| Identification | Back Directory | [Name]
Dihydroxythiobinupharidine | [CAS]
30343-70-5 | [Synonyms]
Dihydroxythiobinupharidine
6,6′-Dihydroxythiobinupharidine
6,6'-Dihydroxythiobinupharidine >=95% (HPLC)
Dispiro[2H-quinolizine-3(4H),2'(3'H)-thiophene-4'(5'H),3''(4''H)-[2H]quinolizine]-4,4''-diol, 6,6''-di-3-furanyldodecahydro-9,9''-dimethyl-, (2'S,3''S,4S,4''R,6S,6''S,9R,9''R,9aS,9''aS)- | [Molecular Formula]
C30H42N2O4S | [MDL Number]
MFCD30738198 | [MOL File]
30343-70-5.mol | [Molecular Weight]
526.73 |
| Chemical Properties | Back Directory | [Boiling point ]
667.3±55.0 °C(Predicted) | [density ]
1.30±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [form ]
powder | [pka]
13.42±0.70(Predicted) |
| Hazard Information | Back Directory | [Uses]
6,6′-Dihydroxythiobinupharidine is a cysteine proteases inhibitor. 6,6′-Dihydroxythiobinupharidine can enhance DNA cleavage mediated by human topoisomerase IIα and IIβ ~8-fold and ~3-fold, respectively[1][2]. | [General Description]
6,6′-Dihydroxythiobinupharidine is an active compound found in Nuphar lutea extract. It is a dimeric sesquiterpene thioalkaloid which presents multiple activities. | [Biochem/physiol Actions]
6,6′-Dihydroxythiobinupharidine inhibits NFκB activation, leading to an induction of apoptosis via cleavage of procaspase-9 and poly (ADP-ribose) polymerase (PARP). It was also found to act synergistically with cytotoxic drugs such as cisplatin and etoposide, enabling their cytotoxic effect at lower concentrations. 6,6′-Dihydroxythiobinupharidine was found to have cytotoxic activity at a concentration of ~10 μM on human leukemia cells (U937), mouse melanoma cells (B16F10), and human fibroblasts (HT1080).In addition, Nuphar lutea extract was effective against both Leishmania promastigote and amastigote forms (IC50?=?2?±?0.12?μg/mL; ID50?=?0.65?±?0.023?μg/mL; LD50?=?2.1?±?0.096?μg/mL, STI?=?3.23). A synergistic antileishmanial activity was demonstrated with the antileishmanial drug, paromomycin.Recently 6,6′-dihydroxythiobinupharidine was found to be active against MRSA and VRE strains with an MIC of 1-4?μg/mL. Inhibition of DNA topoisomerase?IV but not DNA gyrase in S.?aureus was suggested as the mechanism of action. 6,6′-Dihydroxythiobinupharidine was also shown to promote neutrophil effector bactericidal functions. | [References]
[1] Yamahara
J, et al. Potent immunosuppressive principles, dimeric sesquiterpene
thioalkaloids, isolated from nupharis rhizoma, the rhizoma of Nuphar pumilum
(nymphaeaceae): structure-requirement of nuphar-alkaloid for immunosuppressive
activity. Biol Pharm Bull. 1996;19(9):1241-1243. DOI:10.1248/bpb.19.1241
[2] Dalvie
ED, et al. 6,6'-Dihydroxythiobinupharidine as a poison of human type II
topoisomerases. Bioorg Med Chem Lett. 2019;29(15):1881-1885. DOI:10.1016/j.bmcl.2019.06.003 |
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