The design and synthesis of pyrazine amide ligands suitable for the "tiles" approach to molecular weaving with octahedral metal ions

Cockriel, David L.; McClain, James M.; Patel, Kaushal C.; Ullom, Robert; Hasley, Travis R.; Archibald, Stephen J.; Hubin, Timothy J.

doi:10.1016/j.inoche.2007.10.006

New AMD3100 derivatives for CXCR4 chemokine receptor targeted molecular imaging studies: synthesis, anti-HIV-1 evaluation and binding affinities (2015)
Journal Article
Poty, S., Désogère, P., Goze, C., Boschetti, F., D‘huys, T., Schols, D., …Denat, F. (2015). New AMD3100 derivatives for CXCR4 chemokine receptor targeted molecular imaging studies: synthesis, anti-HIV-1 evaluation and binding affinities. Dalton Transactions : an international journal of inorganic chemistry, 44(11), 5004-5016. https://doi.org/10.1039/c4dt02972k

CXCR4 is a target of growing interest for the development of new therapeutic drugs and imaging agents as its role in multiple disease states has been demonstrated. AMD3100, a CXCR4 chemokine receptor antagonist that is in current clinical use as a ha... Read More about New AMD3100 derivatives for CXCR4 chemokine receptor targeted molecular imaging studies: synthesis, anti-HIV-1 evaluation and binding affinities.

CXCR4 chemokine receptor antagonists: nickel(II) complexes of configurationally restricted macrocycles (2012)
Journal Article
Smith, R., Huskens, D., Daelemans, D., Mewis, R. E., Garcia, C. D., Cain, A. N., …Archibald, S. J. (2012). CXCR4 chemokine receptor antagonists: nickel(II) complexes of configurationally restricted macrocycles. Dalton Transactions : an international journal of inorganic chemistry, 41(37), 11369-11377. https://doi.org/10.1039/c2dt31137b

Tetraazamacrocyclic complexes of transition metals provide useful units for incorporating multiple coordination interactions into a single protein binding molecule. They can be designed with available sites for protein interactions via donor atom-con... Read More about CXCR4 chemokine receptor antagonists: nickel(II) complexes of configurationally restricted macrocycles.

Challenges in chelating positron emitting copper isotopes: tailored synthesis of unsymmetric chelators to form ultra stable complexes (2011)
Journal Article
Silversides, J. D., Smith, R., & Archibald, S. J. (2011). Challenges in chelating positron emitting copper isotopes: tailored synthesis of unsymmetric chelators to form ultra stable complexes. Dalton Transactions : an international journal of inorganic chemistry, 40(23), 6289-6297. https://doi.org/10.1039/c0dt01395a

The synthesis of chelators that form high stability complexes with copper(II) isotopes and do not suffer from transchelation in vivo has been a goal for many chemists. Such chelators will facilitate the exploitation of the Cu-64 isotope (t(1/2) = 12.... Read More about Challenges in chelating positron emitting copper isotopes: tailored synthesis of unsymmetric chelators to form ultra stable complexes.

Preparation, structural characterization, and thermal ammonolysis of two novel dimeric transition silylamide complexes (2011)
Journal Article
Cheng, F., Hope, C. N., Archibald, S. J., Bradley, J. S., Clark, S., Francesconi, M. G., …Lefebvre, F. (2011). Preparation, structural characterization, and thermal ammonolysis of two novel dimeric transition silylamide complexes. International Journal of Applied Ceramic Technology, 8(2), 467-481. https://doi.org/10.1111/j.1744-7402.2009.02452.x

The preparation and molecular structures of two novel dimeric transition metal silylamide complexes {Li0.5Zr[NHSi(NMe2)3]1.5[NSi(NMe2)3]0.5[μ -NSi(NMe2)3]}2 and {Li0.5Hf[NHSi(NMe2)3]1.5[NSi(NMe2)3]0.5[μ-NSi(NMe2)3]}2 with a tetrahedral coordination e... Read More about Preparation, structural characterization, and thermal ammonolysis of two novel dimeric transition silylamide complexes.

Synthesis, structure and reactivity of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole (2010)
Journal Article
Sparke, A. E., Fisher, C. M., Mewis, R. E., & Archibald, S. J. (2010). Synthesis, structure and reactivity of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 51(36), 4723-4726. https://doi.org/10.1016/j.tetlet.2010.07.010

The synthesis of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole, which undergoes a nucleophilic substitution with pyridine in the absence of additional base, is reported. The key steps are the reaction of 1,2-phenylenediamine to give exclusively the... Read More about Synthesis, structure and reactivity of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole.

A cellular screening assay using analysis of metal-modified fluorescence lifetime (2010)
Journal Article
Cade, N. I., Fruhwirth, G., Archibald, S. J., Ng, T., & Richards, D. (2010). A cellular screening assay using analysis of metal-modified fluorescence lifetime. Biophysical journal, 98(11), 2752-2757. https://doi.org/10.1016/j.bpj.2010.03.016

Current methods for screening cell receptor internalization often require complex image analysis with limited sensitivity. Here we describe a novel bioassay based on detection of changes in global fluorescence lifetime above a gold substrate, with su... Read More about A cellular screening assay using analysis of metal-modified fluorescence lifetime.

Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives (2010)
Journal Article
Jha, S., Silversides, J. D., Boyle, R. W., & Archibald, S. J. (2010). Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives. CrystEngComm RSC, 12(6), 1730-1739. https://doi.org/10.1039/b924683e

Hydantoins have been known as medicinally active compounds since the 1940s and thiohydantoin derivatives are currently undergoing clinical trials as potent androgen receptor antagonist drugs. Control of solid state properties including the formation... Read More about Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives.

Coordination chemistry of macrocyclic ligands (2009)
Journal Article
Archibald, S. J. (2009). Coordination chemistry of macrocyclic ligands. Annual Reports Section A :Inorganic Chemistry, 105, 297 - 322. https://doi.org/10.1039/b818281g

This chapter reviews the literature published during 2008 on macrocyclic coordination chemistry. Porphyrin ligands and supramolecular chemistry are not covered in this review which primarily focuses on complexes formed with transition metals and lant... Read More about Coordination chemistry of macrocyclic ligands.

MRI contrast agent delivery using spore capsules: controlled release in blood plasma (2009)
Journal Article
Lorch, M., Thomasson, M. J., Diego-Taboada, A., Barrier, S., Atkin, S. L., Mackenzie, G., & Archibald, S. J. (2009). MRI contrast agent delivery using spore capsules: controlled release in blood plasma. Chemical communications : Chem comm / the Royal Society of Chemistry, 6442-6444. https://doi.org/10.1039/b909551a

The exine coatings of spores can be used to encapsulate drug molecules. We have demonstrated that these microcapsules can be filled with a commercial gadolinium(III) MRI contrast agent (in this proof of concept study Gd-DTPA-BMA was used) which is sl... Read More about MRI contrast agent delivery using spore capsules: controlled release in blood plasma.

Synthesis and phototoxicity of polyethylene glycol (PEG) substituted metal-free and metallo-porphyrins: Effect of PEG chain length, coordinated metal, and axial ligand (2009)
Journal Article
Mewis, R. E., Savoie, H., Archibald, S. J., & Boyle, R. W. (2009). Synthesis and phototoxicity of polyethylene glycol (PEG) substituted metal-free and metallo-porphyrins: Effect of PEG chain length, coordinated metal, and axial ligand. Photodiagnosis and Photodynamic Therapy, 6(3-4), 200-206. https://doi.org/10.1016/j.pdpdt.2009.08.002

Treatment of 5,10,15,20-tetra(pentafluorophenyl) porphyrins with polyethylene glycol (PEG) halides and sodium sulfide is a mild and efficient route to water-soluble PEG substituted porphyrins. The method has been used to access a series of free-base... Read More about Synthesis and phototoxicity of polyethylene glycol (PEG) substituted metal-free and metallo-porphyrins: Effect of PEG chain length, coordinated metal, and axial ligand.

CXCR4 antagonists: a new generation of configurationally restricted bis-azamacrocyclic compounds (2009)
Journal Article
Khan, A., Nicholson, G., McRobbie, G., Greenman, J., Pannecouque, C., Daelemans, D., …Archibald, S. J. (2009). CXCR4 antagonists: a new generation of configurationally restricted bis-azamacrocyclic compounds. Antiviral research, 82(2), A59-A60. https://doi.org/10.1016/j.antiviral.2009.02.141

AMD3100 is a bis-azamacrocyclic compound that has been demonstrated to be a highly effective antagonist of the CXCR4 chemokine receptor. The two azamacrocyclic rings have been shown to interact with aspartate residues on the receptor via hydrogen bon... Read More about CXCR4 antagonists: a new generation of configurationally restricted bis-azamacrocyclic compounds.

Binding Optimization through Coordination Chemistry: CXCR4 Chemokine Receptor Antagonists from Ultrarigid Metal Complexes (2009)
Journal Article
Khan, A., Nicholson, G., McRobbie, G., Pannecouque, C., De Clercq, E., Ullom, R., …Greenman, J. (2009). Binding Optimization through Coordination Chemistry: CXCR4 Chemokine Receptor Antagonists from Ultrarigid Metal Complexes. Journal of the American Chemical Society, 131(10), 3416-3417. https://doi.org/10.1021/ja807921k

A new copper(II) containing bis-macrocyclic CXCR4 chemokine receptor antagonist is shown to have improved binding properties to the receptor protein in comparison to the drug AMD3100 (Plerixafor, Mozobil). The interaction of the metallodrug has been... Read More about Binding Optimization through Coordination Chemistry: CXCR4 Chemokine Receptor Antagonists from Ultrarigid Metal Complexes.

Reductive Amination-A convenient method for generating diverse, mono-functionalised 5,10,15,20-tetraphenyl porphyrins (2009)
Journal Article
Welch, C., Archibald, S. J., & Boyle, R. (2009). Reductive Amination-A convenient method for generating diverse, mono-functionalised 5,10,15,20-tetraphenyl porphyrins. SYNTHESIS, 2009(4), 551-556. https://doi.org/10.1055/s-0028-1083335

Formylation followed by reductive amination of 5,10,15,20-tetraphenyl porphyrin (TPP) is shown to be a versatile synthetic procedure for monosubstitution of the porphyrin core re-giospecifically at one β-position. A diverse range of substituents can... Read More about Reductive Amination-A convenient method for generating diverse, mono-functionalised 5,10,15,20-tetraphenyl porphyrins.

Synthesis and characterization of the chromium(III) complexes of ethylene cross-bridged cyclam and cyclen ligands (2008)
Journal Article
Maples, D. L., Maples, R. D., Hoffert, W. A., Parsell, T. H., Asselt, A. V., Silversides, J. D., …Hubin, T. J. (2009). Synthesis and characterization of the chromium(III) complexes of ethylene cross-bridged cyclam and cyclen ligands. Inorganica Chimica Acta, 362(6), 2084-2088. https://doi.org/10.1016/j.ica.2008.09.034

Dichloro(4,10-dimethyl-1,4,7,10-tetraazabicyclo[5.5.2] tetradecane) chromium(III) chloride, Dichloro(4,10-dibenzyl-1,4,7,10-tetraazabicyclo[ 5.5.2] tetradecane) chromium(III) chloride, and Dichloro(4,11-dimethyl- 1,4,8,11-tetraazabicyclo[6.6.2] hexad... Read More about Synthesis and characterization of the chromium(III) complexes of ethylene cross-bridged cyclam and cyclen ligands.

Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: new room temperature blue emitters (2008)
Journal Article
Ilkun, O. T., Archibald, S. J., Barnes, C. L., Gerasimchuk, N., Biagioni, R., Silchenko, S., …Nemykin, V. N. (2008). Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: new room temperature blue emitters. Dalton Transactions : an international journal of inorganic chemistry, 5715-5729. https://doi.org/10.1039/b803846e

A series of five 2-heteroarylcyanoximes such as: α-oximino-(2-benzimidazolyl)acetonitrile (HBIHCO), α-oximino-(N-methy-l-2-benzimidazolyl)acetonitrile (HBIMCO), α-oximino-(2-benzoxazolyl)acetonitrile (HBOCO), α-oximino-(2-benzothiazolyl)acetonitrile... Read More about Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: new room temperature blue emitters.

The design and synthesis of pyrazine amide ligands suitable for the "tiles" approach to molecular weaving with octahedral metal ions (2007)
Journal Article
Cockriel, D. L., McClain, J. M., Patel, K. C., Ullom, R., Hasley, T. R., Archibald, S. J., & Hubin, T. J. (2008). The design and synthesis of pyrazine amide ligands suitable for the "tiles" approach to molecular weaving with octahedral metal ions. Inorganic Chemistry Communications, 11(1), 1-4. https://doi.org/10.1016/j.inoche.2007.10.006

The pyrazine-containing ligands 1 (pyrazine-2-carboxylic acid (pyridine-2-ylmethyl)-amide) and 2 (pyrazine-2,5-dicarboxylic acid bis[(pyridine-2-yimethyl)-amide]) have been synthesized and characterized in order to probe their ability to form polynuc... Read More about The design and synthesis of pyrazine amide ligands suitable for the "tiles" approach to molecular weaving with octahedral metal ions.

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