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ChemicalBook >> CAS DataBase List >>Dihydroxythiobinupharidine

Dihydroxythiobinupharidine

CAS No.
30343-70-5
Chemical Name:
Dihydroxythiobinupharidine
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)-
CBNumber:
CB81120248
Molecular Formula:
C30H42N2O4S
Molecular Weight:
526.73
MDL Number:
MFCD30738198
MOL File:
30343-70-5.mol
MSDS File:
SDS
Last updated:2025-04-18 09:52:47

Dihydroxythiobinupharidine Properties

Boiling point 667.3±55.0 °C(Predicted)
Density 1.30±0.1 g/cm3(Predicted)
storage temp. -20°C
pka 13.42±0.70(Predicted)
form powder
UNSPSC Code 51102829
NACRES NA.76

Dihydroxythiobinupharidine price More Price(1)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SMB00609 6,6′-Dihydroxythiobinupharidine ≥95% (HPLC) 30343-70-5 1mg $545 2024-03-01 Buy
Product number Packaging Price Buy
SMB00609 1mg $545 Buy

Dihydroxythiobinupharidine Chemical Properties,Uses,Production

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

Dihydroxythiobinupharidine Preparation Products And Raw materials

Raw materials

Preparation Products

Dihydroxythiobinupharidine Suppliers

Global( 6)Suppliers
Supplier Tel Email Country ProdList Advantage
Sigma-Aldrich 021-61415566 800-8193336 orderCN@merckgroup.com China 51456 80
Energy Chemical 021-58432009 400-005-6266 marketing@energy-chemical.com China 44918 58
Merck KGaA 21-20338288 ordercn@merckgroup.com China 6394 58
Biosynth Biological Technology (Suzhou) Co Ltd 51288865780 sales@biosynth.com China 6051 58
Dihydroxythiobinupharidine 6,6′-Dihydroxythiobinupharidine 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)- 6,6'-Dihydroxythiobinupharidine >=95% (HPLC) 30343-70-5 C30H42N2O4S