151 results found
Cryer AM, Chan C, Eftychidou A, et al., 2019, Tyrosine Kinase Inhibitor Gold Nanoconjugates for the Treatment of Non-Small Cell Lung Cancer., ACS Appl Mater Interfaces
Gold nanoparticles (AuNPs) have emerged as promising drug delivery candidates that can be leveraged for cancer therapy. Lung cancer (LC) is a heterogeneous disease that imposes a significant burden on society, with an unmet need for new therapies. Chemotherapeutic drugs such as afatinib (Afb), which is clinically approved for the treatment of epidermal growth factor receptor positive LC, is hydrophobic and has low bioavailability leading to spread around the body, causing severe side effects. Herein, we present a novel afatinib-AuNP formulation termed Afb-AuNPs, with the aim of improving drug efficacy and biocompatibility. This was achieved by synthesis of an alkyne-bearing Afb derivative and reaction with azide-functionalized lipoic acid using copper-catalyzed click chemistry, then conjugation to AuNPs via alkylthiol-gold bond formation. The Afb-AuNPs were found to possess up to 3.7-fold increased potency when administered to LC cells in vitro and were capable of significantly inhibiting cancer cell proliferation, as assessed by MTT assay and electric cell-substrate impedance sensing, respectively. Furthermore, when exposed to Afb-AuNPs, human alveolar epithelial type I-like cells, a model of the healthy lung epithelium, maintained viability and were found to release less proinflammatory cytokines when compared to free drug, demonstrating the biocompatibility of our formulation. This study provides a new platform for the development of nontraditional AuNP conjugates which can be applied to other molecules of therapeutic or diagnostic utility, with potential to be combined with photothermal therapy in other cancers.
Ferris T, Carroll L, Mease RC, et al., 2019, Iodination of terminal alkynes using KI/CuSO4 - A facile method with potential for radio-iodination, TETRAHEDRON LETTERS, Vol: 60, Pages: 936-939, ISSN: 0040-4039
Boddy AJ, Cordier CJ, Goldberg K, et al., 2019, Acid-Mediated Ring Expansion of 2,2-Disubstituted Azetidine Carbamates to 6,6-Disubstituted 1,3-Oxazinan-2-ones, ORGANIC LETTERS, Vol: 21, Pages: 1818-1822, ISSN: 1523-7060
Boddy AJ, Affron DP, Cordier CJ, et al., 2019, Rapid Assembly of Saturated Nitrogen Heterocycles in One-Pot: Diazo-Heterocycle "Stitching" by N-H Insertion and Cyclization, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Vol: 58, Pages: 1458-1462, ISSN: 1433-7851
Nielsen CD-T, Mooij WJ, Sale D, et al., 2019, Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes - a reaction at the "oxonium-Prins' vs. "ortho-quinone methide cycloaddition' mechanistic nexus, CHEMICAL SCIENCE, Vol: 10, Pages: 406-412, ISSN: 2041-6520
Nielsen CD-T, Abas H, Spivey AC, 2018, Stereoselective reactions of ortho-quinone methide and ortho-quinone methide imines and their utility in natural product synthesis, SYNTHESIS, Vol: 50, Pages: 4008-4018, ISSN: 0039-7881
Herein presented is a review of the reactivity and synthetic utility of ortho-quinone methides and ortho-quinone methide imines. These versatile intermediates have received significant attention in the literature and new methods for their preparation and reaction as well as recent applications in total synthesis are discussed.
Griffiths K, Tsipis AC, Kumar P, et al., 2017, 3d/4f Coordination Clusters as Cooperative Catalysts for Highly Diastereoselective Michael Addition Reactions, INORGANIC CHEMISTRY, Vol: 56, Pages: 9563-9573, ISSN: 0020-1669
Abas H, Linsdall SM, Mamboury M, et al., 2017, Total Synthesis of (+)-Lophirone H and Its Pentamethyl Ether Utilizing an Oxonium-Prins Cyclization, ORGANIC LETTERS, Vol: 19, Pages: 2486-2489, ISSN: 1523-7060
Murray JI, Floden NJ, Bauer A, et al., 2017, Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Vol: 56, Pages: 5760-5764, ISSN: 1433-7851
Murray JI, Flodén NJ, Bauer A, et al., 2017, Kinetic Resolution of 2-Substituted Indolines by N -Sulfonylation using an Atropisomeric 4-DMAP- N -oxide Organocatalyst, Angewandte Chemie, Vol: 129, Pages: 5854-5858, ISSN: 0044-8249
The first catalytic kinetic resolution by N‐sulfonylation is described. 2‐Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide (4‐DMAP‐N‐oxide) organocatalyst. Use of 2‐isopropyl‐4‐nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
Bodero O, Spivey AC, 2017, An Expedient Synthesis of 2-Aryl-1,4-benzoxazin-3-ones via Tandem Anionic Cyclisation/Alkylation Reactions of N-Boc-O-benzyl-2-aminophenols, SYNLETT, Vol: 28, Pages: 471-474, ISSN: 0936-5214
Frampton CS, Murray JI, Spivey AC, 2017, Crystal structure of 1-methylimidazole 3-oxide monohydrate, ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, Vol: 73, Pages: 372-+, ISSN: 2056-9890
Almond-Thynne J, Blakemore DC, Pryde DC, et al., 2017, Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes, CHEMICAL SCIENCE, Vol: 8, Pages: 40-62, ISSN: 2041-6520
Abas H, Frampton CS, Spivey AC, 2016, Diels-Alder Reactions of alpha-Amido Acrylates with N-Cbz-1,2-dihydropyridine and Cyclopentadiene, JOURNAL OF ORGANIC CHEMISTRY, Vol: 81, Pages: 9947-9956, ISSN: 0022-3263
Murray JI, Heckenast Z, Spivey AC, 2016, Chiral Lewis Base Activation of Acyl and Related Donors in Enantioselective Transformations (n → π*), Lewis Base Catalysis in Organic Synthesis, Pages: 457-526, ISBN: 9783527336180
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA. The role of Lewis bases in acylation reactions has been studied from both synthetic and mechanistic standpoints with a particular recent focus on enantioselective variants mediated by single enantiomer chiral Lewis bases deployed substoichiometrically. The modern-era of research into asymmetric enantioselective nucleophile-catalyzed acyl transfer using designed nucleophiles was initiated in the mid-1990s by the groups of Vedejs and Fu. This group developed chiral ferro-cenyl 4-dialkylaminopyridine derivatives first for the kinetic resolution (KR) of sec-alcohols and for an array of other transformations. Since the 1980s, the synthetic potential of enantioselective acylation has been well established in the context of fine chemical synthesis as a result of the development of biocatalytic processes that rely on hydrolytic enzymes. Cognizant that both bases and nucleophiles catalyze the acylation of alcohols using anhydrides and that alkyl phosphines in particular display weak basicity and strong nucleophilicity, Vedejs and Diver published a study of the utility of phosphines as acyl transfer catalysts.
Murray JI, Spivey AC, 2016, Preparation of 1-Methylimidazole- N-oxide (NMI-O), ORGANIC SYNTHESES, Vol: 93, Pages: 331-+, ISSN: 0078-6209
Murray JI, Spivey AC, 2015, Amines vs. N-Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1-Methylimidazole N-Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols, ADVANCED SYNTHESIS & CATALYSIS, Vol: 357, Pages: 3825-3830, ISSN: 1615-4150
Carroll L, Evans H, Spivey AC, et al., 2015, Mn-salen catalysed benzylic C-H activation for the synthesis of aryl [(18)F]CF3-containing PET probes., Chemical Communications, Vol: 51, Pages: 8439-8441, ISSN: 1364-548X
The development of a Mn-salen complex catalysed oxidative benzylic fluorination of non-activated C-H bonds using [(18)F]fluoride is described for installation of [(18)F]CHRF, [(18)F]CR2F and particularly [(18)F]CF3 containing groups in the presence of other functional groups.
Murray JI, Woscholski R, Spivey AC, 2015, Organocatalytic Phosphorylation of Alcohols Using Pyridine-N-oxide, Synlett, Vol: 26, Pages: 985-990, ISSN: 1437-2096
Murray JI, Woscholski R, Spivey AC, 2014, Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides - towards kinase-like reactivity, CHEMICAL COMMUNICATIONS, Vol: 50, Pages: 13608-13611, ISSN: 1359-7345
Evans HL, Quang-De N, Carroll LS, et al., 2014, A bioorthogonal Ga-68-labelling strategy for rapid in vivo imaging, CHEMICAL COMMUNICATIONS, Vol: 50, Pages: 9557-9560, ISSN: 1359-7345
Evans HL, Carroll L, Aboagye EO, et al., 2014, Bioorthogonal chemistry for Ga-68 radiolabelling of DOTA-containing compounds, JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 57, Pages: 291-297, ISSN: 0362-4803
Pisaneschi F, Slade RL, Iddon L, et al., 2014, Synthesis of a new fluorine-18 glycosylated 'click' cyanoquinoline for the imaging of epidermal growth factor receptor, JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 57, Pages: 92-96, ISSN: 0362-4803
George GPC, Stevens E, Aberg O, et al., 2014, Preclinical evaluation of a CXCR4-specific Ga-68-labelled TN14003 derivative for cancer PET imaging, BIOORGANIC & MEDICINAL CHEMISTRY, Vol: 22, Pages: 796-803, ISSN: 0968-0896
Andrews KG, Spivey AC, 2013, Improving the Accuracy of Computed C-13 NMR Shift Predictions by Specific Environment Error Correction: Fragment Referencing, JOURNAL OF ORGANIC CHEMISTRY, Vol: 78, Pages: 11302-11317, ISSN: 0022-3263
Andrews KG, Frampton CS, Spivey AC, 2013, Structural assignment of a bis-cyclopentenyl--cyanohydrin formed via alkene metathesis from either a triene or a tetraene precursor, ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, Vol: 69, Pages: 1207-+, ISSN: 0108-2701
George GPC, Pisaneschi F, Stevens E, et al., 2013, Scavenging strategy for specific activity improvement: application to a new CXCR4-specific cyclopentapeptide positron emission tomography tracer, JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 56, Pages: 679-685, ISSN: 0362-4803
Carroll L, Evans HL, Aboagye EO, et al., 2013, Bioorthogonal chemistry for pre-targeted molecular imaging - progress and prospects, ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 11, Pages: 5772-5781, ISSN: 1477-0520
Bayly AR, White AJP, Spivey AC, 2013, Design and Synthesis of a Prototype Scaffold for Five-Residue -Helix Mimetics, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol: 2013, Pages: 5566-5569, ISSN: 1434-193X
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