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
Dihydroxythiobinupharidine price More Price(1)
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
| Supplier | Tel | 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 |
| Supplier | Advantage |
|---|---|
| Sigma-Aldrich | 80 |
| Energy Chemical | 58 |
| Merck KGaA | 58 |
| Biosynth Biological Technology (Suzhou) Co Ltd | 58 |