Photo-DHEA - A functional photoreactive dehydroepiandrosterone (DHEA) analog

Steroids

Volumn 76, Issue 5, 2011, Pages 502-507

  Waschatko, Gustav ^a,b   Kojro, Elzbieta ^a   Zahnow, Michael ^a   Gehrig Burger, Katja ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Dehydroepiandrosterone; DHEA; G protein coupled receptor; Photoaffinity labeling; Receptor

Indexed keywords

HORMONE RECEPTOR; HYDROXYL GROUP; PHOTO PRASTERONE; PRASTERONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL ASSAY; CHEMICAL BOND; CHEMICAL STRUCTURE; HORMONE SYNTHESIS; NONHUMAN; PHOTOREACTIVITY; RAT;

DEHYDROEPIANDROSTERONE; HUMANS; MOLECULAR PROBES; PHOTOCHEMISTRY; RECEPTORS, STEROID;

EID: 79952573896     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.01.009     Document Type: Article

References (24)

1. Mukai H, Takata N, Ishii HT, Tanabe N, Hojo Y, Furukawa A, et al. Hippocampal synthesis of estrogens and androgens which are paracrine modulators of synaptic plasticity: synaptocrinology. Neuroscience 2006;138(3):757-64.
2. Maninger N, Wolkowitz OM, Reus VI, Epel ES, Mellon SH. Neurobiological and neuropsychiatric effects of dehydroepiandrosterone (DHEA) and DHEA sulfate (DHEAS). Front Neuroendocrinol 2009;30(1):65-91.
3. Webb S.J. Geoghegan T.E. Prough R.A. Miller K.K.M. The biological actions of dehydroepiandrosterone involves multiple receptors Drug Metabolism Reviews 2006 38 1 2 89-116 DOI 10.1080/03602530600569877, PII L58106516149853 [3] Webb SJ, Geoghegan TE, Prough RA, Michael Miller KK. The biological actions of dehydroepiandrosterone involves multiple receptors. Drug Metab Rev 2006;38(1-2):89-116. (Pubitemid 43739001)
4. Villareal D.T. Holloszy J.O. Effect of DHEA on abdominal fat and insulin action in elderly women and men: A randomized controlled trial Journal of the American Medical Association 2004 292 18 2243-2248 DOI 10.1001/jama.292.18.2243 [4] Villareal DT, Holloszy JO. Effect of DHEA on abdominal fat and insulin action in elderly women and men: a randomized controlled trial. JAMA 2004;292(18):2243-8. (Pubitemid 39473162)
5. Simoncini T. Mannella P. Fornari L. Varone G. Caruso A. Genazzani A.R. Dehydroepiandrosterone modulates endothelial nitric oxide synthesis via direct genomic and nongenomic mechanisms Endocrinology 2003 144 8 3449-3455 DOI 10.1210/en.2003-0044 [5] Simoncini T, Mannella P, Fornari L, Varone G, Caruso A, Genazzani AR. Dehydroepiandrosterone modulates endothelial nitric oxide synthesis via direct genomic and nongenomic mechanisms. Endocrinology 2003;144(8):3449-55. (Pubitemid 36904421)
6. Leblhuber F, Neubauer C, Peichl M, Reisecker F, Steinparz FX, Windhager E, et al. Age and sex differences of dehydroepiandrosterone sulfate (DHEAS) and cortisol (CRT) plasma levels in normal controls and Alzheimer's disease (AD). Psychopharmacology (Berl) 1993;111(1):23-6.
7. Lemcke S, Honnscheidt C, Waschatko G, Bopp A, Lutjohann D, Bertram N, et al. DHEA-Bodipy - a functional fluorescent DHEA analog for live cell imaging. Mol Cell Endocrinol 2010;314(1):31-40.
8. Kramer W, Kurz G. Photolabile derivatives of bile salts synthesis and suitability for photoaffinity labeling. J Lipid Res 1983:24910-23.
9. Bayley H. Photogenerated reagents in biochemistry and molecular biology. In: Work TS, Burdon RH, editors. Laboratory techniques in biochemistry and molecular biology, vol.12, 2nd ed. Amsterdam, The Netherlands: Elsevier Science Publishers B.V.; 1983.
10. 125iodo salicyloyl)-beta-alanyl-beta-alanyl ryanodine (Az-betaAR), a novel photo-affinity ligand for the ryanodine binding site Journal of Labelled Compounds and Radiopharmaceuticals 1994 34 1 33-47 DOI 10.1002/jlcr.2580340106 [10] Bidasee KR, Besch HR, Kwon S, Emmick JT, Besch KT, Gerzon K, et al. C-10-O-Eq-N-(4-azido-5-(125)iodo salicyloyl)-beta-alanyl-beta alanyl ryanodine (az-beta-ar), a novel photo-affinity ligand for the ryanodine binding-site. J Labelled Compd Radiopharm 1994;34(1):33-47. (Pubitemid 24025229)
11. Fisher A. Mann A. Verma V. Thomas N. Mishra R.K. Johnson R.L. Design and synthesis of photoaffinity-labeling ligands of the L-prolyl-L-leucylglycinamide binding site involved in the allosteric modulation of the dopamine receptor Journal of Medicinal Chemistry 2006 49 1 307-317 DOI 10.1021/jm050644n [11] Fisher A, Mann A, Verma V, Thomas N, Mishra RK, Johnson RL. Design and synthesis of photoaffinity-labeling ligands of the L-prolyl-L-leucylglycinamide binding site involved in the allosteric modulation of the dopamine receptor. J Med Chem 2006;49(1):307-17. (Pubitemid 43077343)
12. Felschow D.M. Mi Z. Stanek J. Frei J. Porter C.W. Selective labelling of cell-surface polyamine-binding proteins on leukaemic and solid-tumour cell types using a new polyamine photoprobe Biochemical Journal 1997 328 3 889-895 [12] Felschow DM, Mi Z, Stanek J, Frei J, Porter CW. Selective labelling of cell-surface polyamine-binding proteins on leukaemic and solid-tumour cell types using a new polyamine photoprobe. Biochem J 1997;328(Pt 3):889-95. (Pubitemid 28005790)
13. Adamczyk M. Chen Y.-Y. Gebler J.C. Johnson D.D. Mattingly P.G. Moore J.A. Reddy R.E. Wu J. Yu Z. Evaluation of chemiluminescent estradiol conjugates by using a surface plasmon resonance detector Steroids 2000 65 6 295-303 DOI 10.1016/S0039-128X(00)00091-X, PII S0039128X0000091X [13] Adamczyk M, Chen YY, Gebler JC, Johnson DD, Mattingly PG, Moore JA, et al. Evaluation of chemiluminescent estradiol conjugates by using a surface plasmon resonance detector. Steroids 2000;65(6):295-303. (Pubitemid 30236336)
14. Charalampopoulos I. Tsatsanis C. Dermitzaki E. Alexaki V.-I. Castanas E. Margioris A.N. Gravanis A. Dehydroepiandrosterone and allopregnanolone protect sympathoadrenal medulla cells against apoptosis via antiapoptotic Bcl-2 proteins Proceedings of the National Academy of Sciences of the United States of America 2004 101 21 8209-8214 DOI 10.1073/pnas.0306631101 [14] Charalampopoulos I, Tsatsanis C, Dermitzaki E, Alexaki VI, Castanas E, Margioris AN, et al. Dehydroepiandrosterone and allopregnanolone protect sympathoadrenal medulla cells against apoptosis via antiapoptotic Bcl-2 proteins. Proc Natl Acad Sci USA 2004;101(21):8209-14. (Pubitemid 38698079)
15. Charalampopoulos I. Alexaki V.-I. Lazaridis I. Dermitzaki E. Avlonitis N. Tsatsanis C. Calogeropoulou T. Margioris A.N. Castanas E. Gravanis A. G protein-associated, specific membrane binding sites mediate the neuroprotective effect of dehydroepiandrosterone FASEB Journal 2006 20 3 577-579 http://www.fasebj.org/cgi/reprint/20/3/577 DOI 10.1096/fj.05-5078fje [15] Charalampopoulos I, Alexaki VI, Lazaridis I, Dermitzaki E, Avlonitis N, Tsatsanis C, et al. G protein-associated, specific membrane binding sites mediate the neuroprotective effect of dehydroepiandrosterone. FASEB J 2006;20(3):577-9. (Pubitemid 46671255)
16. Olivo HF, Perez-Hernandez N, Liu D, Iruthayanathan M, O'Leary B, Homan LL, et al. Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA). Bioorg Med Chem Lett 2010;20(3):1153-5.
17. Liu D, O'Leary B, Iruthayanathan M, Love-Homan L, Perez-Hernandez N, Olivo HF, et al. Evaluation of a novel photoactive and biotinylated dehydroepiandrosterone analog. Mol Cell Endocrinol 2010;328(1-2):56-62.
18. i2,3 Journal of Biological Chemistry 2002 277 24 21379-21388 DOI 10.1074/jbc.M200491200 [18] Liu D, Dillon JS. Dehydroepiandrosterone activates endothelial cell nitric-oxide synthase by a specific plasma membrane receptor coupled to Gα(i2,3). J Biol Chem 2002;277(24):21379-88. (Pubitemid 34952278)
19. Tang X, Ma H, Shen Z, Zou S, Xu X, Lin C. Dehydroepiandrosterone activates cyclic adenosine 3′,5′-monophosphate/protein kinase A signalling and suppresses sterol regulatory element-binding protein-1 expression in cultured primary chicken hepatocytes. Br J Nutr 2009:1-7.
20. Yamamoto T. Shimano H. Inoue N. Nakagawa Y. Matsuzaka T. Takahashi A. Yahagi N. Sone H. Suzuki H. Toyoshima H. Yamada N. Protein kinase A suppresses sterol regulatory element-binding protein-1C expression via phosphorylation of liver X receptor in the liver Journal of Biological Chemistry 2007 282 16 11687-11695 http://www.jbc.org/cgi/reprint/282/16/11687 DOI 10.1074/jbc. M611911200 [20] Yamamoto T, Shimano H, Inoue N, Nakagawa Y, Matsuzaka T, Takahashi A, et al. Protein kinase A suppresses sterol regulatory element-binding protein-1C expression via phosphorylation of liver X receptor in the liver. J Biol Chem 2007;282(16):11687-95. (Pubitemid 47100691)
21. Strable MS, Ntambi JM. Genetic control of de novo lipogenesis: role in diet-induced obesity. Crit Rev Biochem Mol Biol 2010;45(3):199-214.
22. Widstrom RL, Dillon JS. Is there a receptor for dehydroepiandrosterone or dehydroepiandrosterone sulfate? Semin Reprod Med 2004;22(4):289-98.
23. Brase S. Gil C. Knepper K. Zimmermann V. Organic azides: An exploding diversity of a unique class of compounds Angewandte Chemie - International Edition 2005 44 33 5188-5240 DOI 10.1002/anie.200400657 [23] Bräse S, Gil C, Knepper K, Zimmermann V. Organic azides: an exploding diversity of a unique class of compounds. Angew Chem Int Ed 2005;44(33):5188-240. (Pubitemid 41223873)
24. Salacinski PR, McLean C, Sykes JE, Clement-Jones VV, Lowry PJ. Iodination of proteins, glycoproteins, and peptides using a solid-phase oxidizing agent, 1,3,4,6-tetrachloro-3′,6′-diphenyl glycoluril (Iodogen). Anal Biochem 1981;117(1):136-46.