Investigating the therapeutic potential of monothiocarbohydrazones: A comprehensive in vitro evaluation of antioxidant, antimicrobial, and cytotoxic activities Scientific paper

Main Article Content

Gorana Mrđan
https://orcid.org/0000-0001-8724-9201
Sanja Vlaisavljević
https://orcid.org/0000-0002-1184-9080
Petar Knežević
https://orcid.org/0000-0003-0353-3892
Isidora Nikolić
https://orcid.org/0000-0001-8958-9912
Dina Tenji
https://orcid.org/0000-0002-7657-943X
Borko Matijević
https://orcid.org/0000-0003-1054-3909

Abstract

Organic compounds, particularly those with nitrogen and sulphur het­eroatoms, constitute over 99 % of clinically approved drugs. Among these, thiocarbohydrazones have been extensively studied, with a focus on sym­met­rical bis-substituted compounds. However, asymmetric and monosubstituted thiocarbohydrazones remain underexplored, despite their demonstrated high biological potential. This study presents an in-depth in vitro evaluation of the antioxidant, antimicrobial, and cytotoxic properties of eighteen previously syn­thesized and characterized monothiocarbohydrazones. The antioxidant poten­tial was assessed using the DPPH assay, while the antimicrobial activity was determined against Gram-positive bacteria using a modified broth microdil­ution susceptibility method. The cytotoxic effect was evaluated on human hep­atocellular carcinoma using the colorimetric MTT assay. The results reveal that the investigated monothiocarbohydrazones exhibit significant antioxidant and antimicrobial activities. Furthermore, their activity and cytotoxicity are influ­enced by the stereochemistry of the molecule and the nature and position of the substituents. These findings provide valuable insights for future in vivo exam­in­ations and underscore the potential of monothiocarbohydrazones in drug dev­elopment.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Article Details

How to Cite
[1]
G. Mrđan, S. Vlaisavljević, P. . Knežević, I. Nikolić, D. Tenji, and B. Matijević, “Investigating the therapeutic potential of monothiocarbohydrazones: A comprehensive in vitro evaluation of antioxidant, antimicrobial, and cytotoxic activities: Scientific paper”, J. Serb. Chem. Soc., vol. 90, no. 1, pp. 1–12, Feb. 2025.
Section
Organic Chemistry

Funding data

References

P. C. Guha, S. C. Dey, J. Indian Chem. Soc. 2 (1925) 225 (https://ia902304.us.archive.org/18/items/sim_journal-of-the-indian-chemical-society_1925_2_index/sim_journal-of-the-indian-chemical-society_1925_2_index.pdf)

J. M. Cano Pavon, A. Garcia de Tores, C. Alcaraz, M. T. Siles Cordero, E. Vereda Alonso, Quimica Analitica. 13 (1994) 5

(https://scholar.google.com/scholar_lookup?journal=Quim.+Anal.&title=Analytical+applications+of+thiocarbohydrazones.+A+review&author=J.M.+Cano+Pavon&author=A.+Garcia+de+Torres&author=E.+Cristofol+Alcaraz&author=M.T.+Siles+Cordero&author=E.+Vereda+Alonso&volume=13&publication_year=1994&pages=5-10&)

D. Rosales, A. G. Asuero, J. L. G. Ariza, The Analyst. 111 (1986) 449 (https://dx.doi.org/10.1039/AN9861100449)

S. P. Chaudhury, S. C. Shome, J. Indian. Chem. Soc. 68 (1991) 430 (https://zenodo.org/record/6160571/files/430-431.pdf)

R. B. Lucena, E. Morales, J. L. Gomez-Ariza, Farmaco. 49 (1994) 291 (https://pubmed.ncbi.nlm.nih.gov/8049011/)

R. B. Lucena, E. Morales, J. L. Gomez-Ariza, Farmaco. 49 (1994) 297 (https://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4270633)

S. B. Zanje, V. J. Suryavanshi, A. N. Kokare, A. A. Ghare, G. S. Kamble, P. N. Kamble, M. A. Anuse, J. Anal. Chem. 73 (2018) 438 (https://dx.doi.org/10.1134/S1061934818050131)

A. V. Sadlapurkar, U. B. Barache, A. B. Shaikh, S. H. Gaikwad, T. N. Lokhande, Int. J. Environ. An. Chem. 103 (2023) 3683 (https://dx.doi.org/10.1080/03067319.2021.1912333)

A. V. Sadlapurkar, U. B. Barache, A. B. Shaikh, P. C. Dhale, S. H. Gaikwad, T. N. Lokhande, Chem. Data Collect. 37 (2022) 100798 (https://dx.doi.org/10.1016/j.cdc.2021.100798)

G. Kiran, T. Maneshwar, Y. Rajeshwar, M. Sarangapani, J. Chem. 2013 (2013) 192039 (https://dx.doi.org/10.1155/2013/192039)

G. Mrđan, A. Tot, M. Vraneš, M. Rašeta, P. Knežević, T. Verbić, B. Matijević, B. Chem. Soc. Jpn. 95 (2022) 185 (https://dx.doi.org/10.1246/bcsj.20210326)

Y. Kaya, A. Ercag, A. Koca, J. Mol. Struct. 1102 (2015) 117 (https://dx.doi.org/10.1016/j.molstruc.2015.08.055)

Y. Kaya, A. Ercag, K. Kaya, J. Coord. Chem. 71 (2018) 3364 (https://dx.doi.org/10.1080/00958972.2018.1516872)

H. Muglu, M. S. Cavus, T. Bakir, H. Yakan, J. Mol. Struct. 1196 (2019) 819 (https://dx.doi.org/10.1016/j.molstruc.2019.07.002)

H. Yakan, T. K. Bakir, M. S. Cavus, H. Muglu, Res. Chem. Intermed. 46 (2020) 5417 (https://dx.doi.org/10.1007/s11164-020-04270-0)

T. K. Bakir, J. B. Lawag, Res. Chem. Intermed. 46 (2020) 2541 (https://dx.doi.org/10.1007/s11164-020-04105-y)

A. Bacchi, M. Carcelli, P. Pelagatti, C. Pelizzi, G. Pelizzi, F. Zani, J. Inorg. Biochem. 75 (1999) 123 (https://dx.doi.org/10.1016/S0162-0134(99)00045-8)

M. Shebl, S. M. E. Khalil, F. S. Al-Gohani, J. Mol. Struct. 980 (2010) 78 (https://dx.doi.org/10.1016/j.molstruc.2010.06.040)

M. T. Gabr, N. S. El-Gohary, E. R. El-Bendary, Ni Nanting, M. I. Shaaban, M. M. El-Kerdawy, Synthetic Commun. 48 (2018) 2899

(https://dx.doi.org/10.1080/00397911.2018.1520889)

A. R. Božić, S. K. Bjelogrlić, I. T. Novaković, N. R. Filipović, P. M. Petrović, A. D. Marinković, T. R. Todorović, I. N. Cvijetić, Chemistryselect. 3 (2018) 2215

(https://dx.doi.org/10.1002/slct.201702691)

K. Gangarapu, S. Manda, A. Jallapally, S. Thota, S. K. Karki, J. Balzarini, E. De Clercq, H. Tokuda, Med. Chem. Res. 23 (2014) 1046 (https://dx.doi.org/10.1007/s00044-013-0684-3)

A. Božić, A. Marinković, S. Bjelogrlić, T. R. Todorović, I. N. Cvijetić, I. Novaković, C. D. Muller, N. R. Filipović, RSC Adv. 6 (2016) 104763 (https://doi.org/10.2298/JSC161220045B)

J. Wang, Y. T. Wang, Y. Fang, Y. L. Lu, M.X. Li, Toxicol. Res. 8 (2019) 862 (https://doi.org/10.1039/C9TX00109C)

M. H. Assaleh, S. K. Bjelogrlic, N. Prlainovic, I. Cvijetic, A. Bozic, I. Arandjelovic, D. Vukovic, A. Marinkovic, Arab. J. Chem. 15 (2022) 103532 (https://doi.org/10.1016/j.arabjc.2021.103532)

M. T. Gabr, N. S. El-Gohary, E. R. El-Bendary, M. M. El-Kerdawy, Ni Nanting, Eur. J. Med. Chem. 128 (2017) 36 (https://doi.org/10.1016/j.ejmech.2017.01.030)

G. Mrdjan, Gy. Vastag, D. Škorić, M. Radanović, T. Verbić, M. Milčić, I. Stoiljković, O. Marković, B. Matijević, Struct. Chem. 32 (2021) 1231 (https://doi.org/10.1007/s11224-020-01700-y)

H. H. J. Gerets, K. Tilmant, B. Gerin, H. Chanteux, B. O. Depelchin, S. Dhalluin, F. A. Atienzar, Cell. Biol. Toxicol. 28 (2012) 69 (https://doi.org/10.1007/s10565-011-9208-4)

S. Yang, M. Ooka, R. J. Margolis, M. Xia, Cell Reports Methods 3 (2023) 100432 (https://doi.org/10.1016/j.crmeth.2023.100432)

C. J. Espin, G. Soler-Rivas, J. H. Wichers, J. Agr. Food Chem. 48 (2000) 648 (https://doi.org/10.1021/jf9908188)

I. Vulin, D. Tenji, I. Teodorovic, S. Kaisarevic, Chem-Biol. Interact. 365 (2022) 110082 (https://doi.org/10.1016/j.cbi.2022.110082)

J. L. Li, X.Y. Liu, J.T. Xie, Y.L. Di, F.X. Zhu, J. Phytopathol. 163 (2015) 239 (http://dx.doi.org/10.1111/jph.12312)

M. S. Cavus, H. Yakan, H. Muglu, T. Bakir, J. Phys. Chem. Solids. 140 (2020) 109362 (http://dx.doi.org/10.1016/j.jpcs.2020.109362)

M. Demurtas, A. Baldisserotto, I. Lampronti, D. Moi, G. Balboni, S. Pacifico, S. Vertuani, S. Manfredini, V. Onnis, Bioorg. Chem. 85 (2019) 568 (https://doi.org/10.1016/j.bioorg.2019.02.007)

D. Saxena, R. Maitra, R. Bormon, M. Czekanska, J. Meiers, A. Titz, S. Verma, S. Chopra, npj Antimicro. Resist. 1 (2023) 17 (https://doi.org/10.1038/s44259-023-00016-1)

R. Tamaian, A. Mot, R. Silaghi-Dumitrescu, I. Ionut, A. Stana, O. Oniga, C. Nastasa, D. Benedec, B. Tiperciuc, Molecules 20 (2015) 22188 (http://dx.doi.org/10.3390/molecules201219841)

J. L. Stigliani, V. Bernardes–Génisson, Ann. Pharm. Francaises 77 (2019) 126 (http://dx.doi.org/10.1016/j.pharma.2018.11.004)

R. K. C. De Paiva, J. F. Da Silva, H. A. Moreira, O. G. Pinto, L. T. F. M. Camargo, P. L. F. Naves, A. J Camargo, L. Ribeiro, L. M. Ramos, J. Brazil. Chem. Soc. 30 (2019) 164 (http://dx.doi.org/10.21577/0103-5053.20180167)

S. Podunavac–Kuzmanović, D. Cvetković, D. Barna, J. Serb. Chem. Soc. 73 (2008) 967 (http://dx.doi.org/10.2298/JSC0810967P)

M. B. Halli, R. B. Sumathi, Arab. J. Chem. 10 (2017) S1748 (https://doi.org/10.1016/j.arabjc.2013.06.025)

C. Bonaccorso, T. Marzo, D. La Mendola, Pharmaceuticals-Base. 13 (2020) 4 (http://dx.doi.org/10.3390/ph13010004)

S. M. Gomha, H. A. Abdelhady, D. Z. H. Hassain, A. H. Abdelmonsef, M. El-Naggar, M. M. Elaasser, H. K. Mahmoud, Drug Des. Dev. Ther. 15 (2021) 659 (http://dx.doi.org/10.2147/DDDT.S291579)

S. Bilginer, H. I. Gul, F. S. Erdal, H. Sakagami, S. Levent, I. Gulcin, C. T. Supuran, J. Enzym. Inhib. Med. Chem. 34 (2019) 1722 (http://dx.doi.org/10.1080/14756366.2019.1670657)

C. Bonaccorso, G. Grasso, N. Musso, V. Barresi, D. F. Condorelli, D. La Mendola, E. Rizzarelli, J. Inorg. Biochem. 182 (2018) 92 (http://dx.doi.org/10.1016/j.jinorgbio.2018.01.019)

Qurat-ul-Ain, M. Munira Taj, M. K. Khanlid, M. I. Choudhary, ArXiv. /abs/2310.00939 (2023) (https://doi.org/10.48550/arXiv.2310.00939).