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(1R, 2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
inhibits in vitro
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
(1R,2R)-2-N-(tetradecanoylamino)-1-(4'-nitrophenyl)-propyl-1,3-O,O-(N,N-dimethylamino)acetate dihydrochloride
i.e. LCL521 or Di-DMG-B13, is a lysosomotropic inhibitor of ACDase, inhibition mechanism, overview. Low dose of LCL521 (0.001 mM) effectively inhibits ACDase in cells, but the effects are transient. A higher dose of LCL521 (0.01 mM) causes profound decrease of sphingosine and increase of ceramide, but additionally affects the processing and regeneration of the ACDase protein, with biphasic and reversible effects on the expression of ACDase, which parallels the long term changes of cellular sphingosine and ceramide. Finally, the higher concentrations of LCL521 also inhibit dihydroceramide desaturase (DES-1, EC 1.14.19.17). LCL521 inhibits ACDase specifically among the ceramidases in vitro, which is reinforced by the lysosomal targeting
(1R,2R)-2-N-myristoylamino-1-(4-nitrophenyl)-1,3-propandiol
(1S, 2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
inhibitor of alkaline ceramidase; inhibitor of alkaline ceramidase; inhibitor of neutral ceramidase
(1S,2R)-2-N-myristoylamino-1-phenyl-1-propanol
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
(2E,4E)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]hexa-2,4-dienamide
-
(2S)-3-keto-dehydrosphingosine
-
mtCDase, weak inhibition
(2S)-3-keto-hexadecanoyl-ceramide
-
mtCDase, IC50: 0.6 mol%
(2S)-3-keto-sphinganine
-
mtCDase, IC50: 0.34 mol%
(E)-4-[(2S,3R)-N-1,3-dihydroxyoctadecan-2-ylamino]4-oxo-2-butenoic acid
-
(E)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]but-2-enamide
-
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide
-
modification of carboxyl groups completely inhibits forward and reverse reaction
1-hexylcarbamoyl-5-fluorouracil
1-O-methyl-D-erythro-sphingosine
-
mtCDase, weak inhibition
12-amino-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]dodecanamide
-
1R,2R-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
1S,2S-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
2,3-Butanedione
-
modification of Arg causes about 50% inhibition of forward and reverse reaction
2-bromo-N-[(2S,3R)-1,3-dihydroxynonadecan-2-yl]acetamide
-
2-bromo-N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
-
2-bromo-N-[(2S,3R,4Z)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
-
2-chloro-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]acetamide
-
2-chloro-N-[(2S,3R,4Z)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
-
2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
3-(6-phenylhexanoyl)-1,3-oxazolidin-2-one
above, pH and temperature not specified in the publication, 9.4% inhibition at 0.02 mM
3-(cyclopropylmethyl)-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
3-benzoyl-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
3-ethyl-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
3-[4-(cyclohexyloxy)benzoyl]-1,3-oxazolidin-2-one
above, pH and temperature not specified in the publication, 18.3% inhibition at 0.02 mM
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
above, pH and temperature not specified in the publication, 14.7% inhibition at 0.02 mM
3-[6-(4-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
above, pH and temperature not specified in the publication, 4.9% inhibition at 0.02 mM
5-(benzyl(methyl)amino)-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
5-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
5-chloro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
5-cyano-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
5-ethyl-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
5-fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
5-fluoro-N-hexyl-3-(2-methylpropanoyl)-2,4-dioxopyrimidine-1-carboxamide
-
5-fluoro-N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide
-
5-fluoro-N-octyl-2,4-dioxopyrimidine-1-carboxamide
-
5-trifluoromethyl-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
6-(4-fluorophenyl)-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
-
6-(4-fluorophenyl)-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide}
in vivo plasma pharmacokinetic profile in mice, overview
6-bromo-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
6-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
ACER2-specific siRNA
-
-
-
beta-D-octyl glucoside
-
almost complete inhibition at 1.5% (v/v)
C16-ceramide
-
ceramide synthesis activity, 10 mol%, 50% inhibition
C18-ceramide
-
mtCDase, competitive inhibition, IC50: 0.62 mol%
C6-urea-ceramide
an nCDase inhibitor
cardiolipin
-
inhibits the ceramide synthesis activity: total inhibition at 2.5-5 mol%, activates the ceramidase activity, mechanism
Ceranib-1
-
i.e. 3-(3-(4-methoxyphenyl)acryloyl)-6-methyl-4-phenylquinolin-2(1H)-one
Ceranib-2
-
i.e. 3-[3-(4-methoxyphenyl)acryloyl]-4-phenyl-1H-quinolin-2-one
cholesterol
-
0.08 mM or below, decreases the hydrolysis of ceramide by a maximum of two-thirds
cis-D-erythro-sphingosine
-
mtCDase, weak inhibition
CuCl2
-
ceramide synthesis activity, 1 mM, total inhibition
D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
D-erythro-dehydrosphingosine
-
mtCDase, IC50: 0.25 mol%
D-erythro-sphinganine
-
mtCDase, IC50: 0.2 mol%
D-erythro-urea-C16-ceramide
-
mtCDase, competitive inhibition, IC50: 0.33 mol%
D-threo-ceramide
-
mt-CDase, IC50: 0.21 mol%
di-isopropyl fluorophosphate
dihydrosphingosine
-
inhibits enzyme activity by up to 40% at 0.25 mM
DL-sphinganine
recombinant CDase
ethyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
Fe3+
-
almost complete inhibition at 10 mM
isobutyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
L-erythro-ceramide
-
mt-CDase, IC50: 0.26 mol%
L-threo-ceramide
-
mt-CDase, IC50: 0.11 mol%
LCL521
a lysosomotropic prodrug inhibitor of acid ceramidase, inhibition in vivo leads to decreased cell viability
lysophosphatidic acid
-
isoenzyme I only
lysophosphatidylcholine
-
ceramide synthesis activity, 10 mol%, moderate inhibition
methyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
methyl 5-fluoro-3-(octylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
myristaldehyde
-
competitively inhibits the ceramide synthesis activity, 2.5-3 mol%, about 50% inhibition
N,N-dimethyl-D-erythro-sphingosine
-
mtCDase, weak inhibition
N-(2-hydroxy-2-phenylethyl)dodecane-1-sulfonamide
-
N-(2-hydroxy-2-phenylethyl)tetradecanamide
N-bromosuccinimide
-
modification of Trp completely inhibits forward and reverse reaction
N-butyl-2,4-dioxopyrimidine-1-carboxamide
-
N-heptyl-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
N-hexyl-2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidine-1(2H)-carboxamide
-
N-hexyl-2,4-dioxo-5-phenylpyrimidine-1-carboxamide
-
N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
N-hexyl-2,4-dioxohexahydropyrimidine-1-carboxamide
-
N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-5,6-dimethyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
N-hexyl-5-(4-methylpiperazin-1-yl)-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-5-(hydroxymethyl)-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-5-bromo-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-5-iodo-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-5-methoxy-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
N-hexyl-5-methyl-2,4-dioxo-pyrimidine-1-carboxamide
N-hexyl-5-methylamino-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-5-morpholino-2,4-dioxopyrimidine-1-carboxamide
-
N-hexyl-N-methyl-2,4-dioxopyrimidine-1-carboxamide
-
N-methyl-D-erythro-sphingosine
-
mtCDase, IC50: 0.13 mol%
N-nonyl-2,4-dioxopyrimidine-1-carboxamide
-
N-octyl-2,4-dioxo-5-(trifluoromethyl)pyrimidine-1-carboxamide
-
N-octyl-2,4-dioxopyrimidine-1-carboxamide
-
N-pentyl-2,4-dioxopyrimidine-1-carboxamide
-
N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]-12-(dimethylamino)dodecanamide
-
N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]dodecane-1-sulfonamide
-
N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]tridecan-1-aminium chloride
-
N-[(1R,2R)-1,3-dihydroxy-1-phenylpropan-2-yl]tridecan-1-aminium chloride
-
N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-12-(1-methylhydrazinyl)dodecanamide
-
N-[(1S,2R)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]dodecane-1-sulfonamide
-
N-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]tetradecanamide
-
N-[(2R)-2-hydroxy-2-(pyridin-3-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
-
N-[(2R)-2-hydroxy-2-(pyridin-4-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
-
N-[(2S 3R)-1,3-dihydroxyoctadecan-2-yl]3-methyl-2-butenamide.
-
N-[(2S)-2-hydroxy-2-(4-methylphenyl)ethyl]tetradecanamide
-
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2,2-dibromoacetamide
strong inhibition
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2-bromoacetamide
strong inhibition
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2-methylacrylamide
strong inhibition
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]acrylamide
-
N-[(2S,3R,4E)-14-azido-1,3-dihydroxytetradec-4-en-2-yl]-2-bromoacetamide
-
N-[2-(4-butylphenyl)-2-hydroxyethyl]tetradecanamide
-
N-[2-(4-ethylphenyl)-2-hydroxyethyl]tetradecanamide
-
N-[2-(4-fluorophenyl)-2-hydroxyethyl]tetradecanamide
-
N-[2-(4-tert-butylphenyl)-2-hydroxyethyl]tetradecanamide
-
N-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(3-methoxyphenyl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(3-methylphenyl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(4-methylphenyl)ethyl]dodecane-1-sulfonamide
-
N-[2-hydroxy-2-(4-methylphenyl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(4-propylphenyl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(pyridin-3-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
-
N-[2-hydroxy-2-(pyridin-3-yl)ethyl]dodecane-1-sulfonamide
-
N-[2-hydroxy-2-(pyridin-3-yl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(pyridin-4-yl)ethyl]dodecane-1-sulfonamide
-
N-[2-hydroxy-2-(pyridin-4-yl)ethyl]tetradecanamide
palmitaldehyde
-
ceramide synthesis activity, 2.5-3 mol%, about 50% inhibition
phorbol myristate acetate
-
phorbol myristate acetate, PMA, decreases the expression of ACER2 in HeLa cells
phosphate
80% inhibition at 100 mM
phosphatidylglycerol
-
ceramide synthesis activity, 10 mol%, moderate inhibition
SABRAC
an acid ceramidase inhibitor
sodium cholate
-
ceramide synthesis
ZnCl2
-
ceramide synthesis activity, 1 mM, total inhibition
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
potent inhibitor of acid ceramidase
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
-
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
the efficacy of (1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol in vitro as well as in intact cells can be enhanced by suitable modification of functional groups; the efficacy of the inhibitor in vitro as well as in intact cells can be enhanced by suitable modification of functional groups
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
-
(1R,2R)-2-N-myristoylamino-1-(4-nitrophenyl)-1,3-propandiol
-
-
(1R,2R)-2-N-myristoylamino-1-(4-nitrophenyl)-1,3-propandiol
-
-
(1S,2R)-2-N-myristoylamino-1-phenyl-1-propanol
-
-
(1S,2R)-2-N-myristoylamino-1-phenyl-1-propanol
-
-
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
-
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
i.e. D-e-MAPP, an alkaline ceramidase inhibitor, that potently and specifically inhibits ACER1, ACER2, and ACER3 activity
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
inhibits in vitro
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
i.e. D-e-MAPP, an alkaline ceramidase inhibitor, that potently and specifically inhibits ACER activity
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
1-hexylcarbamoyl-5-fluorouracil
i.e. carmofur
1-hexylcarbamoyl-5-fluorouracil
i.e. carmofur
1R,2R-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
-
-
1R,2R-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
-
-
1S,2S-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
-
-
1S,2S-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
-
-
2-mercaptoethanol
-
2-mercaptoethanol
-
inhibits both ceramidase and ceramide synthesis activity
2-mercaptoethanol
-
more than 50% inhibition at 100 mM
2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
-
2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
-
5-chloro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
-
5-chloro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
-
5-trifluoromethyl-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
-
5-trifluoromethyl-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
-
6-bromo-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
-
6-bromo-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
-
Ca2+
15% inhibition at 5 mM
Ca2+
-
about 70% residual activity at 5 mM
carmofur
a drug used in treatment of colorectal cancers and a potent in vivo active inhibitor of intracellular acid ceramidase activity. The potent noncompetitive inhibitor enzyme inhibitor has is anti-proliferative effects. Carmofur inhibits acid ceramidase and increases ceramide levels in human SW403 and LNCaP cells
carmofur
a specific ASAH1 inhibitor, inhibition by carmofur contributes to cytotoxicity
carmofur
a drug used in treatment of human colorectal cancers and a potent noncompetitive inhibitor in vivo active inhibitor of intracellular acid ceramidase activity
CHAPS
-
20 mM, 50% inhibition
CHAPS
inhibits in vitro neutral ceramidase activity
Cu2+
-
-
Cu2+
inhibitor of neutral ceramidase
Cu2+
1 mM, 60% inhibition, inhibits in a dose-dependent manner
Cu2+
80% inhibition of 112 kDa CDase from kidney
Cu2+
-
over 80% inhibition at 0.2 mM, reversible by EDTA
Cu2+
-
about 80% inhibition at 10 mM
D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
inhibitor of alkaline ceramidase
D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
inhibitor of alkaline ceramidase
D-erythro-sphingosine
recombinant CDase, more inhibitory than L-erythro-sphingosine
D-erythro-sphingosine
-
IC50: 0.04 mol%, mt-CDase is inhibited by all stereoisomers of sphingosine with IC50 ranging from 0.04 to 0.14 mol%
desipramine
-
acid ceramidase
desipramine
inhibitor of acid ceramidase
di-isopropyl fluorophosphate
the substrate protects against inhibition
di-isopropyl fluorophosphate
the substrate protects against inhibition
dithiothreitol
-
dithiothreitol
-
inhibits both ceramidase and ceramide synthesis activity
dithiothreitol
-
80% inhibition at 100 mM
EDTA
-
at 10 mM
EDTA
recombinant CDase, complete inhibition, Ca2+ restores activity
EDTA
-
about 60% residual activity at 1 mM
EGTA
-
-
EGTA
recombinant CDase, complete inhibition, Ca2+ restores activity
Fe2+
-
Fe2+
inhibitor of neutral ceramidase
Fe2+
-
about 50% residual activity at 5 mM
glycodeoxycholate
-
-
glycodeoxycholate
inhibits in vitro neutral ceramidase activity
Hg2+
50% inhibition at 5 mM
Hg2+
complete inhibition of 112 kDa CDase from kidney
Hg2+
-
complete inhibition at 1 mM
L-erythro-sphingosine
recombinant CDase, 0.02 mM, 20% inhibition, less inhibitory than L-erythro-sphingosine
L-erythro-sphingosine
-
competitive inhibitor of ceramide synthesis activity
LCL385
-
-
LCL385
inhibitor of acid ceramidase
Mg2+
10% inhibition at 5 mM
Mg2+
-
about 72% residual activity at 5 mM
Mn2+
25-30% inhibition at 5 mM
Mn2+
1 mM, 10% inhibition, inhibits in a dose-dependent manner
Mn2+
-
about 90% residual activity at 5 mM
N-(2-hydroxy-2-phenylethyl)tetradecanamide
-
N-(2-hydroxy-2-phenylethyl)tetradecanamide
-
N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
-
N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
-
N-hexyl-5-methyl-2,4-dioxo-pyrimidine-1-carboxamide
-
N-hexyl-5-methyl-2,4-dioxo-pyrimidine-1-carboxamide
-
N-oleoylethanolamine
-
specific inhibition of acid ceramidase
N-oleoylethanolamine
low potency, inhibitor of acid ceramidase
N-oleoylethanolamine
-
inhibitor of acid ceramidase
N-oleoylethanolamine
-
inhibitor of acid ceramidase
N-[2-hydroxy-2-(pyridin-4-yl)ethyl]tetradecanamide
-
N-[2-hydroxy-2-(pyridin-4-yl)ethyl]tetradecanamide
-
oleoylethanolamide
i.e. N-oleylethanolamine; i.e. N-oleylethanolamine
oleoylethanolamide
i.e. N-oleylethanolamine; i.e. N-oleylethanolamine
oleoylethanolamide
i.e. N-oleylethanolamine, inhibits in vitro
phosphatidic acid
-
complete inhibition
phosphatidic acid
-
ceramide synthesis activity, 2.5-5 mol%, total inhibition
phosphatidylcholine
-
complete inhibition
phosphatidylcholine
inhibitor of alkaline ceramidase; inhibitor of alkaline ceramidase; inhibitor of neutral ceramidase
phosphatidylcholine
-
ceramide synthesis activity, 10 mol%, moderate inhibition
phosphatidylserine
-
complete inhibition
phosphatidylserine
-
ceramide synthesis activity, 10 mol%, moderate inhibition
phytosphingosine
-
-
phytosphingosine
recombinant CDase, 0.02 mM, 60% inhibition
siRNA
-
-
-
sphinganine
-
-
sphingomyelin
-
-
sphingomyelin
-
ceramide synthesis activity, 5 mol%, 50% inhibition
sphingosine
-
-
sphingosine
product inhibition in a dose-dependent manner, IC50: 0.08 mM
sphingosine
strong inhibitor
sphingosine
-
and sphingosine analogues
taurocholate
-
20 mM, 50% inhibition
taurocholate
inhibits in vitro neutral ceramidase activity
taurodeoxycholate
-
-
taurodeoxycholate
inhibits in vitro neutral ceramidase activity
taurodeoxycholate
-
ceramide synthesis
TMP
-
-
TMP
-
more than 95% inhibition at 12 mM
Triton X-100
-
-
Triton X-100
2fold activation at 0.1-0.2%, but inhibitory beyond the optimum concentration
UMP
-
-
UMP
-
more than 95% inhibition at 12 mM
urea-hexanoyl-ceramide
-
-
urea-hexanoyl-ceramide
-
-
Zn2+
-
-
Zn2+
inhibitor of neutral ceramidase
Zn2+
1 mM, 60% inhibition, inhibits in a dose-dependent manner
Zn2+
80% inhibition of 112 kDa CDase from kidney
Zn2+
-
over 90% inhibition at 0.2 mM, reversible by EDTA
Zn2+
-
about 87% residual activity at 5 mM
additional information
-
no inhibition by phosphatidylethanolamine, phosphatidylinositol, phosphatidylglycerol
-
additional information
no inhibition by protease inhibitors such as aprotinin, PMSF, leupeptin, and pepstatin
-
additional information
-
no inhibition by protease inhibitors such as aprotinin, PMSF, leupeptin, and pepstatin
-
additional information
-
desipramine downregulates acid ceramidase in cancer cells, which is almost completely reversible by leupeptin and CA074ME, but not by pepstatin A, mechanism, overview
-
additional information
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cellular ACER2 activity is inhibited by depletion of Ca2+ from Golgi lumen
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all stereoisomers of D-erythro-ceramide and sphingosine (L-threo, D-threo, and L-erythro isomers), N-methyl-D-erythro-sphingosine and D-erythro-urea-C16-ceramide show significant inhibitory effects on neural ceramidase; N-methyl ceramide, 1-O-methyl ceramide, cis-D-erythro ceramide or N,N-dimethyl-D-erythrosphingosine have no effect on neutral ceramidase
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additional information
all stereoisomers of D-erythro-ceramide and sphingosine (L-threo, D-threo, and L-erythro isomers), N-methyl-D-erythro-sphingosine and D-erythro-urea-C16-ceramide show significant inhibitory effects on neural ceramidase; N-methyl ceramide, 1-O-methyl ceramide, cis-D-erythro ceramide or N,N-dimethyl-D-erythrosphingosine have no effect on neutral ceramidase
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additional information
all stereoisomers of D-erythro-ceramide and sphingosine (L-threo, D-threo, and L-erythro isomers), N-methyl-D-erythro-sphingosine and D-erythro-urea-C16-ceramide show significant inhibitory effects on neural ceramidase; N-methyl ceramide, 1-O-methyl ceramide, cis-D-erythro ceramide or N,N-dimethyl-D-erythrosphingosine have no effect on neutral ceramidase
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additional information
all stereoisomers of D-erythro-ceramide and sphingosine (L-threo, D-threo, and L-erythro isomers), N-methyl-D-erythro-sphingosine and D-erythro-urea-C16-ceramide show significant inhibitory effects on neural ceramidase; N-methyl ceramide, 1-O-methyl ceramide, cis-D-erythro ceramide or N,N-dimethyl-D-erythrosphingosine have no effect on neutral ceramidase
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DMAPP has no affect on ceramidase activity up to at least 0.3 mM. N-oleoylethanolamine has no affect on ceramidase activity
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a class of benzoxazolone carboxamides act as the first potent and systemically active inhibitors of the acid ceramidase. Prototype members of this class inhibit the enzyme with low nanomolar potency by covalent binding to the catalytic cysteine. No inhibition by N-methyl-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide, 4-phenylbutyl 2-oxo-1,3-benzoxazole-3(2H)-carboxylate, and 3-(6-phenylhexanoyl)-1,3-benzoxazol-2(3H)-one, while 2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carbothioamide is unstable
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amide- and sulfonamide-based compounds as potential inhibitors of ceramidases, synthesis and inhibitory potencies, overview. The hydrophobicity and the steric effects of longer alkyl chains (n-Pr, n-Bu or t-Bu groups) at the phenyl ring are important for an enhanced selectivity towards acid ceramidase over neutral ceramidase
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amide- and sulfonamide-based compounds as potential inhibitors of ceramidases, synthesis and inhibitory potencies, overview. The hydrophobicity and the steric effects of longer alkyl chains (n-Pr, n-Bu or t-Bu groups) at the phenyl ring are important for an enhanced selectivity towards acid ceramidase over neutral ceramidase
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structural modification of the known ceramidase inhibitors (1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol and N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]-12-(dimethylamino)dodecanamide generates more potent ceramidase inhibitors that are active in intact cells and not only elevates the cellular ceramide levels, but also enhances cell death
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structural modification of the known ceramidase inhibitors (1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol and N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]-12-(dimethylamino)dodecanamide generates more potent ceramidase inhibitors that are active in intact cells and not only elevates the cellular ceramide levels, but also enhances cell death
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modifications in the chemical scaffold of carmofur yield acid ceramidase inhibitors that act synergistically with standard antitumoral drugs to prevent cancer cell proliferation, design of chemosensitizing agents, overview
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modifications in the chemical scaffold of carmofur yield acid ceramidase inhibitors that act synergistically with standard antitumoral drugs to prevent cancer cell proliferation, design of chemosensitizing agents, overview
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synthesis of several analogues of SABRAC that are potent irreversible enzyme inhibitors by reaction with the active site Cys143, fluorescent SABRAC analogues are used for enzyme detection
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not inhibited by Mg2+, phytosphingosine, dihydrosphingosine
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not inhibited by Mg2+, phytosphingosine, dihydrosphingosine
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desipramine downregulates the enzyme in fibroblasts
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additional information
a class of benzoxazolone carboxamides act as the first potent and systemically active inhibitors of the acid ceramidase. Prototype members of this class inhibit the enzyme with low nanomolar potency by covalent binding to the catalytic cysteine. No inhibition by N-methyl-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide, 4-phenylbutyl 2-oxo-1,3-benzoxazole-3(2H)-carboxylate, and 3-(6-phenylhexanoyl)-1,3-benzoxazol-2(3H)-one, while 2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carbothioamide is unstable
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not inhibited by 1 mM iodoacetic acid, 0.1 mM 2-mercaptoethanol, 0.05 mM hexadecylsulfonylfluoride, 1 mM p-phenylmethylsulfonylfluoride, 0.2 mM D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol, 0.5 mM N-oleoylethanolamine, L(-)- and D(-)-norephenedrin
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not inhibited by N-methyl-hexadecanoyl-ceramide, 1-O-methyl-hexadecanoyl-ceramide, 3-O-methyl-hexadecanoyl-ceramide, cis-D-erythro-hexadecanoyl-ceramide, 3-O-methyl-D-erythro-sphingosine, requirements for inhibition of mtCDase
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the ceramide synthesis activity is not inhibited in vitro and in cells by fuminosin B1, not inhibited by EDTA or ATP, both up to 10 mM
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EDTA, Mn2+ and Mg2+ have little effect on activity of 112 kDa CDase from kidney
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the enzyme is stable to trypsin and chymotrypsin exposure
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no inhibition by protease inhibitors such as aprotinin, PMSF, leupeptin, and pepstatin
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GMP, GDT, GTP, TDP, TTP, UDP, and UTP, ADP and AMP have no significant effects on the enzyme activity. S-1-P has no inhibitory effect
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synthesis and evaluation of a series of 2,4-dioxopyrimidine-1-carboxamides as acid ceramidase enzyme inhibitors, structural features of uracil derivatives that are critical for inhibition, overview. No inhibition by 7 and 27b, while 4o, 26 and 30 are unstable
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the reverse ceramidase activity in microsomes can only be blocked by a lysine residuespecific reagent when the reagent has access to Ypc1p from the lumenal side
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the reverse ceramidase activity in microsomes can only be blocked by a lysine residuespecific reagent when the reagent has access to Ypc1p from the lumenal side
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additional information
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the reverse ceramidase activity in microsomes can only be blocked by a lysine residuespecific reagent when the reagent has access to Ypc1p from the lumenal side
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