Hermanson G. Bioconjugate Techniques, Second Edition

1150 Index

Cysteine ( continued )

peptide haptens containing , 766

pKa , 10

reaction with

anhydrides , 178

cisplatin , 192

haloacetyl compounds , 182

maleimide-activated BSA ,

769

sodium tetrathionate , 162

reactions , 10

site-directed coupling through ,

22

solvent exposed area , 30

Cystine ,10 , 66 , 80 , 97 , 120

reduction

of , 87

using DTT , 88

Cytochemical staining , 457 , 813

using avidin–biotin

interactions, 904

Cytochrome

b559, 243

Cytochrome b562, 701

Cytochrome C , 961

Cytochrome C reductase , 244

Cytochrome oxidase , 260

Cytochrome P-450 , 239 , 247 ,

256

Cytochrome P-450 reductase ,

256

Cytokeratin , 243

Cytosine ,51 , 412 , 444

activation with bromine com-

pounds, 977

biotin derivative of , 986

hydrazide derivative of , 412

hydrogen bonding , 64

labeling with

Cascade Blue hydrazide ,

457

ﬂ uorescein probes , 414

Lissamine rhodamine B sul-

fonyl hydrazine , 428

Lucifer Yellow CH

, 459

mercuration of

, 57

modiﬁ cation with

AMCA-hydrazide , 439

biotin-hydrazide , 526 , 990

reaction with

bisulﬁ te , 55 , 974

structure and reactivity , 54

thiolation of , 57

transamination of , 976

transamination reactions , 55

Cytotoxic , 514 , 824

Cytotoxic agent

conjugation to dextran , 824

Cytotoxic T cell response , 747

Cytotoxicity , 281 , 832 , 882

mechanism of, for plant

toxins, 827

of

dgA–antibody conjugates ,

830

radioimmunoconjugates ,

498 , 500

single-chain protein toxins ,

829

SMCC conjugated immuno-

toxins, 850

SMPB conjugated immuno-

toxins, 855

optimal ratio of antibody–dgA

conjugates, 840

relationship to use of cleavable

cross-linkers, 847

Czworkowski , 438

Dabbousi , 487

Dade , 256

Daemen , 879

Dahan , 492

Dahlquist , 240

Dakin , 23

Dakshinamurti , 509

Dalen , 403

Damjanovich , 164

Danscher , 924

Dansyl aziridine , 184

Darbandi ,

490

Darzynkiewicz , 400

Das , 305

, 330

Dative binding , 925 , 927

Dative bond , 240 , 687 , 740

with thiols , 188

dATP

derivatives useful for enzymatic

labeling of DNA , 971

Datta , 671

Daum , 1026

Daunomycin

coupling to oxidized dextran ,

857

David , 701

Davidson , 419

Davies , 25 , 28 , 253 , 254 , 559

Davis , 147 , 371 , 708 , 938

Dawson ,

697, 698 , 701

DCC , 118 , 569 , 572

, 631 , 979

general description and use ,

224

in

formation of NHS esters ,

171

formation of NHS-palmi-

tate, 886

preparation of active esters ,

224

reaction with carboxylate-

PEG, 945

rearrangement to N -acylurea ,

225

DCIA

general properties and use ,

436

dCTP , 973

derivatives useful for enzymatic

labeling of DNA , 971

DCU , 225 , 227 , 886

De Araujo , 668 , 669

De Rosario , 90

De Waele , 932

Dean , 171 , 223 , 274

DeBlaquiere , 519

Debye , 54

Deferoxamine , see DFA

Deforming agent , 88

DeFulvio , 503

Deglycosylated ricin A chain ,

839 , 843 , see also dgA

conjugation to antibodies using

Ellman’s reagent , 845

Deglycosylation , 830

Degtyarenko , 189

Dehydration , 102

Dehydroascorbate , 683

Dehydroazepines , 204 , 303 , 311 ,

326 , 337 , 530 , 531 , 987 ,

1018

Index 1151

from phenyl azide photolysis ,

262

Delcroix , 421

DELFIA , 502

Delgado , 937

Della-Penna , 506

Dell’Arciprete , 287 , 828 , 852

DeMar , 194 , 332

Denaturants , 88 , 96 , 99

Dendrimer , 582

2D and 3D structure of , 353

activation with sulfo-NHS-

LC-SPDP , 356

biotinylation of , 376

blocking amine groups on , 363

conjugation methods , 353

construction , 346

coupling to amine-containing ,

356

cystamine core ,

354

DTPA derivative

, 379

epoxy activation , 373

ﬂ uorescent

labeling of , 380

modiﬁ cation of , 358

folate derivative , 359 , 371

fructose derivative , 367

functional groups , 354

generation , 347

glycoprotein coupling to , 361

gold particle modiﬁ cation

using , 389

guest molecules , 353

hexachlorocyclo-triphosp-

hazene (N

3

P

3

Cl

6

)-

containing , 387

manose derivative , 366

metal chelate derivatives ,

383

methotrexate derivative , 371

modiﬁ cation with sugars , 366

mono(lactosylamido) mono

(succinimidyl)suberate

derivative , 368

NHS-PEG-maleimide

activation of , 359

NHS-PEG

4

-biotin derivative ,

379

oligonucleotide , 347

PEG modiﬁ cation of , 365

phosphopeptide conjugation ,

373

poly(propyleneimine)-

containing , 387

Priostar type , 354

quantum dot derivatives , 389

silver nanoclusters , 389

sugar derivatives , 355

surface modiﬁ cation using ,

385

synthesis of , 347

viscosity , 353

dendrimer box , 353

dendrons , 346 , 347 , 371

in convergent synthesis of den-

drimers , 347

Denizli , 612

Denney , 219

Denti , 347

Deoxycholate

for detergent dialysis into lipo-

somes , 888

Deoxynucleoside triphosphates ,

971

Deoxyribonuclease I , 970

 -

D -2-Deoxyribose , 51

2-Deoxyribose , 39

dePont , 239

DePont , 255

Derfus , 492

Derjaguin , 584

Derksen , 754 , 869 , 879 , 895 ,

896

Dermer , 120

Derouiche , 1011

Deryagin , 925

Detergent dialysis , 888

Detergents , 555

use with iodo-beads , 551

Deuterated Crosslinking Agents ,

1008

Deuterium atoms

in mass tags , 650

Deuticke ,

222 , 765

DeVasto , 438

Dewald , 346

Dewey , 283 , 400 , 850 , 896

Dextran , 43 , 125 , 139 , 269 , 270

activation with 1,4-butanediol

diglycidyl ether , 957

amine derivatives , 954

as carrier for antibody

conjugates , 824

carboxyl derivatives , 954

conjugation with haptens , 755

DFA conjugates of , 503

epoxy activation of , 957

general properties and use , 951

hydrazide derivatives , 954

hydroxyl functionalities of ,

936 , 951

in preparation of immunotox-

ins

, 855 , 857

lactone activated derivative

of , 956

modiﬁ cation

of proteins with , 951

with , 936

adipic acid dihydrazide ,

956

bis-hydrazide reagents ,

139

bis-hydrazides , 140

chloroacetic acid , 199

ethylene diamine , 956

oxidation with sodium

periodate , 857

periodate oxidation of , 952 ,

953

polyaldehyde , 954 , 956

reaction with chloroacetic

acid , 954

SPDP modiﬁ ed , 954 , 960

sulfhydryl-reactive derivatives ,

954 , 960

use as carrier , 747 , 754

DFA

general description and use ,

502

DFA–polymer conjugates ,

503

DFDNB

general description and use ,

259

DFDNPS

base cleavability of , 395

general description and use ,

260

dgA , 830 , 839 , 841

conjugation with antibody

using SMPT , 843

1152 Index

1,4-Di-[3  -(2  -pyridyldithio)-

propionamido]butane, see

DPDPB

Diabetes ,49 , 147

Diamandis , 476

Diamines , 115

coupling to aldehydes , 124

modiﬁ cation of carbohydrates ,

122

p -Diaminodiphenyl , see

Benzidine

Diaminodipropylamine , 115 ,

125 , 954

1,6-Diaminohexane , 115 , 125 ,

976 , 978

1,6-Diaminohexyl spacer

of AMCA-HPDP , 434

1,3-Diaminopropane , 115 , 975 ,

976

in

biotin-HPDP , 522

iodoacetyl-LC-biotin , 524

2,6-Diaminopyridine , 538

Diaminopyridine , 153

ﬂ uorescence of , 539

1,3-Diaminourea , see

Carbohydrazide

Diamond , 627 , 639

Diazirine compounds

reactions of , 208

Diazirine derivatives , 302

Diazo bonds , 272

in cleavable cross-linkers , 394

in cleavable reagents , 392

Diazo compounds , 302 , 305

photoreactions of , 207

Diazo group

of PNP-DTP , 323

Diazoalkanes , 680

reaction with carboxylates ,

193

Diazomethane , 193

Diazonium , 127 , 202 , 394

formation from arylamines ,

126

from activation of p -ami-

nobenzoyl biocytin , 534

of o -tolidine, diazotized , 272

reaction with tyrosine , 11

reactivity , 271

side reactions of , 776

using in hapten–carrier

conjugation, 773

Diazonium groups

reactions of , 202

Diazopyruvates , 207

p -nitrophenyl diazopyruvate ,

322

Diazotriﬂ uoropropionate , 207

1,3-Dibromoacetone , 274

DIC

general description and use ,

226

Dicarboxymethyllysine , 110

Dicetylphosphate ,

884

Dickson , 389

Dictyostelium disoideum amoe-

bas, 512

Dicyclohexyl carbodiimide , see

DCC

Dicyclohexyl urea , see DCU

Didenko , 987

Diederich , 634

Diels–Alder reaction , 210 , 667 ,

689

Diene , 210

in Diels–Alder reaction , 667

1,2:3,4-Diepoxybutane , 268

1,2:5,6-Diepoxyhexane , 268

Diethanolamine , 963

Diethyl ether , 887 , 944

7-Diethylamino-3-[(4  -(iodo-

acetyl)amino)phenyl]-4-

methylcoumarin, see DCIA

Diethylenetriaminepentaacetic

anhydride, see DTPA

Diethyl ether , 881 , 928

Diethylmalonate

reaction with fullerenes , 633

4,4-Diﬂ uoro-1,3,5,7-tetram-

ethyl-4-bora-3a,4a-diaza-

s-indacene-8-propionyl

hydrazide, see BODIPY

493/503 C

3

hydrazide

1,5-Diﬂ uoro-2,4-dinitrobenzene ,

see DFDNB

4,4  -Diﬂ uoro-3,3  -dinitrophenyl-

sulfone, see DFDNPS

1,3-Diﬂ uoro-4,6-dinitrobenzene ,

see DFDNB

4,4-Diﬂ uoro-4-bora-3a,4a-diaza-

s-indacene, 440

4,4-Diﬂ uoro-5,7-dimethyl-

4-bora-3a,4a-diaza-s-

indacene-3-propionic acid,

succinimidyl ester , see

BODIPY FL C

3

-SE

4,4-Diﬂ uoro-5,7-dimethyl-

4-bora-3a,4a-diaza-s-

indacene-3-propionyl

hydrazide, see BODIPY FL

C

3

hydrazide

N -(4,4-Diﬂ uoro-5,7-dimethyl-

4-bora-3a,4a-diaza-s-

indacene-3-propionyl)-N  -

iodoacetylethylenediamine ,

see BODIPY FL IA;

BODIPY 530/550 IA

4,4-Diﬂ uoro-5,7-diphenyl-

4-bora-3a,4a-diaza-s-

indacene-3-propionic acid ,

see BODIPY 530/550 C

3

4,4-Diﬂ uoro-5,7-diphenyl-

4-bora-3a,4a-diaza-s-

indacene-3-propionic acid,

succinimidyl ester , see BOD-

IPY 530/550 C

3

-SE

4,4-Diﬂ uoro-5,7-diphenyl-

4-bora-3a,4a-diaza-s-

indacene-3-propionyl

hydrazide, see BODIPY

530/550 C

3

hydrazide

Diﬂ uorobenzene derivatives , 259

Dihazi , 1009

6,7-Dihydrogeranylazide

diphosphate, 695

Dihydrolipoamide

immobilized , 97

Dihydrolipoic acid (DHLA) , 488

2,3-Dihydroxy-1,4-dithiolbu-

tane, see DTT; DTE

Dihydroxyacetone , 38

Dihydroxyphenylalanine

(DOPA) , 28

Di-iodotyrosine , 548

Diisopropyl carbodiimide , see DIC

Diisopropyl- N -acylurea , 227

Diisopropylurea , 227

Diketone group

of APG , 334

Index 1153

2,3-Dimercaptopropanol , 89

4-(2  ,4  -Dimethoxyphenyl-

aminomethyl)phenoxy

linker , 1012

Dimethyl 3,3  -dithiobispropion-

imidate , see DTBP

Dimethyl adipimidate , see DMA

Dimethyl pimelimidate , see

DMP

Dimethyl suberimidate , see DMS

N

4

, N

4

-Dimethyladenine , 51

4-(Dimethylamine)pyridine , see

DMAP

5-Dimethylaminonaphthalene-

2-sulfonyl aziridine , see

Dansyl aziridine

4-(Dimethylamino)pyridine

hydrochloride , 944

3,3  -Dimethylbenzidine , see

o-Tolidine

N , N  -Dimethylcasein , 530

1,2-Dimyristoyl , 865

Dimyristoyl phosphatidic acid ,

see DMPA

Dimyristoyl phosphatidyl

ethanolamine , see DMPE

Ding , 735

2,4-Dinitroﬂ uorobenzene , 175 ,

185 , 800

2,4-Dinitrophenylhydrazine

(DNPH) , 28 , 658

Dintzis

, 128 , 773 , 951

Diols , 526

as cleavable groups in

cross-linkers , 393

Dioxane , 943

Dipalmitoyl phosphatidyl

ethanolamine , see DPPE

Diphtheria toxin , 86 , 827

B chain function of , 828

catalysis of ADP-ribosylation ,

828

coupling to EGF using

cystamine , 844

structure of , 828

Diphtheria toxoid , 748

use as carrier , 753

Dipicolinic acid (DPA) , 482

2,2  -Dipyridyl disulﬁ de , 165 ,

982

4,4  -Dipyridyl disulﬁ de , 71 , 165 ,

186

use with 2-iminothiolane , 166

Disaccharide ,

37 , 44

Discrete PEG Reagents , 707

Distearoyl phosphatidyl

ethanolamine , see DSPE

Disuccinimidyl carbonate , 43 ,

606 , see also DSC

N , N  -Disuccinimidyl carbonate ,

see DSC

Disuccinimidyl glutarate , see

DSG

Disuccinimidyl suberate , see DSS

Disuccinimidyl tartarate , see

DST

Disulﬁ de

formation with pyridyl

disulﬁ des , 257

from pyridyl disulﬁ de

reactions , 325

in immunotoxin conjugates ,

830

of

AMCA-HPDP reactions ,

435

SAED ,

317

SAND , 313

SASD , 306

sulfo-SBED , 338

Disulﬁ de exchange , 89 , 164

in preparation of immuno-

toxins , 833

using

cystamine ,84

Ellman’s reagent , 844

pyridyl disulﬁ des , 186

Disulﬁ de interchange , 166 , 182

prevention by blocking agents ,

156

using cystamine , 844

Disulﬁ de reductants , 156 , 120 ,

278 , 313 , 314 , 940

effect on iodo-beads , 551

immobilized ,97

general description and use ,

87

Disulﬁ de reduction

in immunotoxin action , 830

Disulﬁ des

between protein subunits , 18

cleavable cross-linkers

containing , 392

cyclic , 89

exchange reactions of , 185

formation with

sodium tetrathionate , 161

thiosulfonates , 256

TNB , 256

in

antibody molecules , 784

cleavable reagents , 392

DSP , 238

inhibiting formation of , 67

of DTBP , 255

reduction

in antibodies , 788 , 790

of , 10 , 87

using 2-mercaptoethanol ,

91

using DTT , 88

using immobilized reagents ,

97

using sodium borohydride ,

100

with 2-mercaptoethylamine ,

94

with TCEP , 95

reversibility of , 160

3,6-Disulfonate

4-aminonaphthalimide , 457

Disulfosuccinimidyl tartarate ,

see Sulfo-DST

5,5  -dithio- bis -(2-nitrobenzoic

acid) , 187 , see also

Ellman’s reagent ; DTNB

2,2  -Dithiobis(ethylamine) , see

Cystamine

Dithio bis

(succinimidyl-

propionate) , see DSP

Dithio bis (sulfosuccinimidyl-

propionate) , see DTSSP

2,2 -Dithiodipyridine , 1025

Dithioerythritol , see DTE

Dithionite , see Sodium dithionite

cleavage of diazo bonds , 203

Dithiopyridyl , see also Pyridyl

disulﬁ de

Dithiothreitol , see DTT

Dityrosine , 27

1154 Index

Divinylsulfone , 43

Dixon , 108 , 159

DLVO theory , 584 , 925

DMA

general description and use ,

251

DMAP , 172

DMP

for immobilization of

antibodies, 253

general description and use ,

252

DMPA , 866

DMPC , 884

DMPE , 872

DMS

activation of PE , 892

general description and use ,

253

in conjugation of proteins to

liposomes, 892

DMSO

to solubilize hapten–carrier

conjugates, 749 , 751

DNA , 39

, 146 , 444

activation with

bromine compounds , 976

sodium bisulﬁ te , 974

alkaline phosphatase

conjugation using DSS ,

994

base constituents , 51

base pairing , 64 , 520

biotinylated , 903

biotinylation of , 985

bis-hydrazide modiﬁ cation of ,

974

bisulﬁ te catalyzed

transamination, 976

carbodiimide coupling through

5 phosphate , 978

chemical modiﬁ cation

methods, 973

coupling adipic acid

dihydrazide at the

5 -phosphate end , 980

crosslinking methods , 66

cystamine modiﬁ cation of ,

981

cystamine modiﬁ ed

, 993

detection using avidin-biotin

interactions, 514

diamine modiﬁ cation of , 974

diamine modiﬁ ed

ﬂ uorescent labeling of , 1001

labeling with FITC , 1001

DSS activated , 996

enzymatic labeling methods ,

970

nick translation , 970 , 971

PCR , 970

random primed labeling ,

970 , 973

terminal transferase , 971 ,

973

enzyme conjugation

techniques, 992

ﬂ uorescence detection , 467

ﬂ uorescent labeling of , 998

functional groups , 53

5  -hydrazide modiﬁ ed , 133

hydrazide modiﬁ ed

conjugation to SFB modiﬁ ed

alkaline phosphatase ,

998

labeled with NHS-rhodamine ,

421

labeling at 5  -end , 84

labeling with

AMCA-hydrazide , 438

BODIPY ﬂ uorophores , 441

Cascade Blue hydrazide ,

457

ﬂ uorescein , 414

Lissamine rhodamine B

sulfonyl hydrazine , 428

Lucifer Yellow CH , 459

p -aminobenzoyl biocytin,

diazotized, 535

photobiotin , 531

mapping , 531

modiﬁ cation

and conjugation of , 969

by hydrazide-reactive

probes, 412

of , 50

with

biotin-BMCC , 990

biotin-diazonium , 989

biotin-hydrazide , 990

biotinylation reagents

containing

hydrazides, 525

bis-hydrazides , 146

cystamine , 84

diamines , 124

ﬂ uorescein-5-thiosemi-

carbazide, 412

NHS-LC-biotin , 988

PDITC activated , 997

5  -phosphate group , 869

phosphodiester bonds of , 51

photobiotin modiﬁ cation of ,

987

probe design , 66

psoralen coupling , 209

purine residues of , 58

reaction with

EDC , 62

N -bromosuccinimide

, 978

structure , 62

sugar constituents , 61

sulfhydryl modiﬁ ed

coupling of sulfhydryl-

reactive ﬂ uorescent

probes, 1002

synthesis , 63

thiolation of , 520 , 980

Watson–Crick model , 64

DNA binding proteins , 518

DNA microarrays , 387

DNA polymerase I , 970

DNA probes , 279 , 418

DNase I , 971

DNPH , 658

dNTP , 973

Dombroski , 1032

Domen , 116 , 232 , 750 , 879

Donnelly , 24

Donovan , 219

DOPA , 189

Dordick , 27

Dose , 701

Dot blot , 537

DOTA , 658

general description and use ,

500

in ECAT reagent , 657

Dottavio-Martin , 41

Double helix , 64

Index 1155

Dovichi , 403

Dowben , 862

Dower , 254

Downey , 801

DPDPB

general description and use ,

257

DPPC , 880 , 881

DPPE , 872

activation with

MBS , 875

SMPB , 872 , 881

DPPG , 880 , 881

Draﬂ er , 330

Draper , 412 , 427 , 438 , 444 , 457 ,

460 , 975 , 976

Dreborg , 938

Dried milk

stabilization of colloidal gold

suspensions using

, 926

Drugs

conjugation to toxins , 847

encapsulated in liposomes ,

882

liposome encapsulation , 858

DSC , 40 , 175 , 944

activation of

APTS surfaces using , 572

hydroxyl particles , 606

mPEG using , 943

general description and use ,

249

reaction with hydroxyls , 196

Tween 20 activation using ,

643

DSG , 248 , 249

DSP , 238

dative binding to metallic

surfaces , 240

general description and use ,

238

surface modiﬁ cation , 189

DSPE , 872

DSS , 149 , 996

DNA-alkaline phosphatase

conjugation using , 994

for capturing protein

interactions , 1007

general description and use ,

241

DST , 393

general description and use ,

243

DTBP

general description and use ,

254

DTE , 88 , 97

DTNB , 187 , see also Ellman’s

reagent

DTPA , 479 , 820

dendrimer derivative , 379 ,

383

general description and use ,

499

In-111 labeled carbon

nanotubes , 647

isothiocyanate derivative , 383

isothiocyanatophenyl , 479

DTSSP

general description and use ,

238 , 240

DTT , 87 , 88 , 91 , 97 , 99 , 119 ,

120 , 161 , 163 , 165 , 186 ,

239 , 260 , 279 , 289 , 301 ,

407 , 555 , 834

affect on aryl azides , 305

cleaving disulﬁ de

crosslinkers , 90

for

cleavage of APDP , 326

cleavage of pyridyl

disulﬁ des , 325

cleavage of SADP ,

314

cleavage of SAED , 319

cleavage of SASD , 306

cleaving AMCA-HPDP

derivatives

, 435

reduction of pyridyl

disulﬁ des , 504 , 839

SPDP reduction , 834

partial reduction of

antibodies , 854

reduction of pyridyl

disulﬁ des , 849

general description and use , 88

in

cleaving sulfo-SBED

cross-links , 341

cleavage of aryl-thiol bond ,

185

cleavage of biotin-HPDP

modiﬁ ed proteins , 523

cleavage of sulfo-NHS-SS-

biotin modiﬁ ed pro-

teins , 517

reduction of cystamine , 832

reaction with

SMPT , 78

SPDP , 76

reduction of cystamine-DNA ,

982

DTTA

general description and use ,

501

in time-resolved ﬂ uoro-

immunoassays , 502

Du Vigneaud , 508

Duan , 579

Duband , 423

Dubertret , 492

Duckworth , 686

Duijndam , 413

Dunbar , 92

Duncan , 71 , 795 , 936

Dunn , 228 , 937

Dunnick , 888

Durand , 438

dUTP

derivatives useful for

enzymatic labeling of

DNA , 971

Dye-doped silica nanoparticles ,

625

Dyes

with similar structures to

ﬂ uorophores , 399

DyLight 649 NHS ester

dendrimer labeling , 382

Dysprosium

, 476 , 501

E. coli , 256 , see also

Escherichia coli

E. coli O , 157620 , 626

Eastman , 192

Ebrahim , 509

ECAT , 29

general description and use ,

657

O-ECAT , 658

1156 Index

EDAC , see EDC

EDC, 84, 87, 114, 117, 146, 167 ,

613, 626, 688, 735, 737 ,

765, 890, 979, 980, 982

BMPA activation , 112

coupling to

APTS surfaces using , 570

carboxylated particles , 596

5  -phosphates using , 978

quantum dots , 490

silica particles , 620

cystamine modiﬁ cation of

DNA using , 981

dendrimer conjugation using ,

371

for conjugating

[Met5]-enkephalin to BSA ,

757

[Met5]-enkephalin to OVA ,

757

tyrosyl-lysine to KLH , 757

hydrazides to carboxylates ,

142 , 270

PDTP , 843

for folate coupling to

dendrimers,

372

formation of NHS esters , 172

general description and use ,

216

in

coupling ASBA to carboxy-

lates, 333

hapten–carrier conjugation ,

755

modiﬁ cation of phosphates

with bis-hydrazides , 146

phosphoramidate forma-

tion, 124

preparation of cBSA , 749

levels used with KLH , 762

modiﬁ cation of avidin or

streptavidin with adipic

acid dihydrazide using ,

920

optimal pH for reactions , 217

pH dependence of conjugation

using, 757

plus sulfo-NHS , 219

protein conjugation to

liposomes using , 889

quantum dot conjugation , 494

quenching with 2-mercap-

toethanol, 763

reaction with

AMCA , 432

amine containing Cascade

Blue derivatives

, 455

biotin , 508 , 509

carboxylate-PEG , 945

DFA , 503

phosphate groups of

nucleotides, 62

phosphatidic acid , 869

reactions of , 177

use in

cationization , 116

conjugating tyrosyl-lysine to

BSA, 757

forming hydrazide-protein

derivatives, 967

EDC/NHS , 538

EDC/sulfo-NHS , 585

coupling to carboxylate

particles, 598

EDC/sulfo-NHS reaction , 441 ,

443

in activation of protein

carboxylates, 763

Edelhoch , 256

Edelman , 91

Edsall , 256

EDTA , 98 ,

99 , 111 , 163 , 280 ,

436 , 479 , 523 , 808 , 849 ,

908 , 963

biotin derivative , 1032

for elution from metal chelate

afﬁ nity supports , 815

for prevention of metal-

catalyzed oxidation of

sulfhydryls, 792

iron chelate , 1032

isothiocyanatophenyl , 479

of TMS-EDTA , 575

to prevent metal-catalyzed

disulﬁ de formation

, 769

use to prevent disulﬁ de

formation, 67

Edwards , 14 , 287 , 834

EF2 , 828

Effectomer , 827

Efros , 492

EGF , 86

Egg , 872

Egg lecithin , 879 , see also

Lecithin

Egg-whites , 508

Egg yolk , 864

EGS

hydroxylamine cleavability ,

395

Ehses , 310

Eichman , 352

Eiklid , 827

Eisen , 175 , 185

Eldjarn , 80 ,

97

Electromagnetic radiation , 546

Electron , 546

Electron capture , 546

Electron capture dissociation

(ECD), 662

Electron donating , 548

Electron donating groups

effect on ﬂ uorescence , 398

Electron microscope , 525 ,

924

use of colloidal gold labeling ,

924

Electron withdrawing groups

effect on ﬂ uorescence , 398

Electrons , 397 , 546

Electrophilic , 262

Electrophilic halogen species ,

549

Electrophilic reactions , 10

of tyrosine , 11

Electrophilic species , 819

Electrophilic substitution , 548 ,

549

Electrophilic trap , 691

Electrophoresis , 92 , 117 , 256

Electrospray ionization (ESI) ,

649

Element-coded afﬁ nity tags , see

ECAT

 -Elimination , 153

ELISA , 292 , 750 ,

751 , 754 , 787 ,

793 , 802 , 804 , 807 , 961 ,

965 , 992

use of liposomes in , 883

using avidin–biotin

interactions, 905

Index 1157

Ellerbroek , 519

Ellis , 932

Ellman , 100 , 164 , 187

Ellman’s assay , 111 , 840 , 852

Ellman’s reagent , 68 , 99 , 164 ,

165 , 166 , 1028

for determining level of

maleimide activation , 772

general description and use ,

100 , 164

in

activation of sulfhydryls , 187

measuring maleimide

activation levels , 768

preparation of

immunotoxins , 844

Elsner , 210

Emission

of quantum dots , 486

Emulsiﬁ cation , 896

of lipids

,

862

Emulsion, water-in-oil , 863

Encapsulation , 858

of molecules into liposomes ,

880

Endo F , 153

Endo H , 153

Endocytic vesicles , 827

Endocytosis , 882

Endoglycosidase , 152

Endonuclease , 702

 -Endorphin , 243 , 246

Endorphin , 243

Endosomes , 745

Energy transfer , 400 , 462 , 1000

Engberts , 667

Englund , 162

Enoch , 862

Enol , 42

Enol ester , 228

Enzyme-linked immunosorbent

assay , see ELISA

Enzymes , 783

activation with

bis-hydrazides , 270

glutaraldehyde , 800 , 914

periodate , 800

SMCC , 788 , 906 , 909

sulfo-SMCC , 909

biotinylated , 271

conjugates with antibodies

removal of unconjugated

enzyme , 812

conjugation

to avidin using glutaralde-

hyde , 913

to DNA , 992

with antibodies , 787

creating maleimide-activated

derivatives

, 789

gold labeled , 927

hydrazide-activated , 270 , 805

hydrazide derivatives of

, 968

immobilized , 556

in design of immunotoxic

conjugates , 825

maleimide-activated , 795 ,

797 , 809

conjugation with reduced

antibodies , 790

modiﬁ cation

and conjugation of , 961

with bis-hydrazide reagents ,

139

oxidation with periodate , 802

polymer modiﬁ cation of , 936

reactive derivatives for

conjugation , 966

SPDP activation of , 968

substrates for detection , 961

types and properties , 961

unconjugated , 815

Enzymobeads

in iodination of proteins , 556

Epibromohydrin , 373

Epichlorohydrin

activation of PEG with

, 948

Epidermal growth factor

SPDP conjugation to toxins ,

837

modiﬁ cation with cystamine ,

844

Epitope mapping , 931

Epitopes , 746

Epoxides , 43

chemistry of , 174

general information , 268

modiﬁ cation of dextran , 957

reaction conditions , 269

reaction with

ammonium ion , 174

hydroxyls , 195

pyrimidines

, 55

transformation to an

aldehyde , 174

Epoxy activation

of hydroxylic particles , 615

Epoxy groups

dendrimer activation , 373

of GOPTS , 577

Epps , 185

Ericsson , 418 , 424 , 429

Ernst , 465

Ernsting , 430

Erythrocyte ghosts , 305

Erythrocytes , 240 , 243 , 252 ,

256 , 260 , 314 , 410

Erythropoietin , 243

Erythrose , 38

Escherichia coli , 256 , 964

Eschrich , 430

Ester bonds

hydroxylamine cleavable , 394

Esters , 106

in cleavable reagents , 392

17  -estradiol

conjugation to cBSA using

Mannich reaction , 779

Ethanol

, 862 , 964

Ethanolamine , 167 , 168 , 176 ,

233 , 393 , 801 , 804 , 806

blocking excess glutaraldehyde

with , 913

for

blocking aldehydes , 166

blocking carboxylates , 167

blocking unreacted

aldehydes , 913

quenching glutaraldehyde

reactions , 798 , 800

Ether

formation with epoxides , 268

Ethoxysilane , 563

Ethyl acetate , 950

1-Ethyl-3-(3-dimethylaminopro-

pyl) carbodiimide hydro-

chloride , see EDC

N -Ethyl-3-phenylisoxazolium-

3 -sulfonate , see Wood-

ward’s reagent K

1158 Index

N -Ethyl maleimide , see NEM

Ethylene diamine , 115 , 125 ,

954 , 956

in preparation of cBSA , 749

Ethylene glycol , 708

in cross-bridge of EGS , 395

Ethylene glycol group

cleavability of , 246

Ethylene glycol bis (succinimidyl-

succinate), see EGS

Ethylene glycol bis(sulfosuccinimi-

dylsuccinate), see Sulfo-EGS

Ethylene oxide , 651 , 707 , 708 ,

937

as repeating unit in PEG , 936

Ethylenediamine , 976

dendrimer core of , 347

Ethylenimine , 184

comparison to Aminoethyl -8,

118

general description and use ,

119

produced from 2-bromoethyl-

amine, 120

reaction with pyrimidines , 55

4-Ethyliodoacetamide , 458

N -Ethylmaleimide , 668

Ethylmalonyl chloride , 634

Etzler , 754

Europium , 476 , 501

TMT chelate , 479

Europium chelate

donor with Cy3 in LRET ,

479

Evans , 706

Ewig , 275

Excitation , 397 , 400

Excited-state , 400

Exciton Bohr radius , 486

Expressed protein ligation , 685 ,

702 , 703 , 701

Exteins , 701

Extinction coefﬁ cient , 397

Extrusion (of lipids) , 862

F-actin , 256

F(ab  ) fragments , 809

F(ab  )

2

fragments , 284 , 786 ,

815 , 830

formation of , 807

reduction of , 809

reduction with 2-mercapto-

ethylamine, 94 , 791

preparation of , 807

F/P ratio , 403 , 406 , 419 , 423 ,

425 , 427 , 430 , 434 , 436 ,

438 , 439 , 440

19

F NMR , 1018

Fab fragments , 786 , 815 , 826 ,

830

formation of , 807

preparation of , 808

Fab  fragments , 284 , 292 , 363 ,

786 , 830

conjugation to toxins using

Ellman’s reagent , 845

conjugation with toxins using

S-sulfonates, 846

Fabrics , 938

Factor V , 306

Factor Va , 427

Factor XIII , 529

Factor XIIIa

assay of using 5-(biotinamido)

pentylamine, 529

FAD , 19 , 965

FADH

2

, 965

Fahien , 255

Fairbanks , 171 , 172 , 235 , 238 ,

940

Falke , 409

Fancy , 27 , 1037 , 1039

Farmer , 995

Farnesyl azide , 686

Farnesyl transferase , 694

Farnesylated proteins , 694

Farr , 807

Farries , 244

Fasold , 256 , 258

Fatty acids , 754 , 858

immunogenicity of , 879

in

egg PE , 872

phosphodiglycerides , 864

phospholipids

,

863

of

phosphodiglycerides , 864

sphingolipids , 866

unsaturated , 865

Fatty acid acylation , 693

Fatty acid alcohols , 869

Faulk , 924 , 928

Fauq , 653

Faye , 287 , 293

Fc fragments , 297 , 785 , 786 ,

808

Fc receptors , 243 , 254

Fe(III) (S)-1-(p-bromoacetamido-

benzyl)ethylene diamine

tetraacetic acid , see FeBABE

Fe

 3

, 158

Fe

2

, 25

Fearnley , 268

FeBABE , 23 , 189 , 1032

general description and use ,

505

Feeney , 21

Fehling’s reagent , 37

Fein , 263

Feitler , 225

Felekis , 645 , 647

Feller , 915 , 919

Fenton reaction , 25 , 1035

Ferguson , 413

Ferric hydroxide , 910

Ferritin

conjugation

to avidin using

glutaraldehyde, 913

to avidin using reductive

amination, 910

with avidin or streptavidin ,

905

with avidin using reductive

amination

, 910

general description and use ,

910

modiﬁ cation with bis-

hydrazide reagents , 139

Ferrocyanide , 962

Fibronectin receptors , 423

Ficin , 807

blocking its active site with

sodium tetrathionate , 162

Ficoll , 862

conjugation methods , 755

use as carrier , 754

Field , 121

Fields , 1004 , 1005

Index 1159

Fiete , 311 , 316

Filachione , 263

Filippone , 629

Finlay , 938

Fischer , 641

Fischer–Dimroth rearrangement

of adenine , 59

Fishelson , 834

FITC , 357 , 403 , 623 , 817 , 915 ,

1000

adsorbed onto gold nanoparti-

cles , 620

coupling to diamine modiﬁ ed

DNA , 1001

dendrimer derivative , 371

general properties and use , 401

modiﬁ cation of avidin with ,

915

Fitzgerald , 845

FitzGerald , 579 , 581

Fizgerald

, 837

Flaks , 256 , 258

Flavin adenine dinucleotide , see

FAD

FloDots , 620

Flow cytometry , 424 , 438 , 881

gold labeling in , 924

using ﬂ uorescently-labeled

antibodies , 818

Fluoraldehyde , 93

Fluorescein , 400 , 401 , 448 , 817

aldehyde/ketone and cytosine

reactive derivatives , 412

amine reactive derivatives of ,

401

azido derivative , 685

comparison to

AMCA , 431

Cascade Blue , 453

Lissamine derivatives ,

422

Lucifer Yellow iodo-

acetamide , 459

phycobiliproteins , 462

energy transfer from coumarin

derivatives , 430

general description and use ,

400

hydrazide derivative of , 414

iodoacetamido derivatives ,

406

pH dependence on

ﬂ uorescence , 401

quenching of , 915

silica particle embedded , 623

similarity to phenolphthalein ,

399

sulfhydryl reactive derivatives ,

406

use with

terbium chelates , 485

Texas Red , 424

Fluorescein-5-maleimide , 410

general properties and use ,

408

Fluorescein-5-thiosemicarbazide ,

413 , 414 , 415 , 429 , 430

general description and use ,

412

Fluorescein Isothiocyanate , see

FITC

Fluorescein–maleimide , 668

Fluorescence

effect of

electron donating groups ,

398

electron withdrawing

groups , 398

halogen atoms , 399

heavy atoms , 399

general description , 398

indigenous biological , 461

of OPA reaction with amines ,

129

Fluorescence microscopy , 432

Fluorescence quenching , 405 ,

465

of BODIPY ﬂ uorophores , 441

Fluorescence resonance energy

transfer (FRET) , 463

Fluorescent

aminopyridine derivatives ,

538

Fluorescent in situ hybridization

(FISH) , 1000

Fluorescent labeling

F/P ratio , 403

Fluorescent labels

effect of iodination of , 399

general description and use ,

396

Fluorescent lifetime

of lanthanide chelates , 474

Fluorescent probes

antibody labeling with , 817

coplanar ring structure of , 399

DNA labeling with , 998

effect of environmental con-

stituents on ﬂ uorescence ,

400

hydrazide derivatives , 968

photon absorbing additives ,

403

quenching effects , 400

SAED , 316

similarity to non-ﬂ uorescent

dyes , 399

sulfo-SAMCA , 321

Fluorescent quenching , 452 ,

818 , 1000

of

Cascade Blue derivatives ,

453

TRITC , 418

Fluorescent spectroscopy , 400

Fluorescent transfer

using SAED , 319

Fluorinated aryl azides , 302 , 325

Fluorine , 110

Fluorobenzene derivatives , 175 ,

185

Fluorophenyl esters , 179

Fluorophores

encapsulation into liposomes ,

883 , 885

general characteristics of , 397

general structure of , 398

FMN , 19

Foglesong , 717

Fok , 754

Folate binding protein , 371

Folic acid

coupling to

carbon nanotube , 643

dendrimers , 371

Folk , 330

Forbes , 86 , 844

Ford , 780

Formaldehyde , 130 , 262 , 460 ,

683

general description and use , 263

Hermanson G. Bioconjugate Techniques, Second Edition

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