Synthesis of purine-scaffold fluorescent probes for heat shock protein 90 with use in flow cytometry and fluorescence microscopy

Tony Taldone; Erica M. Gomes-Dagama; Hongliang Zong; Siddhartha Sen; Mary L. Alpaugh; Danuta Zatorska; Raul Alonso-Sabadell; Monica L. Guzman; Gabriela Chiosis

doi:10.1016/j.bmcl.2011.07.026

Synthesis of purine-scaffold fluorescent probes for heat shock protein 90 with use in flow cytometry and fluorescence microscopy

Tony Taldone, Erica M. Gomes-Dagama, Hongliang Zong, Siddhartha Sen, Mary L. Alpaugh, Danuta Zatorska, Raul Alonso-Sabadell, Monica L. Guzman, Gabriela Chiosis

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

19 Scopus citations

Abstract

Fluorescent ligands for the heat shock protein 90 (Hsp90) were synthesized containing either fluorescein isothiocyanate (FITC), 4-nitrobenzo[1,2,5] oxadiazole (NBD) or the red shifted dye sulforhodamine 101 (Texas Red) conjugated to PU-H71. Two of the compounds, PU-H71-FITC2 (9) and PU-H71-NBD1 (8), were shown to be suitable for fluorescence-activated flow cytometry and fluorescence microscopy. Thus these molecules serve as useful probes for studying Hsp90 in heterogeneous live cell populations.

Original language	English (US)
Pages (from-to)	5347-5352
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	18
DOIs	https://doi.org/10.1016/j.bmcl.2011.07.026
State	Published - Sep 15 2011
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported in part by W. H. Goodwin and A. Goodwin and the Commonwealth Cancer Foundation for Research, The Experimental Therapeutics Center of Memorial Sloan-Kettering Cancer Center (MSKCC), the Translational and Integrative Medicine Research Fund of MSKCC, SPORE Pilot Award and Research & Therapeutics Program in Prostate Cancer, Hirshberg Foundation for Pancreatic Cancer Research, 1R01CA155226-01, U01AG032969-01A1, R21AG028811, 3P30CA008748-44S2. G.C. is funded by Leukemia and Lymphoma Society LLS#6114-10 & LLS#6330-11, the Byrne Fund, the Geoffrey Beene Cancer Research Center of MSKCC, grant UL1RR024996 of the Clinical and Translational Science Center at Weill Cornell Medical College and Susan G. Komen for the Cure. T.T. is funded by Susan G. Komen for the Cure and the Department of Defense, Breast Cancer Research Program. M.L.G. is funded by the National Institutes of Health through the NIH Director’s New Innovator Award Program, 1 DP2 OD007399-01 and is a V-Foundation Scholar. We also thank Dr. George Sukenick and Dr. Hui Liu of the NMR Analytical Core Facility at MSKCC for expert mass spectral analysis.

Keywords

Flow cytometry
Fluorescence microscopy
Fluorescent Hsp90 inhibitor
PU-H71
Purine

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Taldone, T., Gomes-Dagama, E. M., Zong, H., Sen, S., Alpaugh, M. L., Zatorska, D., Alonso-Sabadell, R., Guzman, M. L., & Chiosis, G. (2011). Synthesis of purine-scaffold fluorescent probes for heat shock protein 90 with use in flow cytometry and fluorescence microscopy. Bioorganic and Medicinal Chemistry Letters, 21(18), 5347-5352. https://doi.org/10.1016/j.bmcl.2011.07.026

Taldone, T, Gomes-Dagama, EM, Zong, H, Sen, S, Alpaugh, ML, Zatorska, D, Alonso-Sabadell, R, Guzman, ML & Chiosis, G 2011, 'Synthesis of purine-scaffold fluorescent probes for heat shock protein 90 with use in flow cytometry and fluorescence microscopy', Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 18, pp. 5347-5352. https://doi.org/10.1016/j.bmcl.2011.07.026

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abstract = "Fluorescent ligands for the heat shock protein 90 (Hsp90) were synthesized containing either fluorescein isothiocyanate (FITC), 4-nitrobenzo[1,2,5] oxadiazole (NBD) or the red shifted dye sulforhodamine 101 (Texas Red) conjugated to PU-H71. Two of the compounds, PU-H71-FITC2 (9) and PU-H71-NBD1 (8), were shown to be suitable for fluorescence-activated flow cytometry and fluorescence microscopy. Thus these molecules serve as useful probes for studying Hsp90 in heterogeneous live cell populations.",

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author = "Tony Taldone and Gomes-Dagama, {Erica M.} and Hongliang Zong and Siddhartha Sen and Alpaugh, {Mary L.} and Danuta Zatorska and Raul Alonso-Sabadell and Guzman, {Monica L.} and Gabriela Chiosis",

note = "Funding Information: This work was supported in part by W. H. Goodwin and A. Goodwin and the Commonwealth Cancer Foundation for Research, The Experimental Therapeutics Center of Memorial Sloan-Kettering Cancer Center (MSKCC), the Translational and Integrative Medicine Research Fund of MSKCC, SPORE Pilot Award and Research & Therapeutics Program in Prostate Cancer, Hirshberg Foundation for Pancreatic Cancer Research, 1R01CA155226-01, U01AG032969-01A1, R21AG028811, 3P30CA008748-44S2. G.C. is funded by Leukemia and Lymphoma Society LLS#6114-10 & LLS#6330-11, the Byrne Fund, the Geoffrey Beene Cancer Research Center of MSKCC, grant UL1RR024996 of the Clinical and Translational Science Center at Weill Cornell Medical College and Susan G. Komen for the Cure. T.T. is funded by Susan G. Komen for the Cure and the Department of Defense, Breast Cancer Research Program. M.L.G. is funded by the National Institutes of Health through the NIH Director{\textquoteright}s New Innovator Award Program, 1 DP2 OD007399-01 and is a V-Foundation Scholar. We also thank Dr. George Sukenick and Dr. Hui Liu of the NMR Analytical Core Facility at MSKCC for expert mass spectral analysis. ",

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AU - Taldone, Tony

AU - Gomes-Dagama, Erica M.

AU - Zong, Hongliang

AU - Sen, Siddhartha

AU - Alpaugh, Mary L.

AU - Zatorska, Danuta

AU - Alonso-Sabadell, Raul

AU - Guzman, Monica L.

AU - Chiosis, Gabriela

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KW - Flow cytometry

KW - Fluorescence microscopy

KW - Fluorescent Hsp90 inhibitor

KW - PU-H71

KW - Purine

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ER -

Synthesis of purine-scaffold fluorescent probes for heat shock protein 90 with use in flow cytometry and fluorescence microscopy

Abstract

Bibliographical note

Keywords

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