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Tri-functionalized cryptophane biosensors for biomolecular imaging and MRI diagnostics


Brief Description: Cryptophanes with high xenon affinity enable ultrasensitive detection of analytes in solution using Xe-129 NMR/MRI




The Dmochowski lab has developed biosensors comprised of tri-functionalized cryptophane with high affinity for hyperpolarized 129Xe.  These biosensors can be designed to detect molecular markers associated with cancer and other disease.  More specifically, a biosensor has been synthesized that detects matrix metalloproteases (MMPs), which are frequently upregulated in many cancers.  The MMP enzyme cleaves the peptide covalently attached to the 129Xe biosensor, resulting in a change in the chemical environment of 129Xe readily detectable by a 0.5 ppm chemical shift in NMR.  The features of these tri-functionalized cryptophanes enable the detection of picomolar concentrations of cryptophane biosensors by a technique known as Hyper-CEST NMR/MRI.  Additional xenon biosensors have been designed to target integrin receptors, folate receptor, and carbonic anhydrase.  In most cases, binding the cryptophane biosensor to its protein target produces a measureable change in the Xe-129 NMR chemical shift.


From Khan et al, 2015.  Folate-conjugated cryptophane to target cryptophane to membrane-bound folate receptors that are overexpressed in many human cancers.



·         Tri-functionalized cryptophanes well-solubilized in water

·         Highest known affinity for xenon

·         Very favorable Xe exchange kinetics

·         Ultrasensitive analyte detection

·         Tri-functionalized cryptophane biosensors can be designed that each yield distinct 129Xe NMR chemical shifts and can be targeted to different biomarkers



·         Biosensors

·         129Xe MRI diagnostics next-generation platform

·         Biomolecular imaging and enhancement of existing 1H MRI technology


Stage of Development:

·         In vitro proof-of-concept testing


Intellectual Property:

USSN 8,222,022


Reference Media:

Riggle B.A. et al.  JACS, 2015, 137(16), p. 5542-5548.

Taratula O. et al.  Supramol. Chem., 2015, 27(1-2), p. 65-71.

Khan N.S. et al.  Bioconjugate Chem., 2015, 26(1), p. 101-109.

Taratula O. et al.  Organic Letters, 2012, 14(14), p. 3580-3583.

Taratula O. et al.  Organic Letters, 2011, 13(6), p. 1414-1417.

Bai Y. et al.  Analytical Chemistry, 2012, 84, p. 9935-9941.

Hill PA et al.  JACS, 2007, 129(30), p. 9262-9263.


Desired Partnerships:

1.    License

2.    Co-development


Docket #: T4532


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Patent Information:
For Information, Contact:
Joshua Jeanson
Associate Director, SEAS/SAS Licensing Group
University of Pennsylvania
Ivan Dmochowski