New formyl indole derivatives based on thiobarbituric acid and their nano-formulations; synthesis, characterization, parasitology and histopathology investigations
Abstract New formyl indole derivatives based on thiobarbituric acid were designed for targeting parasitological applications. The new compounds (5-((1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (3a), and 5-((1-benzyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H...
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Nature Portfolio
2025-01-01
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| Online Access: | https://doi.org/10.1038/s41598-024-81683-6 |
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| author | Walaa Ali Abdelhalim Ahmed R. Rabee Saied M. Soliman Mohamed Hagar Esraa A. Moneer Basant A. Bakr Assem Barakat Matti Haukka Hanaa A. Rasheed |
| author_facet | Walaa Ali Abdelhalim Ahmed R. Rabee Saied M. Soliman Mohamed Hagar Esraa A. Moneer Basant A. Bakr Assem Barakat Matti Haukka Hanaa A. Rasheed |
| author_sort | Walaa Ali Abdelhalim |
| collection | DOAJ |
| description | Abstract New formyl indole derivatives based on thiobarbituric acid were designed for targeting parasitological applications. The new compounds (5-((1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (3a), and 5-((1-benzyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (3b) were synthesized as thioxodihydropyrimidine derivatives via aldol condensation reaction. The structures of the synthesized compounds were confirmed based on their spectral data via FT-IR, 1H and 13C NMR spectral characterization. In addition, the structure of 3a is confirmed using X-ray crystallography. The synthesized compounds were prepared in nm scale via chitosan as a matrix, and their size was measured via scanning electronic microscope. Interestingly, the newly synthesized nano formulations show higher positive zeta potential (mV) values + 29.6 and + 26.1 for compounds NP-3a, and NP-3b; respectively. These compounds were tested for their parasitological activity. The results revealed that 3b had a great activity against cryptosporidium infection. Moreover, the nano formulation of compound 3b showed a significant reduction percent of oocyst count of cryptosporidium infected mice representing 66%. Furthermore, these compounds were screened by in-vitro hemolytic activity assay (IC50) values (cytotoxicity on RBCs) to assess their cytotoxic potentials and safety profiles. |
| format | Article |
| id | doaj-art-bd597c92e3764d5ca4f4a92cf821fdc1 |
| institution | Kabale University |
| issn | 2045-2322 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj-art-bd597c92e3764d5ca4f4a92cf821fdc12025-01-05T12:16:54ZengNature PortfolioScientific Reports2045-23222025-01-0115111210.1038/s41598-024-81683-6New formyl indole derivatives based on thiobarbituric acid and their nano-formulations; synthesis, characterization, parasitology and histopathology investigationsWalaa Ali Abdelhalim0Ahmed R. Rabee1Saied M. Soliman2Mohamed Hagar3Esraa A. Moneer4Basant A. Bakr5Assem Barakat6Matti Haukka7Hanaa A. Rasheed8Chemistry Department, Faculty of Science, Alexandria UniversityChemistry Department, Faculty of Science, Alexandria UniversityChemistry Department, Faculty of Science, Alexandria UniversityChemistry Department, Faculty of Science, Alexandria UniversityDepartment of Medical Laboratory Technology, Faculty of Applied Health Sciences Technology, Pharos University in AlexandriaDepartment of Zoology, Faculty of Science, Alexandria UniversityDepartment of Chemistry, College of Science, King Saud UniversityDepartment of Chemistry, University of JyväskyläChemistry Department, Faculty of Science, Alexandria UniversityAbstract New formyl indole derivatives based on thiobarbituric acid were designed for targeting parasitological applications. The new compounds (5-((1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (3a), and 5-((1-benzyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (3b) were synthesized as thioxodihydropyrimidine derivatives via aldol condensation reaction. The structures of the synthesized compounds were confirmed based on their spectral data via FT-IR, 1H and 13C NMR spectral characterization. In addition, the structure of 3a is confirmed using X-ray crystallography. The synthesized compounds were prepared in nm scale via chitosan as a matrix, and their size was measured via scanning electronic microscope. Interestingly, the newly synthesized nano formulations show higher positive zeta potential (mV) values + 29.6 and + 26.1 for compounds NP-3a, and NP-3b; respectively. These compounds were tested for their parasitological activity. The results revealed that 3b had a great activity against cryptosporidium infection. Moreover, the nano formulation of compound 3b showed a significant reduction percent of oocyst count of cryptosporidium infected mice representing 66%. Furthermore, these compounds were screened by in-vitro hemolytic activity assay (IC50) values (cytotoxicity on RBCs) to assess their cytotoxic potentials and safety profiles.https://doi.org/10.1038/s41598-024-81683-6Thiobarbituric acidAldol condensationNano formulationParasitologyHistopathology investigation |
| spellingShingle | Walaa Ali Abdelhalim Ahmed R. Rabee Saied M. Soliman Mohamed Hagar Esraa A. Moneer Basant A. Bakr Assem Barakat Matti Haukka Hanaa A. Rasheed New formyl indole derivatives based on thiobarbituric acid and their nano-formulations; synthesis, characterization, parasitology and histopathology investigations Scientific Reports Thiobarbituric acid Aldol condensation Nano formulation Parasitology Histopathology investigation |
| title | New formyl indole derivatives based on thiobarbituric acid and their nano-formulations; synthesis, characterization, parasitology and histopathology investigations |
| title_full | New formyl indole derivatives based on thiobarbituric acid and their nano-formulations; synthesis, characterization, parasitology and histopathology investigations |
| title_fullStr | New formyl indole derivatives based on thiobarbituric acid and their nano-formulations; synthesis, characterization, parasitology and histopathology investigations |
| title_full_unstemmed | New formyl indole derivatives based on thiobarbituric acid and their nano-formulations; synthesis, characterization, parasitology and histopathology investigations |
| title_short | New formyl indole derivatives based on thiobarbituric acid and their nano-formulations; synthesis, characterization, parasitology and histopathology investigations |
| title_sort | new formyl indole derivatives based on thiobarbituric acid and their nano formulations synthesis characterization parasitology and histopathology investigations |
| topic | Thiobarbituric acid Aldol condensation Nano formulation Parasitology Histopathology investigation |
| url | https://doi.org/10.1038/s41598-024-81683-6 |
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