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Journal of Biological Inorganic Chemistry: JBIC

Rebecca N Adamek, Cy V Credille, Benjamin L Dick, Seth M Cohen
Hydroxypyridinethiones (HOPTOs) are strong ligands for metal ions and potentially useful pharmacophores for inhibiting metalloenzymes relevant to human disease. However, HOPTOs have been sparingly used in drug discovery efforts due, in part, to concerns that this scaffold will act as a promiscuous, non-selective metalloenzyme inhibitor, as well as possess poor pharmacokinetics (PK), which may undermine drug candidates containing this functional group. To advance HOPTOs as a useful pharmacophore for metalloenzyme inhibitors, a library of 22 HOPTO isostere compounds has been synthesized and investigated...
July 12, 2018: Journal of Biological Inorganic Chemistry: JBIC
Kaia Tõnsuaadu, Michel Gruselle, Frieda Kriisa, Andres Trikkel, Patrick Gredin, Didier Villemin
Motivated by the role of copper ions in biological processes the aim of this study was to elucidate the impact of copper ions bound to hydroxyapatite on L-serine (L-Ser) and O-phospho-L-serine (O-Ph-L-Ser) adsorption at different acidity of aqueous solutions. The adsorption phenomenon was studied by FTIR, UV, and AA spectroscopy, XRD and thermal analysis methods together with the evolved gases analysis taking into consideration the ionic state of the amino acids as well as the apatite surface state, which are tightly correlated with the solution pH...
July 9, 2018: Journal of Biological Inorganic Chemistry: JBIC
Scott P Fletcher, Asif Noor, James L Hickey, Catriona A McLean, Jonathan M White, Paul S Donnelly
Age-associated deposition of amyloid-β in cerebral blood vessels, a condition referred to as cerebral amyloid angiopathy, can contribute to stroke and dementia. This research aimed to design new radioactive technetium-99 m complexes that bind to amyloid-β plaques that have the potential to assist in diagnosis of cerebral amyloid angiopathy using single-photon-emitted computed tomography (SPECT) imaging. Six new pyridylthiosemicarbazide ligands containing either benzofuran or styrylpyridyl functional groups that are known to selectively bind to amyloid plaques were prepared...
July 7, 2018: Journal of Biological Inorganic Chemistry: JBIC
Loyanne C B Ramos, Fernando P Rodrigues, Juliana C Biazzotto, Sergio de Paula Machado, Leonardo D Slep, Michael R Hamblin, Roberto S da Silva
The rational design of anti-cancer agents includes a new approach based on ruthenium complexes that can act as nitric oxide (NO) donor agents against specific cellular targets. One of the most studied classes of those compounds is based on bis(bipyridine) ruthenium fragment and its derivative species. In this work, we present the chemical and cytotoxicity properties against the liver hepatocellular carcinoma cell line HepG2 of cis-[RuII (NO+ )Cl(dcbpy)2 ]2- conjugated to a polyclonal antibody IgG (anti-VDAC) recognizing a cell surface marker...
July 3, 2018: Journal of Biological Inorganic Chemistry: JBIC
Lizhi Tao, Troy A Stich, Alexandra V Soldatova, Bradley M Tebo, Thomas G Spiro, William H Casey, R David Britt
The multi-copper oxidase (MCO) MnxG from marine Bacillus bacteria plays an essential role in geochemical cycling of manganese by oxidizing Mn2+ (aq) to form manganese oxide minerals at rates that are three to five orders of magnitude faster than abiotic rates. The MCO MnxG protein is isolated as part of a multi-protein complex, denoted as Mnx, which includes one MnxG unit and a hexamer of MnxE3 F3 subunit. During the oxidation of Mn2+ (aq) catalyzed by the Mnx protein complex, an enzyme-bound Mn(III) species was trapped recently in the presence of pyrophosphate (PP) and analyzed using parallel-mode electron paramagnetic resonance (EPR) spectroscopy...
July 2, 2018: Journal of Biological Inorganic Chemistry: JBIC
Wilma Neumann, Elizabeth M Nolan
Bacterial iron uptake machinery can be hijacked for the targeted delivery of antibiotics into pathogens by attaching antibiotics to siderophores, iron chelators that are employed by bacteria to obtain this essential nutrient. We synthesized and evaluated Ent-SS-Cipro, a siderophore-antibiotic conjugate comprised of the triscatecholate siderophore enterobactin and the fluoroquinolone antibiotic ciprofloxacin that contains a self-immolative disulfide linker. This linker is designed to be cleaved after uptake into the reducing environment of the bacterial cytoplasm...
July 2, 2018: Journal of Biological Inorganic Chemistry: JBIC
Julia J Griese, Rui M M Branca, Vivek Srinivas, Martin Högbom
R2-like ligand-binding oxidases contain a dinuclear metal cofactor which can consist either of two iron ions or one manganese and one iron ion, but the heterodinuclear Mn/Fe cofactor is the preferred assembly in the presence of MnII and FeII in vitro. We have previously shown that both types of cofactor are capable of catalyzing formation of a tyrosine-valine ether cross-link in the protein scaffold. Here we demonstrate that Mn/Fe centers catalyze cross-link formation more efficiently than Fe/Fe centers, indicating that the heterodinuclear cofactor is the biologically relevant one...
June 26, 2018: Journal of Biological Inorganic Chemistry: JBIC
Jennifer M McGarry, A Andrew Pacheco
A re-investigation of the interaction with NO of the small tetraheme protein cytochrome c 554 (C554 ) from Nitrosomonas europaea has shown that the 5-coordinate heme II of the two- or four-electron-reduced protein will nitrosylate reversibly. The process is first order in C554 , first order in NO, and second-order overall. The rate constant for NO binding to the heme is 3000 ± 140 M-1 s-1 , while that for dissociation is 0.034 ± 0.009 s-1 ; the degree of protein reduction does not appear to significantly influence the nitrosylation rate...
June 26, 2018: Journal of Biological Inorganic Chemistry: JBIC
Clifford D Hardy, Alison Butler
A growing number of siderophores are found to contain β-hydroxyaspartic acid (β-OH-Asp) as a functional group for Fe(III) coordination, along with the more common catechol and hydroxamic acid groups. This review covers the structures, biosynthesis, and reactions of peptidic β-OH-Asp siderophores. Hydroxylation of Asp in siderophore biosynthesis is predicted to be carried out either through discrete aspartyl β-hydroxylating enzymes or through hydroxylating domains within non-ribosomal peptide synthetases, both of which display sequence homology to known non-heme iron(II), α-ketoglutarate-dependent dioxygenases...
June 26, 2018: Journal of Biological Inorganic Chemistry: JBIC
Rachel Codd, Cho Zin Soe, Amalie A H Pakchung, Athavan Sresutharsan, Christopher J M Brown, William Tieu
Dihydroxamic acid macrocyclic siderophores comprise four members: putrebactin (putH2 ), avaroferrin (avaH2 ), bisucaberin (bisH2 ), and alcaligin (alcH2 ). This mini-review collates studies of the chemical biology and coordination chemistry of these macrocycles, with an emphasis on putH2 . These Fe(III)-binding macrocycles are produced by selected bacteria to acquire insoluble Fe(III) from the local environment. The macrocycles are optimally pre-configured for Fe(III) binding, as established from the X-ray crystal structure of dinuclear [Fe2 (alc)3 ] at neutral pH...
June 26, 2018: Journal of Biological Inorganic Chemistry: JBIC
Xuewu Sui, Erik R Farquhar, Hannah E Hill, Johannes von Lintig, Wuxian Shi, Philip D Kiser
Carotenoid cleavage oxygenases (CCO) are non-heme iron enzymes that catalyze oxidative cleavage of alkene bonds in carotenoid and stilbenoid substrates. Previously, we showed that the iron cofactor of CAO1, a resveratrol-cleaving member of this family, can be substituted with cobalt to yield a catalytically inert enzyme useful for trapping active site-bound stilbenoid substrates for structural characterization. Metal substitution may provide a general method for identifying the natural substrates for CCOs in addition to facilitating structural and biophysical characterization of CCO-carotenoid complexes under normal aerobic conditions...
June 26, 2018: Journal of Biological Inorganic Chemistry: JBIC
Koushik Ghosh, Katherine C Elbert, Eva Rose M Balog, Jennifer S Martinez, Reginaldo C Rocha
An optically active metallo-polymer assembly is demonstrated via conjugation of a genetically engineered elastin-like polypeptide (ELP) and a ruthenium(II) polypyridyl complex. By taking advantage of the phase transition of ELPs in water, photophysical properties of the resultant conjugate are investigated for both phases, below and above the critical transition temperature. Upon coacervation, the luminescence of the metallo-ELP is greatly enhanced as a consequence of local effects on the metal-ligand luminophore...
June 22, 2018: Journal of Biological Inorganic Chemistry: JBIC
Mingjie Li, Kate L Henderson, Salette Martinez, Robert P Hausinger, Joseph P Emerson
Taurine/α-ketoglutarate (αKG) dioxygenase (TauD) is an E. coli nonheme Fe2+ - and αKG-dependent metalloenzyme that catalyzes the hydroxylation of taurine, leading to the production of sulfite. The metal-dependent active site in TauD is formed by two histidine and one aspartate that coordinating to one face of an octahedral coordination geometry, known as the 2-His-1-carboxylate facial triad. This motif is found in many nonheme Fe2+ proteins, but there is limited information on the thermodynamic parameters that govern metal-ion binding to this site...
June 19, 2018: Journal of Biological Inorganic Chemistry: JBIC
Hyo Je Cho, Ha Yeon Cho, Jeen-Woo Park, Oh-Shin Kwon, Hyun-Shik Lee, Tae Lin Huh, Beom Sik Kang
Cadmium (Cd2+ ) is toxic to living organisms because it causes the malfunction of essential proteins and induces oxidative stress. NADP+ -dependent cytosolic isocitrate dehydrogenase (IDH) provides reducing energy to counteract oxidative stress via oxidative decarboxylation of isocitrate. Intriguingly, the effects of Cd2+ on the activity of IDH are both positive and negative, and to understand the molecular basis, we determined the crystal structure of NADP+ -dependent cytosolic IDH in the presence of Cd2+ ...
June 19, 2018: Journal of Biological Inorganic Chemistry: JBIC
M Alfano, J Pérard, R Miras, P Catty, C Cavazza
Carboxydothermus hydrogenoformans is a model microorganism for the study of [NiFe]-CODH, a key enzyme of carbon cycle in anaerobic microorganisms. The enzyme possesses a unique active site (C-cluster), constituted of a distorted [NiFe3 S4 ] cubane linked to a mononuclear Fe(II) center. Both the biogenesis of the C-cluster and the activation of CODH by nickel insertion remain unclear. Among the three accessory proteins thought to play a role in this latter step (CooC, CooJ, and CooT), CooT is identified as a nickel chaperone involved in CODH maturation in Rhodospirillum rubrum...
June 7, 2018: Journal of Biological Inorganic Chemistry: JBIC
Zuzanna Wojdyla, Tomasz Borowski
The Fe(II)/2-oxoglutarate-dependent dioxygenase AsqJ from Aspergillus nidulans catalyses two pivotal steps in the synthesis of quinolone antibiotic 4'-methoxyviridicatin, i.e., desaturation and epoxidation of a benzodiazepinedione. The previous experimental results signal that, during the desaturation reaction, hydrogen atom transfer (HAT) from the benzylic carbon atom (C10) is a more likely step to initiate the reaction than the alternative HAT from the ring moiety (C3 atom). To unravel the origins of this regioselectivity and to explain why the observed reaction is desaturation and not the "default" hydroxylation, we performed a QM/MM study on the reaction catalysed by AsqJ...
June 6, 2018: Journal of Biological Inorganic Chemistry: JBIC
Carlson Alexander, A Nithyakumar, M Wilson Bosco Paul, N Arockia Samy
The synthesis of the platinum(II) complexes, [Pt(AIP)(bpy)](PF6 )2 (1) and [Pt(PIP)(phen)](PF6 )2 (2), of anthracene- and pyrene-conjugated imidazophenanthroline ligands and their in vitro cytotoxicity toward the fibroblast cells and the HeLa cell lines are reported. MTT assay demonstrates their cytotoxicity against the HeLa cell lines with the IC50 values of 1.35 and 1.56 µM, respectively, and the cytotoxicity profiles indicate that the HeLa cell lines show more activity than the fibroblast cells. Trypan blue assay highlights significant damage on the HeLa cell lines with a pronounced reduction on their clonogenicity...
July 2018: Journal of Biological Inorganic Chemistry: JBIC
Deliang Kong, Meng Tian, Lihua Guo, Xicheng Liu, Shumiao Zhang, Yameng Song, Xin Meng, Shu Wu, Lingzi Zhang, Zhe Liu
Organometallic half-sandwich IrIII complexes of the type [(η5 -Cpx )Ir(N^N)Cl]PF6 1-6, where Cpx  = C5 Me5 (Cp*), C5 Me4 C6 H5 (Cpxph ), C5 Me4 C6 H4 C6 H5 (Cpxbiph ), N^N is imionopyridine chelating ligand, were prepared and characterized. The X-ray crystal structure of complex 1 has been determined. Four compounds displayed higher anticancer potency than clinically used anticancer drug cisplatin against A549 cancer cells, especially complex 3 which is 8 times more active than cisplatin. No hydrolysis was observed by NMR and UV-Vis for complexes 3 and 6; however, these complexes show big differences in nucleobase binding, mainly decided by the imionopyridine chelating ligand...
July 2018: Journal of Biological Inorganic Chemistry: JBIC
Hsiao-Wen Huang, Yen-Hung Lin, Min-Hsuan Lin, Ya-Rong Huang, Chih-Hung Chou, Hsiao-Chin Hong, Mei-Ren Wang, Yu-Ting Tseng, Po-Chun Liao, Min-Chuan Chung, Yu-Jie Ma, Shou-Cheng Wu, Yung-Jen Chuang, Horng-Dar Wang, Yun-Ming Wang, Hsien-Da Huang, Tsai-Te Lu, Wen-Feng Liaw
The ubiquitous and emerging physiology function of endogenous nitric oxide in vascular, myocardial, immune, and neuronal systems prompts chemists to develop a prodrug for the controlled delivery of ·NO in vivo and for the translational biomedical application. Inspired by the discovery of natural [Fe(NO)2 ] motif, herein, we develop the synthetic dinitrosyl iron complexes (DNICs) [Fe2 (μ-SR)2 (NO)4 ] (1) as a universal platform for the O2 -triggered release of ·NO, for the regulation of ·NO-release kinetics (half-life = 0...
July 2018: Journal of Biological Inorganic Chemistry: JBIC
Irwin Cassells, Tameryn Stringer, Alan T Hutton, Sharon Prince, Gregory S Smith
A series of bidentate salicylaldimine ligands was prepared and reacted with either [RuCl(µ-Cl)(p-cymene)]2 , [RhCl(µ-Cl)(Cp*)]2 or [IrCl(µ-Cl)(Cp*)]2 . All of the compounds were characterised using an array of spectroscopic and analytical techniques, namely, nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy and mass spectrometry. Single crystal X-ray diffraction (XRD) was used to confirm the bidentate coordination mode of the salicylaldimine ligand to the metal centre. The platinum group metal (PGM) complexes were screened against the MCF7 breast cancer cell line...
July 2018: Journal of Biological Inorganic Chemistry: JBIC
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