BRENDA - Enzyme Database

Inhibition of DNA topoisomerase I by natural and synthetic mono- and dimeric protoberberine alkaloids

Qin, Y.; Pang, J.Y.; Chen, W.H.; Zhao, Z.Z.; Liu, L.; Jiang, Z.H.; Chem. Biodivers. 4, 481-487 (2007)

Data extracted from this reference:

Application
EC Number
Application
Commentary
Organism
5.6.2.1
drug development
dimeric compounds are promising candidates to be further elaborated as anticancer leads
Homo sapiens
Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.6.2.1
10-methoxy-9-{2-[(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium-3-yl)oxy]ethoxy}[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
10-methoxy-9-{3-[(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium-3-yl)oxy]propoxy}[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
10-methoxy-9-{4-[(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium-3-yl)oxy]butoxy}[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
3,3'-[butane-1,4-diylbis(oxy)]bis(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
3,3'-[ethane-1,2-diylbis(oxy)]bis(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium) dichloride
synthetic protoberberine alkaloid, highly active. Strongly stabilize the enzyme-DNA binary complex at low concentration (50100microM). From 0.1 to 1 mM, their ability to stabilize is weak
Homo sapiens
5.6.2.1
3,3'-[propane-1,3-diylbis(oxy)]bis(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[butane-1,4-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[ethane-1,2-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium)dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[heptane-1,7-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[hexane-1,6-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[pentane-1,5-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[propane-1,3-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active. Strongly stabilize the enzyme-DNA binary complex at low concentration (50100microM). From 0.1 to 1 mM, their ability to stabilize is weak
Homo sapiens
5.6.2.1
9-O-(2-aminoethyl)berberine
synthetic protoberberine alkaloid
Homo sapiens
5.6.2.1
9-O-(2-hydroxyethyl)berberine
synthetic protoberberine alkaloid
Homo sapiens
5.6.2.1
9-O-[2-(1H-imidazol-1-yl)ethyl]berberine
synthetic protoberberine alkaloid
Homo sapiens
5.6.2.1
9-O-[2-(4-methylpiperazin-1-yl)ethyl]berberine
synthetic protoberberine alkaloid
Homo sapiens
5.6.2.1
Berberine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
berberrubine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
camptothecin
topoisomerase I poison
Homo sapiens
5.6.2.1
coptisine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
Jatrorrhizine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
jatrorubine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
additional information
series of natural and synthetic protoberberine alkaloid evaluated for their inhibitory activities towards DNA topoisomerase I. Natural, monomeric protoberberine alkaloids and their mono-modified congeners show only minor activities. Most of the dimeric protoberberine alkaloids are highly active
Homo sapiens
5.6.2.1
palmatine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
palmatrubine
natural protoberberine alkaloid
Homo sapiens
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
5.6.2.1
Homo sapiens
-
-
-
Application (protein specific)
EC Number
Application
Commentary
Organism
5.6.2.1
drug development
dimeric compounds are promising candidates to be further elaborated as anticancer leads
Homo sapiens
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.6.2.1
10-methoxy-9-{2-[(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium-3-yl)oxy]ethoxy}[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
10-methoxy-9-{3-[(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium-3-yl)oxy]propoxy}[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
10-methoxy-9-{4-[(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium-3-yl)oxy]butoxy}[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
3,3'-[butane-1,4-diylbis(oxy)]bis(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
3,3'-[ethane-1,2-diylbis(oxy)]bis(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium) dichloride
synthetic protoberberine alkaloid, highly active. Strongly stabilize the enzyme-DNA binary complex at low concentration (50100microM). From 0.1 to 1 mM, their ability to stabilize is weak
Homo sapiens
5.6.2.1
3,3'-[propane-1,3-diylbis(oxy)]bis(2,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[butane-1,4-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[ethane-1,2-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium)dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[heptane-1,7-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[hexane-1,6-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[pentane-1,5-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active
Homo sapiens
5.6.2.1
9,9'-[propane-1,3-diylbis(oxy)]bis(10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium) dichloride
synthetic protoberberine alkaloid, highly active. Strongly stabilize the enzyme-DNA binary complex at low concentration (50100microM). From 0.1 to 1 mM, their ability to stabilize is weak
Homo sapiens
5.6.2.1
9-O-(2-aminoethyl)berberine
synthetic protoberberine alkaloid
Homo sapiens
5.6.2.1
9-O-(2-hydroxyethyl)berberine
synthetic protoberberine alkaloid
Homo sapiens
5.6.2.1
9-O-[2-(1H-imidazol-1-yl)ethyl]berberine
synthetic protoberberine alkaloid
Homo sapiens
5.6.2.1
9-O-[2-(4-methylpiperazin-1-yl)ethyl]berberine
synthetic protoberberine alkaloid
Homo sapiens
5.6.2.1
Berberine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
berberrubine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
camptothecin
topoisomerase I poison
Homo sapiens
5.6.2.1
coptisine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
Jatrorrhizine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
jatrorubine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
additional information
series of natural and synthetic protoberberine alkaloid evaluated for their inhibitory activities towards DNA topoisomerase I. Natural, monomeric protoberberine alkaloids and their mono-modified congeners show only minor activities. Most of the dimeric protoberberine alkaloids are highly active
Homo sapiens
5.6.2.1
palmatine
natural protoberberine alkaloid
Homo sapiens
5.6.2.1
palmatrubine
natural protoberberine alkaloid
Homo sapiens