New organometallic imines of rhenium(<scp>i</scp>) as potential ligands of GSK-3β: synthesis, characterization and biological studies

Muñoz-Osses, Michelle; Godoy, Fernando; Fierro, Angélica; Gómez, Alejandra; Metzler‐Nolte, Nils

doi:10.1039/c7dt04344a

Cited by 37 publications

(25 citation statements)

References 66 publications

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“…As per literature reports, the broad singlet observed at 6.90-6.28 ppm was assigned to the hydrogen nuclei of the SO 2 NH 2 group 42,43 . Moreover, 1 H NMR spectra for 1a-b and 2a-b showed sets of resonances in the region of 6.31-4.92 ppm, which are ascribed to the protons of the cyrhetrenyl and cymantrenyl moieties 44,45 . On this regard, the ferrocenyl derivatives 3a-b exhibited resonances around d 4.82-4.30 due to the non-equivalent alpha and beta protons containing in the substituted Cp ring and a singlet in the region of 4.17-3.99 ppm, which was assigned to the proton resonances of the unsubstituted cyclopentadienyl group 46,47 .…”

Section: Synthesis and Characterisation Of Bioorganometallichydrazones Derivatives From Sulphanilamidementioning

confidence: 98%

Bioorganometallic derivatives of 4-hydrazino-benzenesulphonamide as carbonic anhydrase inhibitors: synthesis, characterisation and biological evaluation

Brichet

Arancibia

Berrino

2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of bio-organometallic-hydrazones of the general formula [{(g 5 -C 5 H 4 )-C(R)¼N-N(H)-C 6 H 4 -4-SO 2 NH 2 }]MLn(MLn ¼ Re(CO) 3 , Mn(CO) 3 , FeCp; R¼H, CH 3 ) were prepared by reaction of formyl/acetyl organometallic precursors with 4-hydrazino-benzenesulphonamide. All compounds were characterized by conventional spectroscopic techniques (infra-red, 1 H and 13 C NMR, mass spectrometry and elemental analysis). Biological evaluation as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors agents was carried out using four human/h) isoforms, hCA I, II, IX and XII. The cytosolic isoforms hCA I and II were effectively inhibited by almost all derivatives with inhibition constants of 1.7-22.4 nM. Similar effects were observed for the tumour-associated transmembrane isoform hCA XII (K I s of 1.9-24.4 nM). hCA IX was less sensitive to inhibition with these compounds. The presence of bio-organometallic or metallo-carbonyl moieties in the molecules of these CAIs makes them amenable for interesting pharmacologic applications, for example for compounds with CO donating properties.

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Section: Synthesis and Characterisation Of Bioorganometallichydrazones Derivatives From Sulphanilamidementioning

confidence: 98%

Bioorganometallic derivatives of 4-hydrazino-benzenesulphonamide as carbonic anhydrase inhibitors: synthesis, characterisation and biological evaluation

Brichet

Arancibia

Berrino

2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Yield: 95%. 1 5-[4-(2-Methoxyphenyl)piperazin-1-yl]pentannitrile (5c) [69,70] Transparent oil. Yield: 88%.…”

Section: -[4-(2-methoxyphenylmentioning

confidence: 99%

Synthesis, in silico, and in vitro studies of novel dopamine D₂ and D₃ receptor ligands

Elek

Djoković

Frank

et al. 2021

Archiv der Pharmazie

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Dopamine is an important neurotransmitter in the human brain and its altered concentrations can lead to various neurological diseases. We studied the binding of novel compounds at the dopamine D 2 (D 2 R) and D 3 (D 3 R) receptor subtypes, which belong to the D 2 -like receptor family. The synthesis, in silico, and in vitro characterization of 10 dopamine receptor ligands were performed. Novel ligands were docked into the D 2 R and D 3 R crystal structures to examine the precise binding mode. A quantum mechanics/molecular mechanics study was performed to gain insights into the nature of the intermolecular interactions between the newly introduced pentafluorosulfanyl (SF 5 ) moiety and D 2 R and D 3 R. A radioligand displacement assay determined that all of the ligands showed moderate-to-low nanomolar affinities at D 2 R and D 3 R, with a slight preference for D 3 R, which was confirmed in the in silico studies. N-{4-[4-(2-Methoxyphenyl)piperazin-1-yl]butyl}-4-(pentafluoro-λ6-sulfanyl)benzamide (7i) showed the highest D 3 R affinity and selectivity (pK i values of 7.14 [D 2 R] and 8.42 [D 3 R]).

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“…A series of CpRe(I)(CO) 3 compounds harboring a piperazine side chain on the Cp ring was found moderately active on HT-29 cancer cells. Based on computational studies, inhibition of the GSK-3β was postulated to be involved in the cytotoxic activity of these complexes [110].…”

Section: Effect Of Rhenium Complexes On Enzymatic Activitiesmentioning

confidence: 99%

Design of Rhenium Compounds in Targeted Anticancer Therapeutics

Collery¹,

Desmaële

Veena

2019

CPD

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Background: Many rhenium (Re) complexes with potential anticancer properties have been synthesized in the recent years with the aim to overcome the clinical limitations of platinum agents. Re(I) tricarbonyl complexes are the most common but Re compounds with higher oxidation states have also been investigated, as well as hetero-metallic complexes and Re-loaded self-assembling devices. Many of these compounds display promising cytotoxic and phototoxic properties against malignant cells but all Re compounds are still at the stage of preclinical studies. Methods: The present review focused on the rhenium based cancer drugs that were in preclinical and clinical trials were examined critically. The detailed targeted interactions and experimental evidences of Re compounds reported by the patentable and non-patentable research findings used to write this review. Results: In the present review, we described the most recent and promising rhenium compounds focusing on their potential mechanism of action including, phototoxicity, DNA binding, mitochondrial effects, oxidative stress regulation or enzyme inhibition. Many ligands have been described that modulating the lipophilicity, the luminescent properties, the cellular uptake, the biodistribution, and the cytotoxicity, the pharmacological and toxicological profile. Conclusion: Re-based anticancer drugs can also be used in targeted therapies by coupling to a variety of biologically relevant targeting molecules. On the other hand, combination with conventional cytotoxic molecules, such as doxorubicin, allowed to take into profit the targeting properties of Re for example toward mitochondria. Through the example of the diseleno-Re complex, we showed that the main target could be the oxidative status, with a down-stream regulation of signaling pathways, and further on selective cell death of cancer cells versus normal cells.

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New organometallic imines of rhenium(i) as potential ligands of GSK-3β: synthesis, characterization and biological studies

Cited by 37 publications

References 66 publications

Bioorganometallic derivatives of 4-hydrazino-benzenesulphonamide as carbonic anhydrase inhibitors: synthesis, characterisation and biological evaluation

Bioorganometallic derivatives of 4-hydrazino-benzenesulphonamide as carbonic anhydrase inhibitors: synthesis, characterisation and biological evaluation

Synthesis, in silico, and in vitro studies of novel dopamine D₂ and D₃ receptor ligands

Design of Rhenium Compounds in Targeted Anticancer Therapeutics

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New organometallic imines of rhenium(i) as potential ligands of GSK-3β: synthesis, characterization and biological studies

Cited by 37 publications

References 66 publications

Bioorganometallic derivatives of 4-hydrazino-benzenesulphonamide as carbonic anhydrase inhibitors: synthesis, characterisation and biological evaluation

Bioorganometallic derivatives of 4-hydrazino-benzenesulphonamide as carbonic anhydrase inhibitors: synthesis, characterisation and biological evaluation

Synthesis, in silico, and in vitro studies of novel dopamine D2 and D3 receptor ligands

Design of Rhenium Compounds in Targeted Anticancer Therapeutics

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Synthesis, in silico, and in vitro studies of novel dopamine D₂ and D₃ receptor ligands