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8α-Tigloyloxyhirsutinolide 13-O-acetate

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8α-Tigloyloxyhirsutinolide 13-O-acetate Basic information

Product Name:
8α-Tigloyloxyhirsutinolide 13-O-acetate
Synonyms:
  • 8α-Tigloyloxyhirsutinolide 13-O-acetate
  • 8alpha-Tigloyloxyhirsutinolide 13-O-acetate
  • 2-Butenoic acid, 2-methyl-, (4S,6R,7S,10R,11E)-3-[(acetyloxy)methyl]-2,4,5,6,7,8,9,10-octahydro-7-hydroxy-6,10-dimethyl-2-oxo-7,10-epoxycyclodeca[b]furan-4-yl ester, (2E)-
  • 8α-Tigloyloxyhirsutinolide13-O-acetate
  • [(1R,2E,8S,10R,11S)-6-(Acetyloxymethyl)-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradeca-2,6-dien-8-yl] (E)-2- methylbut-2-enoate
CAS:
83182-58-5
MF:
C22H28O8
MW:
420.45
Mol File:
83182-58-5.mol
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8α-Tigloyloxyhirsutinolide 13-O-acetate Chemical Properties

Boiling point:
589.6±50.0 °C(Predicted)
Density 
1.28±0.1 g/cm3(Predicted)
pka
12.51±0.70(Predicted)
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8α-Tigloyloxyhirsutinolide 13-O-acetate Usage And Synthesis

Uses

8α-Tigloyloxyhirsutinolide 13-O-acetate (8αTGH) is a potent and orally active STAT3 inhibitor. 8α-Tigloyloxyhirsutinolide 13-O-acetate induces early oxidative stress and pyroptosis, and late DNA damage, cell cycle arrest, apoptosis in the TNBC cells. 8α-Tigloyloxyhirsutinolide 13-O-acetate suppresses tumor cell growth in vitro and tumor growth in vivo[1][2].

in vivo

8α-Tigloyloxyhirsutinolide 13-O-acetate (5?mg/kg, Oral gavage, 5 times per week for 75 days) suppresses tumor growth in mice[1].

Animal Model:Five-week-old female athymic nude mice (injected subcutaneously in the right flank area with MDA-MB-468 cells in 100?μL PBS)
Dosage:5?mg/kg
Administration:Oral gavage, every day, 5 times per week for 75 days
Result:Inhibited MDA-MB-468 xenografts growth in mice, with reduced pY705-STAT3, G6PD, TrxR1, and GSH levels.

IC 50

STAT3; Bcl-2; Bcl-xL; Mcl-1

References

[1] Zhu Y, et al. Natural product preferentially targets redox and metabolic adaptations and aberrantly active STAT3 to inhibit breast tumor growth in vivo. Cell Death Dis. 2022 Dec 6;13(12):1022. DOI:10.1038/s41419-022-05477-2
[2] A Bardón, et al. Glaucolides and related sesquiterpene lactones fromVernonia nudiflora and Chrysolaena propinqua. Phytochemistry, 1992, 31(2):609-613.

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