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Subject Index Subject Index A DNA binding 38-40 DNA strand breaks 37 Scatchard plot 36 ACIMBO 146 effects on nuclear nucleic acid 58 Aclacinomycin 59 and nuclear damage 36 Aclacinomycin A 60,63-5,67 Adriamycin macromolecule complexes and catalase 65,71 79 and DNA binding 64 Adriamycin-ara-C 106 and DNA strand breaks 64 Adriamycin-14-benzoate 94 and DNA synthesis 64 Adriamycin-14-(1-naphthalene acetate) and RNA synthesis 64 94 Acridine orange 2 Adriamycin-14-octanoate 94,120 Acridine yellow 3 Agglutination 25 Acridones 26-9 Aklavine 68 alkaloids 28 Aklavinone 59 nitroacridone 27 Albumin microspheres 79 thioacridone 27 Alcindromycin 66 Acriflavine 1, 2 Aldehyde reductase 109 Acrolein 11 0 Alkaline elution 37,206,316,318, Acronycine 28 335,336,344 and DNA synthesis 28 Alkaline sucrose sedimentation 206, detoxification 28 218,222,316,322 metabolism 28 Alkylated DNA 244 and RNA synthesis 28 Alkylated RNA 244 Actinomycins 24, 104, 148 Alkylating acridines 3, 4 inhibition of RNA synthesis 25 Alkylating agents 233ff, 284 Actinomycin D 37,104,129,150 local administration of 264 DNA damage 105 Alkylation of DNA bases 300 AD32 74,97,104 Alkylation products 300 cell cycle effects 74 7-a1kylguanines 300 AD41 97 Alkyltransferase 346,355 Adamanty1 substituents 385 Allopurinol 111 Adenocarcinoma 386 Ametantrone 82-5 Adriamycin 21,35-53,57-86,94, D-aminoacid oxidase 111 96, 104, 108 L-aminoacid oxidase 111 cardiotoxicity of 57 9-aminoacridine 1,18,22,23 chromatin binding 36-7 imino form 10 chromatin compaction 37 Aminopterin 368,380 395 396 Subject Index AML 121 Ataxia telangiectasia 174 m-AMSA 12-21,37,104,105 Atebrin (see Mepacrine) antitumour spectrum 17 A V3 cells 212 cell division cycle 18 7-aza analogues 381 chromosomal aberrations 18 Azacrine 1 degradation 13 Aziridines 240, 249 DNA binding 14 Aziridinium ion 236 DNA damage 103 5-aziridino-2,4-dinitrobenzamide 272 DNA strand breaks 18 Aziridinyl quinone 326 DNA intercalation 14,18 1-aziridinyl-2,4-dinitrobenzene 250, equilibrium dialysis 20 251 immunosuppressive activity 17 Azo mustards 269, 270 irradiation 18 Azoreductase 268, 269 and leukaemia 17 and lymphoma 17 B mutagenic activity of 17 Scatchard plots 20 Bacteriophage 197 o-AMSA 16 T7 209 Amsacrine 12 Baker's soluble antifo1 385 log P values 12 Baker's triazinate 386 Angelicin 335 Base preference of saframycin Aniline mustard 247,265,274 binding 288 9-anilinoacridines 4, 9, 10-29 Base-propenals 163 and closed circular duplex DNA 12 BCND (see Chloroethylnitrosoureas) Hammett relationship 13 Bifunctional intercalation 129-33, 150 and intercalation with DNA 12, 14 and diacridines 24 pKa values 13 Bioreductive activation 293 and lipophilic-hydrophilic balance 12 Biotransformation of anthracycline 107 and petite mutants in yeast 16 Binding kinetics and diacridines 24 and QSARs 14,16 Bleomycin 157-78,184 X-ray crystallographic studies of 13 activated 169,170 Anthracyclines 286 and DNA damage 105 anaesthetic properties 113 and DNA strand breaks 165,166, biotransformation 107 174 immunosuppressive activity 95 and mutagenesis 176 neurotoxicity 113 Bleomycin-inactivating enzyme 177 reduction 111 Bleomycin-metal complexes 159 selective toxicity 95, 111 Blood-brain barrier 253 semiquinone radicals 111 Bohemic acid complex 65 structural relationships 59-63 N-bromoacetyl daunomycin 45 Anthramycin 288,290,301 5-bromo-2'-deoxyuridine 316 Anthranilic acid 269 7-bromomethylbenz(a)anthracene 222 Anthraquinones 81,84 Burkitt's lymphoma cells, DNA damage Antibacterial tests of TANDEM 130 and cytotoxicity 344 Antifol 363 Butyl ethers 242 Antitumour immunity and platinum drugs 191 c Apoptosis 106 Ara-C 106 Caffeine Arachidonic acid 116 inhibition of post replication repair, Arrhenius plots 148 337 Aryl-2-haloethyltriazenes 294 and toxicity of cis-DDP 217 Subject Index 397 Camptothecin 291 Chromomycin A3 297 Carboxypeptidase G 1 and metho­ Chromophore resonances 44 trexate toxicity 369 Chromosome Carcinomycin (see 4-hydroxydauno­ aberrations mycin) and aclacinomycin 63 Cardiac guany1ate cyclase, inhibition and m-AMSA 18 byanthracyclines 114 and bleomycin 175 Cardiomyopathy 35,95 breaks Carminic acid 85 and mitoxantrone 83 Carminomycin 59,78,94,102,108 and ametantrone 83 Carrier damage of methotrexate 368 staining of 7 protein, and alky1ating agent 276 Cinerubin A and B 65,67 transport 384 Circular dichroism 1 54 Carzinophilin A 303 cis-trans isomerisation 152 Catalase 116, 308 Citrovorum factor (see 5-formyl- and aclacinomycin A 65 tetrahydrofolic acid) CBDCA 263 Collinemycin 66 CCRF-CEM cells and 4-demethoxy­ Colon tumour 350 daunomycin 97 Conformational calculations of dauno- Cell division mycin 46 and AD32 74 Cooperative binding 135, 136 and m-AMSA 18 Cooperative interaction 137 Cell survival and platinum compounds Cooperativity in dissociation 150 200 Cyclic AMP 368 CF (see 5-formy1tetrahydrofo1ic acid) Adriamycin, regulation by 114 Chelate effect 185 and platinum drugs 192 CHIP 201 Cyclic GMP regulation by Adriamycin Chlorambucil 234,237,247,274,276 114 Chlorasquin 382 Cyclic phosphodiesterases regulation Chlorocarcins 288 by Adriamycin 114 p-b is (2-chloroethyl)aminophenol 267 Cyclophosphamide 119,271,272, Ch10roethy1nitrosoureas (CNUS) 345 284,326 2-chloroethylnitrosoureas (CENU) Cytochrome P-450 110,170 284,295,303 reductase 108 1 ,3 -b is-( 2 chloroethyl)-l-nitrosourea Cytotoxicity (BCNU) 253, 254, 272, 284, of DNA damaging agents 352 306,355 of methotrexate 367 1-(2-chloroethyl)-1-nitrosourea (CNU) 356 1-(2-chloroethyl)-3-(trans-4-methyl­ D cYclohexyl)-l-nitrosourea (MeCCNU) 253, 254 DAEP 385 bis(2-chloroethyl)sulphide 234 DAMP 385 Chlorozotocin 255, 351 Daunomycin 35-53,57-86,102,104, Chloroquine 273 111 CH NU 306 N-acetyl- 94, 97 Chromatin N-benzyl- 74 binding binding to with Adriamycin 36-7 chromatin 36-7 with daunomycin 36-7 DNA 38-40,46-8 compaction and Adriamycin 37 biotransformation 108 398 Subject Index conformational calculations 46 crosslinking 8, 316 deoxy- 60 frequency of 318, 322 4-demethoxy- 94,97,102,104, resistance to agents 334 108 and platinum compounds 195 II-deoxy- 78 damage 163,323,339 dihydro- 59 and alky1ating agents 284-6 and DNA unwinding angle 40 and anthracyclines 103 6,11-di-o-methyl- 77 as a depot site 97 N,N-dibenzyl- 75 dissociation 146-7 N,N-dimethyl- 74 A-DNA 197 effects on nuclear nucleic acid 58 melting point of 40 4'-epi- 96 nuc1eosomal 103 and hydrogen-bonding interactions pSMl DNA 198 52 and platinum drugs, reaction with interaction with oligonucleotides 193ff 43,44 polymerase 99,216,328 NMR studies 43 protein crosslinks with 206, 208, polynucleotide interactions 45 319,337 quenching of fluorescence 38 replication, inhibition of 327 self-aggregation 43 strand breaks 166,174,292,303 structural studies 45-53 304,310,318,330,353 and tetranucleotide interaction 43 and AD32 74 toxicity 57 apurinic/apyrimidic sites 174 Daunomycin-dinucleoside complex and ac1acinomycin 64 42, 52 and m-AMSA 18 Daunomycin-hexamer structure 52 and bleomycin 165 Daunomycin-hexanucleotide complex and ethidium 36 41,44 and free radicals 307 Daunomycin-macromolecule studies and and mitoxantrone 83 nuclear damage 36 type 11 307 Daunomycin-oligonucleotide complex strand reassociation 316,321 50-3 structure 41 Daunomycinol 108 supercoiled CCC- 298 Daunomycinone 108 synthesis 174,366,387 Daunorubicin (see Daunomycin) and aclacinomycin A 64 Daunosamine sugar 38 and acronycine 28 I-and 3-deazamethotrexate 381,382 inhibition by anthracyclines of 98 3-deaza-trimethoprim 382 unwinding of 130,131 Density-hybrid method for measuring angle 23,24,26,40,132 DNA interstrand cross linking 316 viral 325 Deoxyribose cleavage by bleomycin Z-DNA 41 172 Deoxyuridy1ate 365 Deoxyribose nucleic acid (DNA) Depsipeptides 146 B-form 41,44,52,132 Depurination 299 binding 163, 173, 200 Depyrimidination 299 and aclacinomycin 64 Detoxification of acronycine 28 and Adriamycin 96 Diacridines 21-6, 129 and anthracyclines 96 bifunctional intercalation 24 and daunomycin 96 binding kinetics 24-5 and quinoxalines 129 mode of binding 22 closed circular duplex 12, 22, 131 and RNA synthesis 25 covalent bonding 10 Dialkyltriazenes 25 Subject Index 399 2,4-diamino-5-adamantyl-6-methyl­ Dunning leukaemia ascites and di­ pyrimidine 368 hydrotriazine 386 2, 4-diamino-5( 3,4-dichloropheny 1)- 6-methy1pyrimidine (DDMP or Metropine) 384 E 2,4-diamino-5,6-dihydro-6,6-di­ Echinomycin 26, 127, 130-50 methyl-5-( 4' methoxypheny1)­ binding to DNA s-triazine (MPT) 374 dissociation of 143-5 2,6-diaminopurine analogues 382 high affinity site of 142 cis-dichlorodiammine platinum (cis­ preferred site of 142 DDP) 37,183-238,261,263, statistical mechanical model of 135 324,332,335,336,337,339, quinoline analogues of 130 352 Electric dichroism 22 trans-DDP 325,335 Electrophilic attack 301 cis-diammine-1 , 1-cyc1o butane dicarb- ELSERTA 146 oxy1ate platinum 11 (CBDCA) 263 Endonuc1eases, Mg2+ -Ca 2+ 105 1,2:5,6-dianhydro-D-mannito1 252 1,2: 5,6-dianhydrogalactito1 253 Epoxides 241 Dibromodu1cito1 252 Ethidium 14,19,26,131,133,297 Dibromomannito1 252 and DNA strand breaks 36 (J-diethy1aminoethy1dipheny1propy1- and DNA unwinding angle 40 acetate 110 Euflavine 1, 2 Difunctionality 244 Excision mechanisms 328,355 Dihydrofo1ate reductase 363-70, Exr gene 216 379,381,382 alterations in 370 F chickenliver 371,374,375,378,387 E. coli 371 Fanconi's anaemia 223,337 inhibition of 363 Fibre diffraction of daunomycin-DNA resistance, toxicity, pharmaco- complex 46 kinetics of 381 Filament formation, in bacteria 188 L. casei 370,371,377,383 Flow dichroism of steffimycin 72 mammalian 385 5-fluorodeoxyuridine monophosphate
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