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RP-1551-1

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Category Bioactive by-products
Catalog number BBF-03372
CAS
Molecular Weight 460.9
Molecular Formula C25H29ClO6

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Product Description

RP-1551-1 is a compound in the class of azaphilone produced by Penicillium sp. SPC-21609. It inhibits the binding of PDGF AA to the extracellular domain of PDGF alpha-receptor potentially via reacting with amino groups on the alpha-receptor extracellular domain.

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IUPAC Name (1S,10S,12S,14S,17R)-8-chloro-5-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-12-hydroxy-10,14-dimethyl-4,11,15-trioxatetracyclo[8.7.0.02,7.012,17]heptadeca-2,5,7-triene-9,16-dione
Canonical SMILES CCC(C)C=C(C)C=CC1=CC2=C(C(=O)C3(C(C2=CO1)C4C(=O)OC(CC4(O3)O)C)C)Cl
InChI InChI=1S/C25H29ClO6/c1-6-13(2)9-14(3)7-8-16-10-17-18(12-30-16)19-20-23(28)31-15(4)11-25(20,29)32-24(19,5)22(27)21(17)26/h7-10,12-13,15,19-20,29H,6,11H2,1-5H3/b8-7+,14-9+/t13-,15-,19+,20-,24-,25-/m0/s1
InChI Key ICFWHHFUXCQUBQ-SYMYOLTFSA-N
Appearance Yellow Powder
Melting Point 124-128°C
1. RP-1551s, a family of azaphilones produced by Penicillium sp., inhibit the binding of PDGF to the extracellular domain of its receptor
S Toki, T Tanaka, Y Uosaki, M Yoshida, Y Suzuki, K Kita, A Mihara, K Ando, N A Lokker, N A Giese, Y Matsuda J Antibiot (Tokyo). 1999 Mar;52(3):235-44. doi: 10.7164/antibiotics.52.235.
Nine azaphilones designated RP-1551-1, -2, -3, -4, -5, -6, -7, -M1, and -M2 were isolated from the culture broth of Penicillium sp. SPC-21609 as inhibitors of PDGF binding to its receptor. RP-1551s inhibit the binding of PDGF AA to the extracellular domain of PDGF alpha-receptor with IC50 values ranging from 0.1 to 2 microM without affecting PDGF BB binding to the extracellular domain of PDGF beta-receptor. PDGF binding was not restored after the PDGF alpha-receptor extracellular domain was washed in an attempt to remove the RP-1551-1 bound to the receptor. This result suggests that RP-1551-1 may irreversibly interact with the PDGF alpha-receptor. Since many azaphilone compounds possess high reactivity with an amino group, RP-1551-1 may prevent PDGF AA binding by reacting with amino groups on the alpha-receptor extracellular domain.

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