Green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer-targeted chemo/radioisotope therapy
Abstract New derivatives of heterocyclic bearing pyrazole moiety were synthesized (eight new compounds from 2 to 9) via green synthesis methods (microwave-assisted and grinding techniques). 4,6-Diamino-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (2) shows high anti-cancer activity against...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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BMC
2023-10-01
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| Series: | BMC Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.1186/s13065-023-01053-7 |
| _version_ | 1797454019675815936 |
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| author | Kurls E. Anwer Galal H. Sayed Basma M. Essa Adli A. Selim |
| author_facet | Kurls E. Anwer Galal H. Sayed Basma M. Essa Adli A. Selim |
| author_sort | Kurls E. Anwer |
| collection | DOAJ |
| description | Abstract New derivatives of heterocyclic bearing pyrazole moiety were synthesized (eight new compounds from 2 to 9) via green synthesis methods (microwave-assisted and grinding techniques). 4,6-Diamino-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (2) shows high anti-cancer activity against both HepG2 and HCT-116 with IC50 of 9.2 ± 2.8 and 7.7 ± 1.8 µM, respectively, which referenced to 5-Fu which is showing activity of 7.86 ± 0.5 and 5.35 ± 0.3 against both HepG2 and HCT-116, respectively. The cytotoxic activity against HCT-116 and HepG2 was slightly decreased and slightly increased, respectively, by a different pyrazole moiety (compound 5). Pharmacokinetics of compound 2 was carried out using the radioiodination technique in tumour-bearing Albino mice which shows good uptake at the tumour site. The biodistribution showed high accumulation in tumour tissues with a ratio of 13.7% ID/g organ after one hour in comparison with 2.97% ID/g organ at normal muscle at the same time point. As I-131 has maximum beta and gamma energies of 606.3 and 364.5 keV, respectively, therefore the newly synthesized compound 2 may be used for chemotherapy and TRT. |
| first_indexed | 2024-03-09T15:31:12Z |
| format | Article |
| id | doaj.art-6dd66ff25aa2490998814111765c445c |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-03-09T15:31:12Z |
| publishDate | 2023-10-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-6dd66ff25aa2490998814111765c445c2023-11-26T12:13:42ZengBMCBMC Chemistry2661-801X2023-10-0117111110.1186/s13065-023-01053-7Green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer-targeted chemo/radioisotope therapyKurls E. Anwer0Galal H. Sayed1Basma M. Essa2Adli A. Selim3Heterocyclic Synthesis Lab, Chemistry Department, Faculty of Science, Ain Shams UniversityHeterocyclic Synthesis Lab, Chemistry Department, Faculty of Science, Ain Shams UniversityRadioactive Isotopes and Generators Department, Egyptian Atomic Energy AuthorityLabelled Compounds Department, Egyptian Atomic Energy AuthorityAbstract New derivatives of heterocyclic bearing pyrazole moiety were synthesized (eight new compounds from 2 to 9) via green synthesis methods (microwave-assisted and grinding techniques). 4,6-Diamino-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (2) shows high anti-cancer activity against both HepG2 and HCT-116 with IC50 of 9.2 ± 2.8 and 7.7 ± 1.8 µM, respectively, which referenced to 5-Fu which is showing activity of 7.86 ± 0.5 and 5.35 ± 0.3 against both HepG2 and HCT-116, respectively. The cytotoxic activity against HCT-116 and HepG2 was slightly decreased and slightly increased, respectively, by a different pyrazole moiety (compound 5). Pharmacokinetics of compound 2 was carried out using the radioiodination technique in tumour-bearing Albino mice which shows good uptake at the tumour site. The biodistribution showed high accumulation in tumour tissues with a ratio of 13.7% ID/g organ after one hour in comparison with 2.97% ID/g organ at normal muscle at the same time point. As I-131 has maximum beta and gamma energies of 606.3 and 364.5 keV, respectively, therefore the newly synthesized compound 2 may be used for chemotherapy and TRT.https://doi.org/10.1186/s13065-023-01053-7MicrowaveGrindingPyrazoleRadioiodinationDual cancer therapy |
| spellingShingle | Kurls E. Anwer Galal H. Sayed Basma M. Essa Adli A. Selim Green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer-targeted chemo/radioisotope therapy BMC Chemistry Microwave Grinding Pyrazole Radioiodination Dual cancer therapy |
| title | Green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer-targeted chemo/radioisotope therapy |
| title_full | Green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer-targeted chemo/radioisotope therapy |
| title_fullStr | Green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer-targeted chemo/radioisotope therapy |
| title_full_unstemmed | Green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer-targeted chemo/radioisotope therapy |
| title_short | Green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer-targeted chemo/radioisotope therapy |
| title_sort | green synthesis of highly functionalized heterocyclic bearing pyrazole moiety for cancer targeted chemo radioisotope therapy |
| topic | Microwave Grinding Pyrazole Radioiodination Dual cancer therapy |
| url | https://doi.org/10.1186/s13065-023-01053-7 |
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