Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.2.1.166 extracted from

  • Gozalbes, R.; Mosulen, S.; Orti, L.; Rodriguez-Diaz, J.; Carbajo, R.J.; Melnyk, P.; Pineda-Lucena, A.
    Hit identification of novel heparanase inhibitors by structure- and ligand-based approaches (2013), Bioorg. Med. Chem., 21, 1944-1951.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression of the His-tagged enzyme from pET-15b expression vector containing a TEV cleavage site in Escherichia coli BL21-DE3 codon plus Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(2E)-N-(3,4-dichlorophenyl)-3-[3-fluoro-4-[5-(2-oxopropyl)-1,3-benzoxazol-2-yl]phenyl]prop-2-enamide
-
Homo sapiens
(3R,5S)-8-nonyl-9-oxo-1,6-dioxaspiro[4.4]non-7-ene-2,2,3-tricarboxylic acid
-
Homo sapiens
(3S,4S,5R,6R)-4,5-dihydroxy-6-[(trifluoroacetyl)amino]piperidine-3-carboxylic acid
-
Homo sapiens
(3S,4S,5R,6R)-6-(acetylamino)-4,5-dihydroxypiperidine-3-carboxylic acid
-
Homo sapiens
(5R)-3-heptadecanoyl-5-(hydroxymethyl)-4-methoxyfuran-2(5H)-one
-
Homo sapiens
(5R)-4-(benzyloxy)-3-heptadecanoyl-5-(hydroxymethyl)furan-2(5H)-one
-
Homo sapiens
(5S)-8-nonyl-9-oxo-1,6-dioxaspiro[4.4]non-7-ene-2,2,3-tricarboxylic acid
-
Homo sapiens
1,3-bis[4-(1H-benzimidazol-2-yl)phenyl]urea
-
Homo sapiens
1,3-bis[4-(5,6-dimethyl-1H-benzimidazol-2-yl)phenyl]urea
-
Homo sapiens
1-[2-([3-[(7-chloroquinolin-4-yl)amino]-5-(hydroxymethyl)benzyl]amino)prop-2-en-1-yl]piperidin-4-ol
-
Homo sapiens
1-[3-[(7-chloroquinolin-4-yl)amino]-5-([[3-(piperidin-1-yl)prop-1-en-2-yl]amino]methyl)benzyl]piperidin-4-ol
-
Homo sapiens
2-[(3-[4-[3-(4-chloro-2-cyclohexylphenoxy)-5-nitrophenoxy]phenyl]propanoyl)amino]ethanesulfonic acid
-
Homo sapiens
2-[2-methoxy-5-(5-phenyl-1,3-benzoxazol-2-yl)-4-(propylamino)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
-
Homo sapiens
2-[3-(1,3-benzoxazol-2-yl)phenyl]-1,3-dioxo-2,3-dihydro-1H-indene-5-carboxylic acid
-
Homo sapiens
2-[3-[5-(4-chlorophenyl)-1,3-benzoxazol-2-yl]-4-(propylamino)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
-
Homo sapiens
2-[3-[5-(4-fluorophenyl)-1,3-benzoxazol-2-yl]-4-(propylamino)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
-
Homo sapiens
2-[4-[4-(6-amino-1H-benzimidazol-2-yl)phenoxy]phenyl]-1H-benzimidazol-5-amine
-
Homo sapiens
3-heptadecanoyl-4-hydroxy-5-(hydroxymethyl)furan-2(5H)-one
-
Homo sapiens
3-[(7-chloroquinolin-4-yl)amino]-N-[2-(dimethylamino)ethyl]-5-([[3-(piperidin-1-yl)prop-1-en-2-yl]amino]methyl)benzamide
-
Homo sapiens
3-[(7-chloroquinolin-4-yl)amino]-N-[2-(morpholin-4-yl)ethyl]-5-([[3-(piperidin-1-yl)prop-1-en-2-yl]amino]methyl)benzamide
-
Homo sapiens
4-[(4-carboxy-3-hydroxy-5-methylphenoxy)carbonyl]-3-hydroxy-5-pentadecylphenyl beta-D-glucopyranosiduronic acid
-
Homo sapiens
4-[(4-carboxy-3-hydroxy-5-methylphenoxy)carbonyl]-3-hydroxy-5-pentadecylphenyl methyl beta-D-glucopyranosiduronate
-
Homo sapiens
4-[(7-chloroquinolin-4-yl)amino]-2-(pyrrolidin-1-ylmethyl)phenol
-
Homo sapiens
4-[(7-chloroquinolin-4-yl)amino]phenol
-
Homo sapiens
4-[[5-(3,6-dibromo-9H-fluoren-9-yl)-4-hydroxy-2-(2-phenylethyl)pentanethioyl]amino]benzenesulfonic acid
-
Homo sapiens
5-bromo-2-hydroxy-N-[(E)-(3-[2-[(4-methylphenyl)amino]-2-oxoethyl]-2-oxo-2,3-dihydro-1H-inden-1-ylidene)methyl]benzamide
-
Homo sapiens
5-[3-(2-methylidenenonadecyl)-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]-2-phenoxybenzenesulfonic acid
-
Homo sapiens
7-chloro-N-[3-([[3-(piperidin-1-yl)prop-1-en-2-yl]amino]methyl)-5-([[3-(piperidin-1-yl)prop-1-en-2-yl]oxy]methyl)phenyl]quinolin-4-amine
-
Homo sapiens
7-chloro-N-[3-[(diethylamino)methyl]-4-(morpholin-4-yl)phenyl]quinolin-4-amine
-
Homo sapiens
7-chloro-N-[4-(furan-2-yl)-3-(pyrrolidin-1-ylmethyl)phenyl]quinolin-4-amine
-
Homo sapiens
7-chloro-N-[4-ethoxy-3-(pyrrolidin-1-ylmethyl)phenyl]quinolin-4-amine
-
Homo sapiens
amodiaquine an antimalarial drug Homo sapiens
astemizole
-
Homo sapiens
cisapride
-
Homo sapiens
hesperidin
-
Homo sapiens
labetalol
-
Homo sapiens
metergoline
-
Homo sapiens
additional information screening of a virtual inhibitor library composed of 27 known heparanase inhibitors and a commercial collection of drugs and drug-like compounds, overview. A subset of fourteen 4-arylaminoquinolines from a global set of 249 analogues of amodiaquine is selected based on the application of in silico models, a QSAR solubility prediction model and a chemical diversity analysis. Some of these compounds displayed binding affinities in the micromolar range. Structure-activity relationships around the amodiaquine scaffold, overview Homo sapiens
N'-[3-[(7-chloroquinolin-4-yl)amino]-5-([[3-(piperidin-1-yl)prop-1-en-2-yl]amino]methyl)benzyl]-N,N-dimethylethane-1,2-diamine
-
Homo sapiens
N-[4-([[4-(1H-benzimidazol-2-yl)phenyl]amino]methyl)phenyl]-3-bromo-4-methoxybenzamide
-
Homo sapiens
N-[4-([[5-(1H-benzimidazol-2-yl)pyridin-2-yl]amino]methyl)phenyl]-3-bromo-4-methoxybenzamide
-
Homo sapiens
N-[4-bromo-3-[(diethylamino)methyl]phenyl]-7-chloroquinolin-4-amine
-
Homo sapiens
naringin
-
Homo sapiens
PI-88
-
Homo sapiens
[2-(2-carboxybenzoyl)-6-(phenylsulfanyl)phenyl](hydroxy)oxoammonium
-
Homo sapiens
[3-[(7-chloroquinolin-4-yl)amino]-5-([[3-(morpholin-4-yl)prop-1-en-2-yl]amino]methyl)phenyl]methanol
-
Homo sapiens
[3-[(7-chloroquinolin-4-yl)amino]-5-([[3-(piperidin-1-yl)prop-1-en-2-yl]amino]methyl)phenyl](morpholin-4-yl)methanone
-
Homo sapiens
[4-(5-[2-chloro-4-[(4-chlorobenzoyl)amino]phenyl]furan-2-yl)-1,3-thiazol-2-yl]acetic acid
-
Homo sapiens
[4-[5-(2,4-dichlorophenyl)furan-2-yl]-1,3-oxazol-2-yl]acetic acid
-
Homo sapiens
[4-[5-(4-[[(2E)-3-(4-bromophenyl)prop-2-enoyl]amino]-2-chlorophenyl)furan-2-yl]-1,3-thiazol-2-yl]acetic acid
-
Homo sapiens

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
8000
-
1 * 45000, glycosylated subunit, + 1 * 8000, non-covalently binding, SDS-PAGE Homo sapiens
45000
-
1 * 45000, glycosylated subunit, + 1 * 8000, non-covalently binding, SDS-PAGE Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli BL21-DE3 codon plus by metal affinity chromatography Homo sapiens

Subunits

Subunits Comment Organism
heterodimer 1 * 45000, glycosylated subunit, + 1 * 8000, non-covalently binding, SDS-PAGE Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
additional information
-
dissociation constants, overview Homo sapiens additional information

General Information

General Information Comment Organism
additional information three-dimensional sequence homology modelling, overview. Two essential acidic residues are Glu225 and Glu343, which are involved in the catalytic mechanism, acting as a proton donor and a nucleophile, respectively Homo sapiens
physiological function heparanase is a key enzyme involved in the dissemination of metastatic cancer cells Homo sapiens