Hermanson G. Bioconjugate Techniques, Second Edition
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1160 Index
Formaldehyde ( continued )
in capture of protein
interactions, 1010
Mannich reaction , 202
use in
fi xing Lucifer Yellow
derivatives, 457
Mannich reaction , 776
Formalin , 264
Formyl , see Aldehydes
N -Formyl peptide receptor , 306 ,
311
Forster , 531 , 987
Förster , 477
Förster radius , 477
Fortes , 413 , 460
Fox , 255 , 305 , 330 , 553 , 555
Fraenkel-Conrat , 102 , 158 , 178
Fraker ,
553
Franklin , 485
Franz , 485
Fréchet , 346 , 347 , 353 , 356
Free radical , 23
Freedberg , 256 , 258
Freedman , 107
Freeland , 162
FRET
use with lanthanide chelates ,
477
using quantum dots , 492
Freund’s adjuvant , 751
Freytag , 284 , 287
Friden , 302
Fried , 128
Friede , 754 , 861 , 863 , 869 , 877
Friedenson ,
162
Friedman , 188 , 403
Friedrich , 413
Friedrichson , 1007 , 1037
Friend virus , 243
Froehner , 512
Fructosamine-3-kinase , 367
Fructose ,38 , 45 , 857
dendrimer derivative , 367
reaction with phenylhydra-
zine, 42
Frytak , 498
Fu , 581
Fucose ,46
Fuji , 74
Fujii , 708
Fujimoto , 337
Fujioka , 334
Fujita , 413
Fujiwara , 292
, 908
Fukui , 263
Fuller , 597 , 628
Fullerenes , 582 , 627
maleimide derivative , 630
modifi cation of , 629
properties of , 627 , 628
reaction with
azomethine ylide , 629
glycine and formaldehyde
derivatives, 629
solubility of , 629
structure of , 627
Fulleropyrrolidines , 629
conjugation to , 630
Functional targets , 3
Amino Acids, Peptides, and
Proteins, 3
carbohydrates , 35
Functionalities
creating specifi c chemical
groups, 66
Fungi , 746
Fv fragments , 826 ,
830 , 855
Gabizon , 882
Gadolinium , 24 , 708
Gadolinium(III) texaphyrin ,
708
Gaertner , 136
Gaffney , 256
Gahmberg , 40
Gailit , 100
-Gal
sulfhydryl , 788
Galactosamine , 38
Galactose , 21 , 38 , 45 , 46 , 124 ,
852 , 878 , 964
coupling to dendrimers , 371
labeling with biocytin-
hydrazide, 529
oxidation with galactose
oxidase
, 132
plant toxin binding of , 827
Galactose cerebroside ,
871
Galactose oxidase , 124 , 132 ,
198 , 529 , 919
-Galactosidase , 290 , 787 , 790
conjugation , 905
general , 964
Galactosidase , 906
conjugation with avidin using
SMCC, 908
-
D -Galactoside , 964
Galardy , 132 , 310
Galium-66 , 498
Galium-67 , 498
Galium-68 , 503
Gamma counter , 551
Gangliosides , 131 , 139 , 866 ,
868 , 869 , 871 , 878
labeling with Lucifer Yellow
CH, 460
Gansow , 383
Gantt , 461
Gao , 492 , 493
Gartner , 654
Garzon , 930
Gastroclonium coulteri , 461
Gaudet , 1016
Gaur , 982
153
Gd , 384
Ge , 484
Geckeler , 629
Gee , 179 , 924
Gegg , 754
Geiger , 423
Gel fi ltration chromatography ,
813
Gel state , 869
Geldanamycin , 708
Gelonin , 827 , 829 , 830 , 847
conjugation using SMCC , 850
modifi cation with 2-imino-
thiolane, 829 , 840
removal of unconjugated , 841
structure of , 829
thiolation with 2-imino-
thiolane, 837
Gelonium multifl orum , 827
Gemeiner , 112
Genetic code
, 50
Gentle Elution Buffer , 814
Geoghegan , 136 , 197 , 473 , 926 ,
929 , 932
Index 1161
Georgakilas , 646
Georges , 474
Geranylazide , 694
Gergely , 220 , 599 , 763
Germain , 746
Gershoni , 139 , 967
Geuze , 927
Ghebrehiwet , 523
Ghetie ,73 , 281 , 830 , 840 , 841 ,
845
Ghosh , 69 , 84 , 124 , 132 , 146 ,
176 , 195 , 215 , 978 , 979 ,
981 , 998
Gibian , 205
, 328
Gilchrist
, 204 , 207 , 303
Gilham , 211 , 676
Gill , 828
Gilles , 177 , 216
Gilligan , 92
Gillitzer , 924 , 934
Gingras , 649
Gioannini , 329 , 739
Girish , 704
Gitlin , 900
Gitman , 292
Givens , 322
Givol , 256 , 275
Glactosyltransferase , 253
Glacy , 427
Glass slides
coupling using expressed
protein ligation , 704
Diels–Alder and click chemis-
try coupling to ,
689
Diels–Alder reaction on , 669
GOPTS modifi cation of , 579
modifi cation with
bis-NHS-PEG compounds ,
714
SHA groups , 679
treatment for silanization , 565
Glass surfaces
dendrimer modifi cation of ,
385
Glazer , 461 , 462 , 773
-
D -Gluconolactone , 965
Glucosamine , 38 , 43 , 147
- d -Glucose , 965
Glucose , 38 , 45 , 173 , 305 , 548 ,
878 , 965
as repeating unit in dextran ,
936
determination of , 965
glycation reaction of , 147
in
dextran polymers , 857
non-enzymatic glycation , 49
of dextran , 951
reaction with phenylhydra-
zine , 41
Glucose oxidase , 160 , 284 , 787
conjugation with avidin or
streptavidin , 905
general description and use ,
965
immobilized , 556
oxidation with periodate , 802
periodate oxidation of , 967
thiolation using SATA , 908
Glucose oxidase/lactoperoxidase
reaction , 548
Glucose-1-phosphate , 39
Glucose-6-phosphate , 39
Glucosylcerebroside , 878 , see
also Sphingomyelin
Glutamate dehydrogenase–
amino transferase , 255
Glutamic acid , 7
oxidation of , 28
pKa , 7
solvent exposed area , 30
Glutamine , 6 , 529
solvent exposed area , 30
Glutaraldehyde , 135
, 235 , 263 ,
460 , 781 , 788 ,
810 , 813 ,
962 , 964 , 965
1-step conjugation protocol ,
798
2-step conjugation procedure ,
798
2-step conjugation protocol ,
800
activation of
enzymes with , 914 , 966
PE , 891
avidin conjugation using , 913
concentration used in cross-
linking , 780
coupling to amine particles ,
601
cyclized , 134
general description and use ,
265
in conjugation of proteins to
liposomes , 890
modifi cation of amines , 134
reaction with adenine , 59
two-step cross-linking , 268
use
for antibody–enzyme
conjugation
, 798
in fi xing Lucifer Yellow
derivatives , 457
in hapten–carrier
conjugation , 779
Glutaric acid , 105
Glutaric anhydride
general description and use ,
106
modifi cation of
APTS surfaces using , 569 ,
570
PEG with , 941 , 945
Glutathione , 89 , 97 , 406 , 425 ,
426 , 436
immobilized , 1020
Glycan , 366
BAP conjugate , 541
BNAH modifi cation of , 541
BAP modifi cation of , 538
containing ketone analogs ,
671
containing sugar analogs
, 671
coupling to dendrimers , 369
coupling to hydrazide
particles , 613
enzymatic release of , 153
fl uorescent labeling of , 153
hydrazide-PEG4-biotin
modifi cation of , 736
labeled with azido-sialic acid
groups , 693
modifi cation
of , 147 , 150
with cyanine dye , 472
Glycan biotinylation reagents ,
537
O -glycanase , 153
Glycated , 173
Glycated hemoglobin , 49
1162 Index
Glycation , 48 , 147
non-enzymatic , 21
Glyceraldehyde , 38
Glycerol , 403 , 414 , 555
for
quenching sodium periodate
reactions, 413 , 440
in phosphodiglycerides , 864
Glycerylphosphate , 754
Glycerylphosphate derivatives ,
859
Glycidol , 364 , 371
for modifi cation of
dendrimers, 364
3-Glycidoxypropyltriethoxysi-
lane, 577
3-Glycidoxypropyltrimethoxysi-
lane, see GOPTS
Glycidyl ether derivative
of PEG , 948
Glycidyl methacrylate , 271
Glycidyloxypropyltrimethoxysi-
lane, see
GOPTS
Glycine , 5801
blocking excess glutaraldehyde
with, 913
for quenching glutaraldehyde
reactions, 798 , 800
in NHS ester reactions , 238
solvent exposed area , 30
Glycobiology , 366
Glycoconjugates , 125 , 131 , 139
detection
using hydrazide-avidin , 919
with lectin–gold probes ,
932
labeling with
biocytin-hydrazide , 528
biotin-hydrazide , 526
Lucifer Yellow hydrazide ,
457
Texas Red hydrazide , 429
lectin binding , 878
Glycoconjugation , 147
Glycogen , 951
Glycogen phosphorylase b , 254
Glycolipids , 46 , 131 , 871
conjugation using lectins , 877
detection with lectin–gold
probes, 932
labeling with Lucifer Yellow
CH, 460
oxidation with sodium
periodate, 869
periodate oxidized , 883
reductive amination
conjugation, 893
Glycols
as cleavable groups in
cross-linkers, 392 , 393
oxidation with periodate , 130
Glycolysis , 39
Glycopeptides , 316
Glycoproteins , 20 , 46 , 123 , 131 ,
166 , 232 , 241 , 292 , 412 ,
413 , 438 ,
446
activation with hydrazide
reagents, 270
avidin , 900
biotinylation of , 538
carbohydrate content , 20
carbohydrate structure , 46
conjugation using
carbonyl and sulfhydryl
reactive cross-linkers ,
297
M
2
C
2
H , 300
MPBH , 298
PDPH , 300
reductive amination , 910
coupling to dendrimers , 362
cyanine dye derivative , 472
detection
using
hydrazide compounds ,
139
hydrazide-protein
derivatives, 967
with
hydrazide probes , 270
hydrazide reagents , 41
lectin–gold probes , 932
gold labeled , 927
labeling with
biocytin-hydrazide , 528
Cascade Blue hydrazide ,
456
fl uorescein-5-thiosemi-
carbazide, 413
Lucifer Yellow CH , 459
modifi cation with
AMBH ,
83
biotin-hydrazide , 527
oxidation with
oxidases , 131
periodate , 197
sodium periodate , 130 , 800
periodate oxidation , 49 , 810
reaction with ABH , 331
specifi c oxidation of sialic acid
residues , 130
Glycosidases
in creating aldehydes , 132
N -Glycosidic , 7
O -Glycosidic , 7
N -Glycosidic bond
in
DNA , 61
nucleic acids , 51
N -Glycosidic linkage , 20 , 45
of purines , 58
O -Glycosidic linkages
, 20 , 45
Glycosphingolipids , 367
conjugation to liposomes by
reductive amination , 893
periodate oxidation of , 870
Glycosyl transferases , 46
Glycosylamines , 149 , 155 , 538
Glycosylation , 20
Glycosylhydrazide , 542
Glyoxals , 262
chemistry of , 173
reaction with arginine , 201, 333
- N -Glyoxylyl , 136
GMBS , 769
analog of , 293
general description and use ,
292
use in antibody–enzyme
conjugation, 788
Goda , 485
Goding, 784 , 819 , 938
Goebel , 147
Gold , 412 , 427 , 438 , 444 , 457 ,
460 , 583 , 975 , 976
dendrimer modifi cation of , 385
Gold nanoparticles , 620 , see
also Colloidal gold
click chemistry coupling to ,
687
Index 1163
dendrimer coating of , 389
Gold particles , 915
Goldman , 489 , 490 , 493
Golds , 260
Golgi apparatus , 46
Gonadotropes , 531
Gonadotropin releasing
hormone , 247
Goodfellow , 322
Goodlad , 275
GOPTS
general description and use ,
577
glass slide modifi cation using ,
579
slide surface modifi cation
using , 387
Gorecki , 97 , 535
Gorin , 160 , 183
Gorman , 330 , 406 , 407 , 425
,
436
Gotoh , 284 , 939 , 940
Gounaris , 103
Goundalkar , 895
Gowda , 333
Grabarek , 220 , 599 , 763
Grabowski , 461
Graft copolymerization , 590
Granata and Kitai , 509
Grant , 531
Graphene sheet , 638
Graphite , 627
Grassetti , 165
Gray , 41 , 781
Grayeski , 438
Grayson , 347
Green , 506
, 508 , 511 , 900 , 901 ,
922
Greenacre , 23
Greene , 407
Greenwood , 548
Gregoriadis , 754 , 824 , 863 , 868 ,
879
Gretch , 514 , 518
Griffi ths , 550 , 552
Grossman , 184
Ground-state , 400
Growth cones , 421
Growth factors , 508
conjugation to toxins , 847
in cytotoxic conjugates , 825
Grubor , 189 , 240
Guanidination , 181 , 650
Guanidine , 88 , 90 , 96 , 99
, 120 ,
393
labeling with p -aminobenzoyl
biocytin, diazotized ,
535
Guanidine hydrochloride , 515
Guanidino
of iminobiotin , 515
Guanidino group , 9
Guanidinyl group
of arginine , 333
Guanine , 51
activation with bromine
compounds , 977
bromination of , 59
electrophilic reactivity , 58
hydrogen bonding , 64
nucleophilic displacement
reactions , 58
reaction with
cisplatin , 192
CMC , 58
structure and reactivity , 58
Guanosine
modifi cation with diazonium
compounds , 989
Gudheti , 423
Guerrero , 1011
Guire , 262
Guo , 639
Gupta , 308 , 824
Gurd , 109 , 183
Gutteridge , 23 , 224 , 1032
Guyot-Sionnest , 487
Gygi , 649 , 651
3
H , 546
H
2
OI + , 547
H
2
O
2
, 556 , see also Hydrogen
peroxide
Ha , 492
Haaijman , 403
HABA , 515 , 922
absorptivity of , 922
determination of biotinylation
level using , 922
HABA assay , 730
Habeeb , 103 , 108 , 128 , 159
Habili , 531
Hackenbrock , 423
Hackeng , 700
Hadi , 549
Hage , 575
Hager , 597
Hahn , 189
Hajdu , 254
Halford , 367
Hall ,
328 , 650 , 658 , 1011
Halliwell , 23 , 1032
-Haloacetamides , 161
Haloacetamides , 183
-Haloacetates
relative reactivity of , 110
Haloacetyl
reactions of , 182 , 274
N -Haloamine derivatives , 548 ,
553
Halogenation
of pyrimidines , 56
Halogens
reactive aromatic , 185
Ham , 120
HAMA , 826
Hamada , 239
Hamaguchi , 807
Hamdan , 649
Hammes , 255 ,
409
Han , 492 , 655
Hanash , 519 , 735
Hand , 254
Handlogten , 735
Häner , 668
Hang , 693
Hansen , 654
Haptens , 116 , 264 , 272 , 745 ,
748
antibody response toward ,
746
conjugation
to liposomes , 754
to MAP , 755
with sulfhydryl containing ,
766
containing an active hydrogen ,
777
defi nition of , 746
1164 Index
Haptens ( continued )
encapsulation into liposomes ,
881
synthetic , 747
Hapten–carrier conjugation , 22 ,
283 , 745
carbodiimide mediated , 755
preparation using active
hydrogens, 773
using
diazonium reactions , 773
glutaraldehyde , 779
homobifunctional NHS
esters, 763
NHS ester–maleimide
cross-linkers, 766
reductive amination , 781
Haptomer , 827
Harding , 149
Hardman , 256 , 258
Hardy , 266 , 798
Harlow , 746 , 784 ,
819
Härmä ,
289
Harper , 590
Harrigan , 863
Harris , 786 , 950
Harrison , 322
Hartman , 234 , 250 , 252
Hartmann , 143
Hashida , 283 , 850 , 896
Hashimoto , 872 , 888 , 905
Hassell , 254
Hatakeyama , 103 , 156
HATU , 371
HAuCl
4
, see Chloroauric acid
Hauenstein , 14
Haugaard , 160
Haugland , 400
Hawker , 347
Hay , 192
4
He , 825
Head groups , 879 , 885
functional derivatives , 869
of
phosphodiglycerides , 864
sphingolipids , 866
Heamagglutinin , 255
Hearn , 196 , 230 , 930 , 946
Heath , 754 , 869 , 870 , 880 , 882 ,
893
Heavy Atom, Deuterated
Crosslinking Agents , 1008
effect on fl uorescence , 399
Heavy chains , 88 , 93 , 784
Hebert , 403
Heetebrij , 192
Heilmann , 256 , 258
Hein, 256 , 258
Heindel , 951 , 953 , 956 , 960
Heinmark , 256
Heitz , 160 , 183
Helenius , 837
Helmeste , 243
HEMA , 583
Heme , 19
Hemiacetal , 37 , 44
Hemiketal , 37
Hemmila , 476 , 502
Hemocyanin , see KLH
Hemoglobin , 256 , 407
Hemoglobin S , 252
Hemoprotein , 962
Henderson , 180 , 342
Henderson–Hasselbalch
equation, 14
Henriksen , 209 , 533
Heparin , 152
Hepatitis B , 367
Herbener , 930 , 931
Hermanson , 43 , 98 , 115 , 134 ,
264 , 268 , 575 , 606 , 750 ,
807 , 808 , 814 , 815 , 843 ,
879
Herpes simplex virus , 367
Herpes virus proteins , 518
Herriott , 193
Hersckovits , 748
Herzberg , 976
HESS , 224
Heterobifunctional reagents ,
788
acid labile
, 108
amine and sulfhydryl reactive ,
277
amine reactive and
photoreactive, 302
arginine reactive and
photoreactive, 333
carbonyl and sulfhydryl
reactive, 297
carbonyl reactive and
photoreactive, 330
carboxylate reactive and
photoreactive, 332
general overview , 276
in
liposome conjugation , 872
multi-step protocols , 33
NHS ester–maleimide
in hapten–carrier
conjugation, 766
PEG-based , 718
sulfhydryl reactive and
photoreactive, 324
use
for crosslinking proteins , 32
in avidin conjugation , 906
Heuck , 427
n
-Hexadecanoic acid , see
Palmitic acid
3,5-Hexadiene phosphoramidite ,
668
2,4-Hexadienyl ester , 669
Hexahydro-2-oxo-1H-
thieno[3,4-d]imidazole-4-
pentanoic acid , see Biotin
Hexose , 37
High content screening assays ,
683
Hilchenbach , 419
Hill , 210 , 668
Hillel , 69
Hines , 96 , 487
Hinge region , 436 , 784 , 786
antibody subclass variation ,
792
Hiratsuka , 275 , 296
Hirsch , 407 , 629 , 634 , 640
6 ×His , 1035
His-tagged proteins , 112 , 575
Histidine ,
7 , 102 , 109 , 422 , 548 ,
553 , 556
iodination of , 549 , 551
iodination reaction of , 203
modifi cation with H
2
OI , 547
oxidation of , 28
reaction with
alkyl halides , 274
anhydrides , 178
cisplatin , 192
Index 1165
diazonium , 272 , 273 , 773
diazonium group , 203
haloacetyl compounds , 182
p -aminobenzoyl biocytin,
diazotized , 534
pKa , 9
reaction with NHS esters ,
171–172 , 237
solvent exposed area , 30
Histones , 407 , 427
HIV , 367
Hixson , 461
HLA A2, 493
Hlavka , 223
Hnatowich , 498 , 499 , 514
Ho , 824
Hoare , 176 , 195 , 215 , 219
, 223
Hochman
, 419
Hodge , 347
Hoffman , 526
Hofmann , 511 , 516
Hohng , 492
Holgate , 924
Holmberg , 498 , 825
Holmgren , 342 , 1028
Höltke , 970
Holzner , 256 , 258
Homoarginine , 181
Homobifunctional reagents
bis-aldehydes , 262
bis-hydrazides , 269 , 270
difl uorobenzene derivatives ,
259
epoxides , 268
general overview , 234
heavy atom, deuterated , 1008
imidoesters
, 250
in
single-step cross-linking
procedures , 235
study of protein
interactions , 1006
NHS ester containing
in hapten–carrier
conjugation , 763
NHS esters , 235
photoreactive , 262
sulfhydryl reactive , 256
use for crosslinking proteins ,
32
Homocysteine , 80 , 110 , 183
Homogeneous assay , 1000
Homogeneous immunoassay ,
419
Homola , 1004
Hong , 371 , 385
Honjo , 828
Hopman , 57
Hopp , 754
Hopwood , 263
Horak , 614
Hordern , 239
Horecker , 107
Horikawa , 509
Horisberger , 924 , 926 , 928
Hormones
gold labeled , 927
in cytotoxic conjugates , 825
Hormonotoxins , 825 , 847
Horney , 1026 , 1027
Hornsey , 174 , 232
Horseradish peroxidase , 49 ,
114 , 131 , see also
HRP
Hou , 171 , 235 , 244 , 940
Howard , 246
Hoyer , 1032
HPLC
, 101 , 128 , 940
Hrapchak , 404
Hrmova , 423
HRP , 114 , 233 , 284 , 787 , 790 ,
810 , 855 , 906 , 964 , 965 ,
981
activation with
periodate , 800 , 802
sulfo-SMCC , 790 , 909
antibody conjugates
purifi cation of , 815
blocking amines on , 156 , 800
color change of , 802
conjugation
to
avidin using reductive
amination , 910
conjugation to PDITC
activated DNA , 997
with
antibodies using
glutaraldehyde , 798
avidin or streptavidin ,
905
controlling size of antibody
conjugates of , 802
coupling to hydrazide
particles , 614
general description and use ,
961
maleimide-activated , 790 , 909
oxidation with
periodate
optimal concentration ,
802
sodium periodate , 131 , 912 ,
962
periodate oxidation of , 788
,
804 , 912 , 967
reductive amination with
antibodies , 804
removal of unconjugated
enzyme , 813
SFB modifi ed , 998
SMCC activated , 962
thiolation using SATA ,
908
HSAB
general description and use ,
308
Hsp , 90708
Huang , 296 , 389 , 862 , 863 , 886
Hudson , 296 , 347
Hughes , 548
Huhtinen , 476 , 477
Huisgen , 680
Huisgen cycloaddition reaction ,
211 , 680
Human anti-mouse antibody , see
HAMA
Human choriogonadotropin ,
305 , 310
Human chorionic gonadotropin
SPDP conjugation to toxins ,
837
Human erythrocyte monosac-
charide transporter protein ,
305
Human Genome Project , 50
Human lymphoblasts
, 311
Human papilloma virus , 367
Human polymorphonuclear leu-
kocytes , 311
Human serum albumin
oxidation of , 27–28
1166 Index
Hummelen , 637 , 638
Humoral immunity , 879
Hunter , 251 , 546 , 557
Hurst , 1026
Hurwitz , 139 , 275 , 824 , 857
Husain , 256 , 274
Huse , 826
Hutchinson , 872 , 875 , 886
Hybridization , 50 , 53 , 66 , 132 ,
526 , 531 , 924 , 969 , 970 ,
973 , 976 , 980 , 982 , 988 ,
990 , 992 , 994 ,
998 ,
1000
Hybridoma , 787
formation of using PEG , 938
Hydrazide-PEG
4
-biotin , 733 ,
736
Hydrazides , 41 , 102 , 131 , 132 ,
143 , 330 , 514 , 787 , 803
biotinylation reagents
containing, 525
coupling using carbodiimides ,
177
detection with TNBS , 128
dextran modifi ed , 954
in homobifunctional reagents ,
269
introduction of , 139
modifi cation
of aldehydes , 140
of carboxylates , 142
of proteins using , 919
with glycans , 150
of
ABH , 331
AMBH , 83
biocytin-hydrazide
, 528
biotin-hydrazide , 990
BODIPY 530/550 C
3
hydrazide, 445
BODIPY FL C
3
hydrazide ,
448
carbonyl reactive heterobi-
functionals, 298
fl uorescein-5-thiosemi-
carbazide, 412
Lissamine rhodamine B
sulfonyl hydrazine ,
427
M
2
C
2
H , 299
MPBH , 298
PDPH , 300
rhodamine derivatives , 427
reaction with
aldehydes , 270
diazopyruvates , 322
glutaraldehdye , 267
periodate oxidized antibod-
ies, 805
transformation to acyl azide ,
171
Hydrazine , 143 , 429 , 438 , 528 ,
990
measurement of , 145
reaction with
aldehydes , 200
nucleotides , 54
Hydrazine–Aldehyde Reagent
Pairs, 669
6-Hydrazinium nicotinate , 671 ,
730
Hydrazinolysis , 153
2-Hydrazinopyridine ,
673
Hydrazone , 131 , 140 , 166 , 200 ,
270 , 271 , 298 , 412 , 413 ,
414 , 427 , 446 , 461 , 504 ,
525 , 527 , 528 , 613 , 669 ,
919 , 990
pH optimum for formation ,
674
reduction of , 527
reduction with sodium
cyanoborohydride, 140 ,
805
Hydrazone linkages , 41
Hydrogen , 100
Hydrogen bonding , 868
of nucleotide base pairs , 64
Hydrogen peroxide (H
2
O
2
) , 23 ,
548 , 961 , 965 , 1032
Hydrogen peroxide oxidoreduct-
ase, see HRP
Hydrogenolysis , 392
4 -Hydroxyazobenzene-2-car-
boxylic acid , see HABA
Hydroperoxyl radical (HO
.
2
) , 23
-Hydroxy aldehydes , 42
-Hydroxy ketones , 42
Hydroxyl groups
activation with
DSC , 249
CDI , 228
cross-linking with PMPI , 171
formation by reduction of
aldehydes, 231
in formation of carbonates ,
175
modifi cation with anhydrides ,
103
nucleophilicity , 43
oxidation of diols with
periodate, 130
reaction with
alkyl halides , 275
anhydrides , 178
chloroacetic acid , 113
epoxides , 174 , 268
glutaric anhydride , 106
isocyanate ,
171, 454
NHS esters , 171 , 237
reactions of , 195
Hydroxyl radical footprinting ,
25 , 1032
Hydroxyl radicals (
·
OH) , 23 ,
505
produced from psoralen , 209
Hydroxylamine , 43 , 797 , 887 ,
984
assay of polyaldehyde-dextran
using, 953
deprotection of
SATA with , 71
SATP , 74
for
cleavage of O -acetyltyro-
sine, 158
cleaving ester bonds , 247
deprotection of SATA-
modifi ed molecules , 795
in
cleavage of ester containing
cross-linkers, 394
in cleavage of esters , 103
reaction with
pyrimidines , 55
SAMSA , 82
use in deblocking citra-
conylated amines , 109
Hydroxylysine, 46
Hydroxymethyl Phosphine
Derivatives, 180 , 342
Index 1167
p -Hydroxyphenylacetic acid
use as an iodination scavenger ,
308
N -Hydroxysuccinimide , see
NHS
N -Hydroxysuccinimide esters ,
114
N -Hydroxysuccinimido-2-imino-
biotin , see NHS-iminobiotin
N -Hydroxysuccinimidyl-4-azido-
benzoate , see HSAB
N -Hydroxysuccinimidyl-4-
azidosalicylic acid , see
NHS-ASA
N -Hydroxysuccinimidyl
chloroformate , 197
reaction with mPEG , 943
N -Hydroxysulfosuccinimide , see
Sulfo-NHS
N -Hydroxysulfosuccinimidyl-
4-azidobenzoate , see
Sulfo-HSAB
Hynes , 46
Hypervariable region , 94
, 785 ,
826
Hypobromous acid (HOBr) , 23
Hypochlorous acid (HOCl) , 23
I
−
, 548
I
2
, 548 , 556
125
I , 262 , 306 , 546 , 549 , 550 ,
553 , 556 , 817 , 819 , 1020
avidin labeled with , 904
comparison to other radio-
isotopes , 546
emission properties , 546
modifi cation of
heterobifunctional
cross-linkers , 561
SHPP with , 557
protein modifi cation with , 547
131
I , 546 , 549 , 553
emission properties , 546
IA antigens , 256
5-IAF 408 , see also 5-(and 6)-
Iodoacetamidofl uorescein
6-IAF 408 , see also 5-(and 6)-
Iodoacetamidofl uorescein
Ibrahim , 124 , 177 , 216
ICAT
acid cleavable , 655
catch-and-release tag , 654
cleavable , 653
general description and use ,
651
hydrazide derivative , 655
solid phase tag , 655
visible tag (VICAT) , 655
Ichihashi , 638
Ichishima , 952
ICl
, 549 , 553
ICPTES
general description and use ,
579
IgA , 785
structure of , 785
IgD , 785
IgE , 241 , 243 , 785
biotinylation of , 511
IgG , 748 , 785
activation with periodate , 803
adsorption density onto
particles , 592
binding to nickel chelate
affi nity column , 815
conjugation
to liposomes , 872
with cBSA , 751
detection using biotinylated
immunoglobulin binding
proteins , 905
digestion with
pepsin , 807
papain , 808
enzymatic digestion of , 786
,
807
gold labeling , 926
isolation of monomeric form ,
842
labeling with
biotin-hydrazide , 526
NHS-fl uorescein , 405
NHS-rhodamine , 421
lysine accessibility , 31
papain digestion of , 808
reduced , 792
reduction
of disulfi des , 88
using TCEP , 96
with 2-mercaptoethylamine ,
93 , 788
reductive amination with
enzymes , 804
IgG 1, 809
IgG
2, 809
IgG 3, 809
IgG 4, 809
Iglesias ,
112
IgM , 785
structure of , 785
Iijima , 638 , 639
Ikada , 177 , 217 , 219
Ikai , 254
Illum , 594 , 602
Ilver , 1025 , 1026
Imagawa , 284
Imaging , 500 , 514 , 819 , 881
Imidate , see Imidoester
Imidazole , 9 , 110 ,
124 , 146 ,
228 , 230 , 231 , 795 , 946 ,
979 , 980 , 981 , 982
in NHS ester reactions , 238
modifi cation with H
2
OI
+
, 547
reaction with
diazonium , 273
reaction with NHS esters ,
172
ring of purines , 58
Imidazole carbamate , 175 , 606 ,
941
hydrolysis of , 231
Imidazolyl carbamate , 196 , 230 ,
946
Imide
as product of a hydrazide
reaction with a
carboxylate , 142
Imidoamide , 176 , see also
amidine
Imidoesters , 67 , 235 , 892
chemistry of , 176
homobifunctional , 250
of
DMA , 251
DMP ,
252
DMS
, 253
DTBP , 254
Imine , 125
2-Imino-imidazole , 515
1168 Index
Iminobiotin , 506
immobilized , 516
NHS ester of , 515
3,3 -Imino bis propylamine , 115 ,
125 , 954 , 976
Iminodiacetic acid
immobilized , 815
Iminophosphorane , 690
2-Iminothiolane , 186 , 503 , 768 ,
793 , 809 , 848 , 850
antibody modifi cation of , 793
for thiolation of toxins , 840
general description and use ,
68
in
modifi cation of gelonin , 830
thiolation of
antibodies , 789
phycobiliproteins
, 462
toxins , 836
modifi cation of
avidin or streptavidin with ,
919
gelonin , 840
gelonin or PAPs , 829
side reactions of , 69
toxin thiolation using , 852
use with 4,4 -dipyridyl
disulfi de , 71 , 166
Immobilization , 162 , 232 , 253 ,
264
using CDI , 230
Immobilized disulfi de
reductants, 97
Immobilized metal affi nity chro-
matography (IMAC) , 575
Immobilized protein A , 807
Immobilized streptavidin , 653
Immonium cation intermediate
in formaldehyde reactions ,
264
Immune complexes ,
254
Immune modulators , 879
Immune response , 745
effect of
liposomal transition
temperature, 879
positively-charged
liposomes, 879
in hapten–carrier system , 746
modulation through PEG
modifi cation , 937
reduction of , 936
toward
cationized molecules , 116
cBSA immunogens , 750
precipitated immunogens ,
749
proteins , 748
Immunity
defi nition of , 745
protective , 747
Immunization , 746 , 753
with liposome carriers , 754
Immunoaffi nity ,
253
Immunoaffi nity chromato
graphy ,
813
protocol , 814
Immunoassay , 279 , 812 , 908
liposome mediated , 858
RIA , 817 , 819
using
avidin–biotin interaction , 514
avidin–biotin reagents , 900
liposome conjugates , 883
Immunochemical blocking agent ,
926
Immunoconjugates
with fullerenes , 634
Immunocytochemical staining ,
931 , 962
Immunocytochemistry , 755
Immunogen , 22 , 292
BMPA conjugation , 112
defi nition of , 745
glycan–streptavidin, 538
gold as carrier
, 927
liposomal , 880
liposome containing , 868
liposomes used as , 858
preparation of , 755
Immunogen conjugate , 218
Immunogen conjugation
using EDC , 217
Immunogenicity , 746 , 747
cross-bridge of
PEG compounds , 718
SMCC , 718
modulation by modifi cation
with dextran , 951
of
cBSA , 750
crosslinker cross-bridges ,
277 , 768
KLH , 748
liposomes , 879
PEG modifi ed molecules , 938
polymerized haptens , 757
Immunogens , 272 , 284 , 287
hapten-polymer conjugates ,
936
Immunoglobulin binding
proteins, 783
biotinylated , 905
gold labeled , 927
gold labeling of , 930
immobilized , 813
Immunoglobulins , 97
activation with periodate , 803
binding to nickel chelate
affi nity column , 815
biotinylation of , 817
class , 785
conjugation
to liposomes by reductive
amination, 893
using carbonyl and
sulfhydryl reactive
cross-linkers, 297
directed against immunotoxin
conjugates in vivo , 826
FITC labeled , 403
gold labeling , 926 , 932
glycosylation sites , 785
labeled , 816
labeling with
AMCA-hydrazide , 439
biotin-hydrazide , 526
modifi cation
and conjugation of , 783
with
DTPA , 499
sulfo-NHS-biotin , 512
on B lymphocytes , 745
optimal fl uorophore
incorporation, 819
radioiodination of , 819
radiolabeling of , 817
reduction
of , 790
Index 1169
using DTT , 90
with 2-mercaptoethylamine ,
93
structure of , 784
subclasses , 792
thiolation
of , 788
using
2-iminothiolane , 793
PDPH , 504
Immunogold staining , 924
Immunohistochemical staining ,
94 , 419 , 802 , 807 , 914 ,
918 , 964 , 965
using fl uorescently-labeled
antibodies , 818
Immunoprecipitation , 727 , 1011
Immunotoxin , 186 , 279 , 281 ,
287 , 292
, 301 , 827 ,
882
conjugation using
intact A–B toxins , 847
PDTP , 843
SPDP , 834
cytotoxicity
of , 830
relative to cleavable
cross-linkers , 847
gel fi ltration isolation of , 843
general description and use ,
824
half-life in vivo , 841
immune response toward , 826
large-scale preparation of , 841
need for cleavable linker in , 830
noncleavable cross-linkers in
preparation of , 830
nonspecifi c binding of , 830
preparation
using
amine- and sulfhydryl-
reactive heterobifunc-
tionals , 847
aromatic maleimide
cross-linkers, 853, 855
cystamine , 844
Ellman’s reagent , 844
MBS , 852
reductive amination , 855
S-sulfonates , 845
SIAB , 848
SMCC , 850
SMPT , 841
via disulfi de exchange , 833
protein toxins used in , 827
removal of unconjugated
toxin , 854
SPDP conjugation , 834
Immunotoxin conjugates
antibody-to-toxin ratio , 832
design of , 829
ideal characteristics , 832
injection of , 826
modifi cation with synthetic
polymers , 826
of protein toxins
, 827
preparation of , 829
preparation strategies , 830
Imperiali , 485
111
In , 379 , 383 , 647
Inada , 937
InCl
3
, 667
Indium-III , 820
Indium-111 , 498
Indium-114 m , 498
Indium-115 , 498
Indol rings , 465 , 467
Indomethacin , 353
Inesi , 410
Infl uenza virus , 255
Ingalls , 512
Initiation factor IF , 2256
Inman , 128 , 773 , 954
Innis , 970
Inorganic substrates
use with silane coupling
agents , 565
Insulin , 86 , 97 , 292 , 336
biotinylation of
, 511
Insulin-dependent protein
kinases , 243
Insulin receptor , 310 , 510
Intein , 191 , 685
native cleavage reaction , 701
Interaction domains , 1004
Interaction surfaces
mapping by hydroxyl radical
footprinting , 1032
Interactome , 1004
Intercalation
of psoralen , 209
Interferon , 243
Interleukin , 2243
Interleukin-3 receptor , 306
Intermediate fi lament , 423
Intraperitoneally , 750
Iodide , 549
Iodination , 1020
changes in proteins as a result
of , 548
controlling reaction , 548
effect on protein activity , 548
groups susceptible toward ,
548
indirect labeling methods , 556
methods , 547
of
APDP , 326
ASBA , 333
ASIB , 325
cross-linkers , 556
histidine , 10
NHS-ASA , 305
SASD , 306
oxidizing agents used with ,
819
process of , 546
scavengers , 308
termination of , 548
using
chloramine-T , 548
Iodo-gen , 553
lactoperoxidase , 556
Iodination Reagents , 546
Iodine ,
289 , 450 , 459 , 557 , 899
radioactive , 819
reaction with tyrosine , 11
reduction of , 548
Iodine-125 , 498
Iodine-131 , 498
Iodoacetamide , 111 , 161 , 373 ,
650 , 665 , 899 , 1016
blocking unreacted sulfhydryl
groups with , 849
of Lucifer Yellow , 457
4-(Iodoacetamido)-2,6-dimethyl-
pyridine dicarboxylate , 482
5-(and 6)-Iodoacetamidofl uo-
rescein
general properties and use ,
406