RK-682

Structure

• InChI=1S/C21H36O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(23)19-20(24)18(16-22)26-21(19)25/h18,22,24H,2-16H2,1H3/t18-/m1/s1
• InChIKey=KZTSLHQKWLYYAC-GOSISDBHSA-N

Synonyms

• JCI10676

Origin

Streptomyces sp. 88-682
Streptomyces sp. AL-462

Biological activities

Inhibition of PTPase

Therapeutic

Anticancer

Target

Protein tyrosine phosphatase (PTPase)
Heparanase
Phospholipase A2
HIV protease

Assay information

Inhibition of dephosphorylation activity (IC₅₀ [μM]): CD45 (54) and VHR (2), Cdc25B (>gt; 100 μM)
Induction of the cell cycle arrest at G1 phase in Ball-1 cells (30 μM)
Heparanase inhibition (IC₅₀ = 17 μM)
Phospholipase A2 inhibition (IC₅₀ = 16 μM)
HIV protease inhibition (IC₅₀ = 84 μM)

References

• Sun Y, Hahn F, Demydchuk Y, Chettle J, Tosin M, Osada H, Leadlay PF
  In vitro reconstruction of tetronate RK-682 biosynthesis.
  Nat Chem Biol, 6(2): 99-101 (2010)  20081823  doi: 10.1038/nchembio.285
• Ishida K, Hirai G, Murakami K, Teruya T, Simizu S, Sodeoka M, Osada H
  Structure-based design of a selective heparanase inhibitor as an antimetastatic agent.
  Mol Cancer Ther, 3(9): 1069-1077 (2004)  15367701
• Ishida K, Teruya T, Simizu S, Osada H
  Exploitation of heparanase inhibitors from microbial metabolites using an efficient visual screening system.
  J Antibiot, 57(2): 136-142 (2004)  15112962
• Hamaguchi T, Sudo T, Osada H
  RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle progression at G1phase.
  FEBS Lett, 372(1): 54-58 (1995)  7556642
• Roggo BE, Petersen F, Delmendo R, Jenny HB, Peter HH, Roesel J
  3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity.
  J Antibiot, 47(2): 136-142 (1994)  8150707
• Shinagawa S, Muroi M, Ito T, Hida T
  (1993). TETRONIC ACID DERIVATIVE, ITS PRODUCTION AND USE. JPH0543568.