Publications by authors named "Jan Janczak"

86 Publications

An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine.

Eur J Med Chem 2021 Apr 10;215:113282. Epub 2021 Feb 10.

Department of Medical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznań, Poland. Electronic address:

Colchicine shows very high antimitotic activity, therefore, it is used as a lead compound for generation of new anticancer agents. In the hope of developing novel, useful drugs with more favourable pharmacological profiles, a series of doubly modified colchicine derivatives has been designed, synthesized and characterized. These novel carbamate or thiocarbamate derivatives of 10-demethoxy-10-methylaminocolchicine have been tested for their antiproliferative activity against four human cancer cell lines. Additionally, their mode of action has been evaluated as colchicine binding site inhibitors, using molecular docking studies. Most of the tested compounds showed greater cytotoxicity (IC in a low nanomolar range) and were characterized by a higher selectivity index than standard chemotherapeutics such as cisplatin and doxorubicin as well as unmodified colchicine. Their pharmacological use in cancer therapy could possibly be accomplished with lower dosages and result in less acute toxicity problems than in the case of colchicine. In addition, we present a QSAR model for predicting the antiproliferative activity of doubly modified derivatives for two tumour cell lines.
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http://dx.doi.org/10.1016/j.ejmech.2021.113282DOI Listing
April 2021

Synthesis and biological evaluation as well as in silico studies of arylpiperazine-1,2-benzothiazine derivatives as novel anti-inflammatory agents.

Bioorg Chem 2021 01 18;106:104476. Epub 2020 Nov 18.

Department of Medicinal Chemistry, Faculty of Pharmacy, Wroclaw Medical University, Borowska 211, 50-556 Wrocław, Poland.

Novel arylpiperazine-1,2-benzothiazine derivatives have been designed and synthesized as potential anti-inflammatory agents. Their structure and properties have been studied using spectroscopic techniques (H NMR, C NMR, FT-IR), MS, elemental analyses, and single-crystal X-ray diffraction (SCXRD, for compound 7b). This study aimed to evaluate the inhibitory activity of new derivatives against both cyclooxygenase isoforms COX-1 and COX-2 due to the similarity of new compounds to oxicams drugs from the NSAIDs group. All new compounds were divided into two series - A and B - with a different linker between thiazine and piperazines nitrogens. Series A included the three-carbon aliphatic linker and series B - two-carbon with a carbonyl group. According to in vitro and molecular docking studies all new compounds exhibited cyclooxygenase inhibitory activity. The series of A compounds included COX-1 inhibitors only. In contrast, the B series showed inhibition of both COX-1 and COX-2, which suggested the importance of the acetoxy linker for COX-2 inhibition. Moreover, the most selective compound 7b, towards COX-2, was non-toxic for the normal human cell line (in concentration of 10 µM) comparable to reference drug meloxicam. Additionally, investigation of influence on model membranes confirmed the ability of the compound 7b to penetrate lipid bilayers which seemed to be important to the influence with membrane protein-cyclooxygenase.
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http://dx.doi.org/10.1016/j.bioorg.2020.104476DOI Listing
January 2021

0D to 3D Pr metal-organic networks crystal engineered for optimal iodine adsorption.

Acta Crystallogr B Struct Sci Cryst Eng Mater 2020 Oct 19;76(Pt 5):779-788. Epub 2020 Aug 19.

Institute of Low Temperature and Structure Research, Polish Academy of Science, PO Box 1410, Wroclaw, 50950, Poland.

Four new praseodymium(III) metal-organic compounds varying in dimensionality from 0D to 3D have been designed and synthesized based on N-heterocyclic polycarboxylic acids, including pyridine-2,6-dicarboxylic acid (Hpydc) and pyrazine-2,3-dicarboxylic acid (Hpzdc). Altering the concentration of piperazine (pip, ancillary ligand) enables control over the dimensionality of the compound by switching between the 0D [Hpip][Hpip][Pr(pydc)]·4HO (I) and the 1D {[Pr(pydc)(Hpydc)(HO)]·4HO} (II) coordination polymer (CP). Upon replacing Hpydc with Hpzdc, CP II is converted to the 2D CP [Pr(pzdc)(Hpzdc)(HO)] (III) and using the metalloligand [Zn(Hpzdc)(HO)], the 3D heterometallic CP {[PrZn(pzdc)(HO)]·2HO} (IV) is formed. Compound IV shows high stability in the absence of uncoordinated solvent molecules and is stable up to 400°C, even in the presence of humidity. Therefore, IV was utilized for iodine adsorption in the vapour phase and in the presence of humidity. The results confirm the remarkable potential of IV for reversible adsorption of iodine vapour.
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http://dx.doi.org/10.1107/S2052520620009336DOI Listing
October 2020

Dopamine Sensing Based on Ultrathin Fluorescent Metal-Organic Nanosheets.

ACS Appl Mater Interfaces 2020 Oct 28;12(40):44499-44507. Epub 2020 Sep 28.

Institute of Low Temperature and Structure Research, Polish Academy of Science, P.O. Box 1410, 50950 Wrocław, Poland.

The importance of dopamine (DA) detection as a biomarker for several diseases, especially Parkinson''s disease, has persuaded scientists to develop new nanomaterials for efficient sensing of DA in clinical samples. Ultrathin metal-organic nanosheets due to their exceptional thickness, large surface area, and flexibility are endowed with many accessible active sites and optimal surface interaction with the target analyte molecules. In this regard, a novel layered fluorescent metal-organic nanomaterial with a honeycomb topology based on europium, [Eu(pzdc)(Hpzdc)(HO)] () (Hpzdc = 2,3-pyrazine dicarboxylic acid), was synthesized. X-ray crystallography revealed that the 3D supramolecular architecture of is constructed from noncovalent interactions of coordinated water molecules between the 2D layers along the axis. These layers that are only ∼4 nm thick were conveniently separated through ultrasound-induced liquid phase exfoliation. Optical studies show that the reduction of thickness enhances the fluorescence intensity and serves as an efficient optical marker for DA detection. nanoflakes exhibited fast response and high selectivity for DA detection in clinical samples. Good linearity for DA detection in the range of 0.1-10 μM with a detection limit of 21 nM proves the potential of nanoflakes in DA sensing applications.
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http://dx.doi.org/10.1021/acsami.0c13166DOI Listing
October 2020

Human plasma protein corona decreases the toxicity of pillar-layer metal organic framework.

Sci Rep 2020 09 3;10(1):14569. Epub 2020 Sep 3.

Department of Chemistry, Faculty of Chemical Science, Firoozabad Branch, Islamic Azad University, P.O. Box 74715-117, Firoozabad, Fars, Iran.

This scenario was designed to investigate the protein corona pattern on the pillar-layer surface of a Cu-based metal-organic framework (MOF) in human plasma. The [Cu(L)(L)].1.3DMA (MOF-1) {L = 4, 4-bipyridine and L = 5-aminoisophthalic acid}, was synthesized through the sonochemical irradiation approach as well as characterized by various techniques like scanning electron microscopy, Fourier-transform infrared spectroscopy, X-ray powder diffraction and single-crystal X-ray diffraction. The space group was determined to be an orthorhombic space group (Pbam) by single-crystal X-ray diffraction. Single-crystal X-ray analyses on MOF-1 showed that Cu ion was 6-coordinated. Besides, to study and clarify interactions between MOFs and biological milieu, human whole blood plasma was selected as a model. Fluorescence spectroscopy and SDS-PAGE techniques were employed to explore quantitative and qualitative in situ characterization of protein corona as well. Furthermore, cell viability in a cancerous cell lines was evaluated by MTT assay in the presence and absence of the corona. The results from SDS-PAGE illustrated that the most adsorbed quantity among plasma proteins belongs to fibrinogen (α, β and γ chains), and this protein showed the maximum frequency on the MOF-1s surface, so the possible interactions of MOF-1s with fibrinogen also studied using fluorescence spectroscopy and corresponding data were plotted. According to the obtained data from MTT assay, these structures have concentration-dependent toxicity. In brief, based on the obtained data in the current study, the designed MOF can be introduced as a new desirable carrier for drug/gen delivery after further prerequisite assessments.
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http://dx.doi.org/10.1038/s41598-020-71170-zDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7471913PMC
September 2020

Crystal engineering of an adenine-decavanadate molecular device towards label-free chemical sensing and biological screening.

Acta Crystallogr B Struct Sci Cryst Eng Mater 2020 Feb 24;76(Pt 1):85-92. Epub 2020 Jan 24.

Institute of Low Temperature and Structure Research, Polish Academy of Science, PO Box 1410, Wroclaw 50950, Poland.

Due to the inherent geometrical interdependencies of nucleic acid structures, the ability to engineer biosensors that rely on the specific interactions of these compounds is of considerable importance. Additionally, sensing or screening in a label-free fashion is a capability of these structures that can be readily achieved by exploiting the fluorescent component. In this work, the [AdH][VO].4(HO) (1) supramolecular structure is introduced using adenine and decavanadate moieties that allow probing of selectivity to specific nucleic acid binding events by optical changes. The structure of (1) is an alternating organic-inorganic hybrid architecture of cationic adeninium (AdH) ribbons and anionic decavanadate (DV)-water sheets. The luminescent screening and anticancer activity of compound (1) on the two human mammary carcinoma cell lines MDA-MB-231 and MCF7 were investigated using fluorescent microscopy and MTT assays, respectively. It was found that compound (1) is cell permeable with no toxicity below 12.5 µM concentration and moderate cytotoxicity at concentrations as high as 200 µM in human breast cancer cell lines, making it a useful tool to study the cell nucleus in real time.
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http://dx.doi.org/10.1107/S2052520619016196DOI Listing
February 2020

Evaluation of 1,2-Benzothiazine 1,1-dioxide Derivatives In Vitro Activity towards Clinical-Relevant Microorganisms and Fibroblasts.

Molecules 2020 Jul 31;25(15). Epub 2020 Jul 31.

Department of Pharmaceutical Microbiology and Parasitology, Faculty of Pharmacy, Medical University of Silesian Piasts in Wroclaw, Borowska 211, 50-556 Wroclaw, Poland.

The global concern related with growing number of bacterial pathogens, resistant to numerous antibiotics, prone scientific environment to search for new antimicrobials. Antiseptics appear to be suitable candidates as adjunctive agents to antibiotics or alternative local treatment option aiming to prevent and treat infections. 1,2-benzothiazines are considered one the most promising of them. In this research twenty 1,2-benzothiazine 1,1-dioxide derivatives were scrutinized with regard to their biological activity. Three of them are new. For evaluation of compounds' activity against microbial pathogens, disk diffusion method and serial microdilution method was applied. To establish the cytotoxicity profile of tested 1,2-benzothiazines 1,1-dioxides derivatives, the cytotoxicity assay using fibroblasts L292 was performed. Antimicrobial activity of all tested compounds against Gram-positive and strains was higher than antimicrobial activity of DMSO solvent, which possesses antimicrobial activity itself. Gram-negative , and have shown susceptibility only to compounds , and . None of tested compounds was effective against Compound has demonstrated the strongest antimicrobial potency (MIC = 0.00975 mg/mL) among compounds of series . Compounds of series , namely , , had the lowest minimum inhibitory concentration (MIC). Compound displayed also the lowest cytotoxic effect against fibroblast cell line among series compounds. All tested derivatives displayed lower MIC against Gram-positive bacteria than commercially applied antiseptic, povidone iodine, which MIC value range for tested Gram-positive bacteria was 1.56-6.25 mg/mL.
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http://dx.doi.org/10.3390/molecules25153503DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7435855PMC
July 2020

Ultrasound-assisted exfoliation of a layered 2D coordination polymer with HER electrocatalytic activity.

Ultrason Sonochem 2021 Jan 30;70:105292. Epub 2020 Jul 30.

Catalan Institute of Nanoscience and Nanotechnology (ICN2), CSIC and BIST, Campus UAB, Bellaterra, 08193 Barcelona, Spain. Electronic address:

Large blue rectangular crystals of the 2D layered coordination polymer 1 have been obtained. The interest for this complex is two-fold. First, complex 1 is made of 2D layers packing along the (0-11) direction favored by the presence of lattice and coordinated water molecules. And second, nanostructures that could be derived by delamination are potentially suitable for catalytic purposes. Therefore it represents an excellent example to study the role of interlayer solvent molecules on the ultrasound-assisted delamination of functionally-active 2D metal-organic frameworks in water, a field of growing interest. With this aim, ultrasound-assisted delamination of the crystals was optimized with time, leading to stable nanosheet colloidal water suspensions with very homogeneous dimensions. Alternative bottom-up synthesis of related nanocrystals under ultrasound sonication yielded similar shaped crystals with much higher size dispersions. Finally, experimental results evidence that the nanostructures have higher catalytic activities in comparison to their bulk counterparts, due to larger metallic center exposition. These outcomes confirm that the combination of liquid phase exfoliation and a suitable synthetic design of 2D coordination polymers represents a very fruitful approach for the synthesis of functional nanosheets with an enhancement of catalytic active sites, and in general, with boosted functional properties.
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http://dx.doi.org/10.1016/j.ultsonch.2020.105292DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7786594PMC
January 2021

Synthesis and crystal structure of a new heteronuclear complex of Fe(iii)-K designed to produce effective catalysts for CO hydrogenation.

Dalton Trans 2020 Aug 21;49(30):10498-10508. Epub 2020 Jul 21.

Department of Chemistry, University of Zabol, P.O. Box 98613-35856, Zabol, Iran.

A new paramagnetic heteronuclear complex formulated as [KFe(μ-ox)(HO)] (1), where ox is oxalate, has been synthesized under hydrothermal condition. The molecular structure of complex 1 was characterized by elemental analysis, Fourier-transform infrared spectroscopy (FT-IR) and single-crystal X-ray diffraction (SCXRD). The results of SC-XRD analysis revealed that complex 1 crystallizes in the centrosymmetric space group P2/c of a monoclinic system with cell dimension a = 7.7175 (4) Å, b = 19.8009 (7) Å, c = 10.2623 (5) Å, and β = 107.634 (5)° at 100 K. The thermal behavior of complex 1 was studied by thermogravimetric analysis (TGA) and differential thermal analysis (DTA). The magnetic behavior of complex 1 was studied at room temperature by a vibration sample magnetometer (VSM). Thermal decomposition of the silica and alumina supports of complex 1 at 650 °C resulted in the main catalysts, FeO-KO/SiO and FeO-KO/AlO. The catalytic activity of the main catalysts was evaluated for CO hydrogenation. For comparative purposes, the reference catalysts of FeO-KO/SiO and FeO-KO/AlO were prepared by the impregnation method. The structure and composition of the catalysts were investigated by FT-IR spectroscopy, powder X-ray diffraction (PXRD), N adsorption-desorption analysis, scanning electron microscopy (SEM), inductively coupled plasma atomic emission spectroscopy (ICP-AES) and energy dispersive X-ray analysis (EDX). We tested all catalysts for hydrogenation of CO at 5 bar of pressure in the temperature range of 593-673 K. It was found that the main catalysts have better CO conversion and selectivity to desired products, such as light olefins, than the reference catalysts.
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http://dx.doi.org/10.1039/d0dt01230kDOI Listing
August 2020

Cathecol and Naphtol Groups in Salphen-Type Schiff Bases for the Preparation of Polynuclear Complexes.

Int J Mol Sci 2020 May 18;21(10). Epub 2020 May 18.

Secció de Química Inorgànica, Departament de Química Inorgànica i Orgànica, C/MArtí i Franqués 1-11, Universitat de Barcelona, 08028, Barcelona, Spain.

In this paper, we show a strategy to modify salphen-type Schiff base ligands with naphtol (SYML1) and pyrocathecol (2,3-dihydroxyphenyl) groups (SYML2), or a combination of both (ASYML). Each of these ligands can be used to obtain polynuclear metal complexes following two different strategies. One relies on using metals that are either too large for the NO cavity or not fond of coordination number 4 and the other one relies on forcing the polynuclear species by adding functional groups to the hydroxybenzaldehayde in order to have extra coordination sites in the ligand. We report and characterize the mononuclear complexes SYML1-Cu and SYML1-Ce, along with the dinuclear complex SYML1-Fe and the tetranuclear species SYML2-Mn. The asymmetric ligand ASYML routinely hydrolyzes into the symmetric ligands in the reaction mixtures. SYML1-Fe displays a nearly linear Fe-O-Fe bridge with very strong antiferromagnetic coupling between the Fe(III) ions.
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http://dx.doi.org/10.3390/ijms21103574DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7278923PMC
May 2020

Synthesis, Antiproliferative Activity and Molecular Docking Studies of Novel Doubly Modified Colchicine Amides and Sulfonamides as Anticancer Agents.

Molecules 2020 Apr 14;25(8). Epub 2020 Apr 14.

Department of Medical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.

Colchicine is a well-known compound with strong antiproliferative activity that has had limited use in chemotherapy because of its toxicity. In order to create more potent anticancer agents, a series of novel colchicine derivatives have been obtained by simultaneous modification at C7 (amides and sulfonamides) and at C10 (methylamino group) positions and characterized by spectroscopic methods. All the synthesized compounds have been tested in vitro to evaluate their cytotoxicity toward A549, MCF-7, LoVo, LoVo/DX and BALB/3T3 cell lines. Additionally, the activity of the studied compounds was investigated using computational methods involving molecular docking of the colchicine derivatives to β-tubulin. The majority of the obtained derivatives exhibited higher cytotoxicity than colchicine, doxorubicin or cisplatin against tested cancer cell lines. Furthermore, molecular modeling studies of the obtained compounds revealed their possible binding modes into the colchicine binding site of tubulin.
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http://dx.doi.org/10.3390/molecules25081789DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7221574PMC
April 2020

Dual-emitting barium based metal-organic nanosheets as a potential sensor for temperature and anthrax biomarkers.

Nanotechnology 2020 Mar 3;31(24):245706. Epub 2020 Mar 3.

School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran.

The development of novel 2D materials, due to the promising applications they have enabled through their unique properties, has attracted increasingly more research interest. In this regard, novel dual-emitting coordination polymer nanosheets were developed by doping Eu and Tb ions into the nanostructures of the [Ba(DPA)(HO)] (DPA = dipicolinic acid) coordination polymer (BCP). Single crystal x-ray crystallography revealed that BCP is a 1D coordination polymer and its three-dimensional supramolecular architecture is constructed with a relatively strong hydrogen bonding in the ac crystallographic plane and weak non-covalent interactions along the b axis. Using energetic ultrasound irradiations, synthesis of nanoscale BCP along with the unzipping of the weak interactions between the ac layers was accomplished. The resulting BCP nanosheets was used as the host lattice and was doped with Eu and Tb ions. Remarkably, the sensing ability of both Eu and Tb doped coordination polymer ([email protected]) nanosheets towards temperature and the DPA anthrax biomarker were investigate. The high relative sensitivity value of 2.42% K and their reusability, makes [email protected] nanosheets an ideal candidate for the nanothermometry. They also exhibited high selective detection characteristics towards the DPA anthrax biomarker with a 0.03 nM detection limit. Therefore, [email protected] nanosheets can also be considered as an efficient multi-responsive optical sensor.
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http://dx.doi.org/10.1088/1361-6528/ab7c4bDOI Listing
March 2020

Water-Involved Hydrogen Bonds in Dimeric Supramolecular Structures of Magnesium and Zinc Phthalocyaninato Complexes.

Authors:
Jan Janczak

ACS Omega 2019 Feb 19;4(2):3673-3683. Epub 2019 Feb 19.

Institute of Low Temperature and Structure Research, Polish Academy of Sciences, Okólna 2 Str., P.O. Box 1410, 50-950 Wrocław, Poland.

Two dimeric supramolecular structures {MgPc(HO)·4-methylmorpholine}-() and {ZnPc(HO)·4-methylmorpholine}-() formed from two molecules of magnesium and zinc aquaphthalocyanines in 4-methylmorpholine solution were revealed by single-crystal X-ray diffraction. Coordinated HO molecules to the metal center of respective Mg or Zn phthalocyanines oriented face-to-face to form two hydrogen bonds, one of them connecting via O-H···N-azamethine atom to form a dimeric structure in the crystals with ring-to-ring distances of 3.412(3) Å in and 3.403(5) Å in , whereas the second hydrogen bonds link the solvent 4-methylpholine molecules to form supramolecular dimeric {MgPc(HO)·4-methylmorpholine}-() and {ZnPc(HO)·4-methylmorpholine}-() structures. The interaction of the metal center of MgPc or ZnPc with O atom of the water molecule results its displacement of ∼0.5 Å from the N-isonodole plane of the phthalocyaninate(2-) macrocycle that adopts a saucer-shape form. To better understand the interactions leading to the existence of the dimeric structures in the crystals, theoretical calculations of dimer stabilization energy composed of two monomers (MgPcHO and ZnPcHO), as well as three-dimensional molecular electrostatic potentials, have been performed using the density functional theoretical method. The calculated absorption spectra of both supramolecular monomers and dimers were compared with the experimental ones in 4-methylmorpholine solution. The water axial ligation of MgPc and ZnPc and the formation of the monomeric and dimeric supramolecular structures only slightly change the energy gap between highest occupied molecular orbital and lowest unoccupied molecular orbital levels that is compared with those of the parent MgPc and ZnPc pigments.
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http://dx.doi.org/10.1021/acsomega.8b03055DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648844PMC
February 2019

Tautomeric polymorphism of the neuroactive inhibitor kynurenic acid.

Acta Crystallogr C Struct Chem 2019 Jun 28;75(Pt 6):793-805. Epub 2019 May 28.

Departament of Chemistry, Wroclaw University of Science and Technology, Wybrzeze Wyspianskiego 27, Wroclaw 50-370, Poland.

Kynurenic acid (KYN; systematic name: 4-hydroxyquinoline-2-carboxylic acid, CHNO) displays a therapeutic effect in the treatment of some neurological diseases and is used as a broad-spectrum neuroprotective agent. However, it is understudied with respect to its solid-state chemistry and only one crystal form (α-KYN·HO) has been reported up to now. Therefore, an attempt to synthesize alternative solid-state forms of KYN was undertaken and six new species were obtained: five solvates and one salt. One of them is a new polymorph, β-KYN·HO, of the already known KYN monohydrate. All crystal species were further studied by single-crystal and powder X-ray diffraction, thermal and spectroscopic methods. In addition to the above methods, differential scanning calorimetry (DSC), in-situ variable-temperature powder X-ray diffraction and Raman microscopy were applied to characterize the phase behaviour of the new forms. All the compounds display a zwitterionic form of KYN and two different enol-keto tautomers are observed depending on the crystallization solvent used.
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http://dx.doi.org/10.1107/S2053229619005990DOI Listing
June 2019

Anti-trypanosomal activity of doubly modified salinomycin derivatives.

Eur J Med Chem 2019 Jul 3;173:90-98. Epub 2019 Apr 3.

Department of Bioorganic Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61‒614, Poznań, Poland.

As a group of biologically active compounds, polyether antibiotics (ionophores) show a broad spectrum of interesting pharmacological properties, ranging from anti-bacterial to anti-cancer activities. There is increasing evidence that ionophores, including salinomycin (SAL), and their semi-synthetic analogues are promising candidates for the development of drugs against parasitic diseases. Our previous studies have shown that esterification and amidation of the C1 carboxylate moiety of SAL provides compounds with potent activity against Trypanosoma brucei, protozoan parasites responsible for African trypanosomiasis. In this paper, we present the synthetic pathways, crystal structures and anti-trypanosomal activity of C1 esters, amides and hydroxamic acid conjugates of SAL, its C20-oxo and propargylamine analogues as well novel C1/C20 doubly modified derivatives. Evaluation of the trypanocidal and cytotoxic activity using bloodstream forms of T. brucei and human myeloid HL-60 cells revealed that the single-modified C20-oxo and propargylamine precursor molecules 10 and 16 were the most anti-trypanosomal and selective compounds with 50% growth inhibition (GI) values of 0.037 and 0.035 μM, and selectivity indices of 252 and 300, respectively. Also the salicylhydroxamic acid conjugate of SAL (compound 9) as well as benzhydroxamic acid and salicylhydroxamic acid conjugates of 10 (compounds 11 and 12) showed promising trypanocidal activities with GI values between 0.032 and 0.035 μM but less favorable selectivities. The findings confirm that modification of SAL can result in derivatives with improved trypanocidal activity that might be interesting lead compounds for further anti-trypanosomal drug development.
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http://dx.doi.org/10.1016/j.ejmech.2019.03.061DOI Listing
July 2019

The salt-cocrystal spectrum in salicylic acid-adenine: the influence of crystal structure on proton-transfer balance.

Acta Crystallogr C Struct Chem 2019 04 13;75(Pt 4):412-421. Epub 2019 Mar 13.

Institute of Low Temperature and Structure Research, Polish Academy of Science, Okólna 2, 50-950 Wrocław, Poland.

At one extreme of the proton-transfer spectrum in cocrystals, proton transfer is absent, whilst at the opposite extreme, in salts, the proton-transfer process is complete. However, for acid-base pairs with a small ΔpK (pK of base - pK of acid), prediction of the extent of proton transfer is not possible as there is a continuum between the salt and cocrystal ends. In this context, we attempt to illustrate that in these systems, in addition to ΔpK, the crystalline environment could change the extent of proton transfer. To this end, two compounds of salicylic acid (SaH) and adenine (Ad) have been prepared. Despite the same small ΔpK value (≈1.2), different ionization states are found. Both crystals, namely adeninium salicylate monohydrate, CHN·CHO·HO, I, and adeninium salicylate-adenine-salicylic acid-water (1/2/1/2), CHN·CHO·2CHN·CHO·2HO, II, have been characterized by single-crystal X-ray diffraction, IR spectroscopy and elemental analysis (C, H and N) techniques. In addition, the intermolecular hydrogen-bonding interactions of compounds I and II have been investigated and quantified in detail on the basis of Hirshfeld surface analysis and fingerprint plots. Throughout the study, we use crystal engineering, which is based on modifications of the intermolecular interactions, thus offering a more comprehensive screening of the salt-cocrystal continuum in comparison with pure pK analysis.
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http://dx.doi.org/10.1107/S2053229619003127DOI Listing
April 2019

Synthesis and pharmacological evaluation of novel arylpiperazine oxicams derivatives as potent analgesics without ulcerogenicity.

Bioorg Med Chem 2019 04 2;27(8):1619-1628. Epub 2019 Mar 2.

Department of Pharmacodynamics, Faculty of Pharmacy, Medical College, Jagiellonian University, Medyczna 9, 30-688 Krakow, Poland.

Gastrotoxicity continues to be a major issue in therapy with nonsteroidal anti-inflammatory drugs (NSAIDs). Medicine is yet to develop absolutely safe analgesics. Numerous strategies are employed to discover new, safer NSAIDs, for example selective inhibition of cyclooxygenase-2, new molecular targets (e.g. microsomal prostaglandin E synthase-1), incorporation of cytoprotective compounds in the drug molecule or modification of the classic NSAIDs currently available on the market. The research presented in this paper is indicative of a current worldwide trend in this area of science, and is an example of the fourth strategy noted above. Two series of new arylpiperazine derivatives of the classic NSAID - piroxicam, were developed by conventional synthesis. The full range of compounds obtained proved to be between two and five times analgesically more potent than the reference drug and, most importantly, they did not show any ulcerogenic activity.
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http://dx.doi.org/10.1016/j.bmc.2019.03.007DOI Listing
April 2019

Three-Photon Absorption of Coordination Polymer Transforms UV-to-VIS Thermometry into NIR-to-VIS Thermometry.

ACS Appl Mater Interfaces 2019 Mar 8;11(11):10435-10441. Epub 2019 Mar 8.

Advanced Materials Engineering and Modelling Group , Wroclaw University of Science and Technology , Wyb. Wyspiańskiego 27 , Wrocław 50370 , Poland.

Lanthanide-based metal-organic frameworks (MOFs) and coordination polymers (CPs) attract much attention as candidates for optical ratiometric thermometry applications. Thus far, excitation of these materials was mainly performed in the ultraviolet that drastically limits their applicability as sensors, e.g., in tissue biological thermometry. As a remedy for this constraint, for the first time, we leverage a nonlinear optical process, the three-photon absorption property of Eu,Tb-CPs to shift the excitation wavelength from ultraviolet into near-infrared region. Experiments demonstrate that three-photon induced thermometric responses of Eu,Tb-CPs follow excellent optical characteristics similar to those determined for one-photon excitation, yet are not identical. The relative sensitivity reaches a very high value of 2.91%K in the physiological temperature region. We put forward a notion that utilizing multiphoton absorption is a general strategy for realizing NIR-to-VIS remote temperature sensing in practically any CP that is designed for UV-to-VIS thermometry.
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http://dx.doi.org/10.1021/acsami.8b21937DOI Listing
March 2019

Tris-chelated complexes of nickel(II) with bipyridine derivatives: DNA binding and cleavage, BSA binding, molecular docking, and cytotoxicity.

J Biomol Struct Dyn 2019 09 5;37(15):3887-3904. Epub 2019 Feb 5.

a Pharmaceutics Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences , Kerman , Iran.

Two nickel(II) complexes with substituted bipyridine ligand of the type [Ni(NN)](ClO), where NN is 4,4'-dimethyl-2,2'-bipyridine (dimethylbpy) () and 4,4'-dimethoxy-2,2'-bipyridine (dimethoxybpy) (), have been synthesized, characterized, and their interaction with DNA and bovine serum albumin (BSA) studied by different physical methods. X-ray crystal structure of shows a six-coordinate complex in a distorted octahedral geometry. DNA-binding studies of and reveal that both complexes sit in DNA groove and then interact with neighboring nucleotides differently; undergoes a partial intercalation. This is supported by molecular-docking studies, where hydrophobic interactions are apparent between and DNA as compared to hydrogen bonding, hydrophobic, and interactions between and DNA minor groove. Moreover, the two complexes exhibit oxidative cleavage of supercoiled plasmid DNA in the presence of hydrogen peroxide as an activator in the order of >. In terms of interaction with BSA, the results of spectroscopic methods and molecular docking show that binds with BSA only via hydrophobic contacts while interacts through hydrophobic and hydrogen bonding. It has been extensively demonstrated that the nature of the methyl- and methoxy-groups in ligands is a strong determinant of the bioactivity of nickel(II) complexes. This may justify the above differences in biomolecular interactions. In addition, the cytotoxicity of the complexes on human carcinoma cells lines (MCF-7, HT-29, and U-87) has been examined by MTT assay. According to our observations, and display cytotoxicity activity against selected cell lines. Communicated by Ramaswamy H. Sarma.
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http://dx.doi.org/10.1080/07391102.2018.1534700DOI Listing
September 2019

Design and Synthesis of a Biocompatible 1D Coordination Polymer as Anti-Breast Cancer Drug Carrier, 5-Fu: In Vitro and in Vivo Studies.

ACS Appl Mater Interfaces 2018 May 17;10(21):17594-17604. Epub 2018 May 17.

Institute of Low Temperature and Structure Research , Polish Academy of Sciences , P.O. Box 1410, Wroclaw 50-950 , Poland.

Designable coordination polymers with suitable chemical diversities and biocompatible structures have been proposed as a promising class of vehicles for drug delivery systems. Here, we hydrothermally synthesized a novel one-dimensional (1D) coordination polymer, [Zn(HO)K(HBTC)(HO)](HBTC)·2HO, where HBTC = benzene-1,3,5-tricarboxylic acid (trimesic acid), cp.1. As the hydrogen bonds stabilized 1D chains in three dimensions, the cp.1 could be a good candidate for delivering small-molecule chemotherapeutics such as 5-fluorouracil (5-Fu). The synthesized cp.1 showed a remarkable 5-Fu loading of 66% with encapsulation efficiency of 98% and almost complete release process. The 5-Fu-loaded cp.1 displayed a time-dependent cytotoxicity effect against breast cancer cell lines MCF-7 and 4T1. The cellular uptake of cp.1 particles was investigated via confocal laser scanning microscopy using fluorescein isothiocyanate and LysoTracker Red staining. Furthermore, the in vivo antitumor impact of 5-Fu-loaded cp.1 was studied on 4T1 breast cancer BALB/c mice model. The intratumor treatment of 5-Fu-loaded cp.1 demonstrated beneficial antitumor efficacy by postponing tumor growth. These results suggest that the 5-Fu-loaded cp.1 microparticles with a great locoregional delivery can be efficient anticancer drug carriers for further clinical treatments.
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http://dx.doi.org/10.1021/acsami.8b03111DOI Listing
May 2018

The role of different nonspecific interactions and halogen contacts in the crystal structure organization of 5-chloroisatoic anhydride.

Acta Crystallogr C Struct Chem 2018 Mar 23;74(Pt 3):372-380. Epub 2018 Feb 23.

Department of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, Wroclaw 50-370, Poland.

The crystal structure of 6-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione (5-chloroisatoic anhydride), CHClNO, has been determined and analysed in terms of connectivity and packing patterns. The compound crystallizes in the noncentrosymmetric space group Pna2 with one molecule in the asymmetric unit. The role of different weak interactions is discussed with respect to three-dimensional network organization. Molecules are extended into one-dimensional helical arrangements, making use of N-H...O hydrogen bonds and π-π interactions. The helices are further organized into monolayers via weak C-H...O and lone pair-π interactions, and the monolayers are packed into a noncentrosymmetric three-dimensional architecture by C-Cl...π interactions and C-H...Cl and Cl...Cl contacts. A Hirshfeld surface (HS) analysis was carried out and two-dimensional (2D) fingerprint plots were generated to visualize the intermolecular interactions and to provide quantitative data for their relative contributions. In addition, tests of the antimicrobial activity and in vitro cytotoxity effects against fitoblast L929 were performed and are discussed.
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http://dx.doi.org/10.1107/S2053229618002280DOI Listing
March 2018

Synthesis and temperature-dependent studies of a perovskite-like manganese formate framework templated with protonated acetamidine.

Dalton Trans 2017 Jul;46(26):8476-8485

Institute of Low Temperature and Structure Research, Polish Academy of Sciences, Box 1410, 50-950 Wrocław 2, Poland.

We report the synthesis, crystal structure, thermal, dielectric, phonon and magnetic properties of the [CHC(NH)][Mn(HCOO)] (AceMn) compound. Our results show that this compound crystallizes in the perovskite-like orthorhombic structure, space group Imma. It undergoes a structural phase transition at 304 K into a monoclinic structure, space group P2/n. X-ray diffraction, dielectric, IR and Raman studies show that the ordering of the acetamidinium cations triggers the phase transition. Low-temperature magnetic studies show that this compound exhibits weak ferromagnetic properties below 9.0 K.
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http://dx.doi.org/10.1039/c7dt01251aDOI Listing
July 2017

Synthesis, structural characterization and computational studies of catena-poly[chlorido[μ-(pyridin-1-ium-3-yl)phosphonato-κO:O':O'']zinc(II)].

Acta Crystallogr C Struct Chem 2017 May 5;73(Pt 5):363-368. Epub 2017 Apr 5.

Department of Chemistry, Wrocław University of Science and Technology, 27 Wybrzeże Wyspiańskiego Street, 50-370 Wrocław, Poland.

Coordination polymers are constructed from two basic components, namely metal ions, or metal-ion clusters, and bridging organic ligands. Their structures may also contain other auxiliary components, such as blocking ligands, counter-ions and nonbonding guest or template molecules. The choice or design of a suitable linker is essential. The new title zinc(II) coordination polymer, [Zn(CHNOP)Cl], has been hydrothermally synthesized and structurally characterized by single-crystal X-ray diffraction and vibrational spectroscopy (FT-IR and FT-Raman). Additionally, computational methods have been applied to derive quantitative information about interactions present in the solid state. The compound crystallizes in the monoclinic space group C2/c. The four-coordinated Zn cation is in a distorted tetrahedral environment, formed by three phosphonate O atoms from three different (pyridin-1-ium-3-yl)phosphonate ligands and one chloride anion. The Zn ions are extended by phosphonate ligands to generate a ladder chain along the [001] direction. Adjacent ladders are held together via N-H...O hydrogen bonds and offset face-to-face π-π stacking interactions, forming a three-dimensional supramolecular network with channels. As calculated, the interaction energy between the neighbouring ladders is -115.2 kJ mol. In turn, the cohesive energy evaluated per asymmetric unit-equivalent fragment of a polymeric chain in the crystal structure is -205.4 kJ mol. This latter value reflects the numerous hydrogen bonds stabilizing the three-dimensional packing of the coordination chains.
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http://dx.doi.org/10.1107/S2053229617004478DOI Listing
May 2017

Sonochemical synthesis of two new zinc(II) 1,10-phenanthroline coordination supramolecular compounds: New precursors to produce nano-sized zinc(II) oxide.

Ultrason Sonochem 2017 Jul 18;37:286-297. Epub 2017 Jan 18.

Institute of Low Temperature and Structure Research, Polish Academy of Sciences, P.O. Box 1410 Okolna 2 Str., 50-950 Wroclaw, Poland.

Nanoparticles of two zinc(II) coordination supramolecule compounds (CSCs), [Zn(L)Cl2] (1) and [Zn(L)Br2] (2) L=1,10-phen=1,10-phenanthroline ligand, have been synthesized by use of a sonochemical process and characterized by scanning electron microscopy (SEM), X-ray powder diffraction (XRPD), Fourier transform infrared (FTIR) spectroscopy and elemental analyses. The single crystal X-ray data of compounds 1 and 2 imply that the Zn ions are four coordinated. Topological analysis shows that the compound 1 and 2 are new topology for net: 1,3M4-1. Nanoparticles of zinc(II) oxide have been prepared by calcination of two different zinc(II) CPs at 500°C that were characterized by scanning electron microscopy (SEM), X-ray powder diffraction (XRD) and IR spectroscopy.
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http://dx.doi.org/10.1016/j.ultsonch.2017.01.020DOI Listing
July 2017

Ultrasonic synthesis of two new zinc(II) bipyridine coordination polymers: New precursors for preparation of zinc(II) oxide nano-particles.

Ultrason Sonochem 2017 Mar 7;35(Pt A):502-513. Epub 2016 Nov 7.

Institute of Low Temperature and Structure Research Polish Academy of Sciences, P.O. Box 1410 Okolna 2 Str., 50-950 Wroclaw, Poland.

Nanoparticles of two zinc(II) coordination polymers (CPs), [Zn(μ-4,4'-bipy)Cl] (1) and [Zn(μ-4,4'-bipy)Br] (2) L=bpy=4,4'-bipyridine ligand, have been synthesized by use of a sonochemical process and characterized by scanning electron microscopy (SEM), X-ray powder diffraction (XRPD), Fourier transform infrared spectroscopy (FTIR) spectroscopy and elemental analyses. The single crystal X-ray data of compounds 1 and 2 imply that the Zn ions are four coordinated. Topological analysis shows that 1D coordination networks of 1 and 2 can be classified as underlying nets of topological types 2C1. Nanoparticles of zinc(II) oxide have been prepared by calcination of two different zinc (II) CPs at 450°C that were characterized by scanning electron microscopy (SEM), X-ray powder diffraction (XRD) and IR spectroscopy.
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http://dx.doi.org/10.1016/j.ultsonch.2016.11.009DOI Listing
March 2017

New polymorphs of an old drug: conformational and synthon polymorphism of 5-nitrofurazone.

Acta Crystallogr B Struct Sci Cryst Eng Mater 2016 Apr 1;72(Pt 2):263-73. Epub 2016 Apr 1.

Department of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, Wroclaw 50-370, Poland.

Two new polymorphic forms of 5-nitrofurazone (5-nitro-2-furaldehyde semicarbazone) have been synthesized and structurally characterized by single-crystal and powder X-ray diffraction methods, vibrational spectroscopy (FT-IR and temperature Raman), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and Hirshfeld surface analysis. The compound crystallizes in three different polymorphic forms P21/a (polymorph α), P21 (polymorph β) and P21/c (polymorph γ), the crystal structures of two of which (polymorphs β and γ) represent new structure determinations. The solid-state molecular organization in the three crystal forms is analyzed and discussed in terms of molecular conformation, crystal packing and hydrogen-bonded networks. All three crystals are formed from trans geometrical isomers, but the molecular conformation of the α-polymorph is syn-anti-anti-anti, while that of β- and γ-polymorphs is syn-anti-syn-syn. As a consequence of this the hydrogen-bond donor and acceptor sites of the molecules are oriented differently, which in turn results in different hydrogen-bond connectivity and packing patterns.
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http://dx.doi.org/10.1107/S2052520615024956DOI Listing
April 2016

Synthesis, antiproliferative activity and molecular docking of Colchicine derivatives.

Bioorg Chem 2016 Feb 12;64:103-12. Epub 2016 Jan 12.

Institut für Medizinische Physik und Biophysik Charité - Universitätsmedizin Berlin, Campus Charité Mitte, Charitéplatz 1, 10117 Berlin, Germany.

In order to create more potent anticancer agents, a series of five structurally different derivatives of Colchicine have been synthesised. These compounds were characterised spectroscopically and structurally and their antiproliferative activity against four human tumour cell lines (HL-60, HL-60/vinc, LoVo, LoVo/DX) was evaluated. Additionally the activity of the studied compounds was calculated using computational methods involving molecular docking of the Colchicine derivatives to β-tubulin. The experimental and computational results are in very good agreement indicating that the antimitotic activity of Colchicine derivatives can be readily predicted using computational modeling methods.
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http://dx.doi.org/10.1016/j.bioorg.2016.01.002DOI Listing
February 2016

Chiral 2 + 3 Keto-Enamine Pseudocyclophanes Derived from 1,3,5-Triformylphloroglucinol.

Org Lett 2016 Jan 14;18(1):12-5. Epub 2015 Dec 14.

Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.

The reactions of 1,3,5-triformylphloroglucinol with (1R,2R)-1,2-diaminocyclohexane, (1R,2R)-1,2-diphenylethylenediamine, or (R)-2,2'-diamino-1,1'-binaphthyl result in the formation of enantiopure [2 + 3] keto-enamine condensation products, in contrast to analogous reactions of 1,3,5-triformylbenzene, where [4 + 6] Schiff base cages are formed. The X-ray crystal structure of the diaminocyclohexane 2 + 3 derivative as well as modeled structures of other compounds of this type show cyclophane-like molecules with close contact between the phloroglucinol rings. Density Functional Theory (DFT) calculations confirm that there is a sizable π-π interaction between these rings influencing the conformation of these molecules.
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http://dx.doi.org/10.1021/acs.orglett.5b02989DOI Listing
January 2016

Trinuclear Cage-Like Zn(II) Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties.

Chemistry 2016 Jan 8;22(2):598-609. Epub 2015 Dec 8.

Department of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383 Wrocław (Poland).

Three zinc(II) ions in combination with two units of enantiopure [3+3] triphenolic Schiff-base macrocycles 1, 2, 3, or 4 form cage-like chiral complexes. The formation of these complexes is accompanied by the enantioselective self-recognition of chiral macrocyclic units. The X-ray crystal structures of these trinuclear complexes show hollow metal-organic molecules. In some crystal forms, these barrel-shaped complexes are arranged in a window-to-window fashion, which results in the formation of 1D channels and a combination of both intrinsic and extrinsic porosity. The microporous nature of the [Zn3 12 ] complex is reflected in its N2 , Ar, H2 , and CO2 adsorption properties. The N2 and Ar adsorption isotherms show pressure-gating behavior, which is without precedent for any noncovalent porous material. A comparison of the structures of the [Zn3 12 ] and [Zn3 32 ] complexes with that of the free macrocycle H3 1 reveals a striking structural similarity. In H3 1, two macrocyclic units are stitched together by hydrogen bonds to form a cage very similar to that formed by two macrocyclic units stitched together by Zn(II) ions. This structural similarity is manifested also by the gas adsorption properties of the free H3 1 macrocycle. Recrystallization of [Zn3 12 ] in the presence of racemic 2-butanol resulted in the enantioselective binding of (S)-2-butanol inside the cage through the coordination to one of the Zn(II) ions.
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http://dx.doi.org/10.1002/chem.201503479DOI Listing
January 2016

Beyond Single-Wavelength SHG Measurements: Spectrally-Resolved SHG Studies of Tetraphosphonate Ester Coordination Polymers.

Inorg Chem 2015 Nov 22;54(22):10568-75. Epub 2015 Oct 22.

Institute of Low Temperature and Structural Research, Polish Academy of Sciences , Okólna 2, P.O. Box 1410, 50-950 Wrocław, Poland.

Powder second-harmonic generation (SHG) efficiencies are usually measured at single wavelengths. In the present work, we provide a proof of concept of spectrally resolved powder SHG measured for a newly obtained series of three non-centrosymmetric coordination polymers (CPs). CPs are constructed from tetrahedral linker-tetraphenylmethane-based tetraphosphonate octaethyl ester and cobalt(II) ions of mixed, octahedral (Oh), and tetrahedral (Td), geometries and different sets of donors (CoO6 vs CoX3O). Isostructurality of the obtained materials allowed for the determination of anion-dependent tunability of SHG optical spectra and their relationship with solid-state absorption spectra.
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http://dx.doi.org/10.1021/acs.inorgchem.5b01939DOI Listing
November 2015
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