Synthesis of theophylline derivatives and study of their activity as antagonists at adenosine receptors.

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Hierrezuelo J, Manuel Lopez-Romero J, Rico R, Brea J, Isabel Loza M, Cai C, Algarra M

Synthesis of theophylline derivatives and study of their activity as antagonists at adenosine receptors.

Bioorg Med Chem. 2010 Mar 15;18(6):2081-8. doi: 10.1016/j.bmc.2010.02.014. Epub 2010 Feb 15.

PubMed ID

20202853 [ View in PubMed

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Abstract

The synthesis of oligo(ethylene glycol)-alkene substituted theophyllines in positions 7 and/or 8 is described. The binding activity at adenosine receptors of selected derivatives was studied. Compound 2 showed high affinity for human A(2B) receptor (K(i) = 4.16 nM) with a selectivity K(iA2A)/K(iA2B) of 24.1, and a solubility in water of 1 mM. The alkenyl substituent in some of the theophylline derivatives allows for covalent attachment of them onto hydrogen-terminated silicon substrate surfaces via hydrosilylation. Alternatively, an azido group was incorporated to an oligo(ethylene glycol)theophylline derivative as an anchor for tethering the molecules on ethynyl presenting surfaces via click reaction.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Theophylline	Adenosine receptor A1	Ki (nM)	10100	N/A	N/A	Details
Theophylline	Adenosine receptor A2a	Ki (nM)	18500	N/A	N/A	Details
Theophylline	Adenosine receptor A2b	Ki (nM)	2700	N/A	N/A	Details