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We describe the preparation and study of novel cavitands, molecular bowls 16+ and 26+, as good binders of the anticancer drug methotrexate (MTX). Molecular bowls are comprised of a curved tribenzotriquinacene (TBTQ) core conjugated to three macrocyclic pyridinium units at the top. The cavitands are easily accessible via two synthetic steps from hexabromo-tribenzotriquinacene in 25% yield. As amphiphilic molecules, bowls 16+ and 26+ self-associate in water by the nucleation-to-aggregation pathway (NMR). The bowls are preorganized, having a semi-rigid framework comprising a fixed bottom with a wobbling pyridinium rim (VT NMR and MD). Further studies, both experimental (NMR) and computational (DFT and MCMM), suggested that a folded MTX occupies the cavity of bowls wherein it forms π-π, C-H-π, and ion pairing intermolecular contacts but also undergoes desolvation to give stable binary complexes (µM) in water. Moreover, a computational protocol is introduced to identify docking pose(s) of MTX inside molecular bowls from NMR shielding data. Both molecular bowls have shown in vitro biocompatibility with liver and kidney cell lines (MTS assay). As bowl 26+ is the strongest binder of MTX reported to date, we envision it as an excellent candidate for further studies on the way toward developing an antidote capable of removing MTX from overdosed cancer patients.
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The creation of new families of intermetallic or Zintl-phase compounds with high-spin orbit elements has attracted a considerable amount of interest due to the presence of unique electronic, magnetic, and topological phenomena in these materials. Here, we establish the synthesis and structural and electronic characterization of KMg4Bi3 single crystals having a new structure type. KMg4Bi3 crystallizes in space group Cmcm having unit cell parameters a = 4.7654(11) Å, b = 15.694(4) Å, and c = 13.4200(30) Å and features an edge-sharing MgBi4 tetrahedral framework that forms cage-like one-dimensional channels around K+ ions. Diffuse reflectance absorption measurements indicate that this material has a narrow band gap of 0.27 eV, which is in close agreement with the electronic structure calculations that predict it to be a trivial insulator. Electronic transport measurements from 80 to 380 K indicate this material behaves like a narrow band gap semiconductor doped to â¼1018 holes/cm-3, with thermopowers of â¼100 µV/K and appreciable magnetoresistance. Electronic structure calculations indicate this material is close to a topological phase transition and becomes a topological insulator when the lattice is uniformly expanded by 3.5%. Overall, this unique structure type expands the landscape of potential quantum materials.
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The realization and discovery of quantum spin liquid (QSL) candidate materials are crucial for exploring exotic quantum phenomena and applications associated with QSLs. Most existing metal-organic two-dimensional (2D) quantum spin liquid candidates have structures with spins arranged on the triangular or kagome lattices, whereas honeycomb-structured metal-organic compounds with QSL characteristics are rare. Here, we report the use of 2,5-dihydroxy-1,4-benzoquinone (X2dhbq, X = Cl, Br, H) as the linkers to construct cobalt(II) honeycomb lattices (NEt4)2[Co2(X2dhbq)3] as promising Kitaev-type QSL candidate materials. The high-spin d7 Co2+ has pseudospin-1/2 ground-state doublets, and benzoquinone-based linkers not only provide two separate superexchange pathways that create bond-dependent frustrated interactions but also allow for chemical tunability to mediate magnetic coupling. Our magnetization data show antiferromagnetic interactions between neighboring metal centers with Weiss constants from -5.1 to -8.5 K depending on the X functional group in X2dhbq linkers (X = Cl, Br, H). No magnetic transition or spin freezing could be observed down to 2 K. Low-temperature susceptibility (down to 0.3 K) and specific heat (down to 0.055 K) of (NEt4)2[Co2(H2dhbq)3] were further analyzed. Heat capacity measurements confirmed no long-range order down to 0.055 K, evidenced by the broad peak instead of the λ-like anomaly. Our results indicate that these 2D cobalt benzoquinone frameworks are promising Kitaev QSL candidates with chemical tunability through ligands that can vary the magnetic coupling and frustration.
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A tetradentate bis(amido)bis(phosphine) FeII complex, (PNNP)Fe, is shown to activate the terminal C-H bond of aryl alkynes across its Fe-Namide bonds. (PNNP)Fe is also shown to catalytically dimerize terminal aryl alkynes to produce 1,3-enynes with Z : E ratios as high as 96 : 4 with yields up to 95% and loadings as low as 1 mol% at 30 °C in 2 h. A plausible metal-ligand cooperative mechanism invoking a vinylidene intermediate is proposed.
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Chiral organic-inorganic metal halides (OIMHs) are attractive for their potential applications in chiral optoelectronics and spintronics, such as circular polarized light emitters, detectors, and chiral-induced spin selectivity. Here, we report three pairs of chiral OIMHs with great water stability constructed from chiral viologens. These OIMHs contain either 1D or 0D structures, however, with small band gaps around 2 eV. Circular dichroism (CD) spectroscopy on transparent thin films of two OIMH pairs showed a wide CD response covering most of the visible light range. Although the chiral center is not directly attached to the pyridinium in these chiral viologens, the chirality is still successfully transferred into both the band gap and the exciton absorption ranges. Liquid and solid CD studies of the chiral viologens further indicate that the chiral induction inside these OIMHs is possibly through chiral crystallization. This work demonstrated the design strategy of water-stable, small band gap chiral OIMHs through chiral viologens. These low-dimensional chiral materials may provide an interesting system to investigate chiral induction, and their broad CD response may enable their potential application as circular photodetectors with a wide detection range.
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Copper(III) aryl species are widely proposed as intermediates in Cu-catalyzed C-C and C-heteroatom bond formation reactions. Despite their wide utility, mechanistic aspects of C-heteroatom formation at CuIII centers as well as factors that lead to byproducts, e.g., Ar-H, Ar-Ar, remain elusive due to the rarity of discrete CuIII-Ar complexes. Herein, we report the synthesis and reactivity of a series of CuII and CuIII aryl complexes that closely mimic the intermediates in Cu-catalyzed C-N coupling reactions. Copper(II) aryl complexes [TBA][LCuII-ArR] were synthesized via the treatment of CuII with a range of aryl donors, such as ZnAr2R, TMS-ArR, and ArR-Bpin. Oxidation of [TBA][LCuII-ArR] produces formal copper(III) aryl complexes LCuIII-ArR. Treatment of copper(III) aryl complexes with neutral nitrogen nucleophiles produces the C-N coupling product in up to 64% yield, along with commonly observed byproducts, such as Ar-H and Ar-Ar. Hammett analysis of the C-N bond formation performed with various N-nucleophiles shows a ρ value of -1.66, consistent with the electrophilic character of LCuIII-ArR. We propose mechanisms for common side reactions in Cu-catalyzed coupling reactions that lead to the formation of Ar-Ar and Ar-H.
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A new series of Rh2(II,II) complexes with the formula cis-[Rh2(DTolF)2(bpnp)(L)]2+, where bpnp = 2,7-bis(2-pyridyl)-1,8-naphthyridine, DTolF = N,N'-di(p-tolyl) formamidinate, and L = pdz (pyridazine; 2), cinn (cinnoline; 3), and bncn (benzo[c]cinnoline; 4), were synthesized from the precursor cis-[Rh2(DTolF)2(bpnp)(CH3CN)2]2+ (1). The first reduction couple in 2-4 is localized on the bpnp ligand at approximately -0.52 V vs Ag/AgCl in CH3CN (0.1 M TBAPF6), followed by reduction of the corresponding diazine ligand. Complex 1 exhibits a Rh2(δ*)/DTolF â bpnp(π*) metal/ligand-to-ligand charge-transfer (1ML-LCT) absorption with a maximum at 767 nm (ε = 1800 M-1 cm-1). This transition is also present in the spectra of 2-4, overlaid with the Rh2(δ*)/DTolF â L(π*) 1ML-LCT bands at 516 nm in 2 (L = pdz), 640 nm in 3 (L = cinn), and 721 nm in 4 (L = bncn). Complexes 2 and 3 exhibit Rh2(δ*)/DTolF â bpnp 3ML-LCT excited states with lifetimes, τ, of 3 and 5 ns, respectively, in CH3CN, whereas the lowest energy 3ML-LCT state in 4 is Rh2(δ*)/DTolF â bncn in nature with τ = 1 ns. Irradiation of 4 with 670 nm light in DMF in the presence of 0.1 M TsOH (p-toluene sulfonic acid) and 30 mM BNAH (1-benzyl-1,4-dihydronicotinamide) results in the production of H2 with a turnover number (TON) of 16 over 24 h. The axial capping of the Rh2(II,II) bimetallic core with the bpnp ligand prevents the formation of an Rh-H hydride intermediate. These results show that the observed photocatalytic reactivity is localized on the bncn ligand, representing the first example of ligand-centered H2 production.
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We describe the preparation, dynamic, assembly characteristics of vase-shaped basket 13- along with its ability to form an inclusion complex with anticancer drug mitoxantrone in abiotic and biotic systems. This novel cavitand has a deep nonpolar pocket consisting of three naphthalimide sides fused to a bicyclic platform at the bottom while carrying polar glycines at the top. The results of 1 H Nuclear Magnetic Resonance (NMR), 1 Hâ NMR Chemical Exchange Saturation Transfer (CEST), Calorimetry, Hybrid Replica Exchange Molecular Dynamics (REMD), and Microcrystal Electron Diffraction (MicroED) measurements are in line with 1 forming dimer [12 ]6- , to be in equilibrium with monomers 1(R) 3- (relaxed) and 1(S) 3- (squeezed). Through simultaneous line-shape analysis of 1 Hâ NMR data, kinetic and thermodynamic parameters characterizing these equilibria were quantified. Basket 1(R) 3- includes anticancer drug mitoxantrone (MTO2+ ) in its pocket to give stable binary complex [MTOâ1]- (Kd =2.1â µM) that can be precipitated inâ vitro with UV light or pH as stimuli. Both inâ vitro and inâ vivo studies showed that the basket is nontoxic, while at a higher proportion with respect to MTO it reduced its cytotoxicity inâ vitro. With well-characterized internal dynamics and dimerization, the ability to include mitoxantrone, and biocompatibility, the stage is set to develop sequestering agents from deep-cavity baskets.
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Antineoplásicos , Mitoxantrona , Mitoxantrona/química , Antineoplásicos/farmacología , Antineoplásicos/química , Espectroscopía de Resonancia MagnéticaRESUMEN
Pathogenic bacteria employ iron-containing enzymes to detoxify nitric oxide (NOâ¢) produced by mammals as part of their immune response. Two classes of diiron proteins, flavodiiron nitric oxide reductases (FNORs) and the hemerythrin-like proteins from mycobacteria (HLPs), are upregulated in bacteria in response to an increased local NO⢠concentration. While FNORs reduce NO⢠to nitrous oxide (N2O), the HLPs have been found to either reduce nitrite to NO⢠(YtfE), or oxidize NO⢠to nitrite (Mka-HLP). Various structural and functional models of the diiron site in FNORs have been developed over the years. However, the NO⢠oxidation reactivity of Mka-HLP has yet to be replicated with a synthetic complex. Compared to the FNORs, the coordination environment of the diiron site in Mka-HLP contains one less carboxylate ligand and, therefore, is expected to be more electron-poor. Herein, we synthesized a new diiron complex that models the electron-poor coordination environment of the Mka-HLP diiron site. The diferrous precursor FeIIFeII reacts with NO⢠to form a diiron dinitrosyl species ({FeNO}72), which is in equilibrium with a mononitrosyl diiron species (FeII{FeNO}7) in solution. Both complexes can be isolated and fully characterized. However, only oxidation of {FeNO}72 produced nitrite in high yield (71%). Our study provides the first model that reproduces the NO⢠oxidase reactivity of Mka-HLP and suggests intermediacy of an {FeNO}6/{FeNO}7 species.
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Óxido Nítrico , Nitritos , Animales , Óxido Nítrico/química , Hierro/química , Oxidación-Reducción , Óxido Nitroso , Bacterias/metabolismo , Mamíferos/metabolismoRESUMEN
Developing K-ion conducting solid-state electrolytes (SSEs) plays a critical role in the safe implementation of potassium batteries. In this work, a chalcogenide-based potassium ion SSE is reported, K3 SbSe4 , which adopts a trigonal structure at room temperature. Single-crystal structural analysis reveals a trigonal-to-cubic phase transition at the low temperature of 50 °C, which is the lowest among similar compounds and thus provides easy access to the cubic phase. The substitution of barium for potassium in K3 SbSe4 leads to the creation of potassium vacancies, expansion of lattice parameters, and a transformation from a trigonal phase to a cubic phase. As a result, the maximum conductivity of K3-2 x Bax SbSe4 reaches around 0.1 mS cm-1 at 40 °C for K2.2 Ba0.4 SbSe4 , which is over two orders of magnitude higher than that of undoped K3 SbSe4 . This novel SSE is successfully employed in a K-O2 battery operating at room temperature where a polymer-laminated K2.2 Ba0.4 SbSe4 pellet serves as a separator between the oxygen cathode and the potassium metal anode. Effective protection of the K metal anode against corrosion caused by O2 is demonstrated.
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The bonding interactions of a synthesized pincer-ligated manganese dicarbonyl complex featuring an N-heterocyclic phosphenium (NHP+) central moiety are explored. The pincer ligand [PPP]Cl was coordinated to a manganese center using Mn(CO)5Br and 254 nm light to afford the chlorophosphine complex (PPClP)Mn(CO)2Br (2) as a mixture of halide exchange products and stereoisomers. The target dicarbonyl species (PPP)Mn(CO)2 (3) was prepared by treatment of 2 with 2 equiv of the reductant KC8. Computational investigations and analysis of structural parameters were used to elucidate multiple bonding interactions between the Mn center and the PNHP atom in 3. The generation of a product of formal H2 addition, (PPHP)Mn(CO)2H (4), was achieved through the dehydrogenation of NH3BH3, affording a 2:1 mixture of 4syn:4anti stereoisomers. The nucleophilic nature of the Mn center and the electrophilic nature of the PNHP moiety were demonstrated through hydride addition and protonation of 3 to produce K(THF)2[(PPHP)Mn(CO)2] (6) and (PPClP)Mn(CO)2H (5), respectively. The observed reactivity suggests that 3 is best described as a Mn-I/NHP+ complex, in contrast to pincer-ligated dicarbonyl manganese analogues typically assigned as MnI species.
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A cardiac glycoside epoxide, (-)-cryptanoside A (1), was isolated from the stems of Cryptolepis dubia collected in Laos, for which the complete structure was confirmed by analysis of its spectroscopic and single-crystal X-ray diffraction data, using copper radiation at a low temperature. This cardiac glycoside epoxide exhibited potent cytotoxicity against several human cancer cell lines tested, including HT-29 colon, MDA-MB-231 breast, OVCAR3 and OVCAR5 ovarian cancer, and MDA-MB-435 melanoma cells, with the IC50 values found to be in the range 0.1-0.5 µM, which is comparable with that observed for digoxin. However, it exhibited less potent activity (IC50 1.1 µM) against FT194 benign/nonmalignant human fallopian tube secretory epithelial cells when compared with digoxin (IC50 0.16 µM), indicating its more selective activity toward human cancer versus benign/nonmalignant cells. (-)-Cryptanoside A (1) also inhibited Na+/K+-ATPase activity and increased the expression of Akt and the p65 subunit of NF-κB but did not show any effects on the expression of PI3K. A molecular docking profile showed that (-)-cryptanoside A (1) binds to Na+/K+-ATPase, and thus 1 may directly target Na+/K+-ATPase to mediate its cancer cell cytotoxicity.
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Antineoplásicos , Glicósidos Cardíacos , Neoplasias Ováricas , Humanos , Femenino , Glicósidos Cardíacos/farmacología , Glicósidos Cardíacos/química , Cryptolepis/metabolismo , Apoptosis , Simulación del Acoplamiento Molecular , Línea Celular Tumoral , ATPasa Intercambiadora de Sodio-Potasio , Antineoplásicos/farmacología , Digoxina/farmacologíaRESUMEN
High-valent metal oxo complexes are prototypical intermediates for the activation and hydroxylation of alkyl C-H bonds. Substituting the oxo ligand with other functional groups offers the opportunity for additional C-H functionalization beyond C-O bond formation. However, few species aside from metal oxo complexes have been reported to both activate and functionalize alkyl C-H bonds. We herein report the first example of an isolated copper(iii) cyanide complex (LCuIIICN) and its C-H cyanation reactivity. We found that the redox potential (E ox) of substrates, instead of C-H bond dissociation energy, is a key determinant of the rate of PCET, suggesting an oxidative asynchronous CPET or ETPT mechanism. Among substrates with the same BDEs, those with low redox potentials transfer H atoms up to a million-fold faster. Capitalizing on this mechanistic insight, we found that LCuIIICN is highly selective for cyanation of amines, which is predisposed to oxidative asynchronous or stepwise transfer of H+/e-. Our study demonstrates that the asynchronous effect of PCET is an appealing tool for controlling the selectivity of C-H functionalization.
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Class Ic ribonucleotide reductases (RNRIc) and R2-like ligand-binding oxidases (R2lox) are known to contain heterobimetallic MnIIFeII cofactors. How these enzymes assemble MnIIFeII cofactors has been a long-standing puzzle due to the weaker binding affinity of MnII versus FeII. In addition, the heterobimetallic selectivity of RNRIc and R2lox has yet to be reproduced with coordination complexes, leading to the hypothesis that RNRIc and R2lox overcome the thermodynamic preference for coordination of FeII over MnII with their carefully constructed three-dimensional protein structures. Herein, we report the selective formation of a heterobimetallic MnIIFeII complex accomplished in the absence of a protein scaffold. Treatment of the ligand Py4DMcT (L) with equimolar amounts of FeII and MnII along with two equivalents of acetate (OAc) affords [LMnIIFeII (OAc)2(OTf)]+ (MnIIFeII) in 80% yield, while the diiron complex [LFeIIFeII(OAc)2(OTf)]+ (FeIIFeII) is produced in only 8% yield. The formation of MnIIFeII is favored regardless of the order of addition of FeII and MnII sources. X-ray diffraction (XRD) of single crystals of MnIIFeII reveals an unsymmetrically coordinated carboxylate ligandâa primary coordination sphere feature shared by both RNRIc and R2lox that differentiates the two metal binding sites. Anomalous XRD studies confirm that MnIIFeII exhibits the same site selectivity as R2lox and RNRIc, with the FeII (d6) center preferentially occupying the distorted octahedral site. We conclude that the successful assembly of MnIIFeII originates from (1) Fe-deficient conditions, (2) site differentiation, and (3) the inability of ligand L to house a dimanganese complex.
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Hierro , Ribonucleótido Reductasas , Hierro/química , Ligandos , Oxidorreductasas/metabolismo , Ribonucleótido Reductasas/química , Compuestos FerrososRESUMEN
Despite the utility of Si-Si bonds, there are relatively few examples of Si-Si bond formation by base metals. In this work, a four-coordinate iron complex, (PNNP)FeII, is shown to strongly activate the Si-H bonds in primary silanes across the Fe-amide bonds in a metal-ligand cooperative fashion. Upon treatment with excess silane, Si-Si dehydrogenative homocoupling is shown to occur across the Fe-Namide bond without concomitant oxidation and spin state changes at the Fe center.
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Hierro , Silanos , Hierro/química , Silanos/química , Metales , Compuestos Ferrosos/químicaRESUMEN
A single bridging phosphinoamide ligand was shown to support a metal-metal triple bond in a Zr/Co heterobimetallic complex. The similarity of the bonding in this compound to previously synthesized Zr/Co species, and therefore the assignment of the Zr/Co triple bond, is supported by the structural parameters of the complex, the electronic structure predicted by density functional theory, and complete-active-space self-consistent-field (CASSCF) calculations. This demonstrates that metal-metal multiple bonds can be realized in heterobimetallic complexes without multiple bridging ligands to enforce the proximity of the two metals.
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The bonding interactions and electronic structure of a diphosphine pincer ligand featuring an N-heterocyclic phosphenium/phosphido (NHP±) central moiety with nickel are explored. Treating Ni(COD)2 with the pincer ligand [PPP]Cl in the presence of a two-electron phosphine donor ligand PMe3 generates chlorophosphine complex (PPClP)Ni(PMe3) (2a). The cationic Ni complex [(PPP)Ni(PMe3)][BPh4] (3a) can be prepared by subsequent halide abstraction from 2a with NaBPh4. The assignment of 3a as a Ni0/NHP+ complex, based on analysis of structural parameters and computational investigations, lies in contrast to its previously reported group 10 MII/NHP- (M = Pd, Pt) analogues. The activation of O-H bonds across the Ni-PNHP bond is demonstrated by the addition of isopropanol to afford the metal hydride species [(PPOiPrP)Ni(PMe3)(H)][BPh4] (4). Notably, the installation of a P-H bond in the NHP unit by treatment of 2a with LiAlH4 yields (PPHP)Ni(PMe3) (6). The ambiphilic nature of the P-H bond was demonstrated through reactivity studies of P-H bond cleavage in comparison to a Pd analogue (PPHP)Pd(PPh3) (8).
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We report Pd-catalyzed cyclotrimerization of (+)-α-bromoenone, obtained from monoterpene ß-pinene, into an enantiopure cyclotrimer. This C3 symmetric compound has three bicyclo[3.1.1]heptane rings fused to its central benzene with each ring carrying a carbonyl group. The cyclotrimer undergoes diastereoselective threefold alkynylation with the lithium salts of five terminal alkynes (41-63 %, de=4-83 %). The addition enabled a rapid synthesis of a small library of novel chiral cavitands that, in shape, resemble a tripod stand. These molecular tripods include a tris-bicycloannelated benzene head attached to three alkyne legs twisted in one direction to form a nonpolar cavity with polar groups as feet. Tripods with methylpyridinium and methylisoquinolinium legs, respectively, form inclusion complexes with anti-inflammatory and chiral drugs (R)/(S)-ibuprofen and (R)/(S)-naproxen. The mode of binding shows drug molecules docked in the cavity of the host through ion-ion, cation-π, and C-H-π contacts that, in addition of desolvation, give rise to complexes having millimolar to micromolar stability in water. Our findings open the door to creating a myriad of enantiopure tripods with tunable functions that, in the future, might give novel chemosensors, catalysts or sequestering agents.
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Benceno , Naproxeno , Naproxeno/química , Éteres CíclicosRESUMEN
In this study, we describe a synthetic method for incorporating arenes into closed tubes that we name capsularenes. First, we prepared vase-shaped molecular baskets 4-7. The baskets comprise a benzene base fused to three bicycle[2.2.1]heptane rings that extend into phthalimide (4), naphthalimide (6), and anthraceneimide sides (7), each carrying a dimethoxyethane acetal group. In the presence of catalytic trifluoroacetic acid (TFA), the acetals at top of 4, 6 and 7 change into aliphatic aldehydes followed by their intramolecular cyclization into 1,3,5-trioxane (1 H NMR spectroscopy). Such ring closure is nearly a quantitative process that furnishes differently sized capsularenes 1 (0.7×0.9â nm), 8 (0.7×1.1â nm;) and 9 (0.7×1.4â nm;) characterized by X-Ray crystallography, microcrystal electron diffraction, UV/Vis, fluorescence, cyclic voltammetry, and thermogravimetry. With exceptional rigidity, unique topology, great thermal stability, and perhaps tuneable optoelectronic characteristics, capsularenes hold promise for the construction of novel organic electronic devices.
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Compounds derived from natural sources have been major contributors to the area of cancer chemotherapy for decades. As part of an ongoing effort to discover anticancer drug leads from tropical plants, a large-scale collection of Glycosmis ovoidea Pierre (Rutaceae), was made at Nui Chua National Park, Vietnam. Activity-guided fractionation of the chloroform-soluble fractions led to the isolation of nine coumarins, including the new compound, 1-(7-methoxy-2-oxo-2H-chromen-8-yl)-3-methyl-1-oxobut-2-en-2-yl (S)-2-methylbutanoate (1). An close analogue of 1, namely, kincuongin (2), was deemed as non-cytotoxic (IC50 > 10 µM) against five different cancer cell lines. However, co-administration of kimcuongin (2) showed an approximately 100 times potentiation of the MCF-7 breast cancer cell cytotoxicity of the previously reported flavonoid, 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone (10). To provide a mechanistic basis for the cancer cell line inhibition enhancement observed, an initial in silico study on compound 10 indicated that it interacts with isoforms of the NF-κB complex. In a confirmatory western blot experiment conducted, kimcuongin (2) was found to potentiate the effects of flavone 10 in inhibiting both NF-κB and PARP-1. In vivo investigations using a zebrafish (Danio rerio) model showed that compounds 2, 3, 5, and 6 did not exhibit any discernible toxicity at concentrations up to 50 µM.