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Olivo HF, Perez-Hernandez N, Liu D, et al. Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA). Bioorg Med Chem Lett. 2009;20(3):1153-5doi: 10.1016/j.bmcl.2009.12.019.
Olivo, H. F., Perez-Hernandez, N., Liu, D., Iruthayanathan, M., O'Leary, B., Homan, L. L., & Dillon, J. S. (2010). Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA). Bioorganic & medicinal chemistry letters, 20(3), 1153-5. https://doi.org/10.1016/j.bmcl.2009.12.019
Olivo, Horacio F, et al. "Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA)." Bioorganic & medicinal chemistry letters vol. 20,3 (2010): 1153-5. doi: https://doi.org/10.1016/j.bmcl.2009.12.019
Olivo HF, Perez-Hernandez N, Liu D, Iruthayanathan M, O'Leary B, Homan LL, Dillon JS. Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA). Bioorg Med Chem Lett. 2010 Feb 01;20(3):1153-5. doi: 10.1016/j.bmcl.2009.12.019. Epub 2009 Dec 06. PMID: 20031404; PMCID: PMC2818606.
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Bioorg Med Chem Lett. 2010 Feb 01;20(3):1153-5. doi: 10.1016/j.bmcl.2009.12.019. Epub 2009 Dec 06.

Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA).

Bioorganic & medicinal chemistry letters

Horacio F Olivo, Nury Perez-Hernandez, Dongmin Liu, Mary Iruthayanathan, Brianne O'Leary, Laurie L Homan, Joseph S Dillon

Affiliations

  1. Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City, IA 52242, USA. [email protected]

PMID: 20031404 PMCID: PMC2818606 DOI: 10.1016/j.bmcl.2009.12.019

Abstract

We have synthesized an analog of dehydroepiandrosterone (DHEA, 1) containing both a benzophenone (BP) and a biotin (Bt) group (DHEA-BP-Bt, 8). Compound 8 was prepared by functionalization on C-17 of 1. Biocytin was reacted with 4-benzoylbenzoic acid and the product was condensed with 1 containing a diamine-hexane linker. We detected specific protein bands of approximately 55, 80, and 150 kDa by SDS-PAGE analysis of vascular endothelial cell plasma membranes which had been photoirradiated in the presence of 8.

Copyright (c) 2009 Elsevier Ltd. All rights reserved.

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