Macrocyclic NHC complexes of group 10 elements with enlarged aromaticity for biological studies

Bernd, Marco A.; Bauer, Elisabeth B.; Oberkofler, Jens; Bauer, Andreas; Reich, Robert M.; Kühn, Fritz E.

doi:10.1039/d0dt02598d

Cited by 20 publications

(18 citation statements)

References 49 publications

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“…A similar trend was observed for the average M–N bond lengths (Ni II 1.90 Å, Pd II 2.06 Å, Pt II 2.05 Å) and the M···M distances (Ni II 3.60 Å, Pd II 3.72 Å, Pt II 3.76 Å). These values are in good agreement with similar mononuclear platinum group–NHC complexes. ,, …”

Section: Resultsmentioning

confidence: 99%

“…These values are in good agreement with similar mononuclear platinum group−NHC complexes. 18,40,45 The macrocyclic nature of the ligand drastically affects the overall structure of the cationic fragments: A related nonmacrocyclic bimetallic Pd II complex reported by the group of Kuḧn, 46 as well as that of Meyer, 42 incorporating two ligands with the same NHC−CH 2 −Pz−CH 2 −NHC binding motif as in L, adopts a flat structure, in which the pyrazolate moieties and both Pd II centers form a plane. This is enabled by the lack of connectivity between both ligands and the steric repulsion of the terminal NHCs introduced thereby.…”

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confidence: 99%

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Bimetallic Platinum Group Complexes of a Macrocyclic Pyrazolate/NHC Hybrid Ligand

Pickl

Pöthig

2021

Organometallics

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We present the synthesis, structural characterization, and photophysical properties of dinuclear Pd II and Pt II − NHC complexes Pd 2 L(PF 6 ) 2 and Pt 2 L(PF 6 ) 2 based on a macrocyclic calix[4]imidazolylidene[2]pyrazolate ligand obtained by in situ deprotonation of the tetraimidazolium salt H 6 L(PF 6 ) 4 . The Pt II congener was also prepared by transmetalation from previously published Ag I pillarplex Ag 8 L 2 (PF 6 ) 4 . NMR spectroscopy ( 1 H, 13 C, 195 Pt) combined with SC-XRD studies elucidated the structure of the Pd II and Pt II complexes in the solid state and in solution. The d 8 metal ions of both congeners are coordinated in a slightly distorted square-planar arrangement. Similar to the previously reported Ni II complex Ni 2 L(PF 6 ) 2 , the heavier metal homologues adopt a bent, saddle-shaped structure. As observed for structurally similar Pt II complexes in solution, bimetallic Pt 2 L(PF 6 ) 2 showed photoluminescence in the blue region. In the solid state, emission was observed at a similar energy with unusually short lifetimes compared to other monometallic Pt II complexes. DFT and TDDFT studies shed light on the nature of the most bathochromic transitions, suggesting a significant pyrazolate-and NHCcentered π−π* character.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Bimetallic Platinum Group Complexes of a Macrocyclic Pyrazolate/NHC Hybrid Ligand

Pickl

Pöthig

2021

Organometallics

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“…The nickel(II) complex (Figure 14: OM2) was not cytotoxic, although both the platinum(II) and palladium(II) complexes were considerably more cytotoxic than cisplatin, and have potential as both helical and quadruplex DNA binders [109]. Silver bis-methyl salen complexes have been investigated as potential anticancer agents and demonstrate promising fluorescent and DNA-binding properties.…”

Section: Other Metal Complexesmentioning

confidence: 99%

Photoactive and Luminescent Transition Metal Complexes as Anticancer Agents: A Guiding Light in the Search for New and Improved Cancer Treatments

McGhie

Aldrich‐Wright

2022

Biomedicines

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Cancer continues to be responsible for the deaths of more than 9 million people worldwide each year. Current treatment options are diverse, but low success rates, particularly for those with late-stage cancers, continue to be a problem for clinicians and their patients. The effort by researchers globally to find alternative treatment options is ongoing. In the present study, we focused on innovations in inorganic anticancer therapies, specifically those with photoactive and luminescent properties. Transition metals offer distinct advantages compared to wholly organic compounds in both chemotherapeutics and luminescence properties. Here we report on the characteristics that result from discrete structural changes that have been expertly used to fine-tune their properties, and how diverse inherent luminescent properties have been widely employed to monitor cellular localization to photodynamic therapy.

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“…So, these ligands also are remarkable in the field of drug discovery due to this excellent synthetic flexibility. In this regard, many carbene ligands have been tested with metals such as platinum, [ 12 ] palladium, [ 13–16 ] ruthenium, [ 17 ] rhodium, [ 18 ] nickel, [ 19 ] iridium, [ 20 ] copper, [ 21 ] gold, [ 22 ] and silver. [ 23,24 ]…”

Section: Introductionmentioning

confidence: 99%

Silver N‐heterocyclic carbene complexes bearing fluorinated benzyl group: Synthesis, characterization, crystal structure, computational studies, and inhibitory properties against some metabolic enzymes

Bal

Demirci

Şen

et al. 2021

Applied Organom Chemis

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A series of the silver N‐heterocyclic carbene (NHC) complexes have been synthesized from the reactions between benzimidazolium salts bearing fluorinated benzyl group and Ag2O via the deprotonation method. All Ag(I)NHC complexes were characterized by known spectroscopic techniques (1H nuclear magnetic resonance [NMR], 13C NMR, and Fourier transform infrared [FT‐IR]) and elemental analysis. The molecular structures of the two complexes were unambiguously elucidated through single‐crystal X‐ray diffraction analysis. Namely, X‐ray studies show that the coordination geometry around the Ag(I) atom in the case of complex 2c is revealed to be almost linear with C–Ag–Cl angle, whereas in complex 2e, it appears as a nonlinear structure. The inhibitory profiles of these new complexes are investigated on some metabolic enzymes. Representatively, the most potent complex against human carbonic anhydrase isoenzymes I and II (hCAs I and II), 2d, was 1.8 times more potent than standard inhibitor acetazolamide against hCAs I and II. On the other hand, complexes 2c and 2b as most potent compounds against both cholinesterase enzymes was around 5 and 1.6 times more potent than tacrine against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively. The most active α‐glucosidase inhibitor 2d had similar activity to acarbose as a standard inhibitor. Furthermore, it confirms its in vitro studies as a result of molecular docking studies for each enzyme with (i) binding energy and inhibition constant values and (ii) the definition of the best conformation and nonbonding interactions of the related complexes (2b, 2c, and 2d) against the different target proteins.

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Macrocyclic NHC complexes of group 10 elements with enlarged aromaticity for biological studies

Abstract: Two sets of macrocyclic, bio-inspired, non-heme ligands are utilized for the synthesis of NiII, PdII and PtII complexes.

Cited by 20 publications

References 49 publications

Bimetallic Platinum Group Complexes of a Macrocyclic Pyrazolate/NHC Hybrid Ligand

Bimetallic Platinum Group Complexes of a Macrocyclic Pyrazolate/NHC Hybrid Ligand

Photoactive and Luminescent Transition Metal Complexes as Anticancer Agents: A Guiding Light in the Search for New and Improved Cancer Treatments

Silver N‐heterocyclic carbene complexes bearing fluorinated benzyl group: Synthesis, characterization, crystal structure, computational studies, and inhibitory properties against some metabolic enzymes

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