Fluorescent Bisphosphonate and Carboxyphosphonate Probes: A Versatile Imaging Toolkit for Applications in Bone Biology and Biomedicine

Shuting Sun; Katarzyna M Błażewska; Anastasia P Kadina; Boris A Kashemirov; Xuchen Duan; James T Triffitt; James E Dunford; R Graham G Russell; Frank H Ebetino; Anke J Roelofs; Fraser Coxon; Mark W Lundy; Charles E McKenna

doi:10.1021/acs.bioconjchem.5b00369

Fluorescent Bisphosphonate and Carboxyphosphonate Probes: A Versatile Imaging Toolkit for Applications in Bone Biology and Biomedicine

Shuting Sun, Katarzyna M Błażewska, Anastasia P Kadina, Boris A Kashemirov, Xuchen Duan, James T Triffitt, James E Dunford, R Graham G Russell, Frank H Ebetino, Anke J Roelofs, Fraser Coxon, Mark W Lundy, Charles E McKenna

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

A bone imaging toolkit of 21 fluorescent probes with variable spectroscopic properties, bone mineral binding affinities, and antiprenylation activities has been created, including a novel linking strategy. The linking chemistry allows attachment of a diverse selection of dyes fluorescent in the visible to near-infrared range to any of the three clinically important heterocyclic bisphosphonate bone drugs (risedronate, zoledronate, and minodronate or their analogues). The resultant suite of conjugates offers multiple options to "mix and match" parent drug structure, fluorescence emission wavelength, relative bone affinity, and presence or absence of antiprenylation activity, for bone-related imaging applications.

Original language	English
Pages (from-to)	329-340
Number of pages	12
Journal	Bioconjugate Chemistry
Volume	27
Issue number	2
Early online date	8 Dec 2015
DOIs	https://doi.org/10.1021/acs.bioconjchem.5b00369
Publication status	Published - 17 Feb 2016

Bibliographical note

Acknowledgment
Compounds 1a–1c were gifts from Warner Chilcott Pharmaceuticals (formerly Procter & Gamble Pharmaceuticals). This work was supported by the University of Southern California and in part by NIH grants 1R01DC009837, 1R21DE023410, 1R43AR067021-01A1, and 1R43DE025524-01. A.J.R. and F.P.C. acknowledge support from Warner Chilcott. J.D. was supported through funding from the Oxford NIHR Biomedical Research Unit.

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Anke Roelofs
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Sun, S., Błażewska, K. M., Kadina, A. P., Kashemirov, B. A., Duan, X., Triffitt, J. T., Dunford, J. E., Russell, R. G. G., Ebetino, F. H., Roelofs, A. J., Coxon, F., Lundy, M. W., & McKenna, C. E. (2016). Fluorescent Bisphosphonate and Carboxyphosphonate Probes: A Versatile Imaging Toolkit for Applications in Bone Biology and Biomedicine. Bioconjugate Chemistry, 27(2), 329-340. https://doi.org/10.1021/acs.bioconjchem.5b00369

Sun, S, Błażewska, KM, Kadina, AP, Kashemirov, BA, Duan, X, Triffitt, JT, Dunford, JE, Russell, RGG, Ebetino, FH, Roelofs, AJ, Coxon, F, Lundy, MW & McKenna, CE 2016, 'Fluorescent Bisphosphonate and Carboxyphosphonate Probes: A Versatile Imaging Toolkit for Applications in Bone Biology and Biomedicine', Bioconjugate Chemistry, vol. 27, no. 2, pp. 329-340. https://doi.org/10.1021/acs.bioconjchem.5b00369

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abstract = "A bone imaging toolkit of 21 fluorescent probes with variable spectroscopic properties, bone mineral binding affinities, and antiprenylation activities has been created, including a novel linking strategy. The linking chemistry allows attachment of a diverse selection of dyes fluorescent in the visible to near-infrared range to any of the three clinically important heterocyclic bisphosphonate bone drugs (risedronate, zoledronate, and minodronate or their analogues). The resultant suite of conjugates offers multiple options to {"}mix and match{"} parent drug structure, fluorescence emission wavelength, relative bone affinity, and presence or absence of antiprenylation activity, for bone-related imaging applications.",

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Fluorescent Bisphosphonate and Carboxyphosphonate Probes: A Versatile Imaging Toolkit for Applications in Bone Biology and Biomedicine

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