Hermanson G. Bioconjugate Techniques, Second Edition

1140 Index

Avidin ( continued )

nonspeciﬁ c binding properties ,

901

optimal ﬂ uorescein labeling

level, 915

optimal molar ratio to enzyme

in conjugates , 912

phycoerythrin conjugation of ,

915

preparation of conjugates , 905

puriﬁ cation using immobilized

iminobiotin, 516

radiolabeled , 904

thiolation

using SATA , 909

with

2-iminothiolane , 919

SATA , 73

toxin conjugate , 825

toxin labeled , 905

structure and properties , 900

Avidin–biotin assay , 530

Avidin–biotin complex , 506

Avidin–biotin Systems , 900

Avigad , 40 , 124 , 132

Avouris , 639

Avrameas , 32 , 234 , 268 , 780 ,

798

Axen , 612

Axon , 421

Ayhan , 589

Aza-ylide , 543 , 691 , 697

Azide , 350 , 680 , 684 , 691 , 963

in click chemistry reaction ,

212 , 680

labeling with biotin-

PEG-phosphine, 543

phosphine reaction of , 690

Azide–Alkyne [3  2] Cycloaddi-

tion, 211 , 680

Azide-Cu(I)-alkyne complex , 683

Azide-nanoparticles , 689

Azide-sialic acid , 693

N -5-Azido-2-nitrobenzoyloxy-

succinimide, see ANB-NOS

N -(4-Azido-2-nitrophenyl)-

aminopropyl-N  -( N -d-

biotinyl-3-aminopropyl)-N  -

methyl-1,3-propanediamine ,

see Photobiotin

4-Azido-2-nitrophenyl-biocytin-

4-nitrophenyl ester , 510 ,

see also BSA

Bower , 256 , 258 , 1025

BOXTO , 467

Boyer , 228 , 824

Boyle , 422 , 424 , 754

Br-BODIPY , 493/503

general description and use ,

452

Braatz , 936

BRAB , 905

Brabec , 638

Bragg , 171 , 235 , 244 , 940

Brajter , 189

Brancia , 181

Brandon , 256

Brandt , 951

Braun , 260 , 419 , 629

Brechbiel , 383 , 501

Breinbauer , 693 , 697

Brennan , 206 , 687 , 689

Breslow , 667

Brettreich , 629

Brew , 14, 253

Brewer , 160 , 183

Briand , 780

Bright , 400

Brij-35 , 93

Brillhart

, 271

Brinkley , 293 , 404

1144 Index

Brocklehurst , 165

Brome mosaic virus , 335

Bromelain , 807

Bromination

of

purines , 59

pyrimidines , 56

Bromine , 549 , 977

reaction with pyrimidines , 57

Bromoacetamidobenzyl-DOTA

(BAD), see ECAT

p -Bromoacetamidobenzyl-TETA ,

501

Bromoacetate , 109

for blocking sulfhydryls , 161

Bromoacetyl

in ECAT reagent , 657

reactions of , 182

Bromoacetyl group

of FeBABE , 505

2-Bromoethylamine , 120

general description and use ,

120

6-Bromohexanoic acid , 199

modiﬁ cation of dextran with ,

954

Bromomethyl , 449 , 452

8-Bromomethyl-4,4-diﬂ uoro-

1,3,5,7-tetramethyl-4-bora-

3a,4a-diaza-3-indacene, see

Br-BODIPY 493/503

Bromophenol blue , 93

N -Bromosuccinimide , 977 , 978

reaction with purines , 59

reaction with pyrimidnes , 57

Bronckers , 934

Bronfman , 737

Brooks , 262

Bross , 826

Brouwers , 383

Brown , 55 , 223 , 1026

Browne , 251

Browning , 247

Bruchez

, 486 ,

487

Brunner , 305

Brunswick , 113 , 199 , 951 , 954 ,

960

BS

2

G-d

0

, 1008

BS

2

G-d

4

, 1008

BS

3

, 711

for capturing protein interac-

tions, 1007

general description and use ,

241 , 243

BS

3

-d

0

, 1008

BS

3

-d

4

, 1008

BSA , 67 , 117 , 550 , 748 , 753 ,

762 , 932

activation with sulfo-SMCC ,

768

adsorption density onto parti-

cles, 592

conjugation with

[Met5]-enkephalin using

EDC, 757

tyrosyl-lysine , 757

functional groups , 749

in stabilization of antibody–

gold sols , 932

maleimide activated

determination of sulfhydryl

coupling capacity , 769

PEG modiﬁ cation of , 937

solubility in presence of

DMSO, 751

stabilization of colloidal gold

suspensions using , 926

use as carrier , 749

BSOCOES

base cleavability of , 395

general description and use

,

244

Buckminsterfullerene , 628

Buckyballs , 582 , 627

Bugawan , 904

Bull , 592

Bunnett , 14

Burgess , 519 , 1018

Burnett , 211 , 676

Burns , 95

Burrows , 239

Burtnick , 403

Buss , 28

1,4-Butanediol diglycidyl ether ,

43 , 269 , 615

general description and use ,

269

modiﬁ cation of dextran with ,

957

Butanol , 838 , 996

Butler , 107 ,

159, 514 , 592

Byrne , 964

13

C

in ICAT design , 653

14

C , 546

C1q , 523

C

60

, 627

Bingel reaction of , 634

diazo-mediated cycloaddition

to, 637

maleimide derivative , 630

reaction with

aziridines , 633

azomethine ylides , 629

C-Phycocyanin , 919

C-terminal

pKa , 7

C-terminal thioester

in expressed protein ligation ,

701

Caamano , 242

Cabacungan , 41 , 174 , 232

CAD protein , 254

Cadaverine

in 5-(biotinamido)pentylamine ,

529

Cai , 205 , 303 , 310

Calcitonin receptors , 246

Calcium , 260

, 529

Calmodulin , 243 , 322

Camarero , 700

Campana , 419

Campbell , 329 , 739 , 748

Cancer , 498 , 817 , 847 , 882

targeting with liposomes ,

858

therapy of , 826

Cantarero , 592

Capaccio , 631

Carbamate , 196 , 199 , 230 , 250 ,

579 , 941

acid cleavable in ICAT

reagent, 653

Carbamate linkages , 175

Carbenes , 207 , 208

formed from photolysis of

diazopyruvates, 322

Carbocyanines ,

465

Index 1145

Carbodiimides , 105 , 114 , 116 ,

122 , 124 , 167 , 270 , 332 ,

455 , 886 , 954

CMC , 223

DCC , 224

DIC , 226

EDC , 216

for coupling hydrazides to

carboxylates , 142

in

coupling ASBA to carboxy-

lates , 333

formation of NHS esters ,

171

liposome conjugation , 870

modiﬁ cation of phosphates

with bis-hydrazides ,

146

modiﬁ cation of proteins with

bis-hydrazide compounds

using , 919

quenching with 2-mercap-

toethanol , 763

reaction with

AMCA ,

432

biocytin , 510

biotin-hydrazide , 526

carboxylate-PEG , 945

cystamine , 844

lipid derivatives , 869

phosphate groups of nucle-

otides , 62

reactions of , 176 , 195

reagents , 215

use in hapten–carrier conjuga-

tion , 755

Carbohydrate antigens

coupling to carriers using a

diazonium reaction , 774

Carbohydrates , 125 , 129 , 271 ,

412 , 414 , 438

activation of hydroxyls , 42

azido , 538

basic sugar components

, 37

biotinylation of , 537

BNAH modiﬁ cation of ,

541

conjugation using

carbonyl and sulfhydryl

reactive cross-linkers ,

297

M

2

C

2

H , 300

MPBH , 298

PDPH , 300

coupling to hydrazide parti-

cles , 613

crosslinking methods , 49

coupling to

carriers by reductive amina-

tion , 781

dendrimers , 369

detection

using

hydrazide-avidin , 919

hydrazide compounds ,

139

with

hydrazide compounds , 41

lectin–gold probes , 932

functional groups , 39

glycoprotein attachment

points , 46

gold labeled , 927

hydrogen bonding , 45

hydroxyl group nucleo-

philicity , 43

immune response against , 148

labeling with

biotin-hydrazide , 526

Cascade Blue hydrazide ,

456

Lucifer Yellow CH , 459

Texas Red hydrazide , 429

modiﬁ cation

of , 147

through

amino-sugars , 44

through phospho-sugars ,

44

with

AMBH , 83

 -( p -aminophenyl)

ethylamine , 41

anhydrides , 103

chloroacetic acid , 43

diamines , 122

epoxides , 43

hydrazide-PEG

4

-biotin ,

735

of

antibody molecules , 787

avidin , 901

on proteins , 20

oxidation

by sodium periodate , 40

with

oxidases , 131

periodate , 197 , 803

sodium periodate , 130

reaction with

ABH , 331

anhydrides , 178

reducing ends , 41

structure , 44

and functionality , 37

thiolation of , 504

thiolation using PDPH , 504

within antibody molecules ,

785

Carbohydrazide

, 139 ,

140 , 142 ,

146 , 613

general description and use ,

271

modiﬁ cation of

avidin or streptavidin with ,

919

phosphates , 146

of Lucifer Yellow CH , 459

reaction with aldehydes , 140

5-(((2-(Carbohydrazino)methyl)-

thio)acetyl)-aminoﬂ uorescein

general properties and use ,

414

Carbon

allotropes of , 627

Carbon dioxide , 228

Carbon nanotubes , 582, 627, 638

cycloaddition reactions of ,

645

detergent or lipid modiﬁ cation

of , 640

DNA aptamer labeled , 645

manufacture of , 639

modiﬁ cation

of , 640

with

CDI-activated Tween , 20 ,

641

phospholipid derivatives ,

643

properties , 638

1146 Index

Carbon nanotubes ( continued )

pyrene modiﬁ cation of , 644

Carbonates , 230

chemistry of , 175

Carbonic acid

diester derivative of , 175

Carbonic dihydrazide , see

Carbohydrazide

Carbonyl

reaction with

M

2

C

2

H , 299

MPBH , 298

PDPH , 300

Carbonyl addition mechanism ,

10

Carbonyl diimidazole , 42 , 606

Carbonylating agent , 228

N , N  -Carbonyldiimidazole ,

114 , see also CDI

Carbonylmetallo-immunoassay

(CMIA), 376

Carbostyril derivatives , 482

Carbostyril-DTPA , 484

Carboxyethylsilanetriol

general description and use ,

573

5,6-Carboxyﬂ uorescein

encapsulation into liposomes ,

885

 -Carboxyl group , 4

Carboxylates

activation with CDI , 228

blocking of , 167

coupling to hydrazides

, 269

formation

of , 101

NHS esters from , 171

using

cyclic anhydrides , 102

succinic anhydride , 103

in formation of anhydrides ,

178

modiﬁ cation with

bis-hydrazides , 139 , 142

diamines , 114

reaction with

ASBA , 333

carbodiimides , 176

diazoalkanes , 194

EDC , 216

reactions of , 9

Carboxylation , 508

Carboxymethylcysteinyl deriva-

tive, 109 , 183

Carboxymethylhomocysteine ,

110 ,

183

6-Carboxytetramethylrhodamine

succinimidyl ester , 357

Cardoza , 409

Carlson , 312

Carlsson , 76 , 172 , 238 , 279 ,

834 , 894

Carpenter , 119

Carraway , 218 , 222 , 763

Carrier proteins , 128 , 260 , 272

Carriers

BSA , 749

cBSA , 749

deﬁ nition of , 746

dextran , 951

KLH , 748

MAP , 755

non-relevant , 751

of low immunogenicity , 748

OVA , 752

proteins , 748

synthetic , 754

thyroglobulin , 751

types , 747

Carter , 783 , 824

Caruthers , 104

Casanova , 324

Cascade Blue acetyl azide

general description and use ,

453

Cascade Blue cadaverine

general description and use ,

455

Cascade Blue ethylenediamine

general description and use ,

455

Cascade Blue ﬂ uorophores

amine reactive derivatives , 453

general description and use ,

453

Cascade Blue hydrazide

general description and use ,

456

use with Lucifer Yellow CH ,

460

Casein

amine-blocked , 156

succinylated , 103

Castaneda , 995

Castor beans , 827

Catch-and-release tag , 654

Cater , 262 , 263

Cationization , 116

Cationized BSA , see cBSA

Cauﬁ eld , 241

CBD fusion tag , 706

cBSA

conjugation

to 17  -estradiol using Man-

nich reaction , 779

with

arginine vasopressin , 750

IgG , 751

phenol red using Mannich

reaction, 778

OVA conjugate , 751

pI of , 750

use as carrier , 749

use in Mannich reaction , 777

CD 4, 73 , 299

CD 8, 493

CDI , 40 , 941

activation of

carboxylate groups , 946

hydroxyl groups , 946

hydroxyl particles , 606

mPEG with , 948

PEG with , 946

silanols using , 387

as zero-length cross-linker ,

230

comparison with succinimidyl

carbonate coupling , 946

general description and use ,

228

hydrolysis rate , 946

in formation of carbonates ,

175

reaction with

carboxylates , 194

hydroxyls

, 196

Tween 20 activation using ,

643

Cech , 1032

Cell death , 824 , 829 , 832 , 882

Index 1147

nonspeciﬁ c , 831 , 832 , 847

Cell sorting

using ﬂ uorescently-labeled

antibodies , 818

Cell surface proteins

labeling with sulfo-NHS-SS-

biotin , 519

Cells

iodination of , 554

malignant , 824

periodate oxidation of , 413

Cellulose , 43 , 45

modiﬁ cation with acetic

anhydride , 103

reaction with acetic anhydride ,

178

Central nervous system , 509

Centrifugal concentrator , 838 ,

839 , 840 , 843 , 994

Centrifugal ﬂ oatation , 895

Ceramide , 866

Cerebrosides ,

869

Chai , 631

Chamberlain , 287

Chamow , 299 , 950

Chan , 486 , 487

Chang , 256 , 258 , 617

Chantler , 256 , 258

Chaotropic agent , 813

Chase , 216

Chattopadhyay , 308

Chaudhuri , 413

Chazotte , 423

Chehab , 420 , 421

Chelating agents

dendrimer derivatives , 383

Chelating compounds , 819 , 820

Chelating polymers

, 500 , 503

Chelation compounds , 814

Chelsky , 240

Chemical groups

creating speciﬁ c

functionalities , 66

Chemiluminescent probe , 1000

Chemoimmunoconjugates

preparation using oxidized

dextran , 857

Chemoselective , 210

Chemoselective Ligation , 143, 666

PEG-based crosslinker for , 722

Chemotactic agent , 825

Chemotherapeutic agents , 824

encapsulation in liposomes ,

882

Chemotherapy , 824

Chen , 112 , 162 , 400 , 410 , 479 ,

640 , 641 , 643 , 651

Cheng , 189 , 403

Chetrit ,

531

Chiang , 639

Chickens , 864

Chien , 1004

Childs , 531

Chitin , 44

immobilized , 703 , 706

Chitin binding domain (CBD) ,

702

Chitosan , 44 , 581

Chlamydia , 367

Chloramine-T , 308 , 548 , 551 ,

556 , 819 , 1020

general description and use ,

548

immobilized , 550

in iodination of SHPP , 559

iodination protocol , 550

Chloramines , 27

Chlorine , 551

Chloroacetic acid , 43 , 199

modiﬁ cation of dextran with ,

954 , 956

general description and use ,

113

Chloroauric acid , 928

reduction with

sodium ascorbate , 929

sodium borohydride , 928

sodium citrate , 928 , 929

white phosphorus , 928

N -Chlorobenzenesulfonamide ,

550

Chloroform , 555 , 861 , 873 , 874 ,

875 , 880 , 887

, 888

Chlorophyll , 461

Chloroplast coupling factor ,

409

Chlorosilanes , 563 , 567

N -Chlorotoluenesulfonamide ,

see Chloramine-T

Chlorotriazine , 832

Cholesterol , 858 , 861 , 868 , 869 ,

871 , 876 , 880 , 881 , 884 ,

889 , 895 , 896

Chong , 701 , 706

Chonn , 868

Chowdhry , 323

Christopoulos , 476

Chromogenic biotin , 727 , 730

Chu , 84 ,

124 , 176 , 195 , 215 ,

216 , 979 , 980 , 981 , 982

Chymotrypsin , 329

Cibacron Blue

immobilized

in puriﬁ cation of

immunotoxins , 843

Cimino , 57

Cis-9-hexadecenoic acid , see

Palmitoleic acid

Cis -tetrahydro-2-oxothieno[3,

4-d]-imidazoline-4-valeric

acid hydrazide , see Biotin-

hydrazide

Cisplatin

reaction with Met and Cys ,

192

Citiolone , see N-acetyl

homocysteine thiolactone

Citraconic acid , 889

Citraconic anhydride

as a reversible blocking agent ,

157

for reversibly blocking amines ,

159

general description and use ,

108

Citraconylamide , 108

Clapp , 489

Clark , 366

Clausen , 403

Cleavable reagent systems , 391

Cleland , 97

Cleland’s Reagent , see DTT; DTE

Clerc , 926

Clevenger , 708

Click chemistry , 569 , 669 , 680

Cu(I) catalyzed , 681

dendrimer modiﬁ cation using ,

386

dendrimer synthesis using , 351

PEG-based reagents for , 722

1148 Index

Click chemistry ( continued )

reaction mechanism , 211

Cloninger , 366 , 371

CMC

general description and use ,

223

reaction with

CMC , 58

uracil , 55

CO

2

, 170 , 175 , 230 , 231 , 249 ,

941 , 946

Cobra venom factor , see also

CVF

conjugation using

SIAB , 848

SMCC , 850

oxidation with sodium

periodate, 855

Cobra venom phospholipase A2 ,

312

Cocco , 407

CoCl

2

, 973

Coenzyme A , 19

Coenzyme R , see Biotin

Cofactors , 19 , 508

of glucose oxidase , 965

Cohen , 288 , 971

Cohen-Anisfeld , 155

Cohn , 597 , 750

Co-immunoprecipitation , 727

Cole , 109 , 119 , 120 , 183 , 828

Coleman , 225

Collagen , 269

Collier , 753 , 828

Collins , 639

Collioud , 208

Collision-induced dissociation

(CID), 662

Colloidal gold

advantages of

, 927

antibody labeling of , 931

as immunogen carrier , 755

assay of gold/protein sol

stability , 927

electrolyte-mediated

coagulation, 925

general properties and use ,

924

labeling with

avidin or streptavidin , 934

protein A , 930

lectin labeling of , 932

monitoring pH of , 929

preparation of , 928

mon-disperse suspensions ,

928

protein complexes of , 924

properties and use , 924

protein labeling guidelines ,

926

silver enhancement , 924

Colloidal suspension , 596

Colman , 164

Colombatti

, 828 ,

834

Colon cancer , 954

Colony-stimulating factor , 239 ,

244

Colvin , 607 , 617

Comley , 477

Complementary sequence , 50

Complimentarity-determining

regions, 784

Concanavalin A (Con A) , 314 ,

366

Condensation , 215

Confocal microscopy , 424

Conjugation

using

multi-step protocols , 32

single-step protocols , 32 ,

235

two-step protocols , 235

Conn , 247

Conrad , 243 , 511

Cooper , 256

Coordination bonds , 474

Coordination complex , 498 ,

499 , 500 , 814

Coordination sites , 814

Copper , 748

Copper-67 , 498

Corneillie , 657

Corynebacterium diphtheriae ,

827 , 828

Coscoy , 316

Cosmetics

liposome encapsulation , 858

Coulter , 786

Coumarin , 319 , 400 , 437 ,

1020

aldehyde and ketone reactive

derivatives, 438

diazoalkane derivative , 194

energy transfer to ﬂ uorescein ,

430

general description and use ,

430

group within SAED , 317

labeling of avidin with , 917

sulfhydryl-reactive derivatives ,

434

Coumarin-maleimide , 668

Coupling factor 1, 255

Covalent chromatography , 256

Cover , 256

Cox , 501

Cramer , 932

Crapps , 708

Cravatt , 683

Creatine kinase , 363

Crestﬁ eld , 110 , 183

Criekinge , 1004

Crissman , 400

Cristea , 181

Crook , 755 , 927

Cross-bridge , 277

cleavable , 277 ,

391

diol cleavable

, 393

disulﬁ de containing , 392

immunogenicity of , 768

of

ABH , 332

ANB-NOS , 312

APDP , 328

APG , 335

ASBA , 333

ASIB , 325

biotinylation reagents , 506

GMBS , 292

HSAB , 309

MBS , 287 , 853

NPIA , 296

SADP , 314

SAED , 317

SANPAH , 311

SIAB , 288

SIAC

, 295

SIAX , 294

SIAXX , 295

SMPB , 291

Index 1149

SMPT , 281

sulfo-LC-SMPT , 282

sulfo-NHS-LC-ASA , 306

sulfo-SAMCA , 321

sulfo-SBED , 338

SAND , 313

used in immunotoxin

conjugates , 830

Crosslinkers

arginine reactive and

photoreactive , 333

base cleavable , 395

carbonyl reactive and

photoreactive , 330

carboxylate reactive and

photoreactive , 332

cleavable , 391

APDP , 326

in immunotoxin conjugate

design , 830

SADP , 314

SAED , 317

SAND , 313

sulfo-SBED , 338

disulﬁ de cleavable

, 392

dithionite cleavable , 394

hydroxylamine cleavable , 394

immunogenicity of , 768

iodinatable , 556

periodate cleavable , 393

sulfhydryl reactive

determination of activity

with SAMSA-

ﬂ uorescein , 410

and photoreactive , 324

trifunctional , 336

zero-length , 215

Crosslinking

multi-step protocols , 277

reagents , 213

site-directed , 277

strategies with proteins , 32

using

homobifunctional reagents ,

32

single-step protocols , 235

two-step protocols , 235

Crosslinking agents

disulﬁ de containing

cleavage using DTT , 91

sulfhydryl reactive , 256

Crosslinking chemistry , 169

Crosslinking reagents

carbonyl and sulfhydryl

reactive , 297

cell permeant and imper-

meant , 237

disulﬁ de containing

cleavage using DTT , 90

heterobifunctional , 276

homobifunctional , 234

iodinatable , 556 , 560

Cruz , 112

Cryoprotectants , 863

Cryoprotection , 936

 -Crystalline , 252

CSF-1 , 242

67

Cu , 383

Cu(I) , 386

as catalyst for click chemistry

reaction , 211 , 680

Cu1  , 25

Cuatrecasas , 104 , 172 , 218 ,

237 , 238 , 256 , 773 , 901 ,

940

Cubie , 905

Cuenoud , 1032

Cumber , 77 , 827 , 831 , 834 , 848 ,

852

Curl , 627

Cusan , 629

CuSO

4

, 683 , 726

CVF , 827

Cy3 , 464

Cy5 , 358 , 464 , 480

as acceptor in LRET , 479

dendrimer labeling , 382

dendrimer modiﬁ cation , 358

tandem dye , 463

Cy5.5 , 465

Cy7 , 464

Cyanide , 963

Cyanine dyes

amine-reactive , 467

carbonyl-reactive , 472

general description and use ,

464

hydrazide-containing , 472

thiol-reactive , 470

Cyanobacteria , 461

Cyanocobalamin , 710

Cyanogen bromide , 42–43

activation of hydroxyl

particles , 612

Cyanuric chloride , 43 , see also

Trichloro-s-triazine

Cyclic AMP , 62

Cycloaddition , 350 , 676 , 681 ,

682

Diels–Alder , 667

of psoralen to thymine , 209

to carbon nanotubes , 646

Cycloaddition reactions , 210 ,

680

Cyclodextrins

fullerene interactions , 629

Cyclohexane , 897 , 906

1-Cyclohexyl-3-(2-morpholi-

noethyl) carbodiimide , see

CMC; CDI

Cyclooctyne ring

in click chemistry reactions

,

690

Cyclopentadiene , 689

Cyclopropanation

, 634

Cystamine , 982 , 990 , 993

coupling to lactose , 832

in preparation of

immunotoxins , 844

modiﬁ cation of

DNA with , 981

oligonucleotides , 87

reaction with proteins , 87

reduction of , 832

use for thiolation , 84

Cysteic acid , 26

Cysteine , 7 , 97 , 102 , 107 , 109 ,

118 , 120 , 289 , 426 , 555 ,

701

, 768 , 808

added during peptide

synthesis , 768

aminoethylated , 119

biotinylation of , 520

blocking

of , 160

with iodoacetamide , 161

using Ellman’s reagent , 101

modiﬁ cation with 2-bromo-

ethylamine , 120

oxidation of , 25

Hermanson G. Bioconjugate Techniques, Second Edition

Подождите немного. Документ загружается.