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Literature DB >> 20031404

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

Horacio F Olivo¹, Nury Perez-Hernandez, Dongmin Liu, Mary Iruthayanathan, Brianne O'Leary, Laurie L Homan, Joseph S Dillon.

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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Year: 2009 PMID： 20031404 PMCID： PMC2818606 DOI： 10.1016/j.bmcl.2009.12.019

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

21 in total

Review 1. Steroid-hormone rapid actions, membrane receptors and a conformational ensemble model.

Authors: Anthony W Norman; Mathew T Mizwicki; Derek P G Norman
Journal: Nat Rev Drug Discov Date: 2004-01 Impact factor: 84.694

2. Synthesis and characterization of novel biotinylated carboxyl-terminal parathyroid hormone peptides that specifically crosslink to the CPTH-receptor.

Authors: Santanu Banerjee; Hafez Selim; Gihan Suliman; Andrew I Geller; Harald Jüppner; F Richard Bringhurst; Paola Divieti
Journal: Peptides Date: 2006-10-05 Impact factor: 3.750

3. Dehydroepiandrosterone inhibits human vascular smooth muscle cell proliferation independent of ARs and ERs.

Authors: Maro R I Williams; Shanhong Ling; Tye Dawood; Kazuhiko Hashimura; Aozhi Dai; He Li; Jun-Ping Liu; John W Funder; Krishnankutty Sudhir; Paul A Komesaroff
Journal: J Clin Endocrinol Metab Date: 2002-01 Impact factor: 5.958

4. Dehydroepiandrosterone sulfate and mortality in elderly men and women.

Authors: D P Trivedi; K T Khaw
Journal: J Clin Endocrinol Metab Date: 2001-09 Impact factor: 5.958

5. Concepts for the syntheses of biotinylated steroids. Part I: testosterone derivatives as immunochemical probes.

Authors: H Hauptmann; B Paulus; T Kaiser; E Herdtweck; E Huber; P B Luppa
Journal: Bioconjug Chem Date: 2000 Mar-Apr Impact factor: 4.774

6. Dehydroepiandrosterone activates endothelial cell nitric-oxide synthase by a specific plasma membrane receptor coupled to Galpha(i2,3).

Authors: Dongmin Liu; Joseph S Dillon
Journal: J Biol Chem Date: 2002-04-04 Impact factor: 5.157

7. The use of the biotinyl estradiol-avidin system for the purification of "nontransformed" estrogen receptor by biohormonal affinity chromatography.

Authors: G Redeuilh; C Secco; E E Baulieu
Journal: J Biol Chem Date: 1985-04-10 Impact factor: 5.157

8. Synthesis of biotin-labelled dexamethasone derivatives. Novel hormone-affinity probes.

Authors: B Manz; A Heubner; I Köhler; H J Grill; K Pollow
Journal: Eur J Biochem Date: 1983-03-15

9. Homogeneous functional insulin receptor from 3T3-L1 adipocytes. Purification using N alpha B1-(biotinyl-epsilon-aminocaproyl)insulin and avidin-sepharose.

Authors: R A Kohanski; M D Lane
Journal: J Biol Chem Date: 1985-04-25 Impact factor: 5.157

10. Synthesis of a beta-estradiol-biotin chimera that potently heterodimerizes estrogen receptor and streptavidin proteins in a yeast three-hybrid system.

Authors: Stephen L Hussey; Smita S Muddana; Blake R Peterson
Journal: J Am Chem Soc Date: 2003-04-02 Impact factor: 15.419

3 in total