Modulation of DNA binding by reversible metal-controlled molecular reorganizations of scorpiand-like ligands.

DNA interaction with scorpiand azamacrocycles has been achieved through modulation of their binding affinities. Studies performed with different experimental techniques provided evidence that pH or metal-driven molecular reorganizations of these ligands regulate their ability to interact with calf thymus DNA (ctDNA) through an intercalative mode. Interestingly enough, metal-driven molecular reorganizations serve to increase or decrease the biological activities of these compounds significantly.

[1]  U. Nir,et al.  Down-regulation of Fer induces ROS levels accompanied by ATM and p53 activation in colon carcinoma cells. , 2012, Cellular signalling.

[2]  P. Sadler,et al.  Metal complexes as DNA intercalators. , 2011, Accounts of chemical research.

[3]  Charles Giardina,et al.  DNA damage response to the Mdm2 inhibitor nutlin-3. , 2010, Biochemical pharmacology.

[4]  M. Teulade‐Fichou,et al.  Macrocyclic DNA-mismatch-binding ligands: structural determinants of selectivity. , 2010, Chemistry.

[5]  K. Gurova,et al.  New hopes from old drugs: revisiting DNA-binding small molecules as anticancer agents. , 2009, Future oncology.

[6]  Peter B. Dervan,et al.  Allosteric modulation of DNA by small molecules , 2009, Proceedings of the National Academy of Sciences.

[7]  C. Macrae,et al.  Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures , 2008 .

[8]  Qiang Xu,et al.  Synthesis, DNA-binding, cleavage, and cytotoxic activity of new 1,7-dioxa-4,10-diazacyclododecane artificial receptors containing bisguanidinoethyl or diaminoethyl double side arms. , 2007, Chemistry.

[9]  E. D. Bransome,et al.  Small molecule intercalation with double stranded DNA: implications for normal gene regulation and for predicting the biological efficacy and genotoxicity of drugs and other chemicals. , 2007, Mutation research.

[10]  S. Linder,et al.  Mechanisms of action of DNA-damaging anticancer drugs in treatment of carcinomas: is acute apoptosis an "off-target" effect? , 2007, Mini reviews in medicinal chemistry.

[11]  E. Garcı́a-España,et al.  Hydrogen and copper ion-induced molecular reorganizations in scorpionand-like ligands. A potentiometric, mechanistic, and solid-state study. , 2007, Inorganic chemistry.

[12]  M. J. Hannon,et al.  Supramolecular DNA recognition. , 2007, Chemical Society reviews.

[13]  C. Kumar,et al.  Contributions of hydroxyethyl groups to the DNA binding affinities of anthracene probes. , 2006, The journal of physical chemistry. B.

[14]  E. Garcı́a-España,et al.  Cu2+ and AMP complexation of enlarged tripodal polyamines. , 2006, Dalton transactions.

[15]  N. Malats,et al.  PIK3CA mutations are an early genetic alteration associated with FGFR3 mutations in superficial papillary bladder tumors. , 2006, Cancer research.

[16]  H. Schneider,et al.  Dramatic selectivity differences in the association of DNA and RNA models with new ethylene- and propylene diamine derivatives and their copper complexes. , 2006, Organic & biomolecular chemistry.

[17]  Xiang Zhou,et al.  Medical applications of macrocyclic polyamines. , 2006, Current medicinal chemistry.

[18]  C. Kumar,et al.  Spectroscopic Identification of Binding Modes of Anthracene Probes and DNA Sequence Recognition† , 2006, Photochemistry and photobiology.

[19]  H. Schneider,et al.  A novel bis-phenanthridine triamine with pH controlled binding to nucleotides and nucleic acids. , 2005, Organic & biomolecular chemistry.

[20]  C. Kumar,et al.  Contributions of a long side chain to the binding affinity of an anthracene derivative to DNA. , 2005, The journal of physical chemistry. B.

[21]  R. Kim,et al.  Recent advances in understanding the cell death pathways activated by anticancer therapy , 2005, Cancer.

[22]  T. Sun,et al.  Differential expression of cell cycle regulators in phenotypic variants of transgenically induced bladder tumors: implications for tumor behavior. , 2005, Cancer research.

[23]  Jian Ding,et al.  Novel Cytotoxic Copper(II) Complexes of 8‐Aminoquinoline Derivatives: Crystal Structure and Different Reactivity towards Glutathione , 2004 .

[24]  P. Gans,et al.  Determination of protonation constants of some fluorinated polyamines by means of 13C NMR data processed by the new computer program HypNMR2000. Protonation sequence in polyamines , 2003, Analytical and bioanalytical chemistry.

[25]  N. Socci,et al.  Molecular profiling of bladder cancer using cDNA microarrays: defining histogenesis and biological phenotypes. , 2002, Cancer research.

[26]  H. Schneider,et al.  Interactions of diaryl-polyamines with nucleic acids. Allosteric effects with dinuclear copper complexes , 2002 .

[27]  H. Schneider,et al.  Copper complexes of polyaza[n]cyclophanes and their interaction with DNA and RNA , 2001 .

[28]  A. Avdeef,et al.  PH-metric log P 11. pKa determination of water-insoluble drugs in organic solvent-water mixtures. , 1999, Journal of pharmaceutical and biomedical analysis.

[29]  A. Bianchi,et al.  Proton Coordination by Polyamine Compounds in Aqueous Solution , 1999 .

[30]  Yoichi Taya,et al.  DNA Damage-Induced Phosphorylation of p53 Alleviates Inhibition by MDM2 , 1997, Cell.

[31]  Terence E. Rice,et al.  Signaling Recognition Events with Fluorescent Sensors and Switches. , 1997, Chemical reviews.

[32]  P. Gans,et al.  Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs. , 1996, Talanta.

[33]  P. Gans,et al.  Nuclear magnetic resonance as a tool for determining protonation constants of natural polyprotic bases in solution. , 1995, Analytical biochemistry.

[34]  I. Haworth,et al.  Multiple DNA binding modes of anthracene-9-carbonyl-N1-spermine. , 1995, Bioorganic & medicinal chemistry.

[35]  J. Chaires,et al.  Criteria for the mode of binding of DNA binding agents. , 1995, Bioorganic & medicinal chemistry.

[36]  H. Schneider,et al.  Anthryl(alkylamino)cyclodextrin Complexes as Chemically Switched DNA Intercalators , 1995 .

[37]  C. Kumar,et al.  DNA binding studies and site selective fluorescence sensitization of an anthryl probe , 1993 .

[38]  J. Barton,et al.  On demonstrating DNA intercalation , 1990 .

[39]  N. Turro,et al.  Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA , 1989 .

[40]  D A Scudiero,et al.  Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. , 1988, Cancer research.

[41]  B. Nordén,et al.  Induced CD of DNA intercalators: Electric dipole allowed transitions , 1987, Biopolymers.

[42]  P. Pallavicini,et al.  N-(aminoethyl)cyclam: a tetraaza macrocycle with a coordinating tail (scorpiand). Acidity controlled coordination of the side chain to nickel(II) and nickel(III) cations , 1987 .

[43]  T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[44]  M. Chanon,et al.  Photoelectron-transfer catalysis: its connections with thermal and electrochemical analogs , 1983 .

[45]  B. Nordén,et al.  Structure of methylene blue–DNA complexes studied by linear and circular dichroism spectroscopy , 1982, Biopolymers.

[46]  D. Crothers,et al.  Studies on interaction of anthracycline antibiotics and deoxyribonucleic acid: equilibrium binding studies on interaction of daunomycin with deoxyribonucleic acid. , 1982, Biochemistry.

[47]  B. Nordén,et al.  Determination of binding geometry of DNA-adduct systems through induced circular dichroism , 1980 .

[48]  C. N. Reilley,et al.  Chemical shifts and protonation shifts in carbon-13 nuclear magnetic resonance studies of aqueous amines , 1975 .

[49]  H. Eisenberg,et al.  Viscosity and sedimentation study of sonicated DNA–proflavine complexes , 1969 .

[50]  F. Rossotti,et al.  Potentiometric titrations using Gran plots: A textbook omission , 1965 .

[51]  W. Wilson,et al.  Quantitative analysis of small molecule-nucleic acid interactions with a biosensor surface and surface plasmon resonance detection. , 2010, Methods in molecular biology.

[52]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[53]  C. Kumar,et al.  Tuning the DNA binding modes of an anthracene derivative with salt , 2006 .

[54]  J. Chaires,et al.  Parsing free energies of drug-DNA interactions. , 2000, Methods in enzymology.

[55]  A. Prasanna de Silva,et al.  Direct visual indication of pH windows: ‘off–on–off’ fluorescent PET (photoinduced electron transfer) sensors/switches , 1996 .

[56]  A. D. Moreton,et al.  Protonation sequence of linear aliphatic polyamines by 13C NMR spectroscopy , 1994 .

[57]  A. Bianchi,et al.  Low-spin six-co-ordinate cobalt(II) complexes. A solution study of tris(violurato)cobaltate(II) ions , 1988 .

[58]  A. D. Moreton,et al.  Deuterium isotope effect in concentrated aqueous solutions. A potentiometric and 13C nuclear magnetic resonance study of acid dissociation constants , 1985 .

[59]  A. P. Silva,et al.  A new class of fluorescent pH indicators based on photo-induced electron transfer , 1985 .

[60]  A. W. Addison,et al.  Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]copper(II) perchlorate , 1984 .

[61]  T. Kaden,et al.  pH-Induced co-ordination geometry change in a macrocyclic nickel(II) complex , 1977 .

[62]  J. Eisinger,et al.  Basic principles in nucleic acid chemistry , 1974 .

[63]  M. Paabo,et al.  Use of the glass electrode in deuterium oxide and the relation between the standardized pD (paD) scale and the operational pH in heavy water , 1968 .

[64]  P. K. Glasoe,et al.  USE OF GLASS ELECTRODES TO MEASURE ACIDITIES IN DEUTERIUM OXIDE1,2 , 1960 .

[65]  G. Gran Determination of the equivalence point in potentiometric titrations. Part II , 1952 .