Staurosporine

Staurosporine
Ball-and-stick model of the staurosporine molecule
Clinical data
ATC code
  • none
Identifiers
  • (9S,10R,11R,13R)-2,3,10,11,12,13-Hexahydro-
    10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-
    1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]
    benzodiazonin-1-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.109.946 Edit this at Wikidata
Chemical and physical data
FormulaC28H26N4O3
Molar mass466.541 g·mol−1
3D model (JSmol)
  • C[C@@]12[C@@H]([C@@H](C[C@@H](O1)n3c4ccccc4c5c3c6n2c7ccccc7c6c8c5C(=O)NC8)NC)OC
  • InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20-,26-,28+/m1/s1 checkY
  • Key:HKSZLNNOFSGOKW-FYTWVXJKSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Staurosporine (antibiotic AM-2282 or STS) is a natural product originally isolated in 1977 from the bacterium Streptomyces staurosporeus.[1] It was the first of over 50 alkaloids that were discovered to share this type of bis-indole chemical structure. The chemical structure of staurosporine was elucidated by X-ray crystalography in 1994.[2]

Staurosporine was discovered to have biological activities ranging from anti-fungal to anti-hypertensive.[3] The interest in these activities resulted in a large investigative effort in chemistry and biology and the discovery of the potential for anti-cancer treatment.

  1. ^ Omura S, Iwai Y, Hirano A, Nakagawa A, Awaya J, Tsuchya H, et al. (April 1977). "A new alkaloid AM-2282 OF Streptomyces origin. Taxonomy, fermentation, isolation and preliminary characterization". The Journal of Antibiotics. 30 (4): 275–282. doi:10.7164/antibiotics.30.275. PMID 863788.
  2. ^ Funato N, Takayanagi H, Konda Y, Toda Y, Harigaya Y, Omura S (1994). "Absolute configuration of staurosporine by X-ray analysis". Tetrahedron Lett. 35 (8): 1251–1254. doi:10.1016/0040-4039(94)88036-0.
  3. ^ Rüegg UT, Burgess GM (June 1989). "Staurosporine, K-252 and UCN-01: potent but nonspecific inhibitors of protein kinases". Trends in Pharmacological Sciences. 10 (6): 218–20. doi:10.1016/0165-6147(89)90263-0. PMID 2672462.