of Novel Heterocyclic Derivatives of Benzamidine against Periodontal Disease Triggering Bacteria |
| title_short | Synthesis, Characterization, Cytotoxicity Analysis and Evaluation of Novel Heterocyclic Derivatives of Benzamidine against Periodontal Disease Triggering Bacteria |
| title_sort | synthesis characterization cytotoxicity analysis and evaluation of novel heterocyclic derivatives of benzamidine against periodontal disease triggering bacteria |
| topic | periodontal disease periodontitis heterocyclics antibacterial benzamidine |
| url | https://www.mdpi.com/2079-6382/12/2/306 |
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