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Literature DB >> 23976791

The synthesis of biologically relevant conjugates of Re(CO)₃ using pyridine-2-carboxyaldehyde.

Roshinee Costa¹, Kullapa Chanawanno, James T Engle, Bertha Baroody, Richard S Herrick, Christopher J Ziegler.

Abstract

The new pyridine-2-carboxaldehyde adduct, Ren class="Chemical">(CO)3(NC6H5C(O)H)Cl 1, and previously reported complex Re(CO)3(NC6H5C(O)H)Br 2 react with aniline derivatives sulfanilamide or 4-aminofluorescein in methanol giving Schiff base conjugates Re(CO)3(pyca-R)X (pyca = pyridinecarbaldehyde imine, X = Cl, Br), 3-6. Pre-isolation of compounds 1 and 2 provides a convenient method for preparing conjugate complexes in addition to the known methods of ligand synthesis and one-pot reactions. All new compounds were completely characterized, and compound 1 and the sulfanilamide derivatives 3 and 4 were structurally elucidated by X-ray crystallography.

Entities: Chemical Disease Gene

Keywords: Carbonyl; Crystal Structures; Fluorescein; Metal conjugate; Rhenium; Sulfonamide

Year: 2013 PMID： 23976791 PMCID： PMC3747572 DOI： 10.1016/j.jorganchem.2012.10.025

Source DB: PubMed Journal: J Organomet Chem ISSN： 0022-328X Impact factor: 2.369

20 in total

Review 1. The role of coordination chemistry in the development of target-specific radiopharmaceuticals.

Authors: Shuang Liu
Journal: Chem Soc Rev Date: 2004-08-16 Impact factor: 54.564

Review 2. New sensing mechanisms for design of fluorescent chemosensors emerging in recent years.

Authors: Jiasheng Wu; Weimin Liu; Jiechao Ge; Hongyan Zhang; Pengfei Wang
Journal: Chem Soc Rev Date: 2011-03-29 Impact factor: 54.564

3. Complexes in context: attempting to control the cellular uptake and localisation of rhenium fac-tricarbonyl polypyridyl complexes.

Authors: Rebeca G Balasingham; Michael P Coogan; Flora L Thorp-Greenwood
Journal: Dalton Trans Date: 2011-09-06 Impact factor: 4.390

4. [(Cp-R)M(CO)3] (M=Re or 99mTc) Arylsulfonamide, arylsulfamide, and arylsulfamate conjugates for selective targeting of human carbonic anhydrase IX.

Authors: Daniel Can; Bernhard Spingler; Paul Schmutz; Filipa Mendes; Paula Raposinho; Célia Fernandes; Fabrizio Carta; Alessio Innocenti; Isabel Santos; Claudiu T Supuran; Roger Alberto
Journal: Angew Chem Int Ed Engl Date: 2012-02-17 Impact factor: 15.336

5. Synthesis and biological evaluation of a 99mTc-labelled sulfonamide conjugate for in vivo visualization of carbonic anhydrase IX expression in tumor hypoxia.

Authors: Vamsidhar Akurathi; Ludwig Dubois; Natasja G Lieuwes; Satish K Chitneni; Bernard J Cleynhens; Daniela Vullo; Claudiu T Supuran; Alfons M Verbruggen; Philippe Lambin; Guy M Bormans
Journal: Nucl Med Biol Date: 2010-04-24 Impact factor: 2.408

6. Synthesis of dimeric Re(I) amino acid conjugate complexes.

Authors: Hira Qayyum; Richard S Herrick; Christopher J Ziegler
Journal: Dalton Trans Date: 2011-06-21 Impact factor: 4.390

7. Rhenium(I) and platinum(II) complexes with diimine ligands bearing acidic phenol substituents: hydrogen-bonding, acid-base chemistry and optical properties.

Authors: Wei Liu; Katja Heinze
Journal: Dalton Trans Date: 2010-08-31 Impact factor: 4.390

8. Steps toward high specific activity labeling of biomolecules for therapeutic application: preparation of precursor [(188)Re(H(2)O)(3)(CO)(3)](+) and synthesis of tailor-made bifunctional ligand systems.

Authors: Roger Schibli; Rolf Schwarzbach; Roger Alberto; Kirstin Ortner; Helmut Schmalle; Cécile Dumas; André Egli; P August Schubiger
Journal: Bioconjug Chem Date: 2002 Jul-Aug Impact factor: 4.774

The synthesis of biologically relevant conjugates of Re(CO)₃ using pyridine-2-carboxyaldehyde.

Review 1. The role of coordination chemistry in the development of target-specific radiopharmaceuticals.

Review 2. New sensing mechanisms for design of fluorescent chemosensors emerging in recent years.

3. Complexes in context: attempting to control the cellular uptake and localisation of rhenium fac-tricarbonyl polypyridyl complexes.

4. [(Cp-R)M(CO)3] (M=Re or 99mTc) Arylsulfonamide, arylsulfamide, and arylsulfamate conjugates for selective targeting of human carbonic anhydrase IX.

5. Synthesis and biological evaluation of a 99mTc-labelled sulfonamide conjugate for in vivo visualization of carbonic anhydrase IX expression in tumor hypoxia.

6. Synthesis of dimeric Re(I) amino acid conjugate complexes.

7. Rhenium(I) and platinum(II) complexes with diimine ligands bearing acidic phenol substituents: hydrogen-bonding, acid-base chemistry and optical properties.

8. Steps toward high specific activity labeling of biomolecules for therapeutic application: preparation of precursor [(188)Re(H(2)O)(3)(CO)(3)](+) and synthesis of tailor-made bifunctional ligand systems.

Review 9. Single amino acid chelates (SAAC): a strategy for the design of technetium and rhenium radiopharmaceuticals.

Review 10. Carbonic anhydrase IX: a new druggable target for the design of antitumor agents.

1. Facile rhenium-peptide conjugate synthesis using a one-pot derived Re(CO)3 reagent.

2. Facile solid phase peptide synthesis with a Re-lysine conjugate generated via a one-pot procedure.

3. Lipophilic Re(CO)₃pyca complexes for Mid-IR imaging applications.