by R. W. Sabnis
Contents
ABOUT THE AUTHOR XIX
ACID FUCHSIN 1
ACRIDINE HOMODIMER 3
ACRIDINE ORANGE 5
ALCIAN BLUE 8GX 8
ALIZARIN 10
ALIZARIN RED S 13
ALLURA RED 16
AMARANTH 19
9-AMINO-6-CHLORO-2-METHOXYACRIDINE (ACMA) 22
ANILINE BLUE (METHYL BLUE) 24
AURAMINE O 27
AZURE A 30
AZURE B 33
BAPTA 37
BAPTA AM 40
BASIC FUCHSIN 43
BISMARK BROWN Y 46
BLUE TETRAZOLIUM (BT) 48
BOBO 1 51
BOBO 3 53
BODIPY FL C5-CERAMIDE 55
BRILLIANT BLUE FCF 57
BRILLIANT CRESYL BLUE 60
BRILLIANT GREEN 61
BSPT 64
BTC 66
BTC AM 68
CALCEIN 71
CALCEIN AM 74
CALCEIN BLUE 78
CALCEIN BLUE AM 80
CALCIUM GREEN 1 81
CALCIUM GREEN 2 84
CALCIUM GREEN 5N 86
CARMINE 88
COELENTERAZINE 92
COELENTERAZINE cp 96
COELENTERAZINE f 98
COELENTERAZINE h 100
COELENTERAZINE hcp 102
COELENTERAZINE n 104
CONGO RED 106
CoroNa GREEN 110
CoroNa GREEN AM 111
CoroNa RED 112
CRESYL VIOLET ACETATE 114
CRYSTAL VIOLET 116
CYANOTOLYL TETRAZOLIUM CHLORIDE (CTC) 120
DAF FM 123
DANSYL CADAVERINE 125
DAPI 127
DARROW RED 129
DASPEI 130
DASPMI 132
Di-2-ANEPEQ 134
Di-4-ANEPPS 135
Di-8-ANEPPS 137
DiBAC4(3) 139
DiBAC4(5) 142
DiD 144
DIHYDROETHIDIUM 146
DIHYDRORHODAMINE 6G 149
DIHYDRORHODAMINE 123 151
DiI 153
DiIC1(5) 156
DiOC2(3) 158
DiOC5(3) 160
DiOC6(3) 162
DiOC7(3) 166
DiSBAC2(3) 167
DiSC3(5) 169
EOSIN B 171
EOSIN Y 173
ERYTHROSIN 177
ETHIDIUM BROMIDE 183
ETHIDIUM HOMODIMER-1 (EthD-1) 186
ETHIDIUM HOMODIMER-2 (EthD-2) 189
ETHIDIUM MONOAZIDE (EMA) 191
ETHYL EOSIN 193
FAST GREEN FCF 195
FLUO 3 198
FLUO 3 AM 201
FLUO 4 203
FLUO 4 AM 205
FLUOZIN 1 207
FLUOZIN 2 208
FLUOZIN 3 209
FM 4-64 211
FURA 2 213
FURA 2 AM 215
FURA 2FF 217
GIEMSA STAIN 219
HEMATOXYLIN 223
HEXIDIUM IODIDE 227
HOECHST 33258 229
HOECHST 33342 233
HOECHST 34580 237
INDIGO CARMINE 239
INDO 1 243
INDO 1 AM 245
IODONITRO TETRAZOLIUM (INT) 247
JANUS GREEN B 249
JC 1 252
JC 9 256
JOJO 1 257
JO-PRO 1 259
LIGHT GREEN SF YELLOWISH 261
LOLO 1 264
LUCIFER YELLOW CH 266
LUCIFER YELLOW VS 269
LUCIGENIN 271
MAG-FURA 2 (FURAPTRA) 275
MAG-FURA 2 AM 278
MAG-INDO 1 281
MAG-INDO 1 AM 283
MAGNESIUM GREEN 284
MALACHITE GREEN 286
MALACHITE GREEN OXALATE SALT 290
MEQ 292
METHYLENE BLUE 293
METHYLENE BLUE TRIHYDRATE 296
METHYLENE VIOLET (METHYLENE VIOLET BERNTHSEN) 298
METHYL GREEN 300
METHYL ORANGE (ORANGE III) 302
METHYLTHIAZOLETETRAZOLIUM (MTT) 305
METHYL VIOLET 2B (METHYL VIOLET) 309
MONOBROMOBIMANE (mBBr) 313
MQAE 316
NBD C6-CERAMIDE 317
NBD METHYLHYDRAZINE 320
NEOTETRAZOLIUM (NT) 322
NEUTRAL RED 324
NEWPORT GREEN DCF 327
NEWPORT GREEN PDX 329
NIGROSIN 330
NILE BLUE A 333
NITRO BLUE TETRAZOLIUM (NBT) 336
NONYL-ACRIDINE ORANGE (NAO) 339
NUCLEAR YELLOW 342
OIL RED O 345
ORANGE II (TROPAEOLIN OOO) 349
ORANGE G 352
ORCEIN 356
OXONOL V 359
OXONOL VI 361
PARAROSANILINE HYDROCHLORIDE 363
PBFI 366
PBFI AM 368
PHEN GREEN SK 369
PHLOXINE B 370
PONCEAU SX 375
POPO 1 378
POPO 3 380
PO-PRO 1 382
PO-PRO 3 384
PROPIDIUM IODIDE 386
PYRONIN B 388
PYRONIN Y 390
QSY 7 CARBOXYLIC ACID, SUCCINIMIDYL ESTER 393
QSY 9 CARBOXYLIC ACID, SUCCINIMIDYL ESTER 396
QSY 21 CARBOXYLIC ACID, SUCCINIMIDYL ESTER 398
QUIN 2 400
QUIN 2 AM 402
REDOXSENSOR RED CC-1 405
RESAZURIN SODIUM SALT 406
RH 237 408
RH 414 410
RH 421 412
RH 795 414
RHODAMINE 6G 415
RHODAMINE 123 418
RHODZIN 3 421
ROSE BENGAL 422
SAFRANIN O 425
SBFI 428
SBFI AM 431
SPQ 433
STAINS-ALL 436
STILBENE ISOTHIOCYANATE SULFONIC ACID (SITS) 438
SUDAN BLACK B 440
SUDAN III 443
SUDAN IV 447
SUNSET YELLOW FCF 450
TARTRAZINE 455
TETRANITRO BLUE TETRAZOLIUM (TNBT) 461
TETRAZOLIUM VIOLET (TV) 463
THIONIN 465
TMRE 467
TMRM 469
TOLUIDINE BLUE O 470
TO-PRO 1 475
TO-PRO 3 477
TO-PRO 5 479
TOTO 1 480
TOTO 3 483
TRIPHENYL TETRAZOLIUM CHLORIDE (TTC) 485
TSQ 488
XTT 491
YO-PRO 1 495
YO-PRO 3 497
YOYO 1 498
YOYO 3 500
ZINQUIN 503
ZINQUIN ESTER 506
APPENDIX A INDEX OF CAS REGISTRY NUMBERS 507
APPENDIX B INDEX OF BIOLOGICAL DYES/STAINS (CERTIFIED BY BIOLOGICAL
STAIN COMMISSION) 511
APPENDIX C INDEX OF FD&C DYES (APPROVED BY FOOD & DRUG ADMINISTRATION) 513
APPENDIX D INDEX OF METAL INDICATORS 515
APPENDIX E INDEX OF NUCLEIC ACID STAINS 517
APPENDIX F INDEX OF ORGANELLE PROBES 519
APPENDIX G INDEX OF pH INDICATORS 521
Preface
Color has been a fascination for individuals for a long time. The book is intended as a reference guide for dyes used in biology, chemistry, histology, cytology, medicine, microscopy, and all color- and medical-related allied fields.
Even though the use of biological dyes is widespread, it is growing rapidly, and has exploded in the last decade, there is no book available in the market directly on these dyes that provides information, such as CAS registry numbers, safety/toxicity data, and various applications, in one source. Hence, there was a need to publish a book that provided an immediate incentive for compiling the notes to update the scientific community with the wealth of information on biological dyes and stains. The dyestuff literature, particularly on biological dyes and stains, is largely in patents. This book, as a reference handbook, provides systematic and up-to-date library of information on 200þ biological dyes and stains. The book is compiled as a resource guide for biologists, chemists, histologists, cytologists, medical professionals, and nonchemists in industry as well as in university.
Biological dyes and stains are arranged alphabetically by the most commonly used name. Again, the choice of primary name is somewhat arbitrary, but an effort has been made to strike a balance between names that are easily recognizable and names that are chemically informative.
The detailed information on each biological dye or stain is covered in the following order: CAS registry number, chemical structure, CA index name, other names, Merck index number (Merck Index 14th Edition, 2006), chemical/ dye class, molecular formula, molecular weight, physical form, solubility, melting point, boiling point, pH range, color change at pH, pKa, absorption (lmax), emission (lmax), synthesis, staining applications, biological applications, industrial applications, safety/toxicity, certification/ approval, and references. Where there are discrepancies between different values, the author has used his judgment on selecting the most likely value.
Numerous recent references have been provided on various synthetic methods, staining applications, biological applications, industrial applications, and safety/toxicity data. Space and format limitations prevent giving all the references for each dye. This is the first ever book that provides safety/toxicity data with reference to acute toxicity, aquatic toxicity, carcinogenicity, cytotoxicity, chronic toxicity, ecotoxicity, genotoxicity, hematotoxicity, hepatotoxicity, immunotoxicity, microbial toxicity, mutagenicity, nephrotoxicity, neurotoxicity, nucleic acid damage, oral toxicity, phototoxicity, phytotoxicity, skin toxicity, reproductive toxicity, and so on. The book also provides Biological Stain Commission (BSC)-certified dyes and Food & Drug Administration (FDA)-approved dyes.
Several appendixes have been provided at the end of the book for scientists to conveniently and easily find a dye as per their need. These appendixes include CAS registry numbers, BSC-certified dyes, FDA-approved dyes, metal indicators, nucleic acid stains, organelle probes, and pH indicators.
Omissions as well as errors of fact and interpretation are inevitable in dealing with so vast a subject as biological dyes. I shall be glad to have my attention drawn to errors and to incorporate suggestions for improvement when a revision becomes possible.
I express my profound respect and appreciation to my guru/mentor/advisor, Prof. D.W. Rangnekar, who brought me to this wonderful world of color science in the Dyestuff Technology Department of Mumbai University Institute of Chemical Technology (MUICT), where I laid the foundation stone for my research career in dye chemistry. It is my pleasure to make grateful acknowledgement to Dr. Alan Fanta, Dr. Ganapati Shankarling, and Dr. Jeffrey Talkington for their extremely useful discussions, encouragement, and inspiration.
Words are inadequate to express my sincere appreciation formywife Madhuri and daughter Anika. It would not have been possible to write this book without their encouragement and patience. It is a great pleasure to express my gratitude to JohnWiley & Sons, Inc. for giving me an opportunity to write this book.