Hermanson G. Bioconjugate Techniques, Second Edition
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1190 Index
SATA ( continued )
phycobiliproteins , 462
modifi cation of
amine-DNA probes , 984
avidin or streptavidin with ,
919
solubility , 73
thiolation of avidin with , 909
thiolation of enzymes with , 908
use in preparing avidin–
enzyme conjugates , 906
Sato , 256 , 258 , 383
SATP
solubility , 74
use for thiolation , 74
Savage , 883
Sawanobori , 194
Sawin , 421
Sawyer , 243
Saxon , 543 , 545 , 684 , 691
, 693 ,
696
Sayre , 23
Schengrund , 367
Schepartz , 1032
Scheraga , 193
Scherphof , 754 , 869 , 879 , 895 ,
896
Scherson , 407
Schewale , 14
Schiel , 617 , 618
Schiff base , 123 , 124 , 129 , 131 ,
134 , 140 , 173 , 200 , 231 ,
393 , 779 , 780 , 798 , 801 ,
855 , 890 , 893 , 910 , 913
,
966
effi ciency of , 912
in non-enzymatic glycation , 48
of arginine/glyoxal reactions ,
333
pH dependence of formation
of , 802
reduction of , 201
reduction with sodium
cyanoborohydride, 174
Schimitschek , 430
Schlom , 498
Schmer , 223
Schmidt , 1009
Schmitt , 311
Schnapp , 205 , 262 , 303
Schneede , 332
Schneider , 253 , 650 , 658
Schroeder , 119
Schuberth , 519
Schwartz , 41
, 671
Schweinberger , 255
Schwinghamer , 92
Scintillation cocktails , 546
SCN-Bzl-DTPA , 383 , 384
Scopes , 92
Scorilas , 477
Scorrano , 632
Scott , 247 , 837
Scouten , 422 , 424 , 676
Sculimbrene , 485
SDS , 88 , 93 , 99
SDS electrophoresis , 407
SDS polyacrylamide gel
electrophoresis, 88 , 92
Seela , 62
Segal , 275
Sehgal , 905
Seitz
, 701
Sela ,
824 , 857
Self-assembled monolayers
(SAMs), 189
Seligsberger , 263
Selvin , 112 , 477 , 479 , 484
Sendai virion envelope , 316
Sendai virus , 292
Senior , 868
Senozan , 748
Sensory receptors , 409
Senter , 825
Serine , 46 , 103 , 106 , 701
N-terminal oxidation with
periodate, 197
oxidation of N-terminal by
periodate, 136
solvent exposed area , 29
Serine , 6
Serum , 528
Severinov , 703 , 706
SFB ,
133 , 674 , 675 , 735
alkaline phosphatase
activation, 998
alkaline phosphatase modifi ed ,
998
chemoselective ligation using ,
672
general description and use ,
132
SFPA , 133
general description and use , 132
Sgro , 335
SHA , 211 , 676 , 677 , 678
Shabarova , 979 , 980
Shacter , 28
Shaheen , 638
Shahum , 754 , 863 , 879
Shaltiel , 175 ,
185 , 260
Shanahan , 305
Shannon , 962
Shapiro , 974
Sharma , 256 , 1025 , 1026
Sharon , 366
Sharpless , 211 , 680 , 681 , 683
Shechter , 112
Sheehan , 216 , 223 , 224 , 404
Sheffrey , 240
Shek , 754 , 869 , 879 , 880
Shephard , 308
Sherry , 501
Shetty , 103 , 108 , 159
Shi , 364
Shiao , 103
Shih , 951
Shimisu , 86
, 844
Shimizu , 86
Shimkus , 518
Shimomura , 263
Shivdasani , 256
SHNH , 143
SHPP
general description and use ,
557
iodination protocol , 559
SHTH , 143
Shukla , 359 , 371 , 372
Sia , 107
SIAB , 290 , 294 , 295 , 297 , 328
activation of ricin , 849
conjugation of proteins to
liposomes using , 897
general description and use ,
288
in coupling antibodies to
liposomes, 883
liposome conjugation using ,
871
Index 1191
SIAC
analog of , 295
conjugation of proteins to
liposomes using , 897
general description and use ,
295
SIACX
general description and use ,
295
Sialic acid , 21 , 39 , 46 , 122 , 131 ,
414 , 472 , 527
ketone analog , 671
labeling with biocytin-
hydrazide , 529
modifi cation with cyanine
dyes , 472
oxidation with sodium
periodate , 40 , 49 , 122 ,
130 , 800
removal with neuraminidase ,
132
Sialidase , 305
SiaNAz , 545
SIAX
analog of , 295
conjugation of proteins to
liposomes using , 897
general description and use ,
293
SIAXX
general description and use ,
295
Sickle cell anemia , 252
Siegenthaler , 255
Siezen , 252
Signal recognition particle , 312
Silane , 490 , 562 , 618 , 714
modifi cation of silica particles ,
618
Silane coupling agent , 562
amino group containing , 568
aqueous deposition , 566
aqueous/organic solvent
deposition , 566
carboxylate group containing ,
573
EDTA group containing
, 575
epoxy group containing ,
577
organic solvent deposition ,
567
reaction strategies , 565
reactions of , 563
substrates for use , 565
uses , 565
vapor phase deposition , 567
Silanol , 563 , 618
Silica bubbles , 620
Silica gel , 873
Silica particles , 618
density of , 618
fl uorescent , 620 , 623
silane functionalization of ,
625
Silicic acid , 873 , 875
Silman , 274
Siloxane , 563
, 618
Silva , 581
Silvaraman
, 629
Silver , 924
Silver mercaptide , 81
Silver nanoclusters , 389
Silver nitrate (AgNO
3
) , 80
Simon , 256 , 258 , 427
Simons , 1007 , 1037
Singer , 256 , 423 , 582
Singh , 69 , 147 , 356 , 357 , 363 ,
364 , 373 , 647 , 825 , 834
Singhal , 147 , 211 , 676 , 824
Single chain antibody , 826 , 855
Single chain Fv protein , 826
Single-walled nanotubes
(SWNTs) , 638
Singlet oxygen (
1
O
2
) , 23
fullerene generated , 628
produced from psoralen
reactions , 209
Singlet state , 399
Sinz , 1009 , 1026
Sipe , 423
Sippel , 436 , 438
Site-directed conjugation
of antibody molecules , 786
Site-directed reactions , 22
Siuzdak , 649
Sivakoff , 908
Skare , 1011
Skold , 268
Slaughter , 530
Slinkin , 500 , 503
Slomkowski , 387
Slot , 927
Slow-release agent , 882
Smalley , 628
SMCC , 184 , 293 , 299 , 718 , 812 ,
962 , 964 , 965
activation of enzymes with ,
967
analogs of , 284
general description and use ,
283
in
coupling antibodies to
liposomes , 883
activation of KLH , 749
conjugation of
phycobiliproteins , 462
liposome conjugation using ,
871
reaction with -galactosidase ,
788
stability of its maleimide
group , 283
use in
antibody–enzyme
conjugation , 788
avidin conjugation , 906
Smith , 41 ,
122 , 130 , 208 , 244 ,
418 , 667 , 680 , 953
SMPB , 766 , 884
activation of
liposomes , 880
PE , 872
analog of , 291
conjugation of proteins to
liposomes using , 895
general description and use ,
291
in
coupling antibodies to
liposomes , 883
conjugation of
phycobiliproteins , 462
liposome conjugation using ,
871 , 872
SMPT
analogs , 282
cleavability of , 392
cross-bridge , 281
general description and use ,
281
1192 Index
SMPT ( continued )
half-life of conjugates in vivo ,
841
preparation of antibody–ricin
A chain conjugates , 843
solubility , 78
use for thiolation , 77
Smyth , 102 , 158 , 160 , 178 , 183 ,
283 , 850 , 896
Snyder , 409
Sodium ascorbate , 683
reduction of chloroauric acid
with, 928 , 929
Sodium bisulfi te , 974 , 976 , 991
Sodium borohydride , 125 , 173 ,
231 , 779 , 781 , 801 , 855 ,
857 , 892
, 911 ,
913 , 914 ,
957
for reducing disulfi des , 100
in
disulfi de bond cleavage , 392
glutaraldehyde conjugation
reactions, 798 , 800
reduction of chloroauric acid
with, 928
Sodium citrate
reduction of chloroauric acid
with, 928 , 929
Sodium cyanoborohydride , 21 ,
41 , 49 , 125 , 134 , 140 , 166 ,
167 , 173 , 231 , 233 , 265 ,
270 , 370 , 385 , 413 , 613 ,
779 , 781 , 782 , 798 , 800
,
801 , 802 , 804
, 805 , 855 ,
857 , 870 , 894 , 910 , 950 ,
952 , 953 , 956 , 962 , 966
5 M in 1 N NaOH , 912
for reducing hydrazone bonds ,
140
in
preparation of immuno-
toxins, 855
reduction of hydrazones ,
41 , 200 , 525 , 527
Sodium deoxycholate , 862
Sodium dithionite
cleavage of diazo bonds , 203 ,
272 , 394 , 535 , 775
for reduction of nitrophenyl
compounds, 126 , 774
Sodium hydrosulfi te , see Sodium
dithionite
Sodium metabisulfi te , 548 , 550 ,
554
Sodium nitrite , 127 , 272 , 273 ,
774
in
activation of p -amino-
benzoyl biocytin , 534
diazotization of o -tolidine ,
776
formation of acyl azides ,
171
formation of diazonium , 203
reaction with p -aminobenzoyl
biocytin, 536 , 989
Sodium periodate , 20 , 40 , 66 ,
122 , 131 , 132 , 166 , 232 ,
270 , 298 , 412 , 427
, 446 ,
447 , 448 , 457 , 459 ,
504 ,
526 , 781 , 800 , 803 , 855 ,
871 , 919
cleavage of DST , 243
comparison to sugar oxidases ,
529
for oxidation of antibody
carbohydrate, 787
general description and use ,
130
glycolipid oxidation , 869
in
enzyme activation , 802
cleavage of diol containing
cross-linkers, 393
oxidation of cell-surface
glycoconjugates, 413
optimal concentration for
HRP oxidation , 802
oxidation of
antibodies , 440 , 810
dextran , 755
ferritin with , 910
glycolipids , 870
glycoproteins in solution ,
414
HRP with , 912 , 962 , 966
N-terminal serine , 136
reaction with
dextran , 952
hydrolyzed epoxides , 268
use in immunotoxin
preparation, 855
Sodium pertechnatate , see 99mTc
Sodium sulfi te (Na
2
SO
3
) , 136 ,
473–474 , 845
Sodium tetrathionate , 161 , 122 ,
162 , 845
Soellner , 696 , 697
Soini , 476 , 484
Sokolovsky , 125 , 774
Solomon , 282
Solvent exposed area (SEA) , 29
Somatotropin , 242
Song , 1004
Sonication , 881 , 888
of lipids , 862
Sorbitol , 863 , 871 , 877
Sorensen , 815
Sorenson , 306
Soundararajan , 205 , 303
Souza , 243
Soybean trypsin inhibitor , 319 ,
339 , 340
Spacer arm , 67 , 104 , 102 , 277
of
NHS-LC-fl uorescein , 405
SIACX , 295
SMPT , 281
zero-length , 215
Spangler , 189 , 709
SPB , 209
SPDP , 91 , 257 , 280 , 717 , 848 ,
964 , 980 , 983
acid precursor of , 843
activation of
antibodies , 839 , 840
liposomes ,
876
PE , 874
toxins , 838
alkaline phosphatase
conjugation to DNA , 993
alkaline phosphatase modifi ed ,
994
analogs , 76 , 279
cleavability of , 392
comparison to SMPB , 291
conjugation of avidin to
phycobiliproteins using ,
919
coupling to amine particles , 602
Index 1193
creation using 2,2 -dipyridyl
disulfi de , 165
dendrimer activation , 358
enzyme activation using , 968
for
creating immunotoxins , 834
modifi cation of toxins , 834
general description and use ,
278
in
biotin-HPDP , 522
coupling antibodies to
liposomes , 883
conjugation of phyco-
biliproteins , 462 , 464
modifi cation of gelonin ,
829
inactivation of gelonin and
PAPs , 840
liposome conjugation using ,
871
modifi cation of
amine-DNA probes , 982
dextran with , 954 , 960
pyridyl disulfi de reactions of
,
186
thiolation of antibodies , 849
use for thiolation , 76
Speakman , 268
Speck , 553
Speers , 683
4-Sphingenine , 866
Sphingolipid , 866 , 868 , 869
types , 866
use in liposomes , 866
Sphingomyelin , 866 , 868 , 879
Sphingosine , 864 , 866 , 877
Spiegal , 131 , 139
Spiegel , 460
Springer , 676
Srikrishna , 151 , 152 , 538
Srinivasachar , 256
, 258
Stable isotope labeling of
amino acids in cell culture
(SILAC) , 1011
Stadtman , 23 , 25
Stahlberg , 502
Stanley , 243
Starch ,45
Stark , 254
Staros , 172 , 219 , 220 , 222 , 224 ,
237 , 240 , 243 , 305 , 596 ,
765
Staudinger , 690
Staudinger ligation , 538 , 569 ,
690 , 691
PEG-based compounds for ,
722
traceless , 695
using biotin-PEG-phosphine ,
543
Staudinger reaction ,
181 , 345 ,
544
Stauffer , 342 , 1028
Stearic acid , 487 , 866
Stears , 376
Stearylamine
functional derivatives , 869
activation with SPDP , 895
Steel , 1026
Steer , 46
Steptavidin
comparison to avidin , 901
thiolation with SATA , 73
Steric hindrance , 405
Sternberger , 914
Stewart , 225 , 457
Stickel , 427
Stilbenedisulfonate receptor
, 409
Stirpe , 829
Stöber , 618 , 620
, 623
Stoke’s Law , 398
Stokes shift , 444 , 451 , 479 , 918
defi nition of , 398
of
AMCA derivatives , 438
BODIPY 493/503 C
3
hydrazide , 447
BODIPY FL C
3
hydrazide ,
449
BODIPY FL C
3
-SE , 442
BODIPY fl uorophores , 441
lanthanide chelates , 474
Lucifer Yellow
fl uorophores , 459
phycobiliproteins , 461
tandem phycobiliprotein
conjugates , 462
Stolowitz , 136 , 474 , 676
Straubinger , 882
Streefkerk , 801
Streptavidin , 303 , 336 , 376 ,
477 , 506 , 512 , 517 , 520 ,
523 , 524 , 526 , 537 , 538 ,
632 , 669 , 693 , 710 , 737 ,
976
, 1032
activation with
bis-hydrazides , 270
sulfo-SMCC , 906
alkaline phosphatase
conjugate , 530
as immunogen carrier for
glycans , 538
binding to
ABNP cross-links , 337
sulfo-SBED cross-links , 337
biotin binding site , 506
conjugation
to
ferritin using glutaral-
dehyde , 913
HRP using reductive
amination , 911
liposomes , 883
using
glutaraldehyde , 913
reductive amination , 910
with
enzymes using SMCC , 906
HRP using reductive
amination , 912
phycoerythrin , 462 , 918
effect of periodate , 393
enzyme labeled , 905
fl uorescent labeling of , 914
gold labeled , 905 , 927
gold labeling of , 934
hydrazide-activated , 270
iminobiotin binding of , 515
immobilized , 338 , 514 , 518 ,
523 , 537 , 651 , 653 , 655 ,
708 , 727 , 1012 , 1027 ,
1031
interactionwith
biotin , 508
biotinylated antibodies , 817
iminobiotin , 506
modifi cation with
AMCA-NHS , 917
FITC , 915
1194 Index
Streptavidin ( continued )
Lissamine rhodamine
sulfonyl chloride , 916
modifi ed with bis-hydrazide
compounds, 919
optimal fl uorescein labeling
level, 915
phycoerythrin conjugate , 376
purifi cation using immobilized
iminobiotin, 516
quantum dot conjugate , 493
rate of biotin interaction with ,
506
structure and properties , 901
thiolation
using SATA , 909
with 2-iminothiolane , 919
Streptavidin-HRP , 1031
Streptomyces avidinii , 901
Streptomyces pilosus , 503
Strickland , 962
Striebel , 376
Strittmatter , 862
Stroh
, 136 , 197 ,
473
Strottmann , 403
Struhl , 1011
Stryer , 462
Stuchbury , 257
Stump , 930
Styrene/4-vinylbenzoic acid
copolymer , 230
Subramanian , 498
Substrates , 961
Subunits
disulfi de linked , 10
Succinaldehyde , 262
succinic acid , 103 , 105 , 106
in cross-bridge of EGS , 395
within EGS , 246
Succinic anhydride , 102 , 178
for blocking amines on
dendrimers, 364
general description and use , 103
modifi cation of
amine particles using ,
626
amines , 105
mPEG with , 946
PEG with , 941 , 945
reaction with amino-dextran ,
954
Succinimidyl 4-(((iodoacetyl)-
amino)methyl)cyclohexane-
1-carboxylate, see SIAC
Succinimidyl 4-formylbenzoate ,
see SFB
Succinimidyl 4-hydrazidotereph-
thalate hydrochloride , see
SHTH
Succinimidyl 4-hydrazinonicoti-
nate acetone hydrazone , see
SANH
Succinimidyl 6-((((4-(iodoacetyl)
amino)methyl)cyclohexane-
1-carbonyl)amino)hexanoate ,
see SIACX
Succinimidyl 6-((iodoacetyl)
amino)hexanoate, see SIAX
Succinimidyl 6-(6-(((4-iodoacetyl)-
amino)hexanoyl)amino)-
hexanoate, see SIAXX
Succinimidyl acetylthiopropion-
ate, see SATP
Succinimidyl carbonate
, 175 ,
196 , 249
comparison with CDI
coupling, 946
formation of , 941 , 943
hydrolysis of , 941
reaction with amines , 941
N -Succinimidyl chloroformate ,
944
Succinimidyl glutarate , 941
Succinimidyl hydraziniumnico-
tinate hydrochloride , see
SHNH
Succinimidyl p -formylbenzoate ,
see SFB
Succinimidyl p -formylphenoxy-
acetate, see SFPA
N -Succinimidyl S-acetylthio-
acetate, see SATA
Succinimidyl succinate , 941
N-Succinimidyl 3-
(2-pyridyldithio)propionate,
see SPDP
N-Succinimidyl-3-(4-hydroxy-
phenyl) propionate
, see SHPP
N -Succinimidyl-(4-azidophenyl)
1,3 -dithiopropionate , see
SADP
N-Succinimidyl(4-iodoacetyl)ami-
nobenzoate, see
SIAB
Succinimidyl-[4-(psoralen-8-
yloxy)]butyrate, see SPB
Succinimidyl-4-( N -maleimido-
methyl)cyclohexane-1-
carboxylate, see SMCC
Succinimidyl-4-( p -maleimido-
phenyl)butyrate, see SMPB
N-Succinimidyl-6-(4-azido-2 -
nitrophenylamino)hexanoate ,
see SANPAH
Succinimidyl-6-
(biotinamido)hexanoate, see
NHS-LC-biotin
Succinimidyl-7-amino-4-methyl-
coumarin-3-acetic acid , see
AMCA-NHS
Succinimidyloxycar-
bonyl- -methyl- -(2-
pyridyldithio)toluene.
(SMPT), see SMPT
Succinylation , 103
of amine dendrimers , 364
Suchanek , 208
Sucrose , 45
Sugar
analogs , 667 , 671 , 684 ,
692
azide analogs , 543
dendrimer conjugates , 367
functional groups , 39
immobilized , 847
labeling with biocytin-
hydrazide, 529
modifi cation with diamines ,
122
reducing , 123 , 173
Sugar balls , 366
Sulfenylthiosulfate , 161 , 162 ,
845
as blocking agent , 163
Sulfhydryls , 120
acetylated , 795
activated with TNB , 187
addition to double bonds , 184
alkylation by maleimides , 183
assay with Ellman’s reagent ,
100
biotinylation of , 520
blocking agents
Index 1195
permanent and reversible ,
160
blocking
of , 156 , 160
with Ellman’s reagent , 164
complexation to metals , 503
conjugation with haptens con-
taining , 766
coupling of radionuclides , 498
creation
by
reduction of disulfi des , 88
reduction using TCEP , 95
reduction with 2-mercap-
toethylamine , 93
of , 279
on
antibodies , 788
antibodies with
2-iminothiolane , 793
using
N -acetyl homocysteine
thiolactone , 80
AMBH , 83
cystamine
, 84
SAMSA , 81
SATA , 71
SATP , 74
SMPT , 78
SPDP , 76
dative binding to gold , 925
deprotection using hydroxyl-
amine of acetylated , 908
detection
using
Ellman’s reagent , 99
using Ellman’s reagent , 99
with TNBS , 128
formation of pyridyl disulfi de
groups , 165
immobilized , 99
in immobilized reductants , 97
introduction of , 67
measurement using Ellman’s
reagent , 164
modifi cation with
2-bromoethylamine , 120
ethylenimine , 119
H
2
OI , 547
of -galactosidase , 788 , 908
oxidation
metal catalyzed , 280
permanent and reversible
linkages with , 256
preventing oxidation to
disulfi des , 67
protected
of SAMSA-fl uorescein , 410
reaction
of , 182
with
alkyl halides , 256 , 274
aminoethyl -8, 118
anhydrides , 178
APDP , 326
aryl azides , 304
aryl halides , 175 , 185
ASIB , 325
aziridines , 184
benzophenone-4-iodo-
acetamide
, 328
benzophenone-4-maleim-
ide , 330
biotin-BMCC , 520
BMH , 259
CMC , 223
difl uorbenzene derivatives ,
260
EDC , 218
epoxides , 174 , 268
glutaric anhydride , 106
GMBS , 293
haloacetyl compounds ,
182
iodoacetate , 109
iodoacetyl-LC-biotin , 524
isothiocyanates , 170
M
2
C
2
H , 299
maleic anhydride , 159
maleimides , 107 , 256
MBS , 286
MPBH , 298
NEM , 160
NHS esters , 171 , 237
NPIA , 296
PDPH , 300
pyridyl disulfi des , 186 ,
279
SIAB , 288
SIAC , 295
SIAX , 294
SMCC , 283
SMPB , 291
SMPT , 281
by disulfi de exchange , 186
Sulfi de , 963
5-Sulfi do-2-nitrobenzoate ,
187 , 844 , see also TNB
Sulfi nic acid , 342 , 1028
Sulfo-BSOCOES
general description and use ,
246
6-Sulfo-cytosine , 974
Sulfo-DST
general description and use ,
244
Sulfo-EGS
general description and use ,
247
Sulfo-GMBS
dendrimer modifi cation using ,
387
general description and use ,
293
Sulfo-HSAB
general description and use ,
310
similarity to sulfo-SAPB , 316
Sulfo-LC-SMPT , 77 , 282
Sulfo-LC-SPDP , 76 , 279 , 280
activation of liposomes
, 876
in conjugation of
phycobiliproteins , 464
use in protein–liposome
conjugation , 895
Sulfo-MBS
general description and use ,
287
Sulfo-NHS , 114 , 157 , 237 , 765
of DTSSP , 240
plus EDC in formation of
active esters , 172
reaction with EDC , 112
use with
EDC , 219 , 757
EDC to activate protein
carboxylates , 763
Sulfo-NHS acetate , 157 , 158 ,
282
for blocking amines , 157
1196 Index
Sulfo-NHS acetate ( continued )
chemistry of , 171
of
SAED , 316
SAND , 312
SASD , 306
sulfo-HSAB , 310
sulfo-SADP , 316
sulfo-SAMCA , 319
sulfo-SAPB , 316
sulfo-SBED , 337
sulfo-SHPP , 559
sulfo-SMCC , 285
Sulfo-NHS-ASA
general description and use ,
306
sulfo-NHS-biotin
dendrimer modifi cation using ,
385
general description and use ,
511
use in protein biotinylation ,
512
Sulfo-NHS esters
of
BS 3, 243
sufo-DST , 244
preparation using EDC , 219
produced using EDC/
sulfo-NHS reaction , 765
Sulfo-NHS-LC-ASA
general description and use ,
306
Sulfo-NHS-LC-biotin , 379
general description and use ,
514
Sulfo-NHS-LC-SPDP , 363
activation of dendrimers , 356
Sulfo-NHS-SS-biotin , 727
general description and use ,
517
labeling cell surface proteins ,
519
Sulfo-SADP
general description and use ,
316
Sulfo-SAMCA
general description and use ,
319
Sulfo-SAND
for studying protein
interactions, 1016
Sulfo-SANPAH , 314
general description and use , 311
for studying protein
interactions, 1016
Sulfo-SAPB
general description and use ,
316
Sulfo-SBED , 340 , 510
derivative containing pyridyl
disulfi de , 1022
functional arms of , 339
general description and use ,
337
in study of protein
interactions, 1021
Sulfo-SFAD , 1018
Sulfo-SHPP
general description and use ,
559
Sulfo-SIAB , 356
general description and use ,
289
Sulfo-SMBP , 559
Sulfo-SMCC , 285 , 356 , 718 ,
768 , 790 , 850
activation of
antibodies using , 850
avidin and streptavidin
with,
906
carrier proteins , 771
enzymes with , 906 , 967
HRP with , 909
coupling to particles , 604
general description and use ,
284
in hapten–carrier conjugation ,
766
quantum dot conjugation , 496
reaction with enzymes , 789
use
in
antibody–enzyme
conjugation, 788
avidin conjugation , 906
with poly-
L -lysine , 754
Sulfo-SMPB
general description and use ,
291
Sulfo-tetrafl uorophenyl (STP)
ester , 179
Sulfonamide linkage , 173
Sulfonate group , 157 , 237 , 244 ,
256 , 284 , 287 , 289 , 291 ,
293 , 306 , 310 , 311 , 312 ,
316
cyanine dye derivatives , 465
fl uorescent dye derivatives ,
400
on particle surfaces , 590
reactive aromatic , 185
Sulfone , 260 , 412
base labile group in cross-
linkers, 395
Sulfone group
cleavability ,
244
in cleavable reagents , 392
Sulfonic acid , 173
Sulfonyl chloride
of
Lissamine rhodamine
sulfonyl chloride , 422
Texas Red sulfonyl chloride ,
423
reactions of , 173
Sulfonylhydrazine
of rhodamine derivatives ,
427
Sulforhodamine , 101 , 453 , see
also Texas Red
hydrazide derivative of , 429
sulfonyl chloride derivative
of, 423
Sulforhodamine B , see Lissamine
rhodamine B
hydrazide derivative of , 427
Sulfosuccinimidyl 2-(7-azido-4-
methylcoumarin-3-
acetamide)ethyl-1,3 -
dithiopropionate, see SAED
Sulfosuccinimidyl 4-( p -
azidophenyl)butyrate, see
Sulfo-SAPB
Sulfosuccinimidyl 7-azido-4-
methylcoumain-3-acetate
,
see Sulfo-SAMCA
Sulfosuccinimidyl(4-iodoacetyl)-
aminobenzoate, see
Sulfo-SIAB
Index 1197
Sulfosuccinimidyl-[perfl uoro-
azidobenzamido]-ethyl-
1,3 -dithiopropionate , see
Sulfo-SFAD
Sulfosuccinimidyl-2-
(biotinamido)ethyl-1,3-
dithiopropionate , see
Sulfo-NHS-SS-biotin
Sulfosuccinimidyl-2-( m -azido- o -
nitrobenzamido)-ethyl-1,3 -
dithiopropionate , see SAND
Sulfosuccinimidyl-2-( p -
azidosalicylamido)ethyl-
1,3 -dithiopropionate , see
SASD
Sulfosuccinimidyl-2-[6-(bioti-
namido)-2-(p-azidoben-
zamido) hexanoamido]
ethyl-1,3 -dithiopropion-
ate) , see Sulfo-SBED
Sulfosuccinimidyl-3-(4-hydroxy-
phenyl)propionate , see
Sulfo-SHPP
Sulfosuccinimidyl-4-(N-maleimid-
omethyl)cyclohexane-1-car-
boxylate , see Sulfo-SMCC
Sulfosuccinimidyl-4-( p -male-
imidophenyl)butyrate , see
Sulfo-SMBP
Sulfosuccinimidyl-6-(4-azido-2 -
nitrophenylamino)hexanoate ,
see
Sulfo-SANPAH
Sulfosuccinimidyl-6-[-methyl- -
(2-pyridyldithio)toluamido]-
hexanoate, see Sulfo-LC-
SMPT
Sulkowski , 814
Sun , 90 , 408 , 460 , 470 , 669 ,
689
Sundberg , 43 , 269 , 615 , 956
Sunlamp , 304 , 987
types , 532
Sunn , 69
Superoxide , 24
produced from psoralen , 209
Superoxide anion (O
2
−
) , 23
Surface
activation of , 188
anthraquinone coupling to , 207
dative bonds with , 189
modifi cation
with
psoralen , 210
silane coupling agents , 563
polymer modifi cation of , 936
Surface plasmon resonance
(SPR) , 1004
Susaki , 149
Suspension arrays , 583
Suter , 514
Sutoh , 296 , 525
Swali , 347
Swanson , 255 , 287 , 457
Sweeley , 48
Sweet clover , 430
Swiss 3T3 cells ,
247
Sykaluk , 73
Sympathetic ganglia , 310
Synthetic polymers
modifi cation with , 936
Sytkowski , 904
Szabo , 915
Szwergold , 367
T-cell , 256
Tabor , 23 , 1032
Tacchini-Vonlanthen , 928
Tada , 493 , 497
Tadayoni , 104
Tager , 260
Tagmatarchis , 645 , 647
Takadate , 454
Takahashi , 334
Talsma ,
863
Tam , 755
Tanaka ,
421
Tandem dyes , 463
Tanford , 14
Tang , 1012 , 1015
Tani , 389
Tanke , 400
Tao , 328 , 373
Taq polymerase , 970
Tarentino , 69
Targeting
liposomal reagents , 881
Tartaric acid
as a cleavable group in
cross-linkers , 393
Tarver , 239
Tauer , 606
Taurine , 121
Tawney , 256 , 258
Taylor , 83 , 427 , 924 , 928
99m
Tc , 504
coupling to sulfhydryls , 503
TCEP , 470 , 665 , 683
cleavage of catch-and-release
mass tag , 654
effect on aryl azides , 305
general description and use ,
95
reduction of antibody
disulfi des , 90
Teale , 292
Technetium-99m , 302 , 498
Tempst , 575
TEOS , 618 , 620 , 623
Terbium , 476 , 501
Terbium chelate
donor with Cy3 in LRET , 479
Terminal deoxynucleotide
transferase , 970
Terminal transferase , 970 , 973 ,
1000
Ternynck , 268
Terpyridine- bis (methylenamine)
tetraacetic acid (TMT) ,
479
Tert -butyl- N -(3-
hydroxypropyl)carbamate ,
634
TES , 408
TETA
general description and use ,
500
Tetanus toxoid , 748
use as carrier , 753
Tetra-pyrrole , 461
1,4,7,10-Tetraazacyclododecane-
N , N , N , N -tetraacetic
acid , see DOTA
1,4,8,11-Tetraazacyclotetra-
decane-N , N , N , N -
tetraacetic acid , see TETA
1,3,4,6-Tetrachloro-3 ,6-diphe-
nylglycouril
, see Iodogen
n -Tetradecanoic acid , see
Myristic acid
1198 Index
Tetraethyl orthosilicate (TEOS) ,
490 , 618
Tetraethylene glycol , 543 , 708
Tetrafl uorophenyl (TFP) ester ,
179
Tetramethylrhodamine , 415 , 429
comparison
to Texas Red , 424
with Lissamine rhodamine
B , 422
isothiocyanate derivative of ,
416
sulfhydryl reactive derivatives ,
425
Tetramethylrhodamine-5-
(and-6)-iodoacetamide, 427
general description and use ,
425
Tetramethylrhodamine-5-
(and 6)-isothiocyanate , see
TRITC
Tetranitromethane , 125 , 127
in nitration of tyrosine , 774
Tetrathionate , see Sodium
tetrathionate
Texaphyrin
, 23
gadolinium chelate , 24
PEG functionalized , 708
Texas red , 400 , 416 , 424 , 817
hydrazide derivatives of , 427
Texas Red hydrazide
general description and use ,
429
Texas Red sulfonyl chloride ,
425 , 1000
coupling to diamine modifi ed
DNA, 1001
general description and use ,
423
hydrazide derivative of , 429
TFMSA , 631
Thakur , 503
Theis , 162
Thelen , 222 , 765
Theorell , 963
Therien , 754 , 863 , 879
Thermochemical , 304
Thermoreactive , 302 , 1016
Thermus aquaticus , 970
Thevenin , 319
Thin-layer chromatography ,
873 , 874
5-Thio-2-nitrobenzoic acid ,
187 , 844 , see also TNB
Thioacetic acid , 371 , 488
Thioctic acid , 189
immobilized , 97
Thioester , 106
C-terminal , 191
formation of , 172
in native chemical ligation ,
697
Thioester-biotin , 705
Thioester bonds
hydroxylamine cleavable , 394
Thioester intein , 685
Thioether
, 120 , 256
formation with
epoxides , 268
maleimides , 259
Thioglycolate , 89
Thioglycolic acid , 97
Thiol , 100 , see also
Sulfhydryls
multivalent , 189
oxidation of , 23
Thiol-mPEG , 709
Thiol-PEG-carboxylate , 709
Thiol-PEG
n
-carboxylate , 740
Thiolate anion , 120 , 160 , 161 ,
183 , 834
Thiolation , 67
at carbohydrate residues in
antibodies, 504
of cytosine , 57
through disulfi de reduction ,
88
using
2-iminothiolane , 68 , 69
AMBH , 83
cystamine , 84
N -acetyl homocysteine
thiolactone, 80
PDPH , 301
SAMSA , 81
SATA , 71
SMPT , 77
SPDP , 76
Thiols, 100, see also
Sulfhydryls
reactions of , 182
Thiolsulfonate , 121
Thionyl chloride , 173
Thiophenol , 698 , 703 , 706
Thiopropionic acid , 371
Thiosulfate , 161
Thiourea linkage , 170
Thomas , 67 , 223 , 256 , 357 , 364 ,
380 , 481
Thompson , 662
Thorpe , 23 , 77 , 281 , 282 , 829 ,
830 , 834 , 841 , 848
THP , 180 , 181
general description and use ,
342
THPP , 181
general description and use ,
342
Threonine , 6 , 46 , 103 , 106 , 701
oxidation of , 28
N-terminal by periodate ,
136
solvent exposed area , 29
Thrombin , 413 , 529
Thylakoid membrane , 255
Thymine , 51
cycloaddition to , 57
hydrogen bonding , 64
psoralen photoreaction , 533
reaction with psoralen , 209
structure and reactivity , 54
Thyroglobulin , 748
use as carrier , 751 , 753
Thyroid gland , 753
Thyroxine
, 753
Tiberi ,
1016
Timberlake , 323
Time-resolved fl uorescence , 112 ,
474
Time-resolved fl uoroimmuno-
assay , 501 , 502
Tinglu , 926
Tirrell , 683
Titus , 425
TMS-EDTA
general description and use ,
575
TNB , 100 , 187 , 256 , 844
absorptivity of , 164
as a sulfhydryl blocking
group, 164
Index 1199
extinction coeffi cient , 100
TNB anion
absorptivity of , 187
TNB-thiol
reactions of , 187
TNBS , 105 , 128
for
determination of amines ,
127
measuring protease activity ,
156
in assay of proteases , 104
TNF , 243
Tokuyasu , 926
o -Tolidine , 776
diazotization of , 776
diazotized , 272
using in preparing hapten–
carrier conjugates ,
775
Tollen’s reagent , 37
Tomalia , 346 , 379 , 380 , 389
Tona
, 668
Toner , 479
Tonka beans , 430
Tonsil antigens , 915
Toomre , 151 , 152 , 538 , 539 ,
540
TOPO (tri-n-octylphosphine
oxide) , 487
Torchilin , 500 , 503
TornØe , 211 , 681 , 683
Tosyl chloride , 42
Toxicity
of liposome-encapsulated
drugs , 882
Toxin , 832
activation with
SIAB , 849
SPDP , 838
conjugation
to
antibodies using oxidized
dextrans , 857
antibodies using SMPT
,
841
antibody using cystamine ,
844
drugs , 847
using
amine-and sulfhydryl-reac-
tive heterobifunction-
als , 847
intact A–B types , 847
MBS , 852
SIAB , 848
SMCC , 850
conjugation
via disulfi de exchange , 833
with antibodies , 824
encapsulated in liposomes ,
882
gold labeled , 927
handling and safety issues,
xxxv , 828 , 829 , 838
in design of immunotoxins , 829
lectin binding properties of ,
827
modifi cation using 2-iminothi-
olane , 850
nicked ,
828
proteins used in immunotoxin ,
-827
role of in immunotoxins , 829
single-chain types , 829
SPDP activation of , 834
thiolation using 2-imino-
thiolane , 836 , 851
two-chain types , 827
Toyokuni , 147
Traceless Staudinger ligation ,
696 , 697
Trail , 847
Traincard , 56 , 976
Trakselis , 1025
Transamination , 412 , 460 , 525 ,
976 , 990
of cytosine , 55
, 457 , 974
Transfer RNA , 51 , 64
Transferrin
in cytotoxic conjugates , 825
SPDP conjugation to toxins ,
837
Transferrin receptor OX-26 , 302
Transglutaminase
assay of using 5-(biotinamido)-
pentylamine, 529
Transition temperature
effect on immune response ,
879
Transmembrane glycoprotein
H-2K
k
, 409
Transthioesterifi cation , 191 ,
685 , 697 , 706
Traut , 67 , 257
Traut’s reagent , see also
2-Iminothiolane
side reactions of , 69
TR-FRET , 477
Tresyl chloride , 42
Tri- n -octylphosphine oxide , see
TOPO
1,4,7-Triazacyclononane-
N , N , N -triacetic acid , see
NOTA
Triazole , 351 , 680 , 682 , 683 ,
684 , 722
from click chemistry reaction ,
211
Trichloro-s-triazine , 336
, see
also TsT
Trichloroacetic acid , 551
Trichloromethylperoxyl radical
(CCl
3
OO·) , 23
Triethanolamine , 70 , 176 , 252 ,
840 , 892
Triethylamine , 172 , 872 , 874 ,
875 , 950
Triethylene glycol , 533
Trifl uoroacetate , 118
Trifl uoromethanesulfonic acid
(TFMSA) , 630
Trifl uoroperazine , 1032
Trifunctional cross-linkers , 336
Trifunctional cross-linking
agents , 184
Trifunctional cross-linking rea-
gents
biocytin containing , 510
Trifunctional Label Transfer
Reagents , 1020
3,5,3 -Triiodo-
L -thyronine , 324
Triiodothyronine , 753
Trimethoxysilyl-propyldiethylen-
etriamine , 620 , 625
N -(Trimethoxysilylpropyl)-
ethylenediamine triacetic
acid , see TMS-EDTA
Trinitrobenzene sulfonic acid ,
156 , see also TNBS