Perfluoro-Tert-Butyl Hydroxyproline
- Detailed Technology Description
- Development of new probes to detect specific molecular events associated with disease would substantially increase theinformation content of MRI. 19F imaging has enormous potential because of its specificity (highsignal to noise due to the absence of fluorine in vivo, itshigh sensitivity compared to proton imaging, and its application using commercial proton magnetic resonance instruments). The potential of 19F magnetic imagingin medicine is currently substantially limitedby a need to achieve increased sensitivity for applications. An ideal approach to enhance specificity and sensitivity of 19F magnetic resonance spectroscopy would involve the incorporation of an intense fluorine signal into native ligands in a manner that is minimally disruptive of structure.This invention incorporates perfluoro-tert-butylgroups, specifically perfluoro-tert-butylhydroxyproline,into peptides as novel amino acids. Perfluoro-tert-butylgroups have 9 equivalent fluorines, andthus have a 9-fold increase in signal-to-noise over single fluorines. At least as importantly, perfluoro-tert-butylgroups are sharp singlets by NMR, further increasing signal-to-noiseand operational simplicity, meaning thatmost existing proton-based instrumentation can be readily adjusted to detect peptides containing perfluoro-tert-butyl groups. Because of its highsignal-to-noise ratio and the ability to be incorporated within peptides and proteins, perfluoro-tert-butyl hydroxyproline has broad potential applications inmagnetic imaging (NMR, MRS, MRI), both in vitro and in vivo. Tert-butyl groups also have broad importance in medicinal chemistry due to theirhydrophobicity and symmetry, leading to enhanced binding to targets.Fig. Full NMR spectrum of peptide Ac-TYP(4R-OC(CF3)3)N-NH2.
- Countries
- United States
- Application No.
- Patent Pending
- *Abstract
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None
- *Inquiry
- Denise M. BierleinUniversity of DelawareOffice of Economic Innovation and PartnershipsLicensing AnalystTelephone: (302) 831-4005Email: deniseb@udel.edu
- *IP Issue Date
- None
- *IP Type
- Utility
- Country/Region
- USA
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