NSAID-Based Coordination Compounds for Biomedical Applications: Recent Advances and Developments

Santos, Ariana C.F.; Monteiro, Luís P. G.; Gomes, Adriana C. C.; Martel, F; Santos, Teresa M.; Ferreira, B.J.M. Leite

doi:10.3390/ijms23052855

Cited by 19 publications

(10 citation statements)

References 158 publications

(221 reference statements)

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“…Except for 1d, all ligands were more active than diclofenac. For the ligand 1d (EC50 = 109.342 ± 0.297 mg/mL) it is also important to mention that the complexation with all used metals gives complexes (2d, 3d, 4d) with an improved anti-inflammatory effect shown in this test (EC50 = 40.620 -52.276 mg/mL) which is in agreement with literature data [34].…”

Section: Erythrocyte Membrane Stabilisation Assaysupporting

confidence: 91%

“…A wide range of metal complexes are reported in the literature, such as Li, Mg, Al, K, Ca, Fe, Co, Ga, As, Sr, Y, Zr, Pd, Ag, Sb, Sm, Lu, Pt, Au, Hg, Bi and Ra complexes, which proved to have important biological effects [18,21]. Recent scientific data supports that NSAID-metal complexes exhibit improved anti-inflammatory properties in comparison to parent NSAIDs and, even more, induce other important biological effects [5,22,29,34,35]. For example, cobalt (II), manganese (II), or zinc (II) complexes of some diclofenac derivatives exhibited very promising anti-inflammatory effects and, in addition, proved to have important antioxidant effects not present in diclofenac [32,33,46].…”

Section: Introductionmentioning

confidence: 99%

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New Metal Complexes With Aril-Acetic Structure: Preparation, Characterization, and in Vitro Antiinflammatory Effects

Focsa¹

2023

FARMACIA

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New tridentate ONO hydrazone Schiff base ligands were synthesised by the condensation reaction of some hydroxybenzaldehydes with diclofenac-hydrazide. Afterward, by complexing the ligands with copper (II), zinc (II), and nickel (II), new dimeric complexes were obtained. The structure of ligands (1a-d) and of corresponding metal complexes (2a-d, 3ad, 4a-d) was established through spectroscopic data (FT-IR, UV-Vis). The thermal behaviour of metal complexes was studied using thermogravimetric analysis (TGA) and derivative thermogravimetry (DTA) in an inert atmosphere. Upon heating, all compounds decompose progressively into metal oxides, which are the final products of pyrolysis. The ligands and their metal complexes were subjected to in vitro anti-inflammatory evaluation using a serum albumin denaturation assay and an erythrocyte membrane stabilisation assay. The obtained results support the improved anti-inflammatory effect of diclofenac through complexation with different bivalent metals via hydrazone Schiff base ligands. Moreover, it was noted that the antiinflammatory effect of the metal complexes increases with concentration. The most active were nickel (II) complexes, which showed appreciable anti-inflammatory effects compared to both ligands and diclofenac, used as a reference drug. RezumatPrin reacția de condesare a unor hidroxi-benzaldehide cu hidrazida diclofenacului au fost sintetizați noi liganzi tridentați ONO de tip baze Schiff. Ulterior, prin complexarea liganzilor obținuti cu cupru (II), zinc (II) și nichel (II), s-au obținut noi complecși metalici dimerici. Structura liganzilor (1a-d) și a complecșilor metalici corespunzători ( 2a-d, 3a-d, 4a-d) a fost stabilită prin metode spectrometrice (FT-IR, UV-Vis). Comportamentul termic al complecșilor metalici s-a studiat cu ajutorul analizei termogravimetrice (TGA) și a derivatei curbei termogravimetrice (DTA), în atmosferă inertă. Prin încălzire, toți compușii se descompun progresiv în oxizi metalici, produșii finali ai pirolizei. Liganzii și complecșii metalici corespunzători au fost evaluați pentru efectul antiinflamator, utilizând teste in vitro -testul denaturării albuminei serice și testul de stabilizare a membranei eritrocitare. Rezultatele obținute susțin intensificarea efectului antiinflamator al diclofenacului prin complexare cu diferiți ioni metalici bivalenți prin intermediul liganzilor de tip baze Schiff. Mai mult decât atât, s-a observat că efectul complecșilor metalici crește odată cu creșterea concentrației. Cei mai activi au fost complecșii pe bază de nichel (II), care au dovedit apreciabile efecte antiinflamatoare, comparativ atât cu liganzii, cât și cu diclofenacul utilizat ca medicament de referință.

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Section: Erythrocyte Membrane Stabilisation Assaysupporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

New Metal Complexes With Aril-Acetic Structure: Preparation, Characterization, and in Vitro Antiinflammatory Effects

Focsa¹

2023

FARMACIA

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“…Our results showed the potential of the Ni(II) complexes as a prototype of new antitumor drugs. Despite anti-cancer activity already having been demonstrated for Ni(II) complexes which targeted DNA ( Zhang et al, 2018 ) and kinase proteins ( Santos et al, 2022 ), this is not a frequent metal in pharmacological studies (Cu and Zn are much more usual to be found in the specialized literature, for example), making Ni(II) complexes an open field of opportunities to be explored.…”

Section: Resultsmentioning

confidence: 99%

Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity: Structural, antitumor and molecular docking study

Cavalcante

Mota

Oliveira

et al. 2023

Front. Mol. Biosci.

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In the search for new metal complexes with antitumor potential, two dithiocarbazate ligands derived from 1,1,1-trifluoro-2,4-pentanedione (H2L1) and (H2L2) and four Ni(II) complexes, [Ni(L1)PPh3] (1), [Ni(L1)Py] (2), [Ni(L2)PPh3] (3), and [Ni(L2)Py] (4), were successfully synthesized and investigated by physical-chemistry and spectroscopic methods. The crystal structure of the H2L1 and the Ni(II) complexes has been elucidated by single-crystal X-ray diffraction. The obtained structure from H2L1 confirms the cyclization reaction and formation of the pyrazoline derivative. The results showed square planar geometry to the metal centers, in which dithiocarbazates coordinated by the ONS donor system and a triphenylphosphine or pyridine molecule complete the coordination sphere. Hirshfeld surface analysis by dnorm function was investigated and showed π–π stacking interactions upon the molecular packing of H2L1 and non-classical hydrogen bonds for all compounds. Fingerprint plots showed the main interactions attributed to H⋅H C⋅H, O⋅H, Br⋅H, and F⋅H, with contacts contributing between 1.9% and 38.2%. The mass spectrometry data indicated the presence of molecular ions [M + H]+ and characteristic fragmentations of the compounds, which indicated the same behavior of the compounds in solution and solid state. Molecular docking simulations were studied to evaluate the properties and interactions of the free dithiocarbazates and their Ni(II) complexes with selected proteins and DNA. These results were supported by in vitro cytotoxicity assays against four cancer cell lines, showing that the synthesized metal complexes display promising biological activity.

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“…The majority of these complexes were NSAID–platinum(IV) complexes. ,,− Also, there were reports of NSAID-based coordination with other metals including copper, cobalt, nickel, etc. Accordingly, the synthesis of metal–NSAID complexes is an attractive chemotherapeutic strategy to overcome multidrug resistance (MDR), improve the immune response, and inhibit inflammation-induced metastatic cancers. , As mentioned above, TrxR inhibitors (e.g., the gold complexes) may be potential ICD inducers, which elicit the DAMP approach for tumor cells, modify the state of tumor cells, and stimulate the immune response. Meanwhile, it has been proved that NSAIDs could improve the immunosurveillance, suppress the proliferation, and induce the ICD effects of colorectal tumor cells .…”

Section: Introductionmentioning

confidence: 99%

NSAID–Au(I) Complexes Induce ROS-Driven DAMPs and Interpose Inflammation to Stimulate the Immune Response against Ovarian Cancer

Min

et al. 2023

J. Med. Chem.

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Inflammation contributes to the development of ovarian cancer, and chemoresistance is a principal obstacle in ovarian cancer treatment. Herein, we designed and synthesized a series of gold(I) complexes derived from NSAIDs or their analogues. Among them, complex B3 (Npx-Au) displayed higher antitumor activity than cisplatin and other gold(I) complexes. Npx-Au could induce oxidative stress and the damage-associated molecular patterns (DAMPs) process by the inhibition of TrxR activity. Mechanistic studies revealed that simultaneous downregulation of COX-2 and PD-L1 was observed after Npx-Au treatment. Interestingly, in vivo experiments demonstrated that Npx-Au treatment could stimulate the immune response via reducing the expression of PD-L1, inducing DC maturation and increasing the infiltration of T (CD4+ and CD8+) cells. Collectively, our studies found that the gold(I) complex Npx-Au could elicit immunogenic cell death (ICD) and provide a promising strategy for chemotherapy combined with immunotherapy in the treatment of ovarian cancer.

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NSAID-Based Coordination Compounds for Biomedical Applications: Recent Advances and Developments

Cited by 19 publications

References 158 publications

New Metal Complexes With Aril-Acetic Structure: Preparation, Characterization, and in Vitro Antiinflammatory Effects

New Metal Complexes With Aril-Acetic Structure: Preparation, Characterization, and in Vitro Antiinflammatory Effects

Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity: Structural, antitumor and molecular docking study

NSAID–Au(I) Complexes Induce ROS-Driven DAMPs and Interpose Inflammation to Stimulate the Immune Response against Ovarian Cancer

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