Name: (S)-3'-hydroxy Blebbistatin
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HIT ID:HIT218832892
Cas No:
Common Name:(S)-3'-hydroxy Blebbistatin
alias:m-hydroxy-Blebbistatin, meta-hydroxy-Blebbistatin, (−)-3'-hydroxy Blebbistatin
alias:m-hydroxy-Blebbistatin, meta-hydroxy-Blebbistatin, (−)-3'-hydroxy Blebbistatin
IUPAC:3a-hydroxy-1-(3-hydroxyphenyl)-6-methyl-1H,2H,3H,3aH,4H-pyrrolo[2,3-b]quinolin-4-one
IUPAC:3a-hydroxy-1-(3-hydroxyphenyl)-6-methyl-1H,2H,3H,3aH,4H-pyrrolo[2,3-b]quinolin-4-one
InChIKey:OJXUBBKNTWQDFQ-UHFFFAOYSA-N

Molecular Formula:C18H16N2O3
Molecular Weight:308.337
Hydrogen Bond Donor (HBD):
Hydrogen Bond Acceptor (HBA):
LogP:
SMILES:Cc1ccc2N=C3N(CCC3(O)C(=O)c2c1)c1cccc(O)c1
SMILES:Cc1ccc2N=C3N(CCC3(O)C(=O)c2c1)c1cccc(O)c1

(S)-3'-hydroxy-Blebbistatin is a more stable and less phototoxic derivative of (–)-blebbistatin, retaining the latter's properties as a selective, cell-permeable inhibitor of non-muscle myosin II ATPases. Unlike its predecessor, (S)-3'-hydroxy-Blebbistatin exhibits reduced fluorescence, improving its utility in live cell imaging applications by diminishing degradation into cytotoxic intermediates under blue light exposure (450-490 nm). It effectively inhibits the Mg-ATPase activity and in vitro motility of non-muscle myosin IIA and IIB across various species with IC₅₀ values ranging from 0.5-5 µM and shows minimal inhibition against smooth muscle myosin with an IC₅₀ of 80 µM. This compound plays a critical role in preventing apoptosis-related bleb formation, directed cell migration, and cytokinesis in vertebrate cells, mirroring the active (–)-blebbistatin enantiomer in mechanism and efficacy.

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