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2'-deoxy-AMP
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decreased IMP cyclohydrolase activity by 10-50%
2,2-dioxo-1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one
construction of 1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxide, the corresponding nucleoside, and the nucleoside monophosphate, as mimics of the tetrahedral intermediate in the cyclization reaction. All compounds are competitive inhibitors against IMPCH, but the simpler heterocycle has a completely different IMPCH binding mode, compared to the nucleosides, and is relocated to the phosphate binding pocket, the aromatic imidazole ring interacts with a helix dipole, inhibitor synthesis, binding structure, and mechanism of inhibition, overview
2-chloroinosine 5'-monophosphate
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potent inhibitor
2-flouroinosine 5'-monophosphate
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IC50-value in cell culture 0.0049 mM; potent inhibitor
2-fluoroadenine arabinoside 5'-monophosphate
2-mercaptoinosine 5'-monophosphate
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most potent competitive inhibitor, precursor of GMP in the purine pathway
5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside
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decreased IMP cyclohydrolase activity by 10-50%
6-mercaptopurine riboside 5'-monophosphate
7-(3,4-dihydroxy-5-hydroxymethyltetrahydrofuran-2-yl)-2,2-dioxo-1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one
construction of 1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxide, the corresponding nucleoside, and the nucleoside monophosphate, as mimics of the tetrahedral intermediate in the cyclization reaction. All compounds are competitive inhibitors against IMPCH, but the simpler heterocycle has a completely different IMPCH binding mode, compared to the nucleosides, and is relocated to the phosphate binding pocket, the aromatic imidazole ring interacts with a helix dipole, inhibitor synthesis, binding structure, and mechanism of inhibition, overview
adenosine N1-oxide 5'-monophosphate
AMP
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decreased IMP cyclohydrolase activity by 10-50%
GMP
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decreased IMP cyclohydrolase activity by 10-50%
N-succino-AMP
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decreased IMP cyclohydrolase activity by 10-50%
N2-acetyl-2'deoxyguanosine 5'-monophosphate
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decreased IMP cyclohydrolase activity by 10-50%
N6-(carboxymethyl)adenosine 5'-monophosphate
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strong competitive inhibitor
phosphoric acid mono-[3,4-dihydroxy-5-(2,2,4-trioxo-1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-7-yl)tetrahydrofuran-2-yl]methyl ester
construction of 1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxide, the corresponding nucleoside, and the nucleoside monophosphate, as mimics of the tetrahedral intermediate in the cyclization reaction. All compounds are competitive inhibitors against IMPCH, but the simpler heterocycle has a completely different IMPCH binding mode, compared to the nucleosides, and is relocated to the phosphate binding pocket, the aromatic imidazole ring interacts with a helix dipole, inhibitor synthesis, binding structure, and mechanism of inhibition, overview
xanthosine 5'-monophosphate
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strong competitive inhibitor
2-fluoroadenine arabinoside 5'-monophosphate
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IC50-value in cell culture 0.0002 mM; strong competitive inhibitor, derivative of anti-cancer drug
2-fluoroadenine arabinoside 5'-monophosphate
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strong competitive inhibitor, derivative of anti-cancer drug
6-mercaptopurine riboside 5'-monophosphate
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IC50-value in cell culture 0.0075 mM; strong competitive inhibitor, derivative of anti-cancer drug
6-mercaptopurine riboside 5'-monophosphate
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strong competitive inhibitor, derivative of anti-cancer drug
adenosine N1-oxide 5'-monophosphate
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IC50-value in cell culture 0.0011 microM; strong competitive inhibitor
adenosine N1-oxide 5'-monophosphate
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strong competitive inhibitor
IMP
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minor 5% IMP contaminant in the substrate found to have no effects on the inosinicase assay
IMP
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decreased IMP cyclohydrolase activity by 10-50%
additional information
not inhibitory: EDTA at 2 mM, iodoacetamide at 20mM, XMP, at 0.05 mM, IMP, at 0.02 mM
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additional information
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not inhibitory: EDTA at 2 mM, iodoacetamide at 20mM, XMP, at 0.05 mM, IMP, at 0.02 mM
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