Exploring Anticancer and (Bio)catalytic Activities of New Oxovanadium(V), Dioxomolybdenum(VI), and Copper(II) Complexes of Amide–Imine Conjugates

An amide–imine conjugate, (E)-N′-((2-hydroxynaphthalen-1-yl) methylene)–4-methylbenzohydrazide (PTANAP), derived from 4-methyl-benzoic acid hydrazide (PTA) and 2-hydroxynapthaldehyde, is explored to prepare dinuclear oxovanadium(V), mononuclear dioxomolydenum(VI), and Cu(II) complexes. Single crystal X-ray structurally characterized complexes have been exploited as catalyst for oxidation of ethylbenzene, catechol, and o-aminophenol. The anticancer properties of the oxo-vanadium complex have been explored against human leukemia cell (K-562) and mouse lymphoma cells (2PK3).

[1]  C. Jérôme,et al.  Organometallic-mediated radical polymerization of 'less activated monomers': fundamentals, challenges and opportunities , 2017 .

[2]  M. Drew,et al.  Subtle Structural Changes in (CuIIL)2MnII Complexes To Induce Heterometallic Cooperative Catalytic Oxidase Activities on Phenolic Substrates (H2L = Salen Type Unsymmetrical Schiff Base). , 2017, Inorganic chemistry.

[3]  S. Arepalli,et al.  Enhanced bioactivity, biocompatibility and mechanical behavior of strontium substituted bioactive glasses. , 2016, Materials science & engineering. C, Materials for biological applications.

[4]  M. Campos,et al.  Copper toxicology, oxidative stress and inflammation using zebrafish as experimental model , 2016, Journal of applied toxicology : JAT.

[5]  Arindam Mukherjee,et al.  Catechol oxidase and phenoxazinone synthase: Biomimetic functional models and mechanistic studies , 2016 .

[6]  J. Hochman,et al.  Highly Effective and Hydrolytically Stable Vanadium(V) Amino Phenolato Antitumor Agents. , 2016, Inorganic chemistry.

[7]  B. Ray,et al.  Methotrexate-Loaded Four-Arm Star Amphiphilic Block Copolymer Elicits CD8+ T Cell Response against a Highly Aggressive and Metastatic Experimental Lymphoma. , 2015, ACS applied materials & interfaces.

[8]  H. A. Rudbari,et al.  Mono- and dioxido-vanadium(V) complexes of a tridentate ONO Schiff base ligand: Synthesis, spectral characterization, X-ray crystal structure, and anticancer activity , 2015 .

[9]  T. Rovis,et al.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes. , 2015, Chemical reviews.

[10]  Xiao‐Feng Wu,et al.  Transition metal‐catalyzed oxidative transformations of methylarenes , 2015 .

[11]  Soon Hyeok Hong,et al.  Tandem Synthesis of Amides and Secondary Amines from Esters with Primary Amines under Solvent‐Free Conditions , 2014 .

[12]  B. Ray,et al.  Targeted Delivery of Doxorubicin-Loaded Poly (ε-caprolactone)-b-Poly (N-vinylpyrrolidone) Micelles Enhances Antitumor Effect in Lymphoma , 2014, PloS one.

[13]  M. Bagherzadeh,et al.  New molybdenum (VI) catalyst for the epoxidation of alkenes and oxidation of sulfides: An experimental and theoretical study , 2014 .

[14]  M. Maurya,et al.  Synthesis, characterization and catalytic activity of dioxidomolybdenum(VI) complexes of tribasic pentadentate ligands , 2014 .

[15]  S. Roy,et al.  Metal-catalyzed amidation , 2012 .

[16]  G. Giacomelli,et al.  One-pot synthesis of amides from aldehydes and amines via C-H bond activation. , 2012, Organic letters.

[17]  Dang Thanh Tuan,et al.  Copper-catalyzed oxidative amidation of aldehydes with amine salts: synthesis of primary, secondary, and tertiary amides. , 2012, The Journal of organic chemistry.

[18]  T. Hirayama,et al.  Near-infrared fluorescent sensor for in vivo copper imaging in a murine Wilson disease model , 2012, Proceedings of the National Academy of Sciences.

[19]  J. Bode,et al.  Rethinking amide bond synthesis , 2011, Nature.

[20]  Jason M. Lynam,et al.  Synthesis and Reactivity of Molybdenum Complexes Containing Functionalized Alkynyl Ligands: A Photochemically Activated CO-Releasing Molecule (PhotoCO-RM) , 2011 .

[21]  M. Chatterjee,et al.  Vanadium in the detection, prevention and treatment of cancer: the in vivo evidence. , 2010, Cancer letters.

[22]  K. Theopold,et al.  C-H bond activations by metal oxo compounds. , 2010, Chemical reviews.

[23]  Lili Lin,et al.  Amide-based bifunctional organocatalysts in asymmetric reactions. , 2009, Chemical communications.

[24]  I. Kostova.  Titanium and vanadium complexes as anticancer agents. , 2009, Anti-cancer agents in medicinal chemistry.

[25]  P. S. Prasad,et al.  Room temperature selective oxidation of toluene over vanadium substituted polyoxometalate catalysts , 2009 .

[26]  A. Batista,et al.  Oxovanadium(IV) and (V) complexes of acetylpyridine-derived semicarbazones exhibit insulin-like activity , 2008 .

[27]  A. J. Blake,et al.  Versatility of 2,6-diacetylpyridine (dap) hydrazones in generating varied molecular architectures: synthesis and structural characterization of a binuclear double helical Zn(II) complex and a Mn(II) coordination polymer. , 2007, Dalton transactions.

[28]  A. Dimoglo,et al.  Synthesis and characterization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. , 2006, European journal of medicinal chemistry.

[29]  C. Sergheraert,et al.  Design, synthesis and in vitro antimalarial activity of an acylhydrazone library. , 2006, Bioorganic & medicinal chemistry letters.

[30]  J. Haveman,et al.  Clonogenic assay of cells in vitro , 2006, Nature Protocols.

[31]  Yanguang Wang,et al.  A novel and selective catalytic oxidation of hydrocarbons to ketones using chloramine-T/O2/Fe(TPP)Cl system , 2005 .

[32]  B. Lai,et al.  Imaging of the intracellular topography of copper with a fluorescent sensor and by synchrotron x-ray fluorescence microscopy. , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[33]  M. Cindrić,et al.  A Series of New Molybdenum(VI) Complexes with the ONS Donor Thiosemicarbazone Ligands , 2005 .

[34]  L. Cavallo,et al.  Steric and electronic properties of N-heterocyclic carbenes (NHC): a detailed study on their interaction with Ni(CO)4. , 2005, Journal of the American Chemical Society.

[35]  E. Castellano,et al.  Vanadium(V) complexes with salicylaldehyde semicarbazone derivatives bearing in vitro anti-tumor activity toward kidney tumor cells (TK-10): crystal structure of [VVO2(5-bromosalicylaldehyde semicarbazone)]. , 2005, Journal of inorganic biochemistry.

[36]  K. Burgess,et al.  Metal-catalyzed epoxidations of alkenes with hydrogen peroxide. , 2003, Chemical reviews.

[37]  Saktiprosad Ghosh,et al.  Synthesis, Structure, and Reactivity of a New Mononuclear Molybdenum(VI) Complex Resembling the Active Center of Molybdenum Oxotransferases , 2003 .

[38]  K. Benkstein,et al.  MOLECULAR RECTANGLES BASED ON RHENIUM(I) COORDINATION CHEMISTRY , 1998 .

[39]  A. Chamberlin,et al.  Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides. , 1997, Chemical reviews.

[40]  M. Battell,et al.  Vanadium compounds as insulin mimics. , 1999, Metal ions in biological systems.

[41]  H. Sakurai,et al.  Mechanism for a new antitumor vanadium complex: hydroxyl radical-dependent DNA cleavage by 1,10-phenanthroline-vanadyl complex in the presence of hydrogen peroxide. , 1995, Biochemical and biophysical research communications.

[42]  K. A. Joergensen.  Transition-metal-catalyzed epoxidations , 1989 .

[43]  B. Halliwell,et al.  Oxygen toxicity, oxygen radicals, transition metals and disease. , 1984, The Biochemical journal.