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11-trimethylamino-undecanoyl-DL-carnitine
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2-[5(4-chlorophenyl)pentyl]-oxirane-2-carboxyl-CoA
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4-hydroxy phenylglyoxylate
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CPT I, greatly reduced inhibition of protease treated enzyme
arachidonic acid
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the enzymatic activity significantly declines by treatment with 0.1 mM for 1 h
Bile acids
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e.g. in cholestatic rats
cardiolipin
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inhibits conversion of palmitoylcarnitine to palmitoyl-CoA, stimulates palmitoylcarnitine formation
carnitine
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CPT I, slightly
chenodeoxycholic acid
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competitive to carnitine
CoA esters of certain oxirane carboxylic acids
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diethyl dicarbonate
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CPT II, strong, linear pseudo-first order kinetic, modification of a histidine residue, reversible by hydroxylamine, decanoyl-CoA and L-carnitine
Digitonin
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CPTo and slightly CPTi
dinitrophenyl analogue of etomoxir
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i.e. 2[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylic acid, DNP-Et, specific inhibitor for liver L-CPT I, identical with the small isoform of heart CPT I, complete inhibition of L-CPT I, but not M-CPT I
gamma-linolenic acid
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inhibits CPT I in vivo and reduces malonyl-CoA sensitivity, decreases affinity for 16:0 acyl-CoA substrate
H2O2
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the enzymatic activity significantly and reversibly declines by 1 mM H2O2
Hemipalmitoylcarnitinium bromide
L-palmitoylcarnitine
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competitive product inhibition
L-sulfocarnitine
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ability to act as substrate or inhibitor of CPT is dependent on the nature of CPT and on the chain length of the acyl-CoA cosubstrate
malonyl CoA
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a physiological CPT1 inhibitor
nagarse
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mitochondria, malonyl-CoA protects
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Palmitoylcholine
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competitive in the forward reaction to both substrates
propionyl-CoA
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CPT I, inhibition is not affected by proteinase treatment
Ro 25-0187
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CPT I, strong, inhibitory effect is drastically reduced by protease treatment of outer mitochondrial membrane; malonyl-CoA analogue
rotenone
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the enzymatic activity significantly declines by treatment with 0.001 mM for 2 h
S-(4-bromo-2,3-dioxobutyl)-CoA
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inhibition of malonyl-CoA sensitive enzyme, malonyl-CoA insensitive enzyme is not inhibited
Short chain-length fatty acylcarnitine derivatives
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-
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succinyl-CoA
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partial proteolysis of CPT I slightly diminishes the inhibitory effect
thiolcarnitine
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ability to act as substrate or inhibitor of CPT is dependent on the nature of CPT and on chain length of the acyl-CoA cosubstrate
trans-2-hexadecenoyl-CoA
competitive
tumor necrosis factor-alpha
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the enzymatic activity significantly declines by treatment with 25 ng/ml for 30 min
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2-bromopalmitoyl-CoA
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irreversible
2-bromopalmitoyl-CoA
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with addition of carnitine
2-bromopalmitoyl-CoA
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no inhibition
2-bromopalmitoyl-CoA
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irreversible; with addition of carnitine
acetyl-CoA
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-
acetyl-CoA
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CPT I, inhibition is not affected by proteinase treatment
C75-CoA
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potent competitive inhibition, IC50: 0.00025 mM in INS(832/13) cells, IC50: 0.00046 in L6E9 myotubes, binds tightly but reversibly to CPT I, C75 applied in vivo is transformed to C75-CoA and inhibits fatty acid oxidation, e.g. in pancreatic INS(823/13), muscle L6E9, or kidney HEK293 cell lines, inhibition mechanism, overview, molecular model of docking of C75-CoA to L-CPT I
C75-CoA
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potent competitive inhibition, binds tightly but reversibly to CPT I, C75 applied in vivo is transformed to C75-CoA and inhibits fatty acid oxidation, a single intraperitoneal injection of C75 in mice produced short-term inhibition of CPT I activity in mitochondria from the liver, soleus, and pancreas, inhibition mechanism, overview
C75-CoA
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potent competitive inhibition, IC50: 0.0007 mM in liver, IC50: 0.00004 in muscle, IC50: 0.00024 mM recombinant isozyme L-CPT I, IC50: 0.00036 recombinant isozyme M-CPT I, binds tightly but reversibly to CPT I, C75 applied in vivo is transformed to C75-CoA and inhibits fatty acid oxidation, inhibition mechanism, overview, molecular model of docking of C75-CoA to L-CPT I
CoA
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CoA
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CPT I, inhibition is not affected by proteinase treatment
CoA esters of certain oxirane carboxylic acids
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irreversible, CPT I but not CPT II
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CoA esters of certain oxirane carboxylic acids
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irreversible, CPT I but not CPT II
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CoA esters of certain oxirane carboxylic acids
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irreversible, CPT I but not CPT II
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CoA esters of certain oxirane carboxylic acids
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irreversible, CPT I but not CPT II
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etomoxir
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etomoxir
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etomoxir is a racemate of two optically active phenoxyalkyloxirane carboxylic acid ethyl esters, of which only the (+), but not the (-)-enantiomer, inhibits CPT-I
etomoxir
high concentrations of etomoxir (200 microM) have an off-target effect of inhibiting complex I of the electron transport chain. When fatty acid oxidation is reduced approximately 90% by low concentrations of etomoxir, the proliferation rate of various cancer cells is unaffected
etomoxir
regional differences in brain fatty acid oxidation may be blocked by irreversible CPT1a inhibitor etomoxir; regional differences in brain fatty acid oxidation may be blocked by irreversible CPT1a inhibitor etomoxir
etomoxiryl-CoA
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IC50: 0.00121 mM in INS(832/13) cells, IC50: 0.00287 in L6E9 myotubes
etomoxiryl-CoA
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IC50: 0.00025 mM in liver, IC50: 0.000015 in muscle, IC50: 0.0041 mM recombinant isozyme L-CPT I, IC50: 0.0031 recombinant isozyme M-CPT I
Hemipalmitoylcarnitinium bromide
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competitve to palmitoyl-carnitine in the reverse reaction; i.e. HPC, 2S,6R:2R,6S-6-carboxymethyl-2-hydroxy-2-pentadecyl-4,4-dimethylmorpholinium bromide
Hemipalmitoylcarnitinium bromide
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CPT I, strong, active-site-directed, inhibition not altered by protease treatment; i.e. HPC, 2S,6R:2R,6S-6-carboxymethyl-2-hydroxy-2-pentadecyl-4,4-dimethylmorpholinium bromide
L-aminocarnitine
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inhibition of CPT II not CPT I
L-aminocarnitine
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ability to act as substrate or inhibitor of CPT is dependent on the nature of CPT and on the chain length of the acyl-CoA cosubstrate
malonyl-CoA
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no inhibition
malonyl-CoA
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inhibition of soluble peroxisomal form, no inhibition of enzyme from inner mitochondrial membrane
malonyl-CoA
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CPT II not inhibited; mitochondrial isozyme CPT I, sensitivity against malonyl-CoA is mediated by a 86 kDa malonyl-CoA binding protein complexed with CPT and other proteins of the beta-oxidation, detergent and salt sensitive
malonyl-CoA
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Triton X-100 protects
malonyl-CoA
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no inhibition
malonyl-CoA
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CPT I; CPT II not inhibited; reversible inhibition
malonyl-CoA
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CPT II not inhibited; CPT I, native and reconstituted in phospholipid micelles
malonyl-CoA
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CPT I; isoforms L-CPT I and M-CPT I
malonyl-CoA
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CPT I; CPT II not inhibited; regulatory role in vivo
malonyl-CoA
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inhibits CPT I not CPT II; isoforms L-CPT I and M-CPT I
malonyl-CoA
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Glu3, Leu23, and Ser24 in M-CPTI are important for malonyl-CoA inhibition and binding but not for calalysis. IC50: 0.00007 mM for wild-type enzyme, 0.01 mM for mutant enzyme E3A, 0.00015 for mutant enzyme H5A, 0.01 mM for mutant enzyme E3A/V19A/L23A/S24A, 0.0068 mM for mutant enzyme E3A/H5A/V19A/L23A/S24A
malonyl-CoA
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the activity of CPT I is largely controlled by cytosolic levels of its biological inhibitor malonyl-CoA, being a key regulator of fatty acid partitioning in skeletal muscle by virtue of its ability to inhibit CPT I
malonyl-CoA
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allosteric inhibition
malonyl-CoA
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has a regulatory role in vivo
malonyl-CoA
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IC50: 0.0005 mM for the recombinant wild-type enzyme, IC50: 0.00052 mM for the recombinant revertant A305C, IC50 values of recombinant mutant isozymes M-CPT I, overview
malonyl-CoA
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IC50: 0.0073 mM for the recombinant wild-type isozyme CPT1A, IC50: 0.0384 mM for CPT1A mutant R243T, IC50 values of other mutants, overview, determination of two binding sites, the A site and the O site, the latter involved residue Arg243, binding structure, interactions between N- and C-terminal residues are involved in malonyl-CoA binding to the A site, isozyme CPT1A in malonyl-CoA molecular docking, overview
malonyl-CoA
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CPT I; CPT II not inhibited; reversible inhibition
malonyl-CoA
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CPT I; isoforms L-CPT I and M-CPT I
malonyl-CoA
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allosteric inhibition
malonyl-CoA
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CPT I; regulatory role in vivo
malonyl-CoA
IC50 for wild-type L-CPT-1 is 0.0298 mM; IC50 for wild-type M-CPT-1 is 0.010 mM
malonyl-CoA
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inhibits CPT I not CPT II; regulatory role in vivo
malonyl-CoA
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CPT I; CPT II not inhibited; reversible inhibition
malonyl-CoA
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similar inhibition of wild-type CPT I and mutants A381D and H473A
malonyl-CoA
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benzyl alcohol, isoamyl alcohol and 2-(2-methoxyethoxy)ethyl-8-(cis-2-n-octylpropyl)octanoate decrease the ability of malonyl-CoA to inhibit CPT I; inhibition is temperature dependent
malonyl-CoA
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mitochondrial isozyme CPT I, sensitivity against malonyl-CoA is mediated by a 86 kDa malonyl-CoA binding protein complexed with CPT and other proteins of the beta-oxidation, detergent and salt sensitive
malonyl-CoA
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a malonyl-CoA insensitive enzyme and a malonyl-CoA sensitive enzyme; enzyme from liver mitochondrial inner membrane becomes inhibitable by malonyl-CoA if reconstituted with outer membrane malonyl-CoA binding protein; mitochondrial isozyme CPT I, sensitivity against malonyl-CoA is mediated by a 86 kDa malonyl-CoA binding protein complexed with CPT and other proteins of the beta-oxidation, detergent and salt sensitive; no inhibition
malonyl-CoA
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mitochondrial isozyme CPT I, sensitivity against malonyl-CoA is mediated by a 86 kDa malonyl-CoA binding protein complexed with CPT and other proteins of the beta-oxidation, detergent and salt sensitive; regulatory role in vivo
malonyl-CoA
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CPT I; regulatory role in vivo
malonyl-CoA
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differences in sensitivity of hepatic and heart enzyme
malonyl-CoA
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CPT I; inhibition is very pH-dependent: malonyl-CoA concentrations causing 50% inhibition at pH 6.0, 6.5, 7.0, 7.5 and 8.0 are 0.00004, 0.001, 0.009, 0.04 and 0.2 mM, respectively
malonyl-CoA
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reversible inhibition
malonyl-CoA
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CPT I; CPT II not inhibited; reversible inhibition
malonyl-CoA
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a malonyl-CoA insensitive enzyme and a malonyl-CoA sensitive enzyme
malonyl-CoA
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inhibition of isoform L-CPT I is increased by 2[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylic acid
malonyl-CoA
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partial proteolysis of CPT I greatly diminishes the inhibitory effect
malonyl-CoA
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inhibition is pH-dependent; inhibition is temperature dependent
malonyl-CoA
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CPT I; CPT I catalytic activity and malonyl-CoA sensitivity is located on 1 single polypeptide; CPT II not inhibited; recombinant CPT I is highly sensitive, recombinant CPT II not
malonyl-CoA
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CPT I; isoforms L-CPT I and M-CPT I
malonyl-CoA
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L-CPT I, recombinant enzyme from Saccharomyces cerevisiae is inhibited only in intact mitochondria, not as solubilized enzyme
malonyl-CoA
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overview: recombinant chimeric proteins of L-CPT I and M-CPT I
malonyl-CoA
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differences in sensitivity of hepatic and heart enzyme; inhibits CPT I not CPT II; isoforms L-CPT I and M-CPT I
malonyl-CoA
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CPT I, sensitivity is reduced in vivo during gamma-linolenic acid treatment; membrane or micelle composition and properties influence the sensitivity of CPT I to inhibition
malonyl-CoA
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sensitivity to inhibition of deletion and chimeric L-CPT I mutants
malonyl-CoA
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CPT I; membrane or micelle composition and properties influence the sensitivity of CPT I to inhibition; regulatory role in vivo
malonyl-CoA
IC50: 0.00339 mM for wild-type enzyme, 0.00021 mM for mutant enzyme E590A, 0.00039 mM for mutant enzyme E590Q, 0.00025 mM for mutant enzyme E590K
malonyl-CoA
IC50: 0.0123 for wild-type enzyme, 0.015 mM for mutant enzyme T314S, 0.0087 mM for mutant enzyme N464D, 0.0395 mM for mutant enzyme A478G, 0.0275 mM for mutant enzyme C608A, 0.319 mM for mutant enzyme M593 mM, 0.155 mM for mutant enzyme M593A, 0.22 mM for mutant enzyme M593E
malonyl-CoA
phosphorylation of the CKII site in the C-terminal end of CPT-I leads to decreased malonyl-CoA sensitivity
malonyl-CoA
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allosteric inhibition
malonyl-CoA
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has a regulatory role in vivo
malonyl-CoA
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CPT I; CPT I, inhibition depends on age; inhibition is temperature dependent; regulatory role in vivo
malonyl-CoA
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sensitivity to inhibition of deletion and chimeric L-CPT I mutants
malonyl-CoA
complete inhibition at 0.05 mM; complete inhibition at 0.05 mM; complete inhibition at 0.05 mM; complete inhibition at 0.05 mM
methylmalonyl-CoA
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inhibits sheep liver CPT I, no inhibition of rat liver and guinea-pig liver mitochondrial CPT I
methylmalonyl-CoA
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CPT I
methylmalonyl-CoA
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inhibits sheep liver CPT I, no inhibition of rat liver and guinea-pig liver mitochondrial CPT I
methylmalonyl-CoA
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inhibits sheep liver CPT I, no inhibition of rat liver and guinea-pig liver mitochondrial CPT I
methylmalonyl-CoA
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partial proteolysis of CPT I slightly diminishes the inhibitory effect
octyl glucoside
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with octanoyl-CoA as substrate, competitive
octyl glucoside
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complete loss of CPT I activity, no loss of CPT II activity
octyl glucoside
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complete loss of CPT I activity, no loss of CPT II activity
octyl glucoside
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complete loss of CPT I activity, no loss of CPT II activity
octyl glucoside
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only CPTo
octyl glucoside
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complete loss of CPT I activity, no loss of CPT II activity
oxfenicine
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-
palmitoyl-CoA
thermally destabilizes bith wild-type and mutant S113L
palmitoyl-CoA
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product inhibition, reverse reaction
palmitoyl-CoA
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substrate inhibition
palmitoyl-CoA
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CPT I, slightly
tetradecylglycidyl-CoA
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CPTo
tetradecylglycidyl-CoA
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and analogues, irreversible
Triton X-100
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mutant CPT
Triton X-100
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erythrocyte enzyme is not affected
Triton X-100
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complete loss of CPT I activity, no loss of CPT II activity
Triton X-100
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recombinant CPT I, complete inactivation at 5%, at least partly reversible
Triton X-100
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complete loss of CPT I activity, no loss of CPT II activity
Triton X-100
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complete loss of CPT I activity, no loss of CPT II activity
Triton X-100
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complete loss of CPT I activity, no loss of CPT II activity
Trypsin
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peroxisomal and mitochondrial isozymes
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Trypsin
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mitochondria, malonyl-CoA protects
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Tween 20
-
-
Tween 20
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only CPTo at 2% and above
additional information
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different sites of inhibition of carnitine palmitoyltransferase by malonyl-CoA, acetyl-CoA and CoA
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additional information
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physiological role of malonyl-CoA in the heart
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additional information
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enzyme inhibitors are used to shift the heart's reliance away from fatty acid oxidation to glucose as energy source to increase cardiac efficiency, overview
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additional information
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no inhibition by choline, hemiacetylcarnitinium
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additional information
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CPT I, 2 independent binding sites for acyl-CoA inhibitors and regulation of fatty acid oxidation, the malonyl-CoA site is located on the cytoplasmic face of the outer mitochondrial membrane, the site for monocarboxylic acids and free CoA is located in the mitochondrial intermembrane space
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additional information
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physiological role of malonyl-CoA in the heart
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additional information
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L-CPT I behaves like a natural chimera of M-CPT I and L-CPT I due to malonyl-CoA sensitivity and Km values compared to the enzymes of other organisms
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