Selecting against S1P3 enhances the acute cardiovascular tolerability of 3-(N-benzyl)aminopropylphosphonic acid S1P receptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 13, 2004, Pages 3501-3505

  Hale, Jeffrey J ^a   Doherty, George ^a,b   Toth, Leslie ^a   Mills, Sander G ^a   Hajdu, Richard ^a   Keohane, Carol Ann ^a   Rosenbach, Mark ^a   Milligan, James ^a   Shei, Gan Ju ^a   Chrebet, Gary ^a   Bergstrom, James ^a   Card, Deborah ^a   Forrest, Michael ^a   Sun, Shu Yu ^a   West, Sarah ^a   Xie, Huijuan ^a   Nomura, Naomi ^a   Rosen, Hugh ^a,c   Mandala, Suzanne ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b ARRAY BIOPHARMA INC   (United States)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (N BENZYL)AMINOPROPYLPHOSPHONIC ACID; IMMUNOSUPPRESSIVE AGENT; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE 1 PHOSPHATE RECEPTOR AGONIST; UNCLASSIFIED DRUG; 3-(N-BENZYL)AMINOPROPYLPHOSPHONIC ACID; BENZYL DERIVATIVE; DRUG DERIVATIVE; G PROTEIN COUPLED RECEPTOR; LYSOPHOSPHOLIPID; ORGANOPHOSPHORUS COMPOUND; PHOSPHORUS; SPHINGOSINE; SPHINGOSINE 1 PHOSPHATE RECEPTOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CARDIOTOXICITY; CARDIOVASCULAR EFFECT; CONTROLLED STUDY; DRUG BINDING; DRUG EFFICACY; DRUG SYNTHESIS; DRUG TOLERABILITY; MOUSE; NONHUMAN; RAT; RODENT; ANIMAL; BINDING SITE; CARDIOVASCULAR SYSTEM; CHEMISTRY; CHO CELL; DRUG ANTAGONISM; DRUG EFFECT; DRUG POTENTIATION; HAMSTER; HEART MUSCLE; HUMAN; IC 50; KINETICS; METABOLISM;

RODENTIA;

ANIMALS; BENZYL COMPOUNDS; BINDING SITES; CARDIOVASCULAR SYSTEM; CHO CELLS; CRICETINAE; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; LYSOPHOSPHOLIPIDS; MICE; MYOCARDIUM; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHORUS RADIOISOTOPES; RATS; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, LYSOSPHINGOLIPID; SPHINGOSINE;

EID: 2942592618     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.04.070     Document Type: Article

References (21)

1. Mandala S., Hajdu R., Bergstrom J., Quackenbush E., Xie J., Milligan J., Thornton R., Shei G.-J., Card D., Keohane C., Rosenbach M., Hale J., Lynch C.L., Rupprecht K., Parsons W., Rosen H. Science. 296:2002;346-349
2. Brinkmann V., Davis M.D., Heise C.E., Albert R., Cottens S., Hof R., Bruns C., Prieschl E., Baumruker T., Hiestand P., Foster C.A., Zollinger M., Lynch K.R. J. Biol. Chem. 277:2002;21453-21457
3. Chiba K., Yanagawa Y., Masubuchi Y., Kataoka H., Kawaguchi T., Ohtsuki M., Hoshino Y. J. Immunol. 160:1998;5037-5044
4. Matloubian M., Lo C.G., Cinamon G., Lesneski M.J., Xu Y., Brinkmann V., Allende M.L., Proia R.L., Cyster J.G. Nature. 427:2004;355-360
5. Allende M., Dreier J.L., Mandala S., Proia R.L. J. Biol. Chem. 2004;. M314291200
6. Forrest M., Sun S.-Y., Hajdu R., Card D., Doherty G., Hale J., Keohane C., Meyers J., Milligan J., Mills S., Nomura N., Rosen H., Rosenbach M., Shei G.-J., Singer I., Tian M., West S., White V., Xie J., Mandala S. J. Pharm. Exp. Ther. 2004;. 103062828-0
7. Sanna M.G., Liao J., Jo E., Alfonso C., Ahn M.-Y., Peterson M.S., Webb B., Lefebvre S., Chun J., Gray N., Rosen H. J. Biol. Chem. 2004;. M311743200
8. Novarik J.M., Burtin P. Exp. Opin. Emerging Drugs. 8:2003;47-62
9. Ebeling, T.; Fishman, M. Novartis 2003 R&D Day, November 19, 2003
10. Budde K., Schmouder R.L., Brunkhorst R., Nashan B., Lucker P.W., Mayer T., Choudhury S., Skerjanec A., Kraus G., Neumayer H.H. J. Am. Soc. Nephrol. 13:2002;1073-1083
11. Hale J.J., Neway W., Mills S.G., Hajdu R., Keohane C.A., Rosenbach M., Milligan J., Shei G.-J., Chrebet G., Bergstrom J., Card D., Koo G.C., Koprak S.L., Jackson J.J., Rosen H., Mandala S. Bioorg. Med. Chem. Lett. 14:2004;3351-3355
12. Hale, J. J.; Doherty, G.; Toth, L.; Li, Z.; Mills, S. G.; Hajdu, R.; Keohane, C. A.; Rosenbach, M.; Milligan, J.; Shei, G.-J.; Chrebet, G.; Bergstrom, J.; Card, D.; Rosen, H.; Mandala, S. Bioorg. Med. Chem. Lett. 2004, 14, preceding paper in this issue. doi:10.1016/j.bmcl.2004.04.069
13. Dess D.B., Martin J.C. J. Am. Chem. Soc. 113:1991;7277-7287
14. Wolfe J.P., Singer R.A., Yang B.H., Buchwald S.L. J. Am. Chem. Soc. 121:1999;9550-9561
15. Liang G.B., Feng D.D. Tetrahedron Lett. 37:1996;6627
16. Bold G., Fässler A., Capraro H.-G., Cozens R., Klimkait T., Lazdins J., Mestan J., Poncioni B., Rösel J., Stover D., Tintelnot-Blomley M., Acemoglu F., Beck W., Boss E., Eschbach M., Hürlimann T., Masso E., Roussel S., Ucci-Stoll K., Wyss D., Lang M. J. Med. Chem. 41:1998;3387-3401
17. 50 values
18. 3
19. 21 would suggest it unlikely that those receptors play roles in the observed toxicity
20. 3. See: Himmel H.M., Heringdorf D.M.Z., Graf E., Dobrev D., Kortner A., Schüler S., Jakobs K.H., Ravens U. Mol. Pharm. 58:2000;449-454
21. Fukushima N., Ishii I., Contos J.J.A., Chun J. Ann. Rev. Pharmacol. Toxicol. 41:2001;507-534