Confined Nanospaces in Metallocages: Guest Molecules, Weakly Encapsulated Anions, and Catalyst Sequestration

Amouri, Hani; Desmarets, Christophe; Moussa, Jamal

doi:10.1021/cr200345v

Cited by 457 publications

(189 citation statements)

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“…14 Ellagic acid (5) encapsulated in metalla-prisms 9, 10, and 11 were readily prepared quantitatively by the reaction of one of the binuclear [Ru 2 (p-iPrC 6 H 4 Me) 2 14 acceptors with the tripyridyl donor 4 42 and ellagic acid (5) in a 3:2:1 ratio (Figure 1). The addition of diethyl ether to the concentrated reaction mixtures resulted in the isolation of analytically pure hexanuclear cages as crystalline solids.…”

Section: Resultsmentioning

confidence: 99%

“…Following our results, we hypothesized that the encapsulation of ellagic acid (5) in hexanuclear metalla-prisms would increase the bioavailability and thereby, also the anticancer activity. We therefore synthesized ellagic acid encapsulated in nano-sized metalla-prisms [ellagic acid⊂Ru 6 (p-iPrC 6 H 4 Me) 6 (tpeb) 2 (11) (where, tpeb is 1,3,5-tris(pyridin-4-ylethynyl) benzene, dobq is 2,5-dioxydo-1,4-benzoquinonato, donq is 5, 8-dihydroxy-1,4-naphthaquinonato and dotq is 6,11-dihydroxy-5,12-naphthacenedionato) with similarly sized cavities but differently sized portals. The antioxidant activities of the compounds were examined by performing an oxygen-radical absorbance capacity (ORAC) assay and the anti-cancer activities by assaying cytokines secreted by macrophages.…”

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confidence: 99%

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Investigation of the biological and anti-cancer properties of ellagic acid-encapsulated nano-sized metalla-cages

Dubey

Park

Kwon

et al. 2015

IJN

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Three new large hexanuclear metalla-prisms 9 – 11 incorporating 1,3, 5-tris(pyridin-4-ylethynyl)benzene (tpeb) 4 and one of the dinuclear arene ruthenium clips [Ru 2 ( p - i PrC 6 H 4 Me) 2 ( OO ∩ OO )][CF 3 SO 3 ] 2 ( OO ∩ OO =2,5-dioxydo-1,4-benzoquinonato [dobq] 1 , 5,8-dihydroxy-1,4-naphthaquinonato (donq) 2 , and 6,11-dihydroxy-5,12-naphthacenedionato [dotq] 3 ), which encapsulate the guest molecule ellagic acid (2,3,7,8-tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione, 5 ) were prepared. All complexes were isolated as triflate salts in good yields and were fully characterized by 1 H NMR spectroscopy and electrospray ionization mass spectrometry. The photophysical properties of these metalla-prisms were also investigated. Compounds 9 and 10 showed potent antioxidant activity, but 10 had the superior ORAC PE value (1.30±0.020). Ellagic acid ( 5 ) and compound 11 showed weaker activity than that of Trolox. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay showed that the metalla-prism compounds exhibit anticancer properties in vitro. Compound 10 inhibited the growth of all cancer cell lines at micromolar concentrations, with the highest cytotoxicity observed against A549 human lung cancer cells (IC 50 =25.9 μM). However, these compounds had a lower anti-cancer activity than that of doxorubicin. In a tumoricidal assay, ellagic acid ( 5 ) and compound 10 induced cytotoxicity in tumor cells, while doxorubicin did not. While free ellagic acid had no effect on the granulocyte-colony stimulating factor and regulated on activation normal T cell expressed and secreted protein, the encapsulated metalla-prism 10 stimulated granulocyte-colony stimulating factor and reduced regulated on activation normal T cell expressed and secreted protein expression in the RAW264.7 macrophage line. Our results show that ellagic acid encapsulated in metalla-prisms inhibited cancer cells via the modulation of mRNA induction and protein expression levels of the granulocyte-colony stimulating factor and regulated on activation normal T cell expressed and secreted protein in macrophages.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Investigation of the biological and anti-cancer properties of ellagic acid-encapsulated nano-sized metalla-cages

Dubey

Park

Kwon

et al. 2015

IJN

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“…12 Currently, MOFs are considered as materials with great potential and with possible industrial applications such as, for example, luminescent materials, 13 sensors, 14 and photocatalysts. 15 With numerous unique properties, MOF-5, which was invented by Yaghi and co-workers 16 in 1999, has become one of the more promising MOFs. A high capacity for hydrogen storage 17,18 and luminescence are just two properties.…”

Section: ■ Introductionmentioning

confidence: 99%

Luminescent Properties of Metal–Organic Framework MOF-5: Relativistic Time-Dependent Density Functional Theory Investigations

et al. 2012

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The electronically excited state and luminescence property of metal−organic framework MOF-5 were investigated using relativistic density functional theory (DFT) and timedependent DFT (TDDFT). The geometry, IR spectra, and UV− vis spectra of MOF-5 in the ground state were calculated using relativistic DFT, leading to good agreement between the experimental and theoretical results. The frontier molecular orbitals and electronic configuration indicated that the luminescence mechanism in MOF-5 follows ligand-to-ligand charge transfer (LLCT), namely, π* → π, rather than emission with the ZnO quantum dot (QD) proposed by Bordiga et al. The geometry and IR spectra of MOF-5 in the electronically excited state have been calculated using the relativistic TDDFT and compared with those for the ground state. The comparison reveals that the Zn 4 O 13 QD is rigid, whereas the ligands BDC 2− are nonrigid. In addition, the calculated emission band of MOF-5 is in good agreement with the experimental result and is similar to that of the ligand H 2 BDC. The combined results confirmed that the luminescence mechanism for MOF-5 should be LLCT with little mixing of the ligandto-metal charge transfer. The reason for the MOF-5 luminescence is explained by the excellent coplanarity between the sixmembered ring consisting of zinc, oxygen, carbon, and the benzene ring.

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“…For synthesis of MOFs with better drugs storage properties, nitrogen containing linkers such as amino acids are the best choices which have no toxic effects [14]. Similarly bio compatible metal cations like copper, nickel and manganese are suitable to synthesize MOFs both for in vitro and in vivo drugs adsorption studies [15].…”

Section: *Corresponding Authors: Tabinda Sattar Phd Scholar Institumentioning

confidence: 99%

Hydrothermally Synthesized Copper Isoleucinate (Bio-MOF-30), Evaluated by Single Crystal XRD Analysis and Drugs Storage Property

Sattar¹,

Athar²

2017

IJAT

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Confined Nanospaces in Metallocages: Guest Molecules, Weakly Encapsulated Anions, and Catalyst Sequestration

Cited by 457 publications

References 185 publications

Investigation of the biological and anti-cancer properties of ellagic acid-encapsulated nano-sized metalla-cages

Investigation of the biological and anti-cancer properties of ellagic acid-encapsulated nano-sized metalla-cages

Luminescent Properties of Metal–Organic Framework MOF-5: Relativistic Time-Dependent Density Functional Theory Investigations

Hydrothermally Synthesized Copper Isoleucinate (Bio-MOF-30), Evaluated by Single Crystal XRD Analysis and Drugs Storage Property

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