Fluorescently labeled risedronate and related analogues: “Magic Linker” Synthesis

Boris A Kashemirov; Joy Lynn F Bala; Xiaolan Chen; F H Ebetino; Zhidao Xia; R Graham G Russell; Fraser Coxon; Anke Jozefien Roelofs; Michael John Rogers; Charles E McKenna

doi:10.1021/bc800369c

Fluorescently labeled risedronate and related analogues: “Magic Linker” Synthesis

Boris A Kashemirov, Joy Lynn F Bala, Xiaolan Chen, F H Ebetino, Zhidao Xia, R Graham G Russell, Fraser Coxon, Anke Jozefien Roelofs, Michael John Rogers, Charles E McKenna

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

51 Citations (Scopus)

Abstract

We report synthesis of the first fluorescently labeled conjugates of risedronate (1), using an epoxide linker strategy enabling conjugation of 1 via its pyridyl nitrogen with the label (carboxyfluorescein). Unlike prior approaches to create fluorescent bisphosphonate probes, the new linking chemistry did not abolish the ability to inhibit protein prenylation in vitro, while significantly retaining hydroxyapatite affinity. The utility of a fluorescent 1 conjugate in visualizing osteoclast resorption in vitro was demonstrated.

Original language	English
Pages (from-to)	2308-2310
Number of pages	3
Journal	Bioconjugate Chemistry
Volume	19
Issue number	12
Early online date	25 Nov 2008
DOIs	https://doi.org/10.1021/bc800369c
Publication status	Published - 1 Dec 2008

Keywords

Animals
Etidronic Acid
Fluorescent Dyes
Magnetic Resonance Spectroscopy
Osteoclasts
Rabbits
Temperature

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10.1021/bc800369c

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title = "Fluorescently labeled risedronate and related analogues: “Magic Linker” Synthesis",

abstract = "We report synthesis of the first fluorescently labeled conjugates of risedronate (1), using an epoxide linker strategy enabling conjugation of 1 via its pyridyl nitrogen with the label (carboxyfluorescein). Unlike prior approaches to create fluorescent bisphosphonate probes, the new linking chemistry did not abolish the ability to inhibit protein prenylation in vitro, while significantly retaining hydroxyapatite affinity. The utility of a fluorescent 1 conjugate in visualizing osteoclast resorption in vitro was demonstrated.",

keywords = "Animals, Etidronic Acid, Fluorescent Dyes, Magnetic Resonance Spectroscopy, Osteoclasts, Rabbits, Temperature",

author = "Kashemirov, {Boris A} and Bala, {Joy Lynn F} and Xiaolan Chen and Ebetino, {F H} and Zhidao Xia and Russell, {R Graham G} and Fraser Coxon and Roelofs, {Anke Jozefien} and Rogers, {Michael John} and McKenna, {Charles E}",

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doi = "10.1021/bc800369c",

language = "English",

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TY - JOUR

T1 - Fluorescently labeled risedronate and related analogues

T2 - “Magic Linker” Synthesis

AU - Kashemirov, Boris A

AU - Bala, Joy Lynn F

AU - Chen, Xiaolan

AU - Ebetino, F H

AU - Xia, Zhidao

AU - Russell, R Graham G

AU - Coxon, Fraser

AU - Roelofs, Anke Jozefien

AU - Rogers, Michael John

AU - McKenna, Charles E

PY - 2008/12/1

Y1 - 2008/12/1

N2 - We report synthesis of the first fluorescently labeled conjugates of risedronate (1), using an epoxide linker strategy enabling conjugation of 1 via its pyridyl nitrogen with the label (carboxyfluorescein). Unlike prior approaches to create fluorescent bisphosphonate probes, the new linking chemistry did not abolish the ability to inhibit protein prenylation in vitro, while significantly retaining hydroxyapatite affinity. The utility of a fluorescent 1 conjugate in visualizing osteoclast resorption in vitro was demonstrated.

AB - We report synthesis of the first fluorescently labeled conjugates of risedronate (1), using an epoxide linker strategy enabling conjugation of 1 via its pyridyl nitrogen with the label (carboxyfluorescein). Unlike prior approaches to create fluorescent bisphosphonate probes, the new linking chemistry did not abolish the ability to inhibit protein prenylation in vitro, while significantly retaining hydroxyapatite affinity. The utility of a fluorescent 1 conjugate in visualizing osteoclast resorption in vitro was demonstrated.

KW - Animals

KW - Etidronic Acid

KW - Fluorescent Dyes

KW - Magnetic Resonance Spectroscopy

KW - Osteoclasts

KW - Rabbits

KW - Temperature

U2 - 10.1021/bc800369c

DO - 10.1021/bc800369c

M3 - Article

C2 - 19032080

SN - 1520-4812

VL - 19

SP - 2308

EP - 2310

JO - Bioconjugate Chemistry

JF - Bioconjugate Chemistry

IS - 12

ER -

Fluorescently labeled risedronate and related analogues: “Magic Linker” Synthesis

Abstract

Keywords

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