WSS2220, a novel cyclic tetrapeptide with a new sulfonoamino acid, exhibits potent and selective inhibitory activity against GlyT1

Tetrahedron Letters

Volumn 49, Issue 19, 2008, Pages 3067-3070

  Terui, Yuichi ^a   Yi wen, Chu ^b   Jun ying, Li ^b   Nozawa, Osamu ^a   Ando, Tsutomu ^a   Fukunaga, Takuya ^a   Aoki, Takeshi ^a   Toda, Yoshihisa ^a   Kawashima, Akira ^a  

^a TAISHO PHARMACEUTICAL CO LTD   (Japan)

^b Sichuan Industrial Institute of Antibiotics   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALX 1393; ALX 5407; GLYCINE TRANSPORTER 1; PROTEIN INHIBITOR; TETRAPEPTIDE; UNCLASSIFIED DRUG; WSS 2220;

ACTINOBACTERIA; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; FERMENTATION; HUMAN; HUMAN CELL; NONOMURAEA; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

NONOMURAEA;

EID: 41649099636     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.054     Document Type: Article

References (21)

1. Depoortère R., Dargazanli G., Estenne-Bouhtou G., Coste A., Lanneau C., Desvignes C., Poncelet M., Heaulme M., Santucci V., Decobert M., Cudennec A., Voltz C., Boulay D., Terranova J.P., Stemmelin J., Roger P., Marabout B., Sevrin M., Vigé X., Biton B., Steinberg R., Françon D., Alonso R., Avenet P., Oury-Donat F., Perrault G., Griebel G., George P., Soubrié P., and Scatton B. Neuropsychopharmacology 30 (2005) 1963-1985
2. Lowe III J.A. Expert Opin. Ther. Patents. 15 (2005) 1657-1662
3. Toda, Y.; Chu, Y.; Li, J.; Terui, Y., Fukunaga, T. WO2003104265.
4. Chu, Y.; Li, J.; Toda, Y. CN1535980.
5. 3 0.2%.
6. 3 0.3%. The pH of the medium was adjusted to 7.0 before sterilization.
7. Fujii K., Ikai Y., Oka H., Suzuki M., and Harada K. Anal. Chem. 69 (1997) 5146-5151
8. FDLA-derivatives were analyzed using a YMC-Pack Pro C18 (100 × 4.6 mm; i.d., 3 μm; YMC) column at 40 °C. Acetonitrile-water containing 5 mM of ammonium formate and 5 mM of formic acid was used as the mobile phase under a linear-gradient elution mode (acetonitrile, 15-85%, 20 min) at a flow rate of 1.0 mL/min with UV detection at 215 nm. l- and d-FDLA derivatives of Phe from 1 were detected at 9.11 min and 14.93 min, respectively. l- and d-FDLA derivatives of Ile from 1 were detected at 10.60 min and 14.93 min, respectively. l-FDLA derivatives of standard l-Ile and l-allo-Ile were detected at 10.62 min and 10.36 min, respectively.
9. 2O): δ 20.6 (q), 46.7 (d), 53.0 (t), 57.5 (d), 82.4 (d), 175.3 (s).
10. Raffauf R.F., Zennie T.M., Onan K.D., and Le Quesne P.W. J. Org. Chem. 49 (1984) 2714-2718
11. Tamura O., Iyama N., and Ishibashi H. J. Org. Chem. 69 (2004) 1475-1480
12. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092-4096
13. 2 and 10 mM glucose.
14. Atkinson B.N., Bell S.C., De Vivo M., Kowalski L.R., Lechner S.M., Ognyanov V.I., Tham C.-S., Tsai C., Jia J., Ashton D., and Klitenick M.A. Mol. Pharmacol. 60 (2001) 1414-1420
15. Xu T.X., Gong N., and Xu T.L. Neuroreport 16 (2005) 1227-1231
16. Matsunaga S., Fusetani S., and Konosu S. J. Nat. Prod. 48 (1985) 236-241
17. Rinken M., Lehmann W.D., and König W.A. Liebigs Ann. Chem. 10 (1984) 1672-1684
18. Kamiyama T., Umino T., Itezono Y., Nakamura Y., Sato T., and Yokose K. J. Antibiot. 48 (1995) 929-936
19. Shinagawa S., Kasahara S., Wada Y., Harada S., and Asai M. Tetrahedron 40 (1984) 3465-3470
20. Ito T., Ezaki N., and Ohba K. J. Antibiot. 35 (1982) 533-535
21. Reshef V., Mizrachi E., Maretzki T., Silberstein C., Loya S., Hizi A., and Carmeli S. J. Nat. Prod. 60 (1997) 1251-1260