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3.1.6.2: steryl-sulfatase

This is an abbreviated version!
For detailed information about steryl-sulfatase, go to the full flat file.

Word Map on EC 3.1.6.2

Reaction

3beta-hydroxyandrost-5-en-17-one 3-sulfate
+
H2O
=
3beta-hydroxyandrost-5-en-17-one
 +
sulfate

Synonyms

3-beta-hydroxysteroid sulfate sulfatase, arylsufatase, arylsulfatase C, ASC, AtsA, cholesterol sulfate sulfohydrolase, CHS-ase, dehydroepiandrosterone sulfatase, dehydroepiandrosterone sulfate sulfatase, DHEAS, E1-STS, ES, estrone sulfatase, More, neurosteroid sulfatase, NSS, oestrone sulfatase, phenolic steroid sulfatase, pregnenolone sulfatase, steroid 3-sulfatase, steroid sulfatase, steroid sulfate sulfohydrolase, steroid sulphatase, sterol sulfatase, sterolsulfate sulfohydrolase, Steryl-sulfate sulfohydrolase, STS, sulfatase, sterol

ECTree

     3 Hydrolases
         3.1 Acting on ester bonds
             3.1.6 Sulfuric-ester hydrolases
                3.1.6.2 steryl-sulfatase

Inhibitors

Inhibitors on EC 3.1.6.2 - steryl-sulfatase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(12aS)-N,N-dihydroxy-12a-methyl-1,3-dioxo-2-propyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-f]isoquinoline-8-sulfinamide
-
-
(17beta)-17-(2,3,4,5,6-pentafluorobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(2-furylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3,5-dibromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-benzyloxybenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-bromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-iodobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-tert-butylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-trifluoromethylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-bromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-iodobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-methyl-2-thienyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-tert-butylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-tert-butylbenzyl)estra-1(10),2,4-triene-3,17-diol
-
estradiol phenolic reversible inhibitor as reference, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 39% inhibition, at 1 microM 62% inhibition
(17beta)-17-(4-trifluoromethylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(cyclohexylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(cyclopropylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(pyridin-3-ylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-benzyl-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-benzylestra-1(10),2,4-triene-3,17-diol
-
estradiol phenolic reversible inhibitor as reference, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 15% inhibition, at 1 microM 48% inhibition
(17beta)-17-[3,5-bis(benzyloxy)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[3,5-bis(tert-butyl)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[3,5-bis(trifluoromethyl)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[3-(dibenzylamino)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[4-(benzyloxy)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-{[2-(2-bromoethyl)cyclopropyl]methyl}estra-1(10),2,4-triene-3,17-diol
-
-
(17beta,17'beta)-17,17'-(2E)-but-2-ene-1,4-diylbisestra-1(10),2,4-triene-3,17-diol
-
reversible non-competitive or mixed inhibition, estradiol dimer with C17-C17 bond, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 42% inhibition, at 1 microM 56% inhibition
(17beta,17'beta)-17,17'-butane-1,4-diylbisestra-1(10),2,4-triene-3,17-diol
-
reversible non-competitive or mixed inhibition, estradiol dimer with C17-C17 bond, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 30% inhibition, at 1 microM 54% inhibition
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)(oxo)acetic acid
-
-
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)acetic acid
-
-
(NH4)2SO4
-
slight
(p-O-sulfamoyl)-N-tetradecanoyl tyramine
(R)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
pure R(+)-enantiomer of 1-[(4-Cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
(S)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
pure S(-)-enantiomer of 1-[(4-Cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
1-indanone 4-O-sulfamate
-
-
1-indanone 5-O-sulfamate
-
-
1-indanone 6-O-sulfamate
-
-
1-tetralone 6-O-sulfamate
-
-
1-tetralone 7-O-sulfamate
-
-
1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
bromo derivative of 1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole does improve aromatase inhibitory activity
1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
meta-chloro derivative of 1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole does increase aromatase inhibition activity
1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
increase of aromatase inhibitory activity due to presence of a para-cyanophenyl moiety
1-[bis-(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
best dual inhibition
1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole
methoxy groups reduce inhibition of aromatase compared to 1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
sulfamate in meta-position increases aromatase inhibition strength compared to para-position
1-[bis-(4-sulfamoyloxy-3-methoxyphenyl)methyl]-1H-[1,2,4]triazole
exchange in positions of methoxy and sulfamate group compared to 1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole fails to improve aromatase inhibitory activity
16alpha-hydroxydehydroepiandrosterone
-
competitive to dihydroepiandrosterone
17-oxoestra-1,3,5(10)-trien-3-yl sulfamate
17alpha-benzyl-17beta-hydroxyestra-1,3,5-(10)-triene-3-boronic acid
-
-
17alpha-benzyl-3,17beta-dihydroxyestra-1,3,5-(10)-triene
-
-
17beta estradiol
-
exposure to 17beta estradiol causes 70% reduction of estrone 3-sulfate sulfatase activity in MCF-7 cells after 6 days, but 9% increase in mammary myoepithelial cells
19,19-difluoro-17-oxo-4,9-cyclo-9,10-secoandrosta-1,3,5(10)-trien-1-yl hydrogen sulfate
-
-
19-fluoro-17-oxo-4,9-cyclo-9,10-secoandrosta-1,3,5(10)-trien-1-yl hydrogen sulfate
-
-
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
-
-
2-(1-adamantyl)-4-oxo-4H-chromen-6-yl sulfamate
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carbaldehyde
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxamide
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylic acid
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromen-6-yl sulfamate
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carbonitrile
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carboxylic acid
-
-
2-(1-adamantyl)-6-(hydroxymethyl)-4H-chromen-4-one
-
-
2-(1-adamantyl)-6-glycoloyl-4H-chromen-4-one
-
-
2-(difluoromethyl)-17-oxoestra-1(10),2,4-trien-3-yl hydrogen sulfate
-
-
2-(fluoromethyl)-17-oxoestra-1(10),2,4-trien-3-yl hydrogen sulfate
-
-
2-bromo-4-[(R)-(4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl]-N,N-dihydroxybenzenesulfinamide
-
-
2-chloro-4-[5-(2,6-difluoro-3-hydroxybenzoyl)thiophen-2-yl]phenyl sulfamate
dual inhibitor, acts both on STS and hydroxy steroid dehydrogenase 17beta-HSD1, reverses estrogen-induced T-47D cell proliferation
2-formyl-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
time- and concentration-dependent inhibitor, shows more or less pseudo-first order behavior at all concentrations
2-methoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
-
-
2-methoxyestrone-3-O-sulfamate
-
potent active site-directed inhibitor, no effect on STS mRNA expression in fibroblasts
2-phenylindole sulfamate
-
2-phenylindole sulfamates with lipophilic side chains in 1- or 5-position of the indole with IC50-values between 2 nM and 0.001 mM, irreversibly inhibits hydrolysis of estrone sulfate in MDA-MB 231 cells, inhibits gene activation in estrogen receptor-positive MCF-7 breast cancer cells in submicromolar concentrations and reduces cell proliferation with IC50 of 0.001 mM
2-t-butyl-4H-1-benzopyran-4-one-6-boronic acid
-
-
2-tert-butyl-6-hydroxy-4H-chromen-4-one
-
-
2-[3-[[(4-[[(aminooxy)sulfinyl]oxy]phenyl)sulfanyl]methyl]-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
-
-
2H1-benzpyran 7-O-disulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
-
68.2% inhibition at 0.01 mM
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
-
-
3'-chloro-5-(1H-1,2,4-triazol-1-ylmethyl)biphenyl-2-carbonitrile
-
-
3,4,8-trimethylcoumarin 7-O-sulfamate
-
-
3,4-dihydro-4-methylcoumarin 7-O-sulfamate
-
-
3,4-dihydrocoumarin 7-O-sulfamate
-
-
3,4-dimethylcoumarin 7-O-sulfate
-
12-fold more potent than COUMATE
3-benzyl-4-methylcoumarin-7-O-sulfamate
-
IC50 value 0.68 nM in intact MCF-7 cells
3-hexyl-4-methylcoumarin-7-O-sulfamate
-
IC50 value 0.68 nM in intact MCF-7 cells
3-nitrophenyl sulfamate
3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate
-
-
3-sulfamoyloxy-N-(1''-pyridin-3''-ylmethyl)-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
-
highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
3-sulfamoyloxy-N-3,3,3-trifluoropropyl-16,17-seco-estra-1,3,4(10)-triene-16,17-imide
3-sulfamoyloxy-N-propyl-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
-
highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
3-[4-(3,4-difluoro-benzoylamino)-phenyl]-coumarin-7-O-sulfamate
compound exhibits poor cytotoxicity
3-[4-[2-(2,5-bis-trifluoromethyl-phenyl)-acetylamino]-phenyl]-coumarin-7-O-sulfamate
compound shows antiproliferative activity against the MCF-7 and T47D cell lines, GI50 value is 15.9 microM and 8.7 microM, respectively
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
-
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
-
4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
-
-
4-(cyclohexanecarboxamido)phenyl sulfamate
55.7% inhibition of isolated enzyme at 0.01 mM, 86.1% inhibition of the STS activity of JEG-3 carcinoma cells at 0.010 mM
4-(trifluoromethyl)coumarin 7-O-sulfamate
-
-
4-fluoro-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
linear mixed-type inhibition, compound is capable of binding at sites both within and outside the active site
4-fluoro-17beta-(3'-trifluoromethylbenzene)sulfonamideestra-1,3,5(10)-trien-3-ol
-
4-methylcoumarin 6,7-O,O-disulfamate
-
-
4-methylcoumarin 7-O-sulfamate
-
COUMATE, also in vivo
4-methylcoumarin-7-O-sulfamate
-
-
4-nitro-17beta-4'-biphenylsulfonamide-1,3,5(10)-estratrien-3-ol
-
4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate
-
-
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
-
665 COUMATE, placental IC50: 200 nM
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
-
5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-(N,N-dimethyl)sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-(N-methyl)sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-sulfamate
-
-
5-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
-
-
5-((1H-1,2,4-triazol-1-yl)methyl)-3'-chloro-4'-hydroxybiphenyl-2-carbonitrile
-
-
5-((1H-1,2,4-triazol-1-yl)methyl)-4'-hydroxybiphenyl-2-carbonitrile
-
-
5-methyl-6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
5-pregnen-3beta,21-diol
-
most potent inhibitor of C21 steroids
5-pregnen-3beta,21-diol-20-one
-
most potent inhibitor of C21 steroids
5alpha-androstane-3alpha-17beta-diol
-
most potent inhibitor of C19 steroids
6-(3-phenylpropoxy)-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-(pentyloxy)-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-methoxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-methoxycoumarin 7-O-sulfamate
-
-
6-oxo-5-(3-phenylpropyl)-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-5-pentyl-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17,18,19-tetradecahydrocyclopentadeca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydrocyclotrideca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15-decahydrocycloundeca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13-octahydrocyclonona[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-ylsulfamide
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-2-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl dimethylsulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclododeca[c]-chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
-
6612 COUMATE, placental IC50: 60 nM
6-oxo-7,8,9,10,11,12,13,14-octahydro-6H-cyclodeca[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
-
6610 COUMATE, placental IC50: 1 nM
6-oxo-7,8,9,10,11,12-hexahydro-6H-cycloocta[c]chromen-3-yl sulfamate
-
i.e. STW64, treatment of postmenopausal women with estrogen receptor-positive metastatic breast cancer. Inhibitor almost completely blocks enzyme activity in peripheral blood lymphocytes and tumor tissues, inhibition is associated with significant reductions in serum concentrations of androstenediol and estrogens. Serum androstenedione concentration also decreases by up to 86%
6-oxo-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
-
668 COUMATE, placental IC50: 30 nM
6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
-
666 COUMATE, placental IC50: 70 nM
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
-
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
-
6613 COUMATE, placental IC50: 75 nM
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
-
6611 COUMATE, placental IC50: 13 nM
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
-
669 COUMATE, placental IC50: 2.4 nM
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
6-oxo-8,9,10,11-tetrahydro-7H-cylohepta-[c][1]benzopyran-boronic acid
-
-
667 COUMATE
-
i.e. 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta(c)chromen-3-yl sulfamate, coadministation of oestrone sulfamate and 667 COUMATE completely blocks enzyme activity and completely abrogates the ability of oestrone sulfamate to stimulate uterine growth
667-coumate
-
-
7,8-dihydronaphthalene 2-O-sulfamate
-
-
7-hydroxy-4-methylcoumarin 6-O-sulfamate
-
-
AgNO3
Ammonium molybdate
-
10 mM, 20% residual activity
anastrozole
-
-
breast cyst fluid
-
-
-
CaCl2
-
slight
calcium chloride
-
5 mM, 36% residual activity
cholesterol
-
1 mM, 57% inhibition
Cl-
-
slight
coumarin 7-O-sulfamate
-
-
cysteine
-
10 mM, 15% inhibition
daidzein-4'-O-sulfate
-
at 0.005 mM
daidzein-7,4'-di-O-sulfate
-
at 0.001 mM
dehydroepiandrosterone
dexamethasone
inhibits STS activity and expression in undifferentiated cells, the glucocorticoid antagonist RU486 reverses dexamethasone inhibition of STS
dithiothreitol
-
5 mM, 45% residual activity
EDTA
-
10% inhibition at 1 mM
estra-1,3,5-(10)-triene-17-one-3-boronic acid
-
competitive
estrone
-
-
estrone 3-O-sulfamate
-
-
Estrone 3-sulfate
estrone-3-O-(N,N-dimethyl)sulfamate
-
-
estrone-3-O-(N-methyl)sulfamate
-
-
estrone-3-O-methylthiophosphonate
-
-
estrone-3-O-sulfamate
estrone-3-sulfamate
glucose
-
slight
glutathione
-
reduced form, 5 mM, 23.5% residual activity
H2PO4-
-
-
human pituitary luteinizing hormone
-
human pituitary LH, reduces activity to 85% of baseline at 5 ng/ml, dose-dependent
-
interleukin-1beta
-
marked inhibition of mRNA expression and STS activity
-
irosustat
KBr
-
slight
KCl
-
slight
KCN
-
slight
KH2PO4
-
5 mM, 25% inhibition
KW-2581
-
active site-directed irreversible steroidal inhibitor
letrozole
-
-
LiCl
-
slight
Metabisulfite
-
-
methyl 2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylate
-
-
MgCl2
-
slight
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
-
N,N-dimethoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
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N-acetylated estrone 3-O-sulfamate
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inhibits the enzyme irreversibly, albeit much less potently than estrone 3-O-sulfamate
Na-metaborate
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Na-tetraborate
Na2B4O7
Na2SO3
Na2SO4
NaCl
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slight
NaF
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slight
NaHSO3
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slight
p-Nitrophenyl sulfate
phosphate
pregnenolone
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1 mM, 10% inhibition
pregnenolone 3-sulfate
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competitive inhibitor, dehydroepiandrosterone 3-sulfate as substrate
Rose bengal
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histidine modification
sodium arsenite
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slight
sodium deoxycholate
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sodium taurocholate
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Steroids
STX213
STX289
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N,N-dimethyl 667 COUMATE, analogue of STX64, inhibition 24 h after oral application: 0.1 mg/kg inhibits liver STS by 45%, skin STS by about 39%, 1 and 10 mg/kg inhibit liver STS completely, skin STS almost completely, inhibition 24 h after topical application to neck skin: 0.1 mg/kg inhibits skin and liver STS by <50%, remote skin STS by about 10%, 1and 10 mg/kg inhibit skin STS by 98%, remote skin STS by about 80 and more than 90% respectively, and liver STS by more than 80 and close by 100% respectively
STX64
sulfamic acid 2-bromo-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
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ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-bromo-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
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propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-bromo-4-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]methyl]phenyl ester
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
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ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethylsulfanyl)phenyl ester
sulfamic acid 2-chloro-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
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propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 3-(((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)methylsulfanyl)phenyl ester
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thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 3-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanyl)phenyl ester
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thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(((4-cyanophenyl)-(1,2,4)triazol-4-ylamino)methylsulfanyl)phenyl ester
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thioether linker, , based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold, best STS inhibitor of tested dual inhibitor compounds
sulfamic acid 4-((2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)methylsulfamoyl)phenyl ester
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N-methylated sulfonamide linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(10-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)decylsulfanyl)phenyl ester
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thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)phenyl ester
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ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanylmethyl)phenyl ester
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thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)-2-fluorophenyl ester
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ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-propyl)-2-fluorophenyl ester
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propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
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propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propylsulfanyl)phenyl ester
sulfamic acid 4-(5-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)pentylsulfanyl)phenyl ester
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thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 5-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]-methyl]-2-fluorophenyl ester
Sulfate esters
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overview, e.g. p-nitrophenyl sulfate
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tricyclic coumarin sulfamate
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in vitro and in vivo inhibition studies with E1-STS from different tissues, structure-activity relationship of a number of tricyclic coumarin sulfamates, the size of the third ring has a marked effect on inhibitor potency
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TX-1299
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TX-1492
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non-steroid Theramex compound, strong inhibitor, IC50: 22.5 nM in JEG-3 cells, 0.07 nM in MCF-7 cells
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TX-1506
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non-steroid Theramex compound, strong inhibitor, IC50: 11.9 nM in JEG-3 cells, 0.06 nM in MCF-7 cells
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vanadium oxide(V)
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50 mM, 51% residual activity
Zinc acetate
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1.25 mM, 53% residual activity
additional information
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