CHELERYTHRINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H18NO4
Molecular Weight	348.3719
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C2C(C=[N+](C)C3=C2C=CC4=CC5=C(OCO5)C=C34)=C1OC

InChI

InChIKey=LLEJIEBFSOEYIV-UHFFFAOYSA-N

InChI=1S/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24380291 | https://www.ncbi.nlm.nih.gov/pubmed/2244923 | https://www.ncbi.nlm.nih.gov/pubmed/12702731 | https://www.ncbi.nlm.nih.gov/pubmed/16936897 | http://www.google.com.pg/patents/WO2002013803A2

Chelerythrine is a kind of benzo[c] phenanthridine alkaloids, which is widely found in plant of Fumariaceae, Papaveraceae, Ranunculaceae and Rutaceae families. Chelerythrine is a potent and specific inhibitor of protein kinase C. In addition chelerythrine inhibits pro-survival protein Bcl(XL) thereby inducing apoptosis. It exerts antitumor properties.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2244923	Inhibitor 8297	0.7 µM [Ki]
Apoptosis regulator Bcl-X 8 Target ID: CHEMBL4625 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17011577 \| https://www.ncbi.nlm.nih.gov/pubmed/12702731	Inhibitor 8297
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26183621	Modulator 828	566.0 nM [IC50]
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28509993 \| https://www.ncbi.nlm.nih.gov/pubmed/28102286	Binding Agent 1064
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://adisinsight.springer.com/drugs/800013523	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: http://www.google.com.pg/patents/WO2002013803A2 http://adisinsight.springer.com/drugs/800013523 https://www.ncbi.nlm.nih.gov/pubmed/28515445 https://www.ncbi.nlm.nih.gov/pubmed/28399187	Primary		Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11786500 https://www.ncbi.nlm.nih.gov/pubmed/28842814 https://www.ncbi.nlm.nih.gov/pubmed/26515544 https://www.ncbi.nlm.nih.gov/pubmed/14768516	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
High calcium and dobutamine positive inotropy in the perfused mouse heart: myofilament calcium responsiveness, energetic economy, and effects of protein kinase C inhibition.	2001	11553322
Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells.	2001	11504450
Evidence for two mechanisms of amino acid osmolyte release from hippocampal slices.	2001 Aug	11512036
The effects of isoflurane on native and chimeric muscarinic acetylcholine receptors: the role of protein kinase C.	2001 Aug	11473864
Diminished alpha1-adrenergic-mediated contraction and translocation of PKC in senescent rat heart.	2001 Aug	11454560
Opioid receptor stimulation acts as mediator of protection in ischaemic preconditioning.	2001 Feb-Mar	11447487
Evidence for a role of protein kinase C in FGF signal transduction in the developing chick limb bud.	2001 Jul	11493562
Backtable heat-enhanced preconditioning: a simple and effective means of improving function of heart transplants.	2001 Jul	11465162
Role of protein kinase C in the reduction of infarct size by N-methyl-1-deoxynojirimycin, an alpha-1,6-glucosidase inhibitor.	2001 Jul	11429386
Activation of extracellular signal-regulated kinase in trabecular meshwork cells.	2001 Jul	11428860
Histamine increases interstitial adenosine concentration via activation of ecto-5'-nucleotidase in rat hearts in vivo.	2001 Jul	11408527
Heat shock prevents simulated ischemia-induced apoptosis in renal tubular cells via a PKC-dependent mechanism.	2001 Jul	11404313
ANG II-mediated inhibition of neuronal delayed rectifier K+ current: role of protein kinase C-alpha.	2001 Jul	11401823
Post-ischemic PKC inhibition impairs myocardial calcium handling and increases contractile protein calcium sensitivity.	2001 Jul	11399253
Chelerythrine and genistein inhibit the endothelin-1-induced increase in myofilament Ca(2+) sensitivity in rabbit ventricular myocytes.	2001 Jul 20	11476754
Inhibition of acetylcholine-activated K(+) current by chelerythrine and bisindolylmaleimide I in atrial myocytes from mice.	2001 Jul 27	11672559
A new diprenyl coumarin and alkaloids from the bark of Zanthoxylum dimorphophyllum (Rutaceae).	2001 Jul-Aug	11531078
Protein kinase A- and C-dependent modulation of murine inducible nitric oxide synthase.	2001 Jun	11642342
Stathmin levels in growth plate chondrocytes are modulated by vitamin D3 metabolites and transforming growth factor-beta1 and are associated with proliferation.	2001 Jun	11572331
Role of protein kinase C and phosphatases in the pulmonary vasculature of neonatal piglets.	2001 Jun	11395610
Vasopressin-induced protein kinase C-dependent superoxide generation contributes to atp-sensitive potassium channel but not calcium-sensitive potassium channel function impairment after brain injury.	2001 Jun	11387506
Protein phosphorylation in mitochondria from human placenta.	2001 May	11373154
Stimulatory effect of isoferulic acid on alpha1A-adrenoceptor to increase glucose uptake into cultured myoblast C2C12 cell of mice.	2001 May 14	11474559
17beta-oestradiol stimulates capacitative Ca2+ entry in human endometrial cells.	2001 May 15	11369445
Capsaicin potentiates 1,25-dihydoxyvitamin D3- and all-trans retinoic acid-induced differentiation of human promyelocytic leukemia HL-60 cells.	2001 May 25	11408028
Involvement of protein kinase C and tyrosine kinase in lipopolysaccharide-induced anorexia.	2001 May-Jun	11420064
Differentiation of bipolar CG-4 line oligodendrocytes is associated with regulation of CREB, MAP kinase and PKC signalling pathways.	2001 Nov	11672834
Activation of PKC decreases myocardial O2 consumption and increases contractile efficiency in rats.	2001 Nov	11668082
Mechanisms of the apoptotic and necrotic actions of trimethyltin in cerebellar granule cells.	2001 Nov	11606804
Novel role of macrophage migration inhibitory factor in angiotensin II regulation of neuromodulation in rat brain.	2001 Nov	11606427
Differential MAP kinase activation and Na(+)/H(+) exchanger phosphorylation by H(2)O(2) in rat cardiac myocytes.	2001 Nov	11600417
Adenosine A(2A) and A(2B) receptor activation of erythropoietin production.	2001 Nov	11592940
Role of protein kinase C in the signal pathways that link Na+/K+-ATPase to ERK1/2.	2001 Nov 9	11562372
Chelerythrine rapidly induces apoptosis through generation of reactive oxygen species in cardiac myocytes.	2001 Oct	11603925
Death by protein kinase C inhibitor: a stressful event.	2001 Oct	11603920
Endothelium-derived endothelin-1 reduces cerebral artery sensitivity to nitric oxide by a protein kinase C-independent pathway.	2001 Oct	11588325
Protein kinase C and changes in manganese superoxide dismutase gene expression in cultured glial cells.	2001 Oct	11553022
Role of Na(+)/H(+) exchanger during O(2) deprivation in mouse CA1 neurons.	2001 Oct	11546657
Regulation and distribution of MAdCAM-1 in endothelial cells in vitro.	2001 Oct	11546645
Characterization of the signal transduction pathways mediating morphine withdrawal-stimulated c-fos expression in hypothalamic nuclei.	2001 Oct 26	11698063
Stimulatory effect of phenylephrine on the secretion of beta-endorphin from rat adrenal medulla in vitro.	2001 Oct 8	11695703
The lysophospholipids sphingosine-1-phosphate and lysophosphatidic acid enhance survival during hypoxia in neonatal rat cardiac myocytes.	2001 Sep	11549349
Src and multiple MAP kinase activation in cardiac hypertrophy and congestive heart failure under chronic pressure-overload: comparison with acute mechanical stretch.	2001 Sep	11549343
Role of calcineurin in insulin-like growth factor-1-induced hypertrophy of cultured adult rat ventricular myocytes.	2001 Sep	11548882
Mechanism of action of angiotensin II in human isolated subcutaneous resistance arteries.	2001 Sep	11522611
Regulation of ATP-sensitive K(+) channels by protein kinase C in murine colonic myocytes.	2001 Sep	11502563
Induction of osteoblast differentiation indexes by PTHrP in MG-63 cells involves multiple signaling pathways.	2001 Sep	11500304
Protein kinase C regulates dopamine D4 receptor-mediated phospholipid methylation.	2001 Sep 14	11557258
A diacylglycerol-activated Ca2+ channel in PC12 cells (an adrenal chromaffin cell line) correlates with expression of the TRP-6 (transient receptor potential) protein.	2001 Sep 15	11535132
Protein kinase C regulation of cell spreading in the molluscan Biomphalaria glabrata embryonic (Bge) cell line.	2001 Sep 26	11583819

Patents

Sample Use Guides

In Vivo Use Guide

Mice injected i.p. with chelerythrine 1-10 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

10 ug/mL of chelerythrine is capable of inducing apoptosis in Dalton's lymphoma (DL) cells.

Name

Type

Language

CHELERYTHRINE

Common Name

English

(1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDINIUM, 1,2-DIMETHOXY-12-METHYL-

Systematic Name

English

CHELERYTHRINE [MI]

Common Name

English

TODDALIN

Common Name

English

1,2-DIMETHOXY-12-METHYL(1,3)DIOXOLO)4',5':4,5)BENZO(1,2-C)PHENANTHRIDINIUM

Common Name

English

CHELERITRINE

Common Name

English

TODDALINE

Common Name

English

BROUSSONPAPYRINE

Common Name

English

Chelerythrine [WHO-DD]

Common Name

English

Code System Code Type Description

FDA UNII

E3B045W6X0