Boron-based dual imaging probes, compositions and methods for rapid aqueous F-18 labeling, and imaging methods using same

Li, Zibo; Gabbai, Francois P.; Conti, Peter S.; Hudnall, Todd W.; Lin, Tzu-Pin; Liu, Shuanglong; Huang, Chiun-Wei

Title: Boron-based dual imaging probes, compositions and methods for rapid aqueous F-18 labeling, and imaging methods using same

Patent · Tue Jun 05 00:00:00 EDT 2018

OSTI ID:1457028

Li, Zibo; Gabbai, Francois P.; Conti, Peter S.; Hudnall, Todd W.; Lin, Tzu-Pin; Liu, Shuanglong; Huang, Chiun-Wei

A composition useful as a PET and/or fluorescence imaging probe a compound a compound of Formula I, including salts, hydrates and solvates thereof: ##STR00001## wherein R.sub.1-R.sub.7 may be independently selected from hydrogen, halogen, hydroxy, alkoxy, nitro, substituted and unsubstituted amino, cycloalkyl, carboxy, carboxylic acids and esters thereof, cyano, haloalkyl, aryl, X is selected from the group consisting of C and N; and A is selected of hydrogen, halogen, hydroxy, alkoxy, nitro, substituted and unsubstituted amino, alkyl, cycloalkyl, carboxy, carboxylic acids and esters thereof, cyano, haloalkyl, aryl, including phenyl and aminophenyl, and heteroaryl.

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Research Organization:: Univ. of Southern California, Los Angeles, CA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: SC0002353

Assignee:: University of Southern California (Los Angeles, CA)

Patent Number(s):: 9,987,380

Application Number:: 13/549,309

OSTI ID:: 1457028

Resource Relation:: Patent File Date: 2012 Jul 13

Country of Publication:: United States

Language:: English

References (12)

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Nanoparticle-mediated drug delivery to tumor vasculature suppresses metastasis Murphy, E. A.; Majeti, B. K.; Barnes, L. A. Proceedings of the National Academy of Sciences, Vol. 105, Issue 27, p. 9343-9348 https://doi.org/10.1073/pnas.0803728105	journal	July 2008
Substitution of hydroxide by fluoride at the boron center of a BODIPY dye Hudnall, Todd W.; Lin, Tzu-Pin; Gabbaï, François P. Journal of Fluorine Chemistry, Vol. 131, Issue 11, p. 1182-1186 https://doi.org/10.1016/j.jfluchem.2010.06.012	journal	November 2010
Synthesis and labelling with ¹⁸F of an MK 801 analogue: [¹⁸F]5-(β-fluoruethyl)-10,11-dihydro-5H-dibenzocycloheptene-5,10-imine Denis, A.; Crouzel, C. Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 27, Issue 9, p. 1007-1013 https://doi.org/10.1002/jlcr.2580270905	journal	September 1989
Trimethylsilyl trifluoromethanesulfonate promoted chemoselective reactions of acyclic acetals in the presence of cyclic acetals Kim, Sunggak; Do, Jung Yun; Kim, Sung Hoon Journal of the Chemical Society, Perkin Transactions 1, Vol. 0, Issue 17, p. 2357-2358 https://doi.org/10.1039/P19940002357	journal	January 1994
Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core Li, Lingling; Nguyen, Binh; Burgess, Kevin Bioorganic & Medicinal Chemistry Letters, Vol. 18, Issue 10, p. 3112-3116 https://doi.org/10.1016/j.bmcl.2007.10.103	journal	May 2008
Synthesis and pharmacological characterization of novel fluorescent histamine H₂-receptor ligands derived from aminopotentidine Xie, Sheng-Xue; Petrache, Georgiana; Schneider, Erich Bioorganic & Medicinal Chemistry Letters, Vol. 16, Issue 15, p. 3886-3890 https://doi.org/10.1016/j.bmcl.2006.05.039	journal	August 2006
Development of dual functional SPECT/fluorescent probes for imaging cerebral β-amyloid plaques Ono, Masahiro; Ishikawa, Manami; Kimura, Hiroyuki Bioorganic & Medicinal Chemistry Letters, Vol. 20, Issue 13, p. 3885-3888 https://doi.org/10.1016/j.bmcl.2010.05.027	journal	July 2010
Fast ¹⁸F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes Ting, Richard; Aguilera, Todd A.; Crisp, Jessica L. Bioconjugate Chemistry, Vol. 21, Issue 10, p. 1811-1819 https://doi.org/10.1021/bc1001328	journal	October 2010
Targeted optical imaging of cancer cells using lectin-binding BODIPY conjugated avidin Hama, Yukihiro; Urano, Yasuteru; Koyama, Yoshinori Biochemical and Biophysical Research Communications, Vol. 348, Issue 3, p. 807-813 https://doi.org/10.1016/j.bbrc.2006.07.169	journal	September 2006
Synthesis of [¹⁸F]BODIPY: Bifunctional Reporter for Hybrid Optical/Positron Emission Tomography Imaging Hendricks, J. Adam; Keliher, Edmund J.; Wan, Dongpeng Angewandte Chemie International Edition, Vol. 51, Issue 19, p. 4603-4606 https://doi.org/10.1002/anie.201107957	journal	April 2012

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