Gregory J McManus

University of South Florida, Tampa, Florida, United States

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Publications (16)67.9 Total impact

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    ABSTRACT: NSC 333003 has been identified from the NCI Diversity Set as an inhibitor of the MDM2-p53 protein-protein interaction by in silico docking (virtual screening). Its potency and chemical characteristics render it well suited for lead optimization studies that can result in more potent analogs with improved drug-like properties. Its synthesis was achieved using an acid catalyzed condensation reaction from commercially available benzothiazole hydrazine and pyridyl phenyl ketone in refluxing methanol. Stereochemical implications for this compound are described.
    Bioorganic & medicinal chemistry letters 06/2009; 19(14):3756-9. · 2.65 Impact Factor
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    ABSTRACT: Imidazolium salts containing salicylaldoxime or salen ligands readily form ionic metal complexes with copper and manganese; hence offering applications in metal extractions and biphasic catalysis.
    Dalton Transactions 10/2008; · 4.10 Impact Factor
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    ABSTRACT: A novel metal-organic network [Cu(4)(5-NH(2)-1,3-bdc)(4)(pyridine)(2)(H(2)O)(2)](n), displaying an unprecedented topology has been constructed utilizing the different coordinating functional groups of 5-NH(2)-1,3-bdc to generate a ternary network based upon vertex-linked triangular, square and tetrahedral molecular building blocks (MBBs).
    Chemical Communications 01/2008; · 6.38 Impact Factor
  • Journal of the American Chemical Society 09/2007; 129(33):10076-7. · 10.68 Impact Factor
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    ABSTRACT: In this report, the photophysical properties of self-assembled [Cu(2)(5-OH-bdc)(2)L(2)](12) [where (5-OH-bdc)(2-) = 5-hydroxybenzene-1,3-dicarboxylate and L is a dimethyl sulfoxide, methanol, or water ligand] hydroxylated nanoballs (OH-nanoball) were examined in methanol using optical absorption and steady-state and time-resolved fluorescence methods. The optical spectrum of the OH-nanoball is dominated by ligand absorbance at 305 nm and a weaker Cu(2+)-to-ligand charge-transfer transition at approximately 695 nm, which are distinct from the absorption of either the free ligand (approximately 312 nm) or Cu(2+)(NO(3))(2) (>750 nm) in methanol. The corresponding emission spectrum of the OH-nanoball originates from the emission of the ligand and is centered at approximately 360 nm with a shoulder at approximately 390 nm. The emission from the OH-nanoball is significantly quenched relative to the free ligand [Phi(5-OH-H(2)bdc) = 0.014 and Phi(OH-nanoball) = (5.6 +/- 0.5) x 10-5]. The addition of bases such as imidazole results in an increase in the emission intensity of the OH-nanoball solution, indicating dissociation of the [Cu(2)(5-OH-bdc)(2)L(2)](12) units. Although the mechanism of (5-OH-bdc)(2-) quenching within the OH-nanoball is not clear, it is likely due to interactions between the ligand pi system and the Cu d orbitals. Fluorescence polarization studies further suggest that the OH-nanoball retains a spherical shape in solution. This is evident by the fact that the fluorescence anisotropy of the nanoball is nearly identical with that of the free ligand, suggesting rapid energy transfer (homogeneous fluorescence resonance energy transfer) between ligands within the OH-nanoball.
    Inorganic Chemistry 08/2007; 46(15):5904-10. · 4.59 Impact Factor
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    ABSTRACT: Coordination polymers based on Zn(II)-4,4'-bipyridine (Zn-bipy) frameworks containing pyrene intercalated between adjacent layers and aromatic solvent molecules enclathrated within the framework cavities have been prepared and characterized for the first time. These compounds are highly fluorescent, and show broad, featureless emission spectra significantly red-shifted relative to pyrene monomer fluorescence; this has been assigned to pyrene-bipy exciplex emission. Single-crystal X-ray structural analysis shows that the presence of the aromatic solvent molecule within the cavities has a profound effect on the architecture of these frameworks: in the case of benzene, toluene, p-xylene, and chlorobenzene, the Zn-bipy framework consists of 1-D ladders, whereas in the case of o-dichlorobenzene (the largest solvent guest), the framework was based on a 2-D square grid. This difference in stoichiometry and architecture was also reflected in significant differences in the fluorescence of these coordination polymers, with three of the four compounds with 1-D ladder geometries having similar fluorescence maxima (ca. 520 nm) and lifetimes (ca. 70 ns), whereas the compound with square grid topology had a significantly blue-shifted maximum (ca. 460 nm) and shorter lifetime (ca. 42 ns). It is proposed that exciplexes form upon excitation of ground-state complexes, involving face-to-face bipy/pyrene complexes (pi-pi stacking interactions) in the case of the 1-D ladder structures, but edge-to-face bipy/pyrene and pyrene/o-dichlorobenzene complexes (C-H...pi interactions) in the case of the 2-D square grid structure.
    Journal of the American Chemical Society 08/2007; 129(29):9094-101. · 10.68 Impact Factor
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    ABSTRACT: Cocrystal-controlled solid-state synthesis (C3S3) of imides occurs via heating of cocrystals formed between anhydride and aromatic amine cocrystal formers.
    Crystal Growth & Design - CRYST GROWTH DES. 03/2007; 7(4).
  • John J Perry, Gregory J McManus, Michael J Zaworotko
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    ABSTRACT: A novel Kagomé lattice that demonstrates the modular nature of metal-organic networks has been prepared and is to our knowledge the first example of a metal-organic coordination polymer that incorporates the sextuplet phenyl embrace as a supramolecular synthon.
    Chemical Communications 12/2004; · 6.38 Impact Factor
  • John J. Perry, Gregory J. McManus, Michael J. Zaworotko
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    ABSTRACT: The synthesis and X-ray crystal structure of [Cu(C7H3NO4)(C6H7NO)], [Cu(dipic)(4-MeO-Py)], (dipic = pyridine-2,6-dicarboxylate, 4-MeO-Py = 4-methoxypyridine), is described. Molecules of [Cu(dipic)(4-MeO-Py)] are formed {via} coordination of the copper(II) cation to two nitrogen atoms, from the dipic and 4-MeO-Py ligands respectively, and to two oxygen atoms from the carboxylate groups of the dipic ligand. The molecules pack in a non-centrosymmetric manner, stacked eclipsed with respect to one another along the b-axis and aligned parallel in a head-to-tail motif. The title compound crystallizes in the orthorhombic space group, Pca2(1), with a = 27.339(3) Å, b = 3.7130(4) Å, c = 11.6859(12) Å, V = 1186.2(2) Å3, and Z = 4. The structure was solved by direct methods and refined by least-squares methods to a final R-factor of 0.0327 for 2648 independent reflections.
    Journal of Chemical Crystallography 01/2004; 34(12). · 0.51 Impact Factor
  • Gregory J. McManus, Zhenqiang Wang, Michael J. Zaworotko
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    ABSTRACT: Nanoball structures decorated by 24 sulfonate or 24 methoxy moieties, 1 and 2, respectively, are able to act as nodes for the generation of infinite networks.
    Crystal Growth & Design 11/2003; 4(1). · 4.69 Impact Factor
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    ABSTRACT: The fundamental precept of crystal engineering is that all the information necessary for the design of a network is already stored in the molecular building blocks used. Coordination polymers represent an example of how crystal engineering has become a paradigm for the synthesis of new architectures and compositions. We report herein ten structures that are supramolecular isomers of one another. The structures are prepared from the same building blocks under mild reaction conditions. The modularity of coordination polymers imparts structural diversity that otherwise would not be possible.
    Macromolecular Symposia 07/2003; 196(1):213 - 227.
  • Brian D Wagner, Gregory J McManus
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    ABSTRACT: Addition of hydroxypropyl-beta-cyclodextrin to o-phthalaldehyde (OPA)-amino acid-thiol reaction mixtures is shown to cause significant enhancement of the fluorescence of the isoindole product for a wide range of amino acids, with the largest effects observed in the cases of glycine and lysine. The largest enhancement observed was a factor of 2.67 in the case of the derivative of glycine. This fluorescence enhancement is the result of the formation of a 1:1 host:guest inclusion complex between the isoindole and the cyclodextrin. Relatively small association constants of 44 and 130 M(-1) were obtained for the inclusion of the derivatives of glycine and lysine, respectively. Inclusion of the isoindole derivative into hydroxypropyl-beta-cyclodextrin was also found to result in a significant stabilization of the isoindole derivatives, contrary to what has been previously reported for inclusion into beta-cyclodextrin. For example, the lifetime of the lysine derivative was found to increase from 42 to 222 min, a factor of 5.3. These results have potential applications in fluorescence-based HPLC and high-performance capillary electrophoresis amino acid analysis methods using OPA derivation. Addition of hydroxypropyl-beta-cyclodextrin to the reaction mixture results in an increase in both the fluorescence and the stability of the isoindole product, providing potentially significant improvements to the method.
    Analytical Biochemistry 07/2003; 317(2):233-9. · 2.58 Impact Factor
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    ABSTRACT: We report the crystal structures of two new coordination polymers that have similar composition but, despite having the same circuit symbol and Schläfli notation, different topologies: a novel 3D topology (USF-1) and a CdSO4-like topology.
    Chemical Communications 07/2003; · 6.38 Impact Factor
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    ABSTRACT: The fluorescence intensity of 7-methoxycoumarin (7MC) in aqueoussolution is found to significantly decrease upon addition of variouscyclodextrins. This observed phenomenon is described asfluorescence suppression, to distinguish it from fluorescencereduction via bimolecular quenching. The decrease in fluorescenceof 7MC is proposed to be the result of the formation of ahost–guest inclusion complex with cyclodextrin. Since 7MC isa polarity-sensitive fluorophore, which is less fluorescent ina nonpolar environment, its fluorescence decreases uponinclusion into the relatively nonpolar internal cavity of thecyclodextrin. The same equation used for extracting the associationconstant in the case of 1 : 1 host–guest inclusion-induced fluorescenceenhancement is shown to be applicable to the case of fluorescencesuppression. In the case of ß-cyclodextrin, the degree of fluorescencesuppression, as well as the value of the binding constant for formationof the inclusion complex, are found to be unaffected by modificationof the cyclodextrin rims, suggesting that the molecule iscompletely included within the ß-cyclodextrin cavity. In the case of?-cyclodextrin, the degree of fluorescence suppression, butnot the value of the binding constant, is found to be significantlyaffected by modification of the cyclodextrin rims, suggesting thatthe molecule is experiencing a less polar environment in the modified?-cyclodextrin cavity. The binding constant is three timeslarger in ß- as compared to ?-cyclodextrin, indicatinga much better size match in the smaller ß-cyclodextrin cavity.
    Journal of Inclusion Phenomena 01/2003; 47(3):187-192. · 1.40 Impact Factor
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    ABSTRACT: We report the first use of fluorescence spectroscopy to probe the environment of the cavities that are present in open framework coordination polymers.
    Chemical Communications 10/2002; · 6.38 Impact Factor
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    ABSTRACT: AbstractMetal complexes of divalent copper (1–2), cobalt (3), and nickel (4) with mixed ligands acetylacetone (acac) and adenine were prepared and characterized by IR, mass spectra, elemental and thermal analysis. The X-ray crystal structures of {[Cu(acac)2(adenine)]·EtOH} complex (1) and {[Cu(acac)2(adenine)]·DMF·H2O} (2) were determined. Compound (1) crystallizes in the triclinic space group P−1 with a=7.547(3) Å, b=7.828(3) Å, c=17.791(6) Å, α=79.538(6)°, β=82.240(7)°, γ=86.010(6)°, V=1023.1(6) Å3, and Z=2. Complex (1) forms a hydrogen bonded 2:2 complex {[Cu(acac)2(adenine)]2:[EtOH]2} arranged in bilayers. Complex (2) crystallizes in the triclinic space group P−1 with a=7.828(2) Å, b=8.095(2) Å, c=16.995(5) Å, α=78.508(5)°, β=84.949(5)°, γ=89.285(5)°, V=1051.2(5) Å3, and Z=2. Complex (2) also forms bilayers with H-bonded DMF. Thermal analysis TG and DSC of the compounds (25–800°C, under N2) reveals the disproportionation of ligands with the associated heat. Graphical AbstractMetal complexes of divalent copper, cobalt, and nickel with mixed ligands acetylacetone (acac) and adenine were prepared and characterized by IR, mass spectra, elemental and thermal analysis. The X-ray crystal structures of {[Cu(acac)2(adenine)]·EtOH} complex (1) and {[Cu(acac)2(adenine)]·DMF·H2O} (2) were determined. Complex (1) forms a hydrogen bonded 2:2 complex {[Cu(acac)2(adenine)]2:[EtOH]2} arranged in bilayers. Complex (2) also forms bilayers with H-bonded DMF.
    Journal of Chemical Crystallography 39(12):853-863. · 0.51 Impact Factor