Synthesis, characterization, DFT calculations and anticancer activity of a new oxidovanadium(<scp>iv</scp>) complex with a ligand derived from <i>o</i>-vanillin and thiophene

Rodríguez, María Rosa; Balsa, Lucía M.; Plá, Julian Del; García–Tojal, Javier; Diez, Reinaldo Pis; Parajón‐Costa, Beatriz S.; León, Ignacio E.; González‐Baró, Ana C.

doi:10.1039/c9nj02092f

Cited by 18 publications

(9 citation statements)

References 52 publications

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“…Finally, our previous results on an oxidovanadium(IV) complex with other thiophenes containing Schiff base ligands, showing a much higher IC 50 value on MG-63 cells than CuHL, demonstrate the importance of the nature and the environment geometry of the metal center in the effectiveness of metallo-drugs [54].…”

Section: Cell Viability Studymentioning

confidence: 66%

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Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene

et al. 2021

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A new Cu(II) complex is synthetized by the reaction of copper nitrate and a N-acylhydrazone ligand obtained from the condensation of o-vanillin and 2-thiophecarbohydrazide (H2L). The solid-state structure of [Cu(HL)(H2O)](NO3)·H2O, or CuHL for simplicity, was determined by X-ray diffraction. In the cationic complex, the copper center is in a nearly squared planar environment with the nitrate interacting as a counterion. CuHL was characterized by spectroscopic techniques, including solid-state FTIR, Raman, electron paramagnetic resonance (EPR) and diffuse reflectance and solution UV-Vis electronic spectroscopy. Calculations based on the density functional theory (DFT) assisted the interpretation and assignment of the spectroscopic data. The complex does not show relevant antioxidant activity evaluated by the radical cation of 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) method, being even less active than the free ligand as a radical quencher. Cytotoxicity assays of CuHL against three human tumor cell lines, namely MG-63, A549 and HT-29, revealed an important enhancement of the effectiveness as compared with both the ligand and the free metal ion. Moreover, its cytotoxic effect was remarkably stronger than that of the reference metallodrug cisplatin in all cancer cell lines tested, a promissory result in the search for new metallodrugs of essential transition metals.

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Section: Cell Viability Studymentioning

confidence: 66%

“…than CuHL, demonstrate the importance of the nature and the environment geometry of the metal center in the effectiveness of metallo-drugs [54].…”

Section: Antioxidant Activitymentioning

confidence: 97%

Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene

et al. 2021

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“…These findings are in good agreement with the previous studies which showed the high cytotoxic activity of thiophene derivatives against cancer cells. [ 36,70 ] In addition, α‐tpys (2,2′:6′,2″‐tpy) and their derivatives displayed stronger cytotoxicity against A‐498, PC‐3, and HT‐29 cancer cell lines than doxorubicin. The furyl and thienyl analogs were more cytotoxic than the corresponding phenyl analog.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, and evaluation of biological activities of new 4′‐substituted ruthenium (II) terpyridine complexes: Prospective anti‐inflammatory properties

Elnagar

Samir

Shaker

et al. 2020

Applied Organom Chemis

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The synthesis and characterization of Ru (II) terpyridine complexes derived from 4′ functionalized 2,2′:6′,2″‐terpyridine (tpy) ligands are reported. The heteroleptic complexes comprise the synthesized ligands 4′‐(2‐thienyl)‐ 2,2′:6′,2″‐terpyridine) or (4′‐(3,4‐dimethoxyphenyl)‐2,2′:6′,2″‐terpyridine and (dimethyl 5‐(pyrimidin‐5‐yl)isophthalate). The new complexes [Ru(4′‐(2‐thienyl)‐2,2′:6′,2″‐terpyridine)(5‐(pyrimidin‐5‐yl)‐isophthalic acid)Cl2] (9), [Ru(4′‐(3,4‐dimethoxyphenyl)‐2,2′:6′,2″‐terpyridine)(5‐(pyrimidin‐5‐yl)‐isophthalic acid)Cl2] (10), and [Ru(4′‐(2‐thienyl)‐2,2′:6′,2″‐terpyridine)(5‐(pyrimidin‐5‐yl)‐isophthalic acid)(NCS)2] (11) were characterized by 1H‐ and 13C‐NMR spectroscopy, C, H, N, and S elemental analysis, UPLC‐ESI‐MS, TGA, FT‐IR, and UV‐Vis spectroscopy. The biological activities of the synthesized ligands and their Ru (II) complexes as anti‐inflammatory, antimicrobial, and anticancer agents were evaluated. Furthermore, the toxicity of the synthesized compounds was studied and compared with the standard drugs, namely, diclofenac potassium and ibuprofen, using hemolysis assay. The results indicated that the ligands and the complex 9 possess superior anti‐inflammatory activities inhibiting albumin denaturation (89.88–100%) compared with the standard drugs (51.5–88.37%) at a concentration of 500 μg g−1. These activities were related to the presence of the chelating N‐atoms in the ligands and the exchangeable chloro‐ groups in the complex. Moreover, the chloro‐ and thiophene groups in complex 9 produce a higher anticancer activity compared with its isothiocyanate derivative in the complex 11 and the 3,4‐dimethoxyphenyl moiety in complex 10. Considering the toxicity results, the synthesized ligands are nontoxic or far less toxic compared with the standard drugs and the metal complexes. Therefore, these newly synthesized compounds are promising anti‐inflammatory agents in addition to their moderate unique broad antimicrobial activity.

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“…[172,173] Recent studies in MDA-MB-231 cells have shown apoptotic and autophagic cell death with notch pathway inhibition of a vanadium-based complex, compound 58, a oxidovanadium (IV) complex by Gonzalez-Baró and co-workers with a chelating ligand made from the condensation reaction of o-vanillin and 2thiophenemethylamine. [174] Cellular studies in MDA-MB-231 cells showed cytotoxicity (IC 50 = 29 � 1.7 μM, 48 h), an apoptotic cell death, antimigratory activity, and increased ROS production. [174]…”

Section: Vanadium Compoundsmentioning

confidence: 95%

“…[174] Cellular studies in MDA-MB-231 cells showed cytotoxicity (IC 50 = 29 � 1.7 μM, 48 h), an apoptotic cell death, antimigratory activity, and increased ROS production. [174]…”

Section: Vanadium Compoundsmentioning

confidence: 95%

Exploring the Potential of Metallodrugs as Chemotherapeutics for Triple Negative Breast Cancer

Nayeem

Contel

2021

Chemistry A European J

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This review focuses on studies of coordination and organometallic compounds as potential chemotherapeutics against triple negative breast cancer (TNBC) which has one of the poorest prognoses and worst survival rates from all breast cancer types. At present, chemotherapy is still the standard of care for TNBC since only one type of targeted therapy has been recently developed. References for metal-based compounds studied in TNBC cell lines will be listed, and those of metal-specific reviews, but a detailed overview will also be provided on compounds studied in vivo (mostly in mice models) and those compounds for which some preliminary mechanistic data was obtained (in TNBC cell lines and tumors) and/or for which bioactive ligands have been used. The main goal of this review is to highlight the most promising metalbased compounds with potential as chemotherapeutic agents in TNBC.

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Synthesis, characterization, DFT calculations and anticancer activity of a new oxidovanadium(iv) complex with a ligand derived from o-vanillin and thiophene

Abstract: New vanadium complex was synthesized and fully characterized showing promising anticancer activity on triple negative breast cancer cells.

Cited by 18 publications

References 52 publications

Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene

Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene

Synthesis, characterization, and evaluation of biological activities of new 4′‐substituted ruthenium (II) terpyridine complexes: Prospective anti‐inflammatory properties

Exploring the Potential of Metallodrugs as Chemotherapeutics for Triple Negative Breast Cancer

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