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September 12, 2022
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Solution chemical properties and anticancer potential of 8-hydroxyquino-line hydrazones and their oxidovanadium(IV) complexes

Publicated to: Journal Of Inorganic Biochemistry. 235 111932- - 2022-10-01 235(), DOI: 10.1016/j.jinorgbio.2022.111932

Authors:

Ribeiro, Nadia; Bulut, Ipek; Posa, Vivien; Sergi, Baris; Sciortino, Giuseppe; Pessoa, Joao Costa; Maia, Luisa B; Ugone, Valeria; Garribba, Eugenio; Enyedy, Eva A; Acilan, Ceyda; Correia, Isabel
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Affiliations

Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Barcelona, Spain - Author
CNR, Ist Chim Biomol, Trav La Crucca 3, I-07100 Sassari, Italy - Author
FCT NOVA, LAQV, REQUIMTE, NOVA Sch Sci & Technol, Campus Caparica, P-2829516 Caparica, Portugal - Author
Koc Univ, Res Ctr Translat Med KUTTAM, Istanbul, Turkey - Author
Koc Univ, Sch Med, Istanbul, Turkey - Author
Univ Lisbon, Ctr Quim Estrutural, Inst Mol Sci, Inst Super Tecn, Av Rovisco Pais 1, P-1049001 Lisbon, Portugal - Author
Univ Lisbon, Inst Super Tecn, Dept Engn Quim, Av Rovisco Pais 1, P-1049001 Lisbon, Portugal - Author
Univ Sassari, Dipartimento Med Chirurg & Farm, Viale San Pietro, I-07100 Sassari, Italy - Author
Univ Szeged, MTA SZTE Lendulet Funct Met Complexes Res Grp, Dept Inorgan & Analyt Chem, Dom Ter 7, H-6720 Szeged, Hungary - Author
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Abstract

We report the synthesis and characterization of a family of benzohydrazones (L-n, n = 1-6) derived from 2-car-baldehyde-8-hydroxyquinoline and benzylhydrazides containing different substituents in the para position. Their oxidovanadium(IV) complexes were prepared and compounds with 1:1 and 1:2 metal-to-ligand stoichiometry were obtained. All compounds were characterized by elemental analyses and mass spectrometry as well as FTIR, UV-visible absorption, NMR (ligand precursors) and EPR (complexes) spectroscopies, and by DFT computational methods. Proton dissociation constants, lipophilicity and solubility in aqueous media were determined for all ligand precursors. Complex formation with V(IV)O was evaluated by spectrophotometry for L-4 (Me-substituted) and L-6 (OH-substituted) and formation constants for mono [VO(HL)](+), [VO(L)] and bis [VO(HL)(2)], [VO(HL) (L)], [VO(L)(2)](2- )complexes were determined. EPR spectroscopy indicates the formation of [VO(HL)](+) and [VO (HL)(2)], with this latter being the major species at the physiological pH. Noteworthy, the EPR data suggest a different behaviour for L-4 and L-6, which confirm the results obtained in the solid state. The antiproliferative activity of all compounds was evaluated in malignant melanoma (A-375) and lung (A-549) cancer cells. All complexes show much higher activity on A-375 (IC50 < 6.3 mu M) than in A-549 cells (IC50 > 20 mu M). Complex 3 (F-substituted) shows the lowest IC50 on both cell lines and lower than cisplatin (in A-375). Studies identified this compound as the one showing the highest increase in Annexin-V staining, caspase activity and induction of double stranded breaks, corroborating the cytotoxicity results. The mechanism of action of the complexes involves reactive oxygen species (ROS) induced DNA damage, and cell death by apoptosis.
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Keywords

8-hydroxyquinoline derivativesanticanceroxidovanadium(iv) complexesschiff basessolution stability8-hydroxyquinoline derivativesAnticancerBasis-setsCell-cycleClioquinolCopper(ii) complexesDna-binding propertiesMechanismMedicinal chemistryMycobacterium-tuberculosisOxidovanadium(iv) complexesOxovanadium(iv)Schiff basesSolution stabilitySpeciationV-iv

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Journal Of Inorganic Biochemistry due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2022, it was in position 8/42, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Inorganic & Nuclear.

From a relative perspective, and based on the normalized impact indicator calculated from World Citations provided by WoS (ESI, Clarivate), it yields a value for the citation normalization relative to the expected citation rate of: 1.77. This indicates that, compared to works in the same discipline and in the same year of publication, it ranks as a work cited above average. (source consulted: ESI Nov 13, 2025)

Specifically, and according to different indexing agencies, this work has accumulated citations as of 2025-12-24, the following number of citations:

  • WoS: 21
  • Google Scholar: 13
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Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-12-24:

  • The use, from an academic perspective evidenced by the Altmetric agency indicator referring to aggregations made by the personal bibliographic manager Mendeley, gives us a total of: 21.
  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 20 (PlumX).

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 2.
  • The number of mentions on the social network X (formerly Twitter): 4 (Altmetric).

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

  • The work has been submitted to a journal whose editorial policy allows open Open Access publication.
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Leadership analysis of institutional authors

This work has been carried out with international collaboration, specifically with researchers from: Hungary; Italy; Portugal; Turkey.

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Awards linked to the item

This work was supported by Centro de Quimica Estrutural, which is financed by national funds from Fundacao para a Ciencia e Tecnologia (FCT), projects UIDB/00100/2020, UIDP/00100/2020 and LA/P/0056/2020, and Programa Operacional Regional de Lisboa 2020. We also thank project PTDC/QUI-QIN/0586/2020 and N. Ribeiro acknowledges FCT for SFRH/BD/135797/2018 grant. The Portuguese NMR and Mass spectrometry IST-UL are acknowledged for the access to the equipment. This work was supported by the Portuguese-Hungarian Scientific & Technological Cooperation TET-PT-2018-00002, UNKP-21-3-SZTE-455 (to V. Posa) New National Excellence Program Ministry of Human Capacities. The support of the `Lendulet' Programme (ELKH, LP2019-6/2019) and the COST ActionCA18202, NECTAR-Network for Equilibria and Chemical Thermodynamics Advanced Research is also acknowledged. This work was also supported by Koc University School of Medicine (KUSOM) and the authors gratefully acknowledge use of the services and facilities of the Koc University Research Center for Translational Medicine (KUTTAM), funded by the Presidency of Turkey, Presidency of Strategy and Budget. The content is solely the responsibility of the authors and does not necessarily represent the official views of the Presidency of Strategy and Budget. G. Sciortino, V. Ugone, E. Garribba thank Fondazione di Sardegna (grant FdSGarribba2017) and Regione Autonoma della Sardegna (grant RASSR79857); G. Sciortino also thanks MICINN' Juan de la Cierva program, FJC2019-039135-I for the financial support. L. Maia thanks the Associate Laboratory for Green Chemistry -LAQV, which is financed by national funds from Fundacao para a Ciencia e a Tecnologia, MCTES (FCT/MCTES; UIDB/50006/2020 and UIDP/50006/2020).
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