Coordinatively Unsaturated Lanthanide(III) Helicates: Luminescence Sensors for Adenosine Monophosphate in Aqueous Media.

Coordinatively unsaturated double-stranded helicates [(H2 L)2 Eu2 (NO3 )2 (H2 O)4 ](NO3 )4 , [(H2 L)2 Tb2 (H2 O)6 ](NO3 )6 , and [(H2 L)2 Tb2 (H2 O)6 ]Cl6 (H2 L=butanedioicacid-1,4-bis[2-(2-pyridinylmethylene)hydrazide]) are easily obtained by self-assembly from the ligand and the corresponding lanthanide(III) salts. The complexes are characterized by X-ray crystallography showing the helical arrangement of the ligands. Co-ligands at the metal ions can be easily substituted by appropriate anions. A specific luminescence response of AMP in presence of ADP, ATP, and other anions is observed. Specificity is assigned to the perfect size match of AMP to bridge the two metal centers and to replace quenching co-ligands in the coordination sphere.

[1]  Feng-Xu Wu,et al.  Fluorescence sensing of ADP over ATP and PPi in 100% aqueous solution. , 2015, The Analyst.

[2]  Claudia Caltagirone,et al.  Applications of Supramolecular Anion Recognition. , 2015, Chemical reviews.

[3]  S. Tomić,et al.  Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by a combination of aromatic, hydrogen bond and electrostatic interactions. , 2015, Organic & biomolecular chemistry.

[4]  Partha Mahata,et al.  Optical detection of submicromolar levels of nitro explosives by a submicron sized metal–organic phosphor material , 2014 .

[5]  Y. Zhang,et al.  A pyrene-functionalized Zinc(II)–BPEA complex: sensing and discrimination of ATP, ADP and AMP , 2014 .

[6]  Shengjun Yang,et al.  Discrimination of adenine nucleotides and pyrophosphate in water by a zinc complex of an anthracene-based cyclophane. , 2014, Organic & biomolecular chemistry.

[7]  P. S. Subramanian,et al.  Sensing of phosphates by using luminescent Eu(III) and Tb(III) complexes: application to the microalgal cell Chlorella vulgaris. , 2014, Chemistry.

[8]  Marie C. Heffern,et al.  Lanthanide probes for bioresponsive imaging. , 2014, Chemical reviews.

[9]  P. Mukherjee,et al.  Modification of extended open frameworks with fluorescent tags for sensing explosives: competition between size selectivity and electron deficiency. , 2014, Chemistry.

[10]  Li Wang,et al.  Determination of tetracycline in milk by using nucleotide/lanthanide coordination polymer-based ternary complex. , 2013, Biosensors & bioelectronics.

[11]  E. Jankowsky,et al.  AMP sensing by DEAD-box RNA helicases. , 2013, Journal of molecular biology.

[12]  K. Ghosh,et al.  Pyridinium-based tripodal chemosensor in visual sensing of AMP in water by indicator displacement assay (IDA). , 2013, Organic & biomolecular chemistry.

[13]  T. Lu,et al.  Highly selective recognition and fluorescence imaging of adenosine polyphosphates in aqueous solution. , 2013, Inorganic chemistry.

[14]  Genhua Wu,et al.  Coordination assembly of helicate and mesocate with two-armed carbohydrozine ligand: Synthesis, structure and fluorescence , 2013 .

[15]  P. S. Subramanian,et al.  Lanthanide(III) complexes of bis-semicarbazone and bis-imine-substituted phenanthroline ligands: solid-state structures, photophysical properties, and anion sensing. , 2012, Chemistry.

[16]  Yang Chen,et al.  Luminescence Nucleotide/Eu3+ Coordination Polymer Based on the Inclusion of Tetracycline , 2012 .

[17]  J. Sessler,et al.  Artificial receptors for the recognition of phosphorylated molecules. , 2011, Chemical reviews.

[18]  A. Bianchi,et al.  Binding and recognition of AMP, ADP, ATP and related inorganic phosphate anions by a tren-based ligand containing a pyrimidine functionality , 2011 .

[19]  Narinder Singh,et al.  Tetrapodal receptors for selective fluorescent sensing of AMP: analyte-induced conformational restriction to persuade fluorescence enhancement , 2011 .

[20]  Hannes Y. Kuchelmeister,et al.  Nucleotide recognition in water by a guanidinium-based artificial tweezer receptor. , 2011, Chemistry.

[21]  E. Gendaszewska-Darmach,et al.  Nucleotide receptors as targets in the pharmacological enhancement of dermal wound healing , 2011, Purinergic Signalling.

[22]  W. Junger,et al.  Immune cell regulation by autocrine purinergic signalling , 2011, Nature Reviews Immunology.

[23]  H. Lin,et al.  A supramolecular optic sensor for selective recognition AMP , 2010 .

[24]  K. Kaneko,et al.  Selective inclusion of anionic quantum dots in coordination network shells of nucleotides and lanthanide ions. , 2010, Chemical communications.

[25]  N. Kimizuka,et al.  Switching on luminescence in nucleotide/lanthanide coordination nanoparticles via synergistic interactions with a cofactor ligand. , 2010, Chemistry.

[26]  N. Kimizuka,et al.  Confining molecules within aqueous coordination nanoparticles by adaptive molecular self-assembly. , 2009, Angewandte Chemie.

[27]  Geoffrey Burnstock,et al.  The double life of ATP. , 2009, Scientific American.

[28]  C. McCoy,et al.  Formation of Novel Dinuclear Lanthanide Luminescent Samarium(III), Europium(III), and Terbium(III) Triple-Stranded Helicates from a C2-Symmetrical Pyridine-2,6-dicarboxamide-Based 1,3-Xylenediyl-Linked Ligand in MeCN , 2009 .

[29]  Yujun Song,et al.  Rapid and ultra-sensitive detection of AMP using a fluorescent and magnetic nano-silica sandwich complex. , 2009, Chemical communications.

[30]  Makoto Hashizume,et al.  Nanoparticles of adaptive supramolecular networks self-assembled from nucleotides and lanthanide ions. , 2009, Journal of the American Chemical Society.

[31]  K. Kaneko,et al.  Controlled self-assembly of nucleotide-lanthanide complexes: specific formation of nanofibers from dimeric guanine nucleotides. , 2008, Chemical communications.

[32]  J. Bünzli,et al.  A versatile method for quantification of DNA and PCR products based on time-resolved EuIII luminescence. , 2008, The Analyst.

[33]  R. Fröhlich,et al.  Highly efficient near-IR emitting Yb/Yb and Yb/Al helicates. , 2007, Journal of the American Chemical Society.

[34]  R. Fröhlich,et al.  Diastereoselective formation of luminescent dinuclear lanthanide(III) helicates with enantiomerically puretartaric acid derived bis(β-diketonate) ligands , 2007 .

[35]  Y. Shao,et al.  A chronocoulometric aptamer sensor for adenosine monophosphate. , 2007, Chemical communications.

[36]  F. Amano,et al.  Highly selective recognition of adenine nucleobases by synthetic hosts with a linked five-six-five-membered triheteroaromatic structure and the application to potentiometric sensing of the adenine nucleotide. , 2006, Chemistry.

[37]  J. Bünzli,et al.  Taking advantage of luminescent lanthanide ions. , 2005, Chemical Society reviews.

[38]  M. Albrecht,et al.  Künstliche molekulare doppelsträngige Helices , 2005 .

[39]  Markus Albrecht,et al.  Artificial molecular double-stranded helices. , 2005, Angewandte Chemie.

[40]  G. Bernardinelli,et al.  Tuning the decay time of lanthanide-based near infrared luminescence from micro- to milliseconds through d-->f energy transfer in discrete heterobimetallic complexes. , 2005, Chemistry.

[41]  P. B. Glover,et al.  Highly luminescent, triple- and quadruple-stranded, dinuclear Eu, Nd, and Sm(III) lanthanide complexes based on bis-diketonate ligands. , 2004, Journal of the American Chemical Society.

[42]  J. Bünzli,et al.  Supramolecular recognition of heteropairs of lanthanide ions: a step toward self-assembled bifunctional probes. , 2004, Inorganic chemistry.

[43]  M. J. Hannon,et al.  Helices and Helicates: Beautiful Supramolecular Motifs with Emerging Applications , 2004 .

[44]  G. Bernardinelli,et al.  Extending lifetimes of lanthanide-based near-infrared emitters (Nd, Yb) in the millisecond range through Cr(III) sensitization in discrete bimetallic edifices. , 2003, Journal of the American Chemical Society.

[45]  M. Han,et al.  Visual detection of AMP and real-time monitoring of cyclic nucleotide phosphodiesterase (PDE) activity in neutral aqueous solution. Chemosensor-coupled assay of PDE and PDE inhibitors. , 2003, Bioorganic & medicinal chemistry letters.

[46]  J. Bünzli,et al.  Lanthanide-containing molecular and supramolecular polymetallic functional assemblies. , 2002, Chemical reviews.

[47]  G. Bernardinelli,et al.  The first self-assembled trimetallic lanthanide helicate: different coordination sites in symmetrical molecular architectures. , 2002, Chemical communications.

[48]  H. Schneider,et al.  Phenanthridinium cyclobisintercalands. Fluorescence sensing of AMP and selective binding to single-stranded nucleic acids , 2001 .

[49]  M. Albrecht,et al.  "Let's twist again"--double-stranded, triple-stranded, and circular helicates. , 2001, Chemical reviews.

[50]  E. Sletten,et al.  Intramolecular DNA Coiling Mediated by a Metallo-Supramolecular Cylinder. , 2001, Angewandte Chemie.

[51]  W. Horrocks,et al.  Supramolecular coordination chemistry in aqueous solution: lanthanide ion-induced triple helix formation. , 2000, Inorganic chemistry.

[52]  J. Bünzli,et al.  Lanthanide Helicates Self-Assembled in Water: A New Class of Highly Stable and Luminescent Dimetallic Carboxylates , 1999 .

[53]  Gérald Bernardinelli,et al.  Helicates as Versatile Supramolecular Complexes. , 1997, Chemical reviews.

[54]  J. Siegel,et al.  Spontaneous assembly of double-stranded helicates from oligobipyridine ligands and copper(I) cations: structure of an inorganic double helix. , 1987, Proceedings of the National Academy of Sciences of the United States of America.

[55]  T. Mansour.  Studies on Heart Phosphofructokinase: Purification, Inhibition, and Activation , 1963 .

[56]  Joel H. Hildebrand,et al.  A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons , 1949 .

[57]  Manoj Kumar,et al.  Highly selective fluorescent probe for detection and visualization of palladium ions in mixed aqueous media , 2013 .

[58]  Wei Sun,et al.  Application of a hydroxyl functionalized ionic liquid modified electrode for the sensitive detection of adenosine-5′-monophosphate , 2012 .

[59]  M. Gijs,et al.  Bioconjugated lanthanide luminescent helicates as multilabels for lab-on-a-chip detection of cancer biomarkers. , 2010, The Analyst.

[60]  G. Bernardinelli,et al.  Isolated d-f pairs in supramolecular complexes with tunable structural and electronic properties , 2000 .

[61]  J. Bünzli,et al.  Mono- and polymetallic lanthanide-containing functional assemblies: a field between tradition and novelty , 1999 .

[62]  E. Garcı́a-España,et al.  Multifunctional molecular recognition of ATP, ADP and AMP nucleotides by the novel receptor 2,6,10,13,17,21-hexaaza[22]metacyclophane , 1995 .

[63]  C. Cori,et al.  THE ROLE OF ADENYLIC ACID IN THE ACTIVATION OF PHOSPHORYLASE. , 1964, Proceedings of the National Academy of Sciences of the United States of America.

[64]  University of Huddersfield Repository Asymmetric triplex metallohelices with high and selective activity against cancer cells , 2022 .