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Fluorescent purine nucleobase analogues

Synthetic methodology for generating a range of fluorescent purine nucleobase analogues with tuneable photophysical properties (e.g. absorption wavelength, Stokes’ shift) for use in ensemble-averaged and single-molecule fluorescence applications.

York scientists have designed a range of purine nucleobases (adenosines and guanosines) with conjugated rigid-rod type organic moieties attached. This enables electronic communication via a π-conjugated network between the heterocyclic purine ring and the attached substituted (or unsubstituted) cyclic group.

The chemical composition of the non-bulky cyclic group can be altered to tune the photophysical properties of the analogue (e.g. absorption wavelength, Stokes’ shift). Construction of a combinatorial fluorophore library allows for the selection of a probe with optimal properties for the required fluorescence application.

Benefits

• The nucleobase analogues can also be phosphorylated for use as biological substrates
• The unphosphorylated compounds are soluble at micromolar concentrations in aqueous media and are readily absorbed by cells.

Applications

• These compounds have potential as fluorescent substrates to monitor the activity of enzymes involved in the synthesis, modification, binding, polymerisation or hydrolysis of purine ribonucleotide triphosphate (NTP)
• After chemical or enzymatic incorporation into an oligonucleotide or a polynucleotide, the analogue can be used as a specific fluorescent probe of base pairing or mispairing in a double-stranded sequence. The resulting labelled nucleotide chains can be easily quantified using a variety of fluorescence detection methods
• The adenosine and guanosine compounds of this invention also have potential as inhibitors of pathogen (e.g. viral) replication (by directly inhibiting the replicative viral polymerase) and cell proliferation (e.g. cancerous cells).

Investment readiness status

Available for licensing

IP status

Pending in the US and Europe