APPENDIX: SOME TAURINE ANALOGUES REFERRED TO IN THIS BOOK (a) Some metabolites and natural analogues TAURINE 2-aminoethane-sulfonic acid NH2-CH2-CH2-SO3H N-chlorotaurine NH(CI)-CH2-CH2-SO3H (TAURINE- MONOCHLOROAMINE) 2-hydroxyethane-SUI fonic HO-CH2-CH2-SO3H acid (ISETHIONIC ACID) 2-aminoethane-sulfinic acid NH2-CH2-CH2-SO2H (HYPOTAURINE) 2-amino-3-sulfo-propionic HOOC-CH(NH2)-CH2-SO3H acid (CYSTEIC ACID) cysteinesulfinic acid HOOC-CH(NH2)-CH2-SO2H y-L-glutamyl-taurine COOH-CH(NH2)-CH2-CH2-CO-NH-CH2-CH2-SO3H (LITORALON) 2-amino-3-hydroxy-1- NH2-( OH-CH2)CH-CH2-SO3H propanesulfonic acid N-(2,3-dihydroxy-n- NH-(CH2-CHOH-CH2OH)-CH2-CH2-SO3H propyl)taurine 633 634 Appendix Decanoylsarcosyl-taurine CH3-(CH2)8-CO-N(CH3)-CH2-CO-NH-CH2-CH2-SO3H N-(1-carboxyethyl)-taurine COOH-(CH3)CH-NH-CH2-CH2-SO3H cerilipin R2-CH(OH)-CO2-CH(R1)-CH2-CO-NH-CH((CH2)3NH2) CO-NH-CH2-CH2-SO3H γDPLQREXW\ULF acid NH2-CH2-CH2- CH2- COOH (GABA) (b) Substitutions and simple modifications -NH2 GROUP MODIFIED N-methyltaurine NH(CH3)-CH2-CH2-SO3H N,N-dimethyltaurine N(CH3)2-CH2-CH2-SO3H + N, N, N-trimethyltaurine N(CH3)3-CH2-CH2-SO3- guanidinoethanesulfonic acid NH=C(NH2)-NH-CH2-CH2-SO3H guanidinoethanesulfinic acid NH=C(NH2)-NH-CH2-CH2-SO2H N-(2-acetamido)-2- CH3COCH2NH-CH2-CH2-SO3H aminoethanesulfonic acid -SO3 GROUP MODIFIED 2-aminoethylphosphonic acid NH2-CH2-CH2-PO3H2 2-aminoethylarsonic acid NH2-CH2-CH2-AsO3H2 3-aminopropionic acid NH2-CH2-CH2-COOH (ß-ALANINE) ethanolamine-O-sulphate NH2-CH2-CH2-O-SO3H Appendix 635 CARBON CHAIN-LENGTH ALTERED aminomethanesulfonic acid NH2-CH2-SO3H 3-aminopropanesulfonic acid NH2-CH2-CH2-CH2-SO3H (HOMOTAURINE) (c) Cyclic analogues pyridine-3-sulfonic acid piperidine-3-sulfonic acid aniline-2-sulfonic acid (±)-2-aminocyclohexanesulfonic acid (cis and trans) N-[ 1 '-aza-cyclohepten-2'-y1]-2- aminoethane-sulfonic acid and N-[ 1 '-aza-cyclopenten-2 '-yl]-2- aminoethane-sulfonic acid 636 Appendix N- [1'-aza-cyclohepten-2 '-yl]-3- aminopropane-sulfonic acid and N-[1'-aza-cyclopenten-2'-yl]-3- aminopropane-sulfonic acid 2-aminocyclopentanesulfonic acid piperazine-N, N '-bis( 2-ethanesulfonic acid) R= -CH2CH2SO3- quinoline-8-sulfonic acid 1,2,3,4-tetrahydroquinoline-8-sulfonic acid norbornene derivatives 3-amino-bicyclo[2.2.1]heptane- 2-sulfonic acid Appendix 63 7 (d) Others 6-aminomethyl-3-methyl-4H-1,2,4- benzotiadiazine-1,1-dioxyde (TAG) aminoacetic acid (GLYCINE) retinylidentaurine (TAURET) Taurocholic acid 3-acetamido-1-propanesulfonic acid (calcium salt) (ACAMPROSATE) INDEX A23187, 542, 591, 593 AIDA, 259 Acamprosate, 1, 377, 379, 380, 637 ß-Alanine, 37, 345, 349, 353, 404 ACAT: see Acyl-coenzyme A:cholesterol cardiac TAUT and, 530, 532 acyltransferase cardiomyopathy and, 58, 59, 62, 66 ACE inhibitors, 64 chemical formula, 634 N-(2-Acetamido)-2-aminoethanesulfonic acid DNA damage protection and, 355, 357, 360, (ACES) 361, 364, 365 chemical formula, 634 erythrocyte damage protection and, 412, 413, H2O2-induced erythrocyte damage and, 412, 414, 421, 423, 425, 505, 511, 512, 515, 413, 417, 418, 419, 420, 423, 424-425 516, 519 PHZ-induced erythrocyte damage and, 505, hypochlorous acid and, 563, 567, 568 510, 511, 512, 513, 514, 516, 518 PDGF-BB and, 591, 592 thermoregulation and, 274, 277 retinal taurine transport and, 433 Acetylcholine, 325 streptozotocin-induced diabetes and, 571-576, N-Acetylcysteine (NACYS) 579, 580 H2O2-induced erythrocyte damage and, 412, supraoptic nucleus taurine release and, 233 413, 419, 420, 421 TAUT activity in macrophages and, 127, 128, ,N%α and, 558 129, 130 PHZ-induced erythrocyte damage and, 505, thermoregulation and, 274, 276, 277 510, 513, 516, 518 Alcohol: see Ethanol N-Acetylhomotaurine, 375 Alcohol dehydrogenase (ADH), 205 Actin, 63,64 Alcoholism, 1 Actinomycin D, 128 Aldose reductase, 240, 241, 242, 243, 244, 245- Acyl-coenzyme A:cholesterol acyltransferase 246, 247 (ACAT), 177, 179, 180-181,183, 184 Alkenes, 397-401 Adenosine triphosphate (ATP) Alzheimer’s disease, 9, 356 detrusor muscle and, 325 Amiloride, 251, 253 myocardial ischemia and, 111, 112, 113 3-Amino-bicyclo(2.2.1)heptane-2-sulfonic acid, 636 retina and, 465, 466, 469, 470, 471, 472, 474, ß-Aminobutyric acid, 128 475,477,480, 481,482,483 γ$PLQREXW\ULF acid: see GABA sulfur biochemistry and, 4, 6, 7 2-Aminocycloalkanesulfonic acids, 397-401 swelling-induced taurine efflux and, 489-490, 2-Aminocyclopentanesulfonic acid, 636 494 2-Aminoethane thiosulfate, 124 Adenosine triphosphate (ATP)-dependent potas- 2-Aminoethylarsonic acid (AEA), 274, 276, 634 sium channels (KATP), 46, 50-51,53, 54 S-Aminoethylcysteine, 28 S-Adenosylhomocysteine, 5 S-Aminoethylcysteine ketimine, 29 S-Adenosylmethionine, 6, 37 2-Aminoethylphosphonic acid (AEP), 274, 276, AEP: see 2-Aminoethylphosphonic acid 327, 328, 330, 331, 634 Agarose gel electrophoresis, 189 2-Amino-3-hydroxy-1-propanesulfonic acid, 633 639 640 Index 2-Amino-6,8,hydroxypurine: see 8-hydroxy gua- Atherosclerosis nine apoliprotein E deficiency and, 193-200 Aminomethanesulfonic acid (AMSA), 274 high-fat diet, taurine treatment and, 177-184 chemical formula, 635 in Japan and China, 143-148 H2O2-induced erythrocyte damage and, 412, PDGF-BB and, 589-594 413, 417, 418, 419, 420, 422 ATP see Adenosine triphosphate PHZ-induced erythrocyte damage and, 505, Atropine, 326, 328 510,511, 512, 513,514,516,518 AVP: see Arginine vasopressin 3-Aminopropanesulphonic acid (OMO), 274, 276 2-Azidosulfonic acids, 401 Aminopyridine, 250, 251, 253 2-Aminosulfonic acids, 401 Baclofen, 260, 262, 274 Ammonia Bacteria, 3, 4, 12, 383 hepatic encephalopathy and, 305-311 Bay-K 8644, 340 treatment of poisoning with taurine and bcl-2 gene, 94 unithiol, 627-630 Bepridil hydrochloride, 284, 288, 290 AMPA, 293-295 Betaine, 239, 246, 247 AMSA: see Aminomethanesulfonic acid Betaine-GABA transporter (BGTI), 240, 241, Angiotensin 11, 64-66, 111 242, 243,244, 245,246 Aniline-2-sulfonic acid (ANSA), 274, 278, 635 BHT, 169 6-Anilino-5,8-quinolinedione: see LY83583 Bile acid, 182-183 Anoxia, 325-332 conjugation of, 187, 192, 199 Anthracene-9-carboxylic acid, 46 Bile salt conjugation, 12-15 Antidepressants, 6 Bleomycin, 545-559 Antidiuresis, 243 Blood-brain barrier, 214, 314 Antioxidants, 12, 29, 163-164,364 endogenous cryogens and, 336 L-AP3, 259 ethanol and, 210 L-AP4, 260 taurine transport mechanism through, 321-324 Apolipoprotein A-1, 169, 184 BO-653, 199 Apolipoprotein E, 193-200 Brain, 35 Apoptosis, 110, 111, 113-114, 115, 504 cysteine and, 7, 8-9 3-APPA, 260 cysteine sulfinate decarboxylase and, 11 APV, 265, 267, 268, 269, 271, 290 ethanol and, 203-204, 207, 208, 210 AQP4, 235 extracellular taurine in glioma of, 621-624 Arachidonic acid, 488, 490-494 hypotaurine and, 12 Arginine, 432 phospholipid-taurine interactions in, 18 Arginine vasopressin (AVP), 222, 228, 232, 233, subarachnoid hemorrhage in, 595-602 234, 338, 339 synthetic taurine derivative effect on, 313-318 Aromatic-amino-acid decarboxylase (AADC), 373 taurine biosynthesis in, 36-37 Arthritis, 6 TauT gene expression in, 241-242 ASBA: see a-Sulfo-palanine Brain ischemia Ascorbic acid, 169-174, 564 ion channels in taurine release and, 249-254 Aspartate, 9 subarachnoid hemorrhage and, 595, 596, 599, brain ischemia and, 253 601-602 heat stress and, 336, 337, 340 8-Bromoadenine, 357 hepatic encephalopathy and, 305-311 8-Bromo-adenosinecyclic 3'5' monophosphate, isovolumic regulation and, 221, 222-224 527, 530 subarachnoid hemorrhage monitoring and, 595, 596 CA: see Cysteic acid taurine-metal ion interaction and, 347, 348-349 Cadmium, 471, 475 Aspartate aminotransferase, 9-10, 11 CAHS: see cis-2-Aminocyclohexane sulfonic acid Astrocytes Calcium, 15, 16-17,20, 21 isovolumic regulation and, 222, 224 brain ischemia and, 249, 252-253, 254 taurine release from hippocampal, 213-218 cardiomyopathy and, 57, 58-62, 64 taurine release from supraoptic nucleus. 227, cerebral insult monitoring and, 271 229-231 heart disease and, 33 TauT gene expression in, 239, 240-241,245 heat stress and, 339-340 Index 641 Calcium (cont.) Cell volume matrix metalloproteinases and, 391 in HELA cells, 487-494 mitochondrial permeability transition and, 87, in hepatic encephalopathy, 305-311 88-89, 91, 92, 93, 94 Central nervous system (CNS), 35-41 myocardial ischemia and, 114 Cerebral cortex PDGF-BB and, 593 hepatic encephalopathy and, 305-311 reperfusion injury and. 327, 332 post-operative monitoring of hemorrhage in, retina uptake of, 466, 469-475, 477-484 595-602 sarcoplasmic reticulum uptake of, 403, 405, Cerebral insults, on-line monitoring of, 265-271 406,407-408 Cerebrospinal fluid (CSF), 335-342 in skeletal muscle, 45-46, 51-52, 53, 54 Cerilipin, 634 supraoptic nucleus taurine release and, 229, c-fos gene, 64, 65, 590-593 23 1 Chelation, 19 swelling-induced taurine efflux and, 491,494 Chelerythrine (CHT), 462, 465, 466 synaptic potentiation and, 283, 285-288, 290- China, 143-148 292 Chlordiazepoxide, 377, 378-380 taurine biosynthesis and, 35, 38, 40-41 Chloride, 219, 564 taurine interaction with ions, 345, 353 Chloride channels TAUT and, 132, 133 brain ischemia and, 254 TauT gene regulation and, 535-543 skeletal muscle, 45, 46-48, 53, 54 Calcium acetyl taurine, 375-376 supraoptic nucleus taurine release and, 230, 232 Calcium ATPase, 51 swelling-induced taurine efflux and, 487-489, Calcium channels 494 brain ischemia and, 252, 253 3-Chloronorbomane-2-sulfonic acid sodium salt, hippocampal taurine release and, 257 400,401 synaptic potentiation and. 286, 290 m-Chloroperbenzoic acid (MCPBA), 397,401 Calmidazolium, 127, 128, 129, 133 2-Chlorosulfonate, 397 Calmodulin 2-Chlorosulfonic acids, 400-401