Literature summary for 4.2.1.1 extracted from

Winum, J.Y.; Vullo, D.; Casini, A.; Montero, J.L.; Scozzafava, A.; Supuran, C.T.
Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors (2003), J. Med. Chem., 46, 2197-2204.

Application

Application	Comment	Organism
medicine	design of novel antitumor properties, mainly for hypoxic tumors that overexpress CA IX	Homo sapiens

Cloned(Commentary)

Cloned (Comment)	Organism
CA I and CA II cDNA expressed in Escherichia coli BL21 (DE3), cDNA hCA IX PCR amplified	Homo sapiens

Inhibitors

Inhibitors	Comment	Organism
1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose 6-sulfamate	-	Homo sapiens
1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose 3-sulfamate	-	Homo sapiens
2,4,6-trichlorophenyl sulfamate	-	Homo sapiens
2-naphthyl sulfamate	-	Homo sapiens
2-naphthylsulfamate	-	Homo sapiens
3-methylphenylsulfamate	-	Homo sapiens
4-acetylamidophenyl sulfamate	-	Homo sapiens
4-bromophenyl sulfamate	-	Homo sapiens
4-chlorophenyl sulfamate	best CA IX inhibitor	Homo sapiens
4-cyanophenyl sulfamate	-	Homo sapiens
4-iodophenyl sulfamate	-	Homo sapiens
4-methoxyphenyl sulfamate	-	Homo sapiens
4-methylphenyl sulfamate	-	Homo sapiens
4-nitrophenyl sulfamate	-	Homo sapiens
4-phenoxyphenyl sulfamate	-	Homo sapiens
4-phenylphenyl sulfamate	-	Homo sapiens
4-t-butylphenyl sulfamate	-	Homo sapiens
4-trichloromethylphenyl sulfamate	-	Homo sapiens
5-pentylresorcinylsulfamate	-	Homo sapiens
acetazolamide	-	Homo sapiens
dehydroepiandrosterone sulfamate	-	Homo sapiens
EMATE	-	Homo sapiens
estradiol 17 beta-sulfamate	-	Homo sapiens
estradiol 3,17 beta-disulfamate	CA II inhibitor	Homo sapiens
estrone sulfamate	-	Homo sapiens
ethoxzolamide	-	Homo sapiens
methazolamide	-	Homo sapiens
n-octyl sulfamate	-	Homo sapiens
pentachlorophenyl sulfamate	-	Homo sapiens
pentafluorophenyl sulfamate	-	Homo sapiens
phenylsulfamate	best CA I inhibitor	Homo sapiens
sulfamate	-	Homo sapiens
sulfamic acid	-	Homo sapiens
topiramate	-	Homo sapiens

Localization

Localization	Comment	Organism	GeneOntology No.	Textmining
cytosol	-	Homo sapiens	5829	-
membrane	transmembrane isozyme IX	Homo sapiens	16020	-

Metals/Ions

Metals/Ions	Comment	Organism	Structure
Zn2+	zinc enzyme	Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
H2CO3	Homo sapiens	-	CO2 + H2O	-	r

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	-	-	-

Purification (Commentary)

Purification (Comment)	Organism
-	Homo sapiens

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
4-nitrophenyl acetate + H2O	-	Homo sapiens	4-nitrophenol + acetate	-	?
H2CO3	-	Homo sapiens	CO2 + H2O	-	r

Synonyms

Synonyms	Comment	Organism
CA	-	Homo sapiens
CA I	-	Homo sapiens
CA II	-	Homo sapiens
CA IX	-	Homo sapiens
carbonic anhydrase	-	Homo sapiens
carbonic anhydrase isozyme I	-	Homo sapiens
carbonic anhydrase isozyme II	-	Homo sapiens
carbonic anhydrase isozyme IX	-	Homo sapiens

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism
0.0000013	-	phenylsulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.0000019	-	3-methylphenyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.0000021	-	phenylsulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.0000027	-	n-octyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.0000029	-	4-t-butylphenyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.0000035	-	n-octylsulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.0000038	-	3-methylphenylsulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.0000038	-	4-iodophenyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.0000046	-	4-chlorophenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000005	-	topiramate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000005	-	estradiol 3,17beta-disulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000006	-	estradiol 3,17beta-disulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.0000073	-	4-bromophenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000008	-	ethoxzolamide	pH 7.4, 25°C, hCA II	Homo sapiens
0.0000095	-	4-iodophenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.00001	-	estrone sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000012	-	acetazolamide	pH 7.4, 25°C, hCA II	Homo sapiens
0.000013	-	estradiol 17beta-sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000014	-	methazolamide	pH 7.4, 25°C, hCA II	Homo sapiens
0.000015	-	estradiol 17beta-sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000015	-	1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose 3-sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000018	-	4-acetylamidophenyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000018	-	4-chlorophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000019	-	4-bromophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000023	-	sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000023	-	4-iodophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000025	-	ethoxzolamide	pH 7.4, 25°C, hCA I	Homo sapiens
0.000025	-	acetazolamide	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000025	-	n-octylsulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000026	-	sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000027	-	dehydroepiandrosterone sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000027	-	methazolamide	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000028	-	sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000029	-	1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose 6-sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.00003	-	estrone sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000031	-	dehydroepiandrosterone sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000032	-	1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose 6-sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000032	-	estradiol 17beta-sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000033	-	4-methoxyphenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000033	-	4-t-butylphenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000034	-	ethoxzolamide	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000034	-	4-methoxyphenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000036	-	4-nitrophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000037	-	4-acetylamidophenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000037	-	estrone sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000037	-	2,4,6-trichlorophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000039	-	1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose 3-sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000039	-	pentachlorophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.00004	-	4-nitrophenylsulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.00004	-	2-naphthyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000041	-	4-cyanophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000043	-	4-t-butylphenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000043	-	5-pentylresorcinylsulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000045	-	4-acetylamidophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000047	-	pentafluorophenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.00005	-	4-biphenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000051	-	4-phenoxyphenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000054	-	dehydroepiandrosterone sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000054	-	4-trifluoromethylphenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000058	-	estradiol 3,17beta-disulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000059	-	4-methylphenyl sulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000063	-	2-naphthyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000063	-	phenylsulfamate	pH 7.4, 25°C, hCA IX	Homo sapiens
0.000076	-	5-pentylresorcinylsulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000095	-	4-biphenyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000098	-	p-phenoxyphenylsulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000103	-	2-naphthylsulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000105	-	5-pentylresorcinyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000113	-	4-biphenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000113	-	pentafluorophenyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000115	-	4-phenoxyphenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000125	-	pentachlorophenylsulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000138	-	2,4,6-trichlorophenyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000138	-	4-trifluoromethylphenyl sulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.000149	-	4-cyanophenylsulfamate	pH 7.4, 25°C, hCA II	Homo sapiens
0.00025	-	topiramate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000278	-	1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose 3-sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000315	-	1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose 6-sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000369	-	p-trifluoromethylphenylsulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000415	-	pentafluorophenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000432	-	pentachlorophenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.000454	-	2,4,6-trichlorophenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.00048	-	4-cyanophenyl sulfamate	pH 7.4, 25°C, hCA I	Homo sapiens
0.00078	-	methazolamide	pH 7.4, 25°C, hCA I	Homo sapiens
0.0009	-	acetazolamide	pH 7.4, 25°C, hCA I	Homo sapiens
0.021	-	sulfamic acid	pH 7.4, 25°C, hCA I	Homo sapiens
0.097	-	sulfamic acid	pH 7.4, 25°C, hCA II	Homo sapiens