Sanguinarine - CAS 2447-54-3
Catalog number: 2447-54-3
Category: Inhibitor
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Molecular Formula:
C20H14NO4+
Molecular Weight:
332.33
COA:
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Targets:
Others
Description:
Sanguinarine caused cell death in a dose dependent manner in all neuroblastoma cell lines except SK-N-BE(2) with rates of 18% in SH-SY5Y and 21% in Kelly human neuroblastoma cells. Treatment with sanguinarine, but not berberine, inhibited the proliferation of Rac1b cells, which was accompanied by significantly increased the level of PARP-89, and decreased both the level of cyclin-D1 and the percentage of BrdU positive cells. Sanguinarine treatment resulted in a reduction of cell migration, in a dose-dependent inhibition of cell viability and in the induction of cell death by apoptosis in both human (MDA-MB-231 cells) and mouse (A17 cells) in vitro models of BLBC. SG pretreatment significantly increased the survival rate of mice from 25% to 58%, 75% and 91% respectively. The production of PGE2 in BALF, the lung MPO activity and the (W/D) weight ratios were also markedly reduced. In addition, immunohistochemical analysis showed that the expression of COX-2 was significantly suppressed in vivo. oral administration of sanguinarine reduced the development and growth of A17 transplantable tumors in FVB syngeneic mice.
Purity:
>98%
Synonyms:
Pseudochelerythrine; Sanguinarin
MSDS:
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InChIKey:
INVGWHRKADIJHF-UHFFFAOYSA-N
InChI:
InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
Canonical SMILES:
C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
1. Molecular recognition of poly(A) targeting by protoberberine alkaloids: in vitro biophysical studies and biological perspectives
Prabal Giri* and Gopinatha Suresh Kumar. Mol. BioSyst., 2010, 6, 81–88
Due to extensive biological activities, alkaloids have occupied a lead position in medicinal chemistry. Medicinal plants may represent valuable, untapped source of drugs. Protoberberine alkaloids, which are readily extractable from Chinese and Korean medicinal plants, have been shown to possess diverse biochemical and pharmacological actions while being nontoxic to humans even at high dosages. Needless to say, protoberberine alkaloids that are most widely distributed in several botanical families have a long history of use world-wide in folk medicine. They exhibit myriad therapeutic applications. The naturally occurring berberine, palmatine, jatrorrhizine, sanguinarine and the synthetic coralyne are the representatives of the protoberberine group so far known to be medically important. These protoberberine alkaloids are among the most widely distributed alkaloids of the isoquinoline series and they are also the main active components of some Chinese herbal medicines such as Rhizoma coptidis and Cortex phellodendri. Berberine and palmatine are distributed in many plants such as the Chinese herb huanglian (Coptis chinesis), goldensal (Hydrastis canadensis), Turkish berberis and the roots of species belonging to the Malagasy genus Burasaia, Menispermaceae. Sanguinarine, on the other hand, is a benzophenanthridine alkaloid derived from the root of Sanguinaria canadenis and other poppy-fumaria species. Sanguinarine also has a long history of use world-wide in folk medicine. Berberine and palmatine bear the same tetracyclic structure but differ in the nature of the substituents on the benzo ring (ring A, Fig. 2), these being methylene dioxy for berberine and dimethoxy for palmatine.
2. Binding of the anticancer alkaloid sanguinarine to double stranded RNAs: Insights into the structural and energetics aspects
Sebanti Roy Chowdhury, Md. Maidul Islamz and Gopinatha Suresh Kumar*. Mol. BioSyst., 2010, 6, 1265–1276
Sanguinarine (Fig. 1), a benzophenanthridine alkaloid, is a potential lead compound in cancer therapy inducing apoptosis in a variety of cancer cells via cell cycle arrest, caspase activation, depletion of cellular GSH, modulation of the family of Bcl-2, down-regulation of ERKs, up-regulation of DR-5 etc. Sanguinarine exhibits strong DNA intercalating properties and the binding specificity has been shown to be towards guanine-cytosine sequences. Poly(A) binding aspects of sanguinarine have been investigated recently in our laboratory. Sanguinarine has exceptionally strong affinity to single stranded poly(A) molecules and the binding induces formation of parallel stranded self-structure of poly(A). On the other hand, it has relatively weak affinity to low pH induced ds poly(A) structure. We have recently shown that the isoquinoline alkaloids berberine, palmatine and coralyne bind strongly to ds RNA polynucleotides. Of these three alkaloids the synthetic coralyne binds with remarkably high affinity to the ds RNAs. But coralyne has high aggregation tendency that critically limits its use in biological applications. Our long standing interest in molecular recognition of nucleic acids by small molecule interactions led us to search for potential ds RNA binding natural alkaloids.
3. Inclusion complex formation of sanguinarine alkaloid with cucurbit[7]uril: inhibition of nucleophilic attack and photooxidation
Zsombor Miskolczy, Monika Megyesi, Gabor T´ arkanyi, Reka Mizsei and Laszlo Biczok*. Org. Biomol. Chem., 2011, 9, 1061
Several studies have dealt with the effect of encapsulation in CBn on the protonation of guests, but it is unknown how the encapsulation influences the nucleophilic attack of organic compounds. In the present work, we focus on sanguinarine, a natural benzo[c]phenanthridine alkaloid (Scheme 1), which exhibits anticancer, antimicrobial, antifungal properties and interactswith nucleic acids. ApHdependent reversible transition occurs between its iminium (SA+) and alkanolamine (SAOH) forms. Since the carbon atomof SA+ at the position 6 has lowpelectron density, it is susceptible to nucleophilic addition of OH-. The biological activity is associatedwith the SA+ form, whereas the conversion to SAOHenhances the lipophilicity improving thereby the cellular availability. The latter formundergoes an irreversible oxidation in the singlet-excited state to produce oxysanguinarine. The main goal of the present studies was to reveal how the interaction with CB7 affects the fluorescent properties, photostability and the basicity of sanguinarine. Moreover, we demonstrate that SA+ can associate with not only one but also two CB7 macrocycle.
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CAS 2447-54-3 Sanguinarine

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