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RES-1149-1

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Category Bioactive by-products
Catalog number BBF-03363
CAS
Molecular Weight 386.5
Molecular Formula C23H30O5

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Fermentation Lab

4 R&D and scale-up labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

RES-1149-1 is an endothelin type B receptor antagonist produced by Aspergillus sp. RE-1149. It selectively inhibits the ET-1 binding to endothelin type B receptor with IC50 value of 1.5 µmol/L.

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IUPAC Name [(1R,4S,4aS,8aS)-3,4-diformyl-4-hydroxy-4a,8,8-trimethyl-5,6,7,8a-tetrahydro-1H-naphthalen-1-yl] (2E,4E,6E)-octa-2,4,6-trienoate
Canonical SMILES CC=CC=CC=CC(=O)OC1C=C(C(C2(C1C(CCC2)(C)C)C)(C=O)O)C=O
InChI InChI=1S/C23H30O5/c1-5-6-7-8-9-11-19(26)28-18-14-17(15-24)23(27,16-25)22(4)13-10-12-21(2,3)20(18)22/h5-9,11,14-16,18,20,27H,10,12-13H2,1-4H3/b6-5+,8-7+,11-9+/t18-,20+,22+,23-/m1/s1
InChI Key ZWNZDIPJNHSCRQ-MOHQOPMHSA-N
1. RES-1149-1 and -2, novel non-peptidic endothelin type B receptor antagonists produced by Aspergillus sp. I. Taxonomy of producing strain, fermentation, isolation, and physico-chemical and biological properties
T Ogawa, K Ando, T Tanaka, Y Uosaki, Y Matsuda J Antibiot (Tokyo). 1996 Jan;49(1):1-5. doi: 10.7164/antibiotics.49.1.
RES-1149-1 and -2, novel and non-peptidic endothelin antagonists, were isolated from the cultured broth of a fungus, Aspergillus sp. RE-1149. RES-1149-1 and -2 selectively inhibited the ET-1 binding to endothelin type B receptor (ETB receptor) with IC50 values of 1.5 microM and 20 microM, respectively. Taxonomy of producing strains, fermentation, isolation, and physico-chemical properties of RES-1149-1 and -2 are described.
2. RES-1149-1 and -2, novel non-peptidic endothelin type B receptor antagonists produced by Aspergillus sp. II. Structure determination and derivatization
Y Uosaki, M Yoshida, T Ogawa, Y Saitoh J Antibiot (Tokyo). 1996 Jan;49(1):6-12. doi: 10.7164/antibiotics.49.6.
The structures of two novel non-peptidic endothelin type B receptor antagonists, RES-1149-1 and -2 were determined by spectroscopic methods. Several derivatives were synthesized from RES-1149-1 for biological assay.
3. RES-1149-1 and -2, novel non-peptidic endothelin type B receptor antagonists produced by Aspergillus sp. III. Biochemical properties of RES-1149-1, -2 and structure-activity relationships
T Ogawa, Y Uosaki, T Tanaka, E Tsukuda, A Mihara, Y Matsuda J Antibiot (Tokyo). 1996 Feb;49(2):168-72. doi: 10.7164/antibiotics.49.168.
RES-1149-1 and -2, produced by Aspergillus sp. RE-1149, were found to be non-peptidic antagonists for endothelin type B receptor (ET(B) receptor). RES-1149-1 and -2 selectively inhibited the endothelin-1 (ET-1) binding to ET(B) receptor in a competitive manner with IC50 values of 1.5 microM and 20 microM, respectively. RES-1149-1 inhibited the increase in intracellular Ca2+ concentration elicited by 1 nM ET-1 in COS-7 cells expressing human ET(B) receptor, but not in the case of cells expressing ET(A) receptor. In addition, some structure-activity relationships are described.

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