5578-73-4 Usage
Uses
Different sources of media describe the Uses of 5578-73-4 differently. You can refer to the following data:
1. Sanguinarium Chloride is a natural product with antimicrobial, anti-inflammatory, and anti-oxidant properties. Sanguinarium Chloride has antiproliferative, pro-apoptosis effects in some cancer cell lines.
2. antineoplastic, antiplaque agent
3. Sanguinarine chloride hydrate was tested for anti-schistosomal activities against Schistosoma mansoni.9 It was tested for anti-lipase activity against Candida rugosa lipase.10
General Description
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Biological Activity
sanguinarine chloride is a potent and specific inhibitor of pp2c with ki value of 0.68 μm, and is also a selective and cell-active inhibitor of mkp-1 with ic50 value of 10 μm. sanguinarine is also an allosteric activator of ampk [1][2][3].protein phosphatase 2c (pp2c) is a serine/threonine-specific phosphatase, the activity of which is dependent on mg2+ or mn2+. pp2c dephosphorylates a number of substrates such as cyclin-dependent kinase, mitogen-activated kinase (mapk) and bad. mitogen-activated protein kinase phosphatase-1 (mkp-1) is a dual specificity phosphatase. amp-activated protein kinase (ampk) plays an important role in the regulation of cellular metabolism [1][2][3].sanguinarine chloride is an inhibitor of pp2c and mkp-1, and also an allosteric activator of ampk with antibiotic and antitumor activity. sanguinarine competed with α-casein to inhibit pp2c and exhibited selectivity for pp2c as compared with pp1, pp2a and pp2b. in human promyelocytic leukemia cell line hl60, sanguinarine exhibited cytotoxicity with ic50 value of 0.37 μm and induced apoptosis via a caspase-3/7-dependent mechanism involving the phosphorylation of p38, a pp2c substrate [1]. sanguinarine inhibited mkp-1 and mkp-l with ic50 values of 17.3 and 12.5 μm. in panc-1 human pancreatic cancer cells, sanguinarine increased erk and jnk/sapk phosphorylation [2]. in the mda mb-231 cell line, sanguinarine caused ampk and the downstream acetyl-coa carboxylase (acc) phosphorylation [3]. in lncap and du145 cells, sanguinarine inhibited cell growth, induced g0/g1 phase arrest and apoptosis [4].
Biochem/physiol Actions
Sanguinarine is a benzophenanthridine alkaloid isolated from plants belonging to the family Papaveracea. It exhibits anti-bacterial, anti-fungal, anti-inflammatory and anti-cancer properties. It induces cell cycle arrest and sensitizes cancer cells to apoptosis by activating TNF-related apoptosis inducing ligand.6,7 It inhibits STAT3, MMP-2, MMP-9, interacts with glutathione, induces generation of ROS, disrupts the microtubule assembly and causes DNA damage resulting the death of the cancer cells.6,7,8
references
[1]. aburai n, yoshida m, ohnishi m, et al. sanguinarine as a potent and specific inhibitor of protein phosphatase 2c in vitro and induces apoptosis via phosphorylation of p38 in hl60 cells. biosci biotechnol biochem, 2010, 74(3): 548-552. [2]. vogt a, tamewitz a, skoko j, et al. the benzo[c]phenanthridine alkaloid, sanguinarine, is a selective, cell-active inhibitor of mitogen-activated protein kinase phosphatase-1. j biol chem, 2005, 280(19): 19078-19086. [3]. choi j, he n, sung mk, et al. sanguinarine is an allosteric activator of amp-activated protein kinase. biochem biophys res commun, 2011, 413(2): 259-263. [4]. adhami vm, aziz mh, reagan-shaw sr, et al. sanguinarine causes cell cycle blockade and apoptosis of human prostate carcinoma cells via modulation of cyclin kinase inhibitor-cyclin-cyclin-dependent kinase machinery. mol cancer ther, 2004, 3(8): 933-940.
Check Digit Verification of cas no
The CAS Registry Mumber 5578-73-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,7 and 8 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5578-73:
(6*5)+(5*5)+(4*7)+(3*8)+(2*7)+(1*3)=124
124 % 10 = 4
So 5578-73-4 is a valid CAS Registry Number.
InChI:InChI=1/C20H14NO4.ClH/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;1H/q+1;/p-1
5578-73-4Relevant articles and documents
Inclusion complex formation of sanguinarine alkaloid with cucurbit[7]uril: Inhibition of nucleophilic attack and photooxidation
Miskolczy, Zsombor,Megyesi, Monika,Tarkanyi, Gabor,Mizsei, Reka,Biczok, Laszlo
, p. 1061 - 1070 (2011)
The inclusion of sanguinarine, a biologically active natural benzophenanthridine alkaloid, in cucurbit[7]uril (CB7) was studied by NMR and ground-state absorption spectroscopy, as well as steady-state and time-resolved fluorescence measurements in aqueous solution. The iminium form of sanguinarine (SA+) produces very stable 1:1 inclusion complex with CB7 (K = 1.0 × 106 M-1), whereas the equilibrium constant for the binding of the second CB7 is about 3 orders of magnitude smaller. Marked fluorescence quantum yield and fluorescence lifetime enhancements are found upon encapsulation of SA+ due to the deceleration of the radiationless deactivation from the single-excited state, but the fluorescent properties of 1:1 and 1:2 complexes barely differ. The equilibrium between the iminium and alkanolamine forms is shifted 3.69 pK unit upon addition of CB7 as a consequence of the preferential encapsulation of the iminium form and the protection of the 6 position of sanguinarine against the nucleophilic attack by hydroxide anion. On the basis of thermodynamic cycle, about 225 M-1 is estimated for the equilibrium constant of the complexation between the alkanolamine form of sanguinarine (SAOH) and CB7. The confinement in the CB7 macrocycle can be used to impede the nucleophilic addition of OH- to SA+ and to hinder the photooxidation of SAOH.
New methods for the synthesis of naphthyl amines; Application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C
Tatton, Matthew R.,Simpson, Iain,Donohoe, Timothy J.
, p. 11314 - 11316 (2014/11/07)
A new method for preparing naphthyl amines from 1,5 unsaturated dicarbonyl precursors is described; the utility of this new method was proven in the syntheses of several natural products, all containing the benzo[c]phenanthridine core and enabled by a radical promoted cyclisation of the naphthyl amine products formed in the key cyclisation. the Partner Organisations 2014.
Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: Application to the total synthesis of benzo[c]phenanthridine alkaloids
Lv, Pei,Huang, Kanglun,Xie, Longguan,Xu, Xiaohua
supporting information; experimental part, p. 3133 - 3135 (2011/05/15)
A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.
