Ir para o conteúdo principal Ir para o menu de navegação principal Ir para o rodapé
Scientific Electronic Archives
Ciências da Saúde
DOI: 10.36560/17320241919
Enviado: 2024-03-17
Publicado: 2024-04-30

Preliminary evaluation of the interaction with Albumin/DNA and in vitro evaluation of the antioxidant properties promoted by thiosemicarbazones and thiazole compounds

Federal University of Pernambuco
Federal University of Pernambuco
Federal University of Pernambuco
Federal University of Pernambuco
Federal University of Pernambuco
Federal University of Pernambuco
Federal University of Pernambuco
antioxidante, macromoléculas, potencial biológico

Resumo

Tiosemicarbazonas e tiazóis são conhecidos por suas diversas atividades biológicas. Este estudo introduziu duas séries de moléculas, 4-(3-(4-nitrofenil)-4-feniltiazol-2(3H)-ilideno)-hidrazina)-metil)-fenol e 4-(3-(4-clorofenil)- 4-feniltiazol-2(3H)-ilideno)-hidrazina)-metil)-fenol, que apresentam potencial biológico como agentes antioxidantes. O estudo também avaliou a interação desses compostos com diversas macromoléculas de HSA/DNA. Os resultados da atividade antioxidante mostraram que os tiazóis no ensaio DPPH exibiram valores de IC50 variando de 439,4 a 691,67 µM. No ensaio ABTS, as tiosemicarbazonas exibiram atividade significativa, variando de 39,19 a 50,03 µM. Os ensaios de interação foram realizados com albumina sérica humana (HSA) e DNA. Todos os compostos foram capazes de interagir tanto com DNA (interação baixa a moderada) quanto com HSA (interação moderada a alta).

Referências

  1. ALMEIDA LC ET AL. 2021. DNA damaging agents and DNA repair: From carcinogenesis to cancer therapy. Cancer Genet 252 6-24. https://doi.org/10.1016/j.cancergen.2020.12.002. CEZE L ET AL. 2019.Molecular digital data storage using DNA. Nat Rev Genet 20(8) 456-466. https://doi.org/10.1038/s41576-019-0125-3.
  2. ALVES JEF ET AL. 2021. Novel indole-thiazole and indole-thiazolidinone derivatives as DNA groove binders. Int J Biol Macromol 170 622-635. https://doi.org/10.1016/j.ijbiomac.2020.12.153.
  3. AMADO AM ET AL. 2017. Borissevitch. Acridine orange interaction with DNA: Effect of ionic strength. Biochim. Biophys. Acta Gen Subj 1861(4) 900-909. https://doi.org/10.1016/j.bbagen.2017.01.023.
  4. BASCHIERI A & AMORATI R. 2021. Methods to determine chain-breaking antioxidant activity of nanomaterials beyond DPPH•. A review. Antioxidants, 10(10) 1551. https://doi.org/10.3390/antiox10101551.
  5. BINGUL M ET AL. 2019. Synthesis, photophysical and antioxidant properties of carbazole-based bis-thiosemicarbazones. Res Chem Intermed 45(9) 4487-4499. https://doi.org/10.1007/s11164-019-03844-x
  6. GERONIKAKI AA ET AL. 2013. Thiazoles and thiazolidinones as antioxidants. Curr Med Chem 20 (36) 4460-4480. https://doi.org/10.2174/09298673113209990143.
  7. GUZAEV M. Comparison of nucleic acid gel stains cell permeability, safety, and sensitivity of ethidium bromide alternatives. Online at https://biotium. com/wp-content/uploads/2017/02/Gel-Stains-Comparison. pdf, 2017.
  8. HANIFA B ET AL. 2022. Three isomeric 4-[(n-bromophenyl) carbamoyl] butanoic acids (n= 2, 3, and 4) as DNA intercalator: Synthesis, physicochemical characterization, antimicrobial activity, antioxidant potential, and in silico study. J. Mol. Struct. 1262: 133033. https://doi.org/10.1016/j.molstruc.2021.133033.
  9. HOOGENBOEZEM EN & DUVALL CL. 2018. Harnessing albumin as a carrier for cancer therapies. Adv Drug Deliv Rev 130 73-89. https://doi.org/10.1016/j.addr.2018.07.011.
  10. LAKOWICZ JR. 2006. Principles of Fluorescence Spectroscopy, third ed., Springer. https://doi.org/10.1007/978-0-387-46312-4_2.
  11. JACOB IT Et Al. 2023. Interaction study with DNA/HSA, anti-topoisomerase IIα, cytotoxicity and in vitro antiproliferative evaluations and molecular docking of indole-thiosemicarbazone compounds. Int. J. Biol. Macromol. 234:123606.https://doi.org/10.1016/j.ijbiomac.2023.123606.
  12. MADSEN M & GOTHELF KV 2019. Chemistries for DNA nanotechnology. Chem Rev 119(10) 6384-6458. https://doi.org/10.1021/acs.chemrev.8b00570.
  13. MARC G ET AL. 2021. Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening. Antioxidants, 10(11) 1707. https://doi.org/10.3390/antiox10111707.
  14. MENG Y ET AL. 2012. Interaction study on DNA, single-wall carbon nanotubes and acridine Orange. Mater Sci Eng B 177(11) 887-891. https://doi.org/10.1016/j.mseb.2012.03.055.
  15. MIC M ET AL. 2021. Synthesis and molecular interaction study of a diphenolic hidrazinyl-thiazole compound with strong antioxidant and antiradical activity with HSA. J Mol Struct 1244 131278. https://doi.org/10.1016/j.molstruc.2021.131278.
  16. MOHARRAM HA & YOUSSEF MM. 2014. Methods for determining the antioxidant activity: a review. Alex J Fd Sci & Technol 11(1) 31-42.
  17. OLIVEIRA FILHO GB ET AL. 2017. Structural design, synthesis and pharmacological evaluation of thiazoles against Trypanosoma cruzi. Eur J Med Chem 141 346-361. https://doi.org/10.1016/j.ejmech.2017.09.047.
  18. OLIVEIRA JF ET AL. 2015. Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities. Eur J Med Chem 104 148-156. https://doi.org/10.1016/j.ejmech.2015.09.036.
  19. PARAMESWARAN P ET AL. 2021. Bacterial rRNA A-site recognition by DAPI: Signatures of intercalative binding. Biophys Chem 274 106589. https://doi.org/10.1016/j.bpc.2021.106589.
  20. PETROU A ET AL.2021. Thiazole ring—A biologically active scaffold. Molecules 26(11) (2021), 3166. https://doi.org/10.3390/molecules26113166.
  21. PRICOPIE A-I ET AL. 2020. Novel 2, 4-disubstituted-1, 3-thiazole derivatives: synthesis, anti-candida activity evaluation and interaction with bovine serum albumin. Molecules 25(5) 1079. https://doi.org/10.3390/molecules25051079.
  22. RAHMAN Y ET AL. 2017. Unravelling the interaction of pirenzepine, a gastrointestinal disorder drug, with calf thymus DNA: An in vitro and molecular modelling study. Arch Biochem Biophys 625 1-12. https://doi.org/10.1016/j.abb.2017.05.014.
  23. RIBEIRO AG ET AL. 2019. Novel 4-quinoline-thiosemicarbazone derivatives: Synthesis, antiproliferative activity, in vitro and in silico biomacromolecule interaction studies and topoisomerase inhibition. Eur. J. Med. Chem. 182: 111592. https://doi.org/10.1016/j.ejmech.2019.111592.
  24. RIBEIRO AG ETAL. 2021. Albumin roles in developing anticancer compounds. Med Chem Res 30(8) 1469-1495. https://doi.org/10.1007/s00044-021-02748-z.
  25. SALAR U ET AL. 2019. New hybrid scaffolds based on hydrazinyl thiazole substituted coumarin; As novel leads of dual potential; in vitro α-amylase inhibitory and antioxidant (DPPH and ABTS radical scavenging) activities. Med Chem 15(1) 87-101. https://doi.org/10.2174/1573406414666180903162243.
  26. SAYED M ET AL. 2021. Unraveling the salt induced modulation in the photophysical behavior of acridine orange dye on its interaction with natural DNA. J Mol Liq 336 116146. https://doi.org/10.1016/j.molliq.2021.116146.
  27. SHAFIEI M ET AL. 2020. History of the development of antifungal azoles: A review on structures, SAR, and mechanism of action. Bioorg Chem 104: 104240. https://doi.org/10.1016/j.bioorg.2020.104240.
  28. SHARMA CS ET AL. 2009. Synthesis, anticonvulsant activity and in silico study of some novel amino acids incorporated bicyclo compounds. S J Pharm Sci 2(2) 42-47. https://doi.org/10.3329/sjps.v2i2.2607.
  29. SIDDIQUI EJ ET AL. 2019. Thiosemicarbazone complexes as versatile medicinal chemistry agents: a review. J drug deliv ther 9(3) 689-703. https://doi.org/10.22270/jddt.v9i3.2888.
  30. SILVA FILHO FA ET AL. 2019. Topoisomerase inhibition and albumin interaction studies of acridine thiosemicarbazone derivatives. Int J Biol Macromol 138 582-589. https://doi.org/10.1016/j.ijbiomac.2019.07.097.
  31. SOUSA G ET AL. 2022. Synthesis and Evaluation of Antiproliferative Activity, Topoisomerase IIα Inhibition, DNA Binding and Non-Clinical Toxicity of New Acridine–Thiosemicarbazone Derivatives. Pharmaceuticals 15(9): 1098. https://doi.org/10.3390/ph15091098.
  32. SZYMASZEK P ET AL. 2022. Molecular interactions of bovine serum albumin (BSA) with pyridine derivatives as candidates for non-covalent protein probes: a spectroscopic investigation. J Mol Liq 347 118262. https://doi.org/10.1016/j.molliq.2021.118262.
  33. WANG W ET AL. 2021. Interactions of isoorientin and its Semi-synthetic analogs with human serum albumin. Bioorg Chem 116 105319. https://doi.org/10.1016/j.bioorg.2021.105319.
  34. YANG L ET AL. 2020. Antioxidant properties of camphene-based thiosemicarbazones: Experimental and theoretical evaluation. Molecules, 25(5) 1192. https://doi.org/10.3390/molecules25051192.
  35. YILDIZ M ET AL. 2022. Dimethoxyindoles based thiosemicarbazones as multi-target agents; synthesis, crystal interactions, biological activity and molecular modeling. Bioorg Chem 120 105647. https://doi.org/10.1016/j.bioorg.2022.105647.
  36. YOUSEF TA & EL-REASH GMA. 2020. Synthesis, and biological evaluation of complexes based on thiosemicarbazone ligand. J Mol Struct 1201 127180. https://doi.org/10.1016/j.molstruc.2019.127180.

Como Citar

Nascimento, P. H. do B. ., Santos, K. L. dos ., Pereira, . A. V. L. A. ., Santos, J. C. B. dos ., Santa Clara Marques, D., Cruz Filho, I. J. da ., & Lima, M. do C. A. de . (2024). Preliminary evaluation of the interaction with Albumin/DNA and in vitro evaluation of the antioxidant properties promoted by thiosemicarbazones and thiazole compounds. Scientific Electronic Archives, 17(3). https://doi.org/10.36560/17320241919