Combining advantages of homogeneous organocatalysis and heterogeneous catalysis with thermosensitive single-chain nanoparticles in a representative tetrahydropyranilation of alcohols

Publication date: 31 January 2018
Source:Polymer, Volume 136
Author(s): Misha Rumyantsev, Sergey Rumyantsev
A significant scientific problem solved in this work is the development of effective polymer catalysts that allow carrying out organic reactions under homogeneous conditions with high rates and to remove catalyst from the system as a heterophase without the use of special treatment, thus combining the advantages of both homogeneous and heterogeneous catalysis. Kinetic experiments show high catalytic activity of the synthesized catalyst in homogeneous regime even at low dosage of the catalyst. Thus, it was demonstrated that tetrahydropyranilation of methanol was completed in nearly quantitative yield of the corresponding ether in 80 min at 60 °C with a dosage of the polymeric catalyst as low as 0.2 mol%. On the other hand anomalous decrease in the values of the effective rate constant was observed when the reaction was run at temperatures below the phase transition temperature. Kinetic data were used along with thermodynamic calculations to discuss the effect of the synthesized polymeric catalyst on the stabilization of the transition state. The high activity of the catalyst is complemented by its high sedimentation ability; thus, it usually takes a few minutes for the polymer to precipitate from the alcohol solution when cooled below the phase-transition temperature after the completion of the reaction. It was also revealed via dynamic light scattering that catalytic polymers adopt a thermodynamically stable conformation of the single-chain nanoparticles with average hydrodynamic radius in the range 2–2.5 nm.

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Selective synthesis of highly soluble cyclic olefin copolymers with pendant vinyl groups using 1,5-hexadiene as a comonomer

Publication date: 31 January 2018
Source:Polymer, Volume 136
Author(s): Ryo Tanaka, Akane Sasaki, Takuma Takenaka, Yuushou Nakayama, Takeshi Shiono
Copolymerization of norbornene (NB) and 1,5-hexadiene (HD) was performed using a fluorenylamido-ligated titanium catalyst which conducts copolymerization of NB and 1-alkene. The obtained copolymers possessed pendant vinyl groups, of which content was varied from 0 to 9.4% by the initial feed ratio of the monomers. The copolymers were soluble in various solvents even at high conversion (>85%), showing that the crosslinking of pendant vinyl groups was negligible. The glass transition temperature of the copolymer was changed from 79 °C to over 300 °C, depending on the comonomer composition. Post-functionalization of the pendant vinyl groups with 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene via ruthenium-catalyzed metathesis reaction was also performed and fluoroalkyl-functionalized cyclic olefin copolymer was successfully obtained. The fluorinated copolymer film showed higher contact angle than the unfunctionalized copolymer.

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Effects of pH on the photophysics of conjugated polyelectrolyte complexes

Publication date: 31 January 2018
Source:Polymer, Volume 136
Author(s): Pamela Schleissner, Alexander L. Ayzner
We have previously reported the formation of complexes between oppositely charged, conjugated polyelectrolytes (CPECs), resulting in electronic energy transfer between the donor and acceptor components. The ionic self-assembly process that forms CPECs is heavily influenced by environmental circumstances including solvent composition, temperature, and pH. In this article, we report the effect of polyelectrolyte chain protonation on complex formation and resulting energy transfer. The particular polyelectrolytes used in this study were a pH inactive energy donor and an acceptor polymer with protonatable sidechains. We find that over a large range of acidic pH, the optical properties do not change appreciably up to precipitation (pH 3). Surprisingly in the basic regime where the acceptor polymer is fully deprotonated, complex formation is hindered. However, at pH 11, which corresponds to an excess ion concentration of 0.001 M, the photophysical properties of the complex begin to once again resemble that of the neutral or acidic environments. Our results show that the CPEC displays impressive stability over a relatively broad range of proton concentrations, which may have implications for the construction of supramolecular light-harvesting assemblies.

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Near infrared hyperspectral dataset of healthy and infected apple tree leaves images for the early detection of apple scab disease

Publication date: February 2018
Source:Data in Brief, Volume 16
Author(s): Maroua Nouri, Nathalie Gorretta, Pierre Vaysse, Michel Giraud, Christian Germain, Barna Keresztes, Jean-Michel Roger
This dataset presents two series of hyperspectral images of healthy and infected apple tree leaves acquired daily, from two days after inoculation until an advanced stage of infection (11 days after inoculation). The hyperspectral images were calibrated by reflection correction and registered to match the geometry of one reference image. On the last experiment day, scab positions are provided.



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Fibroblast and keratinocyte gene expression following exposure to extracts of neem plant (Azadirachta indica)

Publication date: February 2018
Source:Data in Brief, Volume 16
Author(s): Takao Someya, Katsura Sano, Kotaro Hara, Yoshimasa Sagane, Toshihiro Watanabe, R.G.S. Wijesekara
This data article provides gene expression profiles, determined by using real-time PCR, of fibroblasts and keratinocytes treated with 0.01% and 0.001% extracts of neem plant (Azadirachta indica), local name "Kohomba" in Sri Lanka, harvested in Sri Lanka. For fibroblasts, the dataset includes expression profiles for genes encoding hyaluronan synthase 1 (HAS1), hyaluronan synthase 2 (HAS2), hyaluronidase-1 (HYAL1), hyaluronidase-2 (HYAL2), versican, aggrecan, CD44, collagen, type I, alpha 1 (COL1A1), collagen, type III, alpha 1 (COL3A1), collagen, type VII, alpha 1 (COL7A1), matrix metalloproteinase 1 (MMP1), acid ceramidase, basic fibroblast growth factor (bFGF), fibroblast growth factor-7 (FGF7), vascular endothelial growth factor (VEGF), interleukin-1 alpha (IL-1α), cyclooxygenase-2 (cox2), transforming growth factor beta (TGF-β), and aquaporin 3 (AQP3). For keratinocytes, the expression profiles are for genes encoding HAS1, HAS2, HYAL1, HYAL2, versican, CD44, IL-1α, cox2, TGF-β, AQP3, Laminin5, collagen, type XVII, alpha 1 (COL17A1), integrin alpha-6 (ITGA6), ceramide synthase 3 (CERS3), elongation of very long chain fatty acids protein 1 (ELOVL1), elongation of very long chain fatty acids protein 4 (ELOVL4), filaggrin (FLG), transglutaminase 1 (TGM1), and keratin 1 (KRT1). The expression profiles are provided as bar graphs.



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Data on a single oral dose of camu camu (Myrciaria dubia) pericarp extract on flow-mediated vasodilation and blood pressure in young adult humans

Publication date: February 2018
Source:Data in Brief, Volume 16
Author(s): Tadayoshi Miyashita, Ryosuke Koizumi, Takao Myoda, Yoshimasa Sagane, Koichi Niwa, Toshihiro Watanabe, Kazuhiro Minami
This data article describes the flow-mediated vasodilation (FMD) responses, represented by changes in arterial diameter, and blood pressure changes in young adults after a single oral dose of camu camu (Myrciaria dubia) pericarp extract or placebo (cross-over design). Ten healthy men and 10 healthy women participated in this study. Ultrasonic diagnostic equipment was used to monitor arterial diameter changes, indicative of FMD, for 110s after the administration of the camu camu extract or placebo. In addition, the systolic and diastolic blood pressure values were recorded.



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Data on a delivery of biomolecules into Nicothiana benthamiana leaves using different nanoparticles

Publication date: February 2018
Source:Data in Brief, Volume 16
Author(s): Antonida V. Makhotenko, Ekaterina A. Snigir, Natalia O. Kalinina, Valentin V. Makarov, Michael E. Taliansky
Nanoparticles (NPs) have a number of unique properties associated with their ultrasmall size and exhibit many advantages compared with existing plant biotechnology platforms for delivery of proteins, RNA and DNA of various sizes into the plant cells (Arruda et al., 2015; Silva et al., 2010; Martin-Ortigosa et al., 2014; Mitter et al., 2017) [1–4]. The data presented in this article demonstrate a delivery of biomolecules into Nicotiana benthamiana plant leaves using various types of NPs including gold, iron oxide and chitosan NPs and methods of biolistic bombardment and infiltration. The data demonstrate physical characteristics of NPs coated with fluorescently labeled protein and small RNA (size and zeta-potential) and visualization of nanocomplexes delivery into cells of N. benthamiana leaves by fluorescence microscopy.



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Molecular imaging of tumor photoimmunotherapy: Evidence of photosensitized tumor necrosis and hemodynamic changes

Publication date: 20 February 2018
Source:Free Radical Biology and Medicine, Volume 116
Author(s): Shun Kishimoto, Nobu Oshima, Kazutoshi Yamamoto, Jeeva Munasinghe, Jan Henrik Ardenkjaer-Larsen, James B. Mitchell, Peter L. Choyke, Murali C. Krishna
Near-infrared photoimmunotherapy (NIR PIT) employs the photoabsorbing dye IR700 conjugated to antibodies specific for cell surface epidermal growth factor receptor (EGFR). NIR PIT has shown highly selective cytotoxicity in vitro and in vivo. Cell necrosis is thought to be the main mode of cytotoxicity based mainly on in vitro studies. To better understand the acute effects of NIR PIT, molecular imaging studies were performed to assess its cellular and vascular effects.In addition to in vitro studies for cytotoxicity of NIR PIT, the in vivo tumoricidal effects and hemodynamic changes induced by NIR PIT were evaluated by ¹³C MRI using hyperpolarized [1,4-¹³C2] fumarate, R2* mapping from T2*-weighted MRI, and photoacoustic imaging. In vitro studies confirmed that NIR PIT resulted in rapid cell death via membrane damage, with evidence for rapid cell expansion followed by membrane rupture. Following NIR PIT, metabolic MRI using hyperpolarized fumarate showed the production of malate in EGFR-expressing A431 tumor xenografts, providing direct evidence for photosensitized tumor necrosis induced by NIR PIT. R2* mapping studies showed temporal changes in oxygenation, with an accompanying increase of deoxyhemoglobin at the start of light exposure followed by a sustained decrease after cessation of light exposure. This result suggests a rapid decrease of blood flow in EGFR-expressing A431 tumor xenografts, which is supported by the results of the photoacoustic imaging experiments. Our findings suggest NIR PIT mediates necrosis and hemodynamic changes in tumors by photosensitized oxidation pathways and that these imaging modalities, once translated, may be useful in monitoring clinical treatment response.

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Targeting protein-protein interaction between MLL1 and reciprocal proteins for leukemia therapy

Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2
Author(s): Zhi-Hui Wang, Dong-Dong Li, Wei-Lin Chen, Qi-Dong You, Xiao-Ke Guo
The mixed lineage leukemia protein-1 (MLL1), as a lysine methyltransferase, predominantly regulates the methylation of histone H3 lysine 4 (H3K4) and functions in hematopoietic stem cell (HSC) self-renewal. MLL1 gene fuses with partner genes that results in the generation of MLL1 fusion proteins (MLL1-FPs), which are frequently detected in acute leukemia. In the progress of leukemogenesis, a great deal of proteins cooperate with MLL1 to form multiprotein complexes serving for the dysregulation of H3K4 methylation, the overexpression of homeobox (HOX) cluster genes, and the consequent generation of leukemia. Hence, disrupting the interactions between MLL1 and the reciprocal proteins has been considered to be a new treatment strategy for leukemia. Here, we reviewed potential protein-protein interactions (PPIs) between MLL1 and its reciprocal proteins, and summarized the inhibitors to target MLL1 PPIs. The druggability of MLL1 PPIs for leukemia were also discussed.

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Current knowledge on the nucleotide agonists for the P2Y2 receptor

Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2
Author(s): Pengfei Xu, Xi Feng, Hongyu Luan, Jubo Wang, Raoling Ge, Zhiyu Li, Jinlei Bian
P2Y receptors are G-protein-coupled receptors (GPCRs) for extracellular nucleotides. There are eight mammalian P2Y receptor subtypes (P2Y1, P2Y2, P2Y4, P2Y6, P2Y11, P2Y12, P2Y13, and P2Y14). P2Y2 receptors are widely expressed and play important roles in multiple functionalities. Diquafosol tetrasodium, known as INS365, which was the first P2Y2 receptor agonists that had been approved in April 2010 and launched in Japan by Santen Pharmaceuticals. Besides, a series of similar agonists for the P2Y2 receptor are undergoing development to cure different diseases related to the P2Y2 receptor. This article illustrated the structure and functions of the P2Y2 receptor and focused on several kinds of agonists about their molecular structures, research progress and chemical synthesis methods. Last but not the least, we summarized the structures-activity relationship (SAR) of agonists for the P2Y2 receptor and expected more efficient agonists for the P2Y2 receptor.

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Editorial Board

Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2





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Selective inhibition of β-N-acetylhexosaminidases by thioglycosyl–naphthalimide hybrid molecules

Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2
Author(s): Wei Chen, Shengqiang Shen, Lili Dong, Jianjun Zhang, Qing Yang
To develop selective inhibitors for β-N-acetylhexosaminidases which are involved in a myriad of physiological processes, a series of novel thioglycosyl–naphthalimide hybrid inhibitors were designed, synthesized and evaluated for inhibition activity against glycosyl hydrolase family 20 and 84 (GH20 and GH84) β-N-acetylhexosaminidases. These compounds which incorporate groups with varied sizes and lengths at the linker region between thioglycosyl moiety and naphthalimide moiety are designed to improve the selectivity and stacking interactions. The GH84 human O-GlcNAcase (hOGA) was sensitive to the subtle changes in the linker region and the optimal choice is a small size linker with six atoms length. And the GH20 insect β-N-acetylhexosaminidase OfHex1 could tolerate compounds with a hydrophobic bulky linker. Especially, the compound 5c (hOGA, Ki = 3.46 μM; OfHex1, Ki > 200 μM) and the compound 6f (hOGA, Ki > 200 μM; OfHex1, Ki = 21.81 μM) displayed high selectivity. The molecular docking results indicated that the inhibition mechanism was different between the two families due to their different structural characteristics beyond the active sites. These results provide some promising clues to improve selectivity of potent molecules against β-N-acetylhexosaminidases.

Graphical abstract

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Immunoproteasome inhibition and bioactivity of thiasyrbactins

Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2
Author(s): Nicole A. Bakas, Chad R. Schultz, Lisette P. Yco, Christopher C. Roberts, Chia-en A. Chang, André S. Bachmann, Michael C. Pirrung
A family of macrodilactam natural products, the syrbactins, are known proteasome inhibitors. A small group of syrbactin analogs was prepared with a sulfur-for-carbon substitution to enhance synthetic accessibility and facilitate modulation of their solubility. Two of these compounds surprisingly proved to be inhibitors of the trypsin-like catalytic site, including of the immunoproteasome. Their bound and free conformations suggest special properties of the thiasyrbactin ring are responsible for this unusual preference, which may be exploited to develop drug-like immunoproteasome inhibitors. These compounds show greater selectivity than earlier compounds used to infer phenotypes of immunoproteasome inhibition, like ONX-0914.

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Monoterpene indole alkaloid azine derivatives as MDR reversal agents

Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2
Author(s): Angela Paterna, Ruttiros Khonkarn, Silva Mulhovo, Alexis Moreno, Patricia Madeira Girio, Hélène Baubichon-Cortay, Pierre Falson, Maria-José U. Ferreira
Aiming at generating a library of bioactive indole alkaloid derivatives as multidrug resistance (MDR) reversers, two epimeric indole alkaloids (1 and 2) were submitted to chemical transformations, giving rise to twenty-four derivatives (5-28), bearing new aromatic or aliphatic azine moieties. The structure of the compounds was established by 1D and 2D NMR (COSY, HMBC, HMQC and NOESY) experiments. Two different strategies were employed for assessing their anti-MDR potential, namely through the evaluation of their activity as inhibitors of typical MDR ABC transporters overexpressed by cell transfection, such as ABCB1 (P-gp), ABCC1 (MRP1), and ABCG2 (BCRP), or by evaluating their ability as collateral sensitivity (CS) agents in cells overexpressing MRP1. A considerable MDR reversing activity was observed for compounds bearing the aromatic azine moiety. The strongest and most selective P-gp inhibition was found for the epimeric azines 5 and 6, bearing a para-methylbenzylidene moiety. Instead, compounds 17 and 18 that possess a di-substituted benzylidene portion with methoxy and hydroxyl groups, selectively inhibited MRP1 drug-efflux. None of these compounds inhibited BCRP. Compounds 5, 6 and 18 were further investigated in drug combination experiments, which corroborated their anti-MDR potential. Moreover, it was observed that compound 12, with an aromatic azine moiety, and compounds 23-26, sharing a new aliphatic substituent, displayed a CS activity, selectively killing MRP1-overexpressing cells. Among these last compounds, it could be established that addition of 19, 23 and 25 to MRP1-overexpressing cells led to glutathione depletion triggering cell death through apoptosis.

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Design, synthesis and pharmacological evaluation of new acyl sulfonamides as potent and selective Bcl-2 inhibitors

Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2
Author(s): Xiaohua Liu, Yu Zhang, Wenjing Huang, Wenfu Tan, Ao Zhang
The antiapoptotic protein Bcl-2, overexpressed in many tumor cells, is an attractive target for potential small molecule anticancer drug discovery. Herein, we report a different structural modification approach on ABT-263 by merging the piperazinyl-phenyl fragment into a bicyclic framework leading to a series of novel analogues, among which tetrahydroisoquinoline 13 was nearly equally potent against Bcl-2 as ABT-263. Further SAR in the P4-interaction pocket affored the difluoroazetidine substituted analogue 55, which retained good Bcl-2 activity with improved Bcl-2/Bcl-xL selectivity.

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Evaluation of 18F-labeled exendin(9-39) derivatives targeting glucagon-like peptide-1 receptor for pancreatic β-cell imaging

Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2
Author(s): Hiroyuki Kimura, Yu Ogawa, Hiroyuki Fujimoto, Eri Mukai, Hidekazu Kawashima, Kenji Arimitsu, Kentaro Toyoda, Naotaka Fujita, Yusuke Yagi, Keita Hamamatsu, Takaaki Murakami, Atsushi Murakami, Masahiro Ono, Yuji Nakamoto, Kaori Togashi, Nobuya Inagaki, Hideo Saji
β-cell mass (BCM) is known to be decreased in subjects with type-2 diabetes (T2D). Quantitative analysis for BCM would be useful for understanding how T2D progresses and how BCM affects treatment efficacy and for earlier diagnosis of T2D and development of new therapeutic strategies. However, a noninvasive method to measure BCM has not yet been developed.We developed four ¹⁸F-labeled exendin(9-39) derivatives for β-cell imaging by PET: [¹⁸F]FB9-Ex(9-39), [¹⁸F]FB12-Ex(9-39), [¹⁸F]FB27-Ex(9-39), and [¹⁸F]FB40-Ex(9-39). Affinity to the glucagon-like peptide-1 receptor (GLP-1R) was evaluated with dispersed islet cells of ddY mice. Uptake of exendin(9-39) derivatives in the pancreas as well as in other organs was evaluated by a biodistribution study. Small-animal PET study was performed after injecting [¹⁸F]FB40-Ex(9-39).FB40-Ex(9-39) showed moderate affinity to the GLP-1R. Among all of the derivatives, [¹⁸F]FB40-Ex(9-39) resulted in the highest uptake of radioactivity in the pancreas 30 min after injection. Moreover, it showed significantly less radioactivity accumulated in the liver and kidney, resulting in an overall increase in the pancreas-to-organ ratio. In the PET imaging study, pancreas was visualized at 30 min after injection of [¹⁸F]FB40-Ex(9-39).[¹⁸F]FB40-Ex(9-39) met the basic requirements for an imaging probe for GLP-1R in pancreatic β-cells. Further enhancement of pancreatic uptake and specific binding to GLP-1R will lead to a clear visualization of pancreatic β-cells.

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Publication date: 15 January 2018
Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2





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Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2





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Source:Bioorganic & Medicinal Chemistry, Volume 26, Issue 2





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Thalassemia

Publication date: Available online 30 December 2017
Source:Hematology/Oncology Clinics of North America
Author(s): Ali T. Taher




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Comparison of detection methods for HPV status as a prognostic marker for loco-regional control after radiochemotherapy in patients with HNSCC

Publication date: Available online 30 December 2017
Source:Radiotherapy and Oncology
Author(s): Annett Linge, Ulrike Schötz, Steffen Löck, Fabian Lohaus, Cläre von Neubeck, Volker Gudziol, Alexander Nowak, Inge Tinhofer, Volker Budach, Ali Sak, Martin Stuschke, Panagiotis Balermpas, Claus Rödel, Hatice Bunea, Anca-Ligia Grosu, Amir Abdollahi, Jürgen Debus, Ute Ganswindt, Kirsten Lauber, Steffi Pigorsch, Stephanie E. Combs, David Mönnich, Daniel Zips, Gustavo B. Baretton, Frank Buchholz, Mechthild Krause, Claus Belka, Michael Baumann
ObjectiveTo compare six HPV detection methods in pre-treatment FFPE tumour samples from patients with locally advanced head and neck squamous cell carcinoma (HNSCC) who received postoperative (N = 175) or primary (N = 90) radiochemotherapy.Materials and methodsHPV analyses included detection of (i) HPV16 E6/E7 RNA, (ii) HPV16 DNA (PCR-based arrays, A-PCR), (iii) HPV DNA (GP5+/GP6+ qPCR, (GP-PCR)), (iv) p16 (immunohistochemistry, p16 IHC), (v) combining p16 IHC and the A-PCR result and (vi) combining p16 IHC and the GP-PCR result. Differences between HPV positive and negative subgroups were evaluated for the primary endpoint loco-regional control (LRC) using Cox regression.ResultsCorrelation between the HPV detection methods was high (chi-squared test, p < 0.001). While p16 IHC analysis resulted in several false positive classifications, A-PCR, GP-PCR and the combination of p16 IHC and A-PCR or GP-PCR led to results comparable to RNA analysis. In both cohorts, Cox regression analyses revealed significantly prolonged LRC for patients with HPV positive tumours irrespective of the detection method.ConclusionsThe most stringent classification was obtained by detection of HPV16 RNA, or combining p16 IHC with A-PCR or GP-PCR. This approach revealed the lowest rate of recurrence in patients with tumours classified as HPV positive and therefore appears most suited for patient stratification in HPV-based clinical studies.



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Precision medicine in ALK rearranged NSCLC: A rapidly evolving scenario

Publication date: Available online 30 December 2017
Source:Critical Reviews in Oncology/Hematology
Author(s): Addeo Alfredo, Tabbò Fabrizio, Robinson Tim, Buffoni Lucio, Novello Silvia




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Loco-regional treatment for castration-resistant prostate cancer: is there any rationale?A critical review from the AFU-GETUG

Publication date: Available online 30 December 2017
Source:Critical Reviews in Oncology/Hematology
Author(s): Jean-Baptiste Beauval, Yohann Loriot, Christophe Hennequin, François Rozet, Philippe Barthelemy, Delphine Borchiellini, Friederike Schlürmann Constans, Emmanuel Gross, Denis Maillet, Gilles Pasticier, Géraldine Pignot, Marc-Olivier Timsit, Sébastien Vincendeau, Guillaume Ploussard, Paul Sargos
Emerging evidence from population-based and retrospective series suggests a potential improvement of clinical outcomes in metastatic prostate cancer. Moreover, metastasis-directed treatment has shown encouraging results in this setting. There is an increasing interest in exploring the potential of local therapies in advanced prostate cancer, but this has rarely been specifically addressed in the castration-resistant state, whether non-metastatic or metastatic. A review of relevant articles was performed on the oncologic benefit of local treatment of the primary tumor or metastasis-targeted treatment in castration-resistant prostate cancer patients. The main goal of this strategy is to delay introduction of a new systemic agent to maintain quality of life and potentially to limit resistance. Further investigation is required to provide high-level evidence for the oncologic benefit of this treatment modality.



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