Skip to content
2000
Volume 22, Issue 5
  • ISSN: 1570-1786
  • E-ISSN: 1875-6255

Abstract

Metal ion sensing properties of thiophene based hydrazone () have been studied using UV-Vis and DFT studies. In comparison to heavy transition metal ions, especially binds to Cu2+ and Fe3+ ions. The lower limit of detection (LOD) of the compound is 6 μM and 9 μM for Cu2+ and Fe3+ ions respectively. The binding constant for the compound: Cu2+ and compound: Fe3+ complexes are obtained as 3 x 104 M-1 and 4.5 x 103 M-1 respectively using the Benesi-Hildebrand plot. The stoichiometry ratio for compound: Cu2+ complex 2:1 is obtained using Job's plot. The complex is more stable than the free compound and is validated through computation of HOMO-LUMO orbital energy and band gap of compound and complex using density functional theory. exhibits antioxidant properties against the DPPH radical with IC: 23 μM. The possible mechanism of quenching of radical is suggested through single electron transfer followed by a proton transfer mechanism. From the above studies, it can be concluded that the hydrazone detects both Cu2+ and Fe3+ ions up to micromolar concentration and quenches the DPPH radical with IC comparable to vitamin E.

© 2025 Bentham Science Publishers
Loading

Article metrics loading...

/content/journals/loc/10.2174/0115701786337428241125091159
2025-01-07
2025-08-24

  • From This Site

    /content/journals/loc/10.2174/0115701786337428241125091159
    dcterms_title,dcterms_subject,pub_keyword
    -contentType:Contributor -contentType:Concept -contentType:Institution
    10
    5
Loading full text...

Full text loading...

References

  1. ZhouZ. ChenS. HuangY. GuB. LiJ. WuC. YinP. ZhangY. LiH. Biosens. Bioelectron.202219811385810.1016/j.bios.2021.113858 34871835
     [Google Scholar]
  2. RamosJ.C. SerranoG. RosalesL. MurilloR. MagañaY. BernalJ.P. GuzmánF. AzuaraL. Eur. J. Inorg. Chem.20172017121728173610.1002/ejic.201601199
     [Google Scholar]
  3. Ruiz-AzuaraL. Bravo-GómezM.E. Curr. Med. Chem.201017313606361510.2174/092986710793213751 20846116
     [Google Scholar]
  4. SaleemM. LeeK.H. RSC Advances2015588721507228710.1039/C5RA11388A
     [Google Scholar]
  5. GoshishtM.K. PatraG.K. TripathiN. Mater. Adv.2022326122669
     [Google Scholar]
  6. NigamA. KumarM. Sens. Actuators A Phys.2021330112879
     [Google Scholar]
  7. StrausakD. MercerJ.F.B. DieterH.H. StremmelW. MulthaupG. Brain Res. Bull.200155217518510.1016/S0361‑9230(01)00454‑3 11470313
     [Google Scholar]
  8. KlompL.W.J. WijmengaC. KampingaH.H. SluisB. PLoS One20149e9240810.1371/journal.pone.0092408 24691167
     [Google Scholar]
  9. PalA. SiottoM. PrasadR. SquittiR. J. Alzheimers Dis.201544234335410.3233/JAD‑141194 25261447
     [Google Scholar]
  10. MadsenE. GitlinJ.D. Annu. Rev. Neurosci.200730131733710.1146/annurev.neuro.30.051606.094232 17367269
     [Google Scholar]
  11. EskiciG. AxelsenP.H. Biochemistry201251326289631110.1021/bi3006169 22708607
     [Google Scholar]
  12. RasheedT. Sci. Total Environ.2018640174193 29859435
     [Google Scholar]
  13. FuY. FanC. LiuG. PuS. Sens. Actuators B Chem.201723929530310.1016/j.snb.2016.08.020
     [Google Scholar]
  14. IlanchelianM. RajendranS.P. Spectrochim. Acta A Mol. Biomol. Spectrosc.2019214170176 30776718
     [Google Scholar]
  15. MéndezA.A.E. ArgüelloJ.M. SonciniF.C. ChecaS.K. J. Biol. Chem.2024300310571010.1016/j.jbc.2024.105710 38309504
     [Google Scholar]
  16. CobineP.A. BradyD.C. Mol. Cell202282101786178710.1016/j.molcel.2022.05.001 35594843
     [Google Scholar]
  17. CorselloS.M. LutsenkoS. KanarekN. SantagataS. GolubT.R. Science202237512541261 35298263
     [Google Scholar]
  18. LakovidisI. DelimarisI. PiperakisS.M. Mol. Biol. Int.2011201159452910.4061/2011/594529 22091409
     [Google Scholar]
  19. HuY. QianY. WeiJ. JinT. KongX. CaoH. DingK. Front. Pharmacol.202112752825 34887757
     [Google Scholar]
  20. MoQ. DengJ. LiuY. HuangG. LiZ. YuP. GouY. YangF. Eur. J. Med. Chem.2018156368380 30015073
     [Google Scholar]
  21. KanchanadeviS. FronczekF.R. DavidC.I. NandhakumarR. MahalingamV. Inorg. Chim. Acta2021526120536
     [Google Scholar]
  22. SharmaS. GhoshK.S. Spectrochim. Acta A Mol. Biomol. Spectrosc.2021254119610 33684850
     [Google Scholar]
  23. SrishtiK. NegiO. HotaP.K. J. Fluoresc.20243410.1007/s10895‑024‑03587‑y
     [Google Scholar]
  24. ParrZ.S. NielsenC.B. Mater. Chem. Front.2020423702377
     [Google Scholar]
  25. YasmeenS. SumrraS.H. AkramM.S. ChohanZ.H. J. Enzyme Inhib. Med. Chem.2017321106112 27766891
     [Google Scholar]
  26. ZafarW. SumrraS.H. HassanA.U. ChohanZ.H. J. Coord. Chem.202376546580
     [Google Scholar]
  27. SumrraS.H. ZafarW. ImranM. ChohanZ.H. J. Coord. Chem.202275293334
     [Google Scholar]
  28. GuoZ. NiuQ. LiT. SunT. ChiH. Spectrochim. Acta A Mol. Biomol. Spectrosc.201921397103 30684885
     [Google Scholar]
  29. LiuY.L. YangL. LiP. LiS.J. LiL. PangX.X. YeF. FuY. Spectrochim. Acta A Mol. Biomol. Spectrosc.202022711754010.1016/j.saa.2019.117540 31680040
     [Google Scholar]
  30. ChenZ. ZhouH. GuW. LiuT. XieZ. YangL. MaL.J. J. Photochem. Photobiol. Chem.201937951010.1016/j.jphotochem.2019.05.007
     [Google Scholar]
  31. MohammadiA. GhasemiZ. Spectrochim. Acta A Mol. Biomol. Spectrosc.202022811773010.1016/j.saa.2019.117730 31718972
     [Google Scholar]
  32. PadhanS.K. MurmuN. MahapatraS. DalaiM.K. SahuS.N. Mater. Chem. Front.20193112437244710.1039/C9QM00394K
     [Google Scholar]
  33. ChenZ.E. QiQ. ZhangH. Spectrochim. Acta A Mol. Biomol. Spectrosc.202023811838410.1016/j.saa.2020.118384 32445979
     [Google Scholar]
  34. KumarN. KumarJ. HotaP.K. J. Fluoresc.20172751729173810.1007/s10895‑017‑2111‑5 28477137
     [Google Scholar]
  35. SinghA.K. HotaP.K. Res. Chem. Intermed.2005311-38510110.1163/1568567053146832
     [Google Scholar]
  36. KumarN. HotaP.K. Kumar.J. Lett. Org. Chem.201815647948410.2174/1570178614666171129161030
     [Google Scholar]
  37. HotaP.K. SinghA.K. J. Fluoresc.2018281212810.1007/s10895‑014‑1430‑z 25063230
     [Google Scholar]
  38. KumarJ. KumarN. HotaP.K. Indian J. Chem. B201857301307
     [Google Scholar]
  39. GusainA. KumarN. KumarJ. PandeyG. HotaP.K. J. Fluoresc.2021311516110.1007/s10895‑020‑02629‑5 33057974
     [Google Scholar]
  40. KumarN. GusainA. KumarJ. SinghR. HotaP.K. J. Lumin.202123011772510.1016/j.jlumin.2020.117725
     [Google Scholar]
  41. KumarJ. KumarN. SatiN. HotaP.K. New J. Chem.202044218960897010.1039/D0NJ01317J
     [Google Scholar]
  42. HuongD.Q. NamP.C. DuongT. J. Mol. Struct.2023128513553710.1016/j.molstruc.2023.135537
     [Google Scholar]
  43. SpiegelM. Sroka.Z. Theor. Chem. Acc.2022141116110.1007/s00214‑022‑02922‑5
     [Google Scholar]
  44. AhmedS.A. KusumaningsihT. J. Mol. Struct.2024130213749810.1016/j.molstruc.2024.137498
     [Google Scholar]
  45. PrasetyoW.E. AdmojoB.T. KusumaningsihT. MarliyanaS.D. WibowoF.R. FirdausM. Free Radic. Res.202357317419410.1080/10715762.2023.2225731 37315300
     [Google Scholar]
  46. MasuriS. CabidduM.G. CadoniE. PivettaT. New J. Chem.20214524107491076010.1039/D1NJ01232K
     [Google Scholar]
  47. ShalabyM.A. FahimA.M. RizkS.A. RSC Advances20231321145801459310.1039/D3RA02393A 37197676
     [Google Scholar]
  48. JobP. Ann. Chim.192810113203
     [Google Scholar]
  49. BenesiH.A. HildebrandJ.H. J. Am. Chem. Soc.19497182703270710.1021/ja01176a030
     [Google Scholar]
  50. MarinovaG. BatchvarovV. Bulg. J. Agric. Sci.2011171124
     [Google Scholar]
  51. NeeseF. Wiley Interdiscip. Rev. Comput. Mol. Sci.201221737810.1002/wcms.81
     [Google Scholar]
  52. WeigendF. AhlrichsR. Phys. Chem. Chem. Phys.20057183297330510.1039/b508541a 16240044
     [Google Scholar]
  53. AlbertoM.E. RussoN. GrandA. GalanoA. Phys. Chem. Chem. Phys.201315134642465010.1039/c3cp43319f 23423333
     [Google Scholar]
  54. KleinE. LukešV. J. Mol. Struct.20078051-315316010.1016/j.theochem.2006.11.002
     [Google Scholar]
/content/journals/loc/10.2174/0115701786337428241125091159
Loading
Metal Sensing and Radical Quenching Properties of Thiophene-based Hydrazone
Lett. Org. Chem. 22, 387 (2025); https://doi.org/10.2174/0115701786337428241125091159
/content/journals/loc/10.2174/0115701786337428241125091159
/content/journals/loc/10.2174/0115701786337428241125091159
Loading

Data & Media loading...

Supplements

Supplementary material is available on the publisher’s website along with the published article. UV-Vis absorption spectra and binding energy table are provided as a supporting information (SI).

file format download Download

  • Article Type:     Research Article
Keyword(s): Antioxidant; cupric ion; density functional theory; hydrazone; radical quenching mechanism; sensor; thiophene; UV-Vis

Most Cited Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test