CONJUGATION OF A POLYAMINE TO THE BIFUNCTIONAL ALKYLATING AGENT CHLORAMBUCIL DOES NOT ALTER THE PREFERRED CROSS-LINKING SITE IN DUPLEX DNA
We report here that chlorambucil introduces interstrand cross-links preferentially between two guanine residues in the sequence 5'-GNC, as has been observed for mechlorethamine and in line with the prediction of Millard et al. We also report that the site of cross-linking is not perturbed when...
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| Published in | Journal of the American Chemical Society Vol. 117; no. 30; pp. 8033 - 8034 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
Amer Chemical Soc
02.08.1995
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| Abstract | We report here that chlorambucil introduces interstrand cross-links preferentially between two guanine residues in the sequence 5'-GNC, as has been observed for mechlorethamine and in line with the prediction of Millard et al. We also report that the site of cross-linking is not perturbed when chlorambucil is conjugated to either spermidine or spermine to give conjugates 2 and 3, respectively. The results have important implications for the nature of interaction between DNA and polyamines. |
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| AbstractList | We report here that chlorambucil introduces interstrand cross-links preferentially between two guanine residues in the sequence 5'-GNC, as has been observed for mechlorethamine and in line with the prediction of Millard et al. We also report that the site of cross-linking is not perturbed when chlorambucil is conjugated to either spermidine or spermine to give conjugates 2 and 3, respectively. The results have important implications for the nature of interaction between DNA and polyamines. |
| Author | WEAVER, R CULLIS, PM MERSONDAVIES, L |
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| References | DREW, HR (WOS:A1981MJ92600009) 1981; 151 COHEN, GM (WOS:A1992HH97100006) 1992 SEILER, N (WOS:A1990CU88700002) 1990; 22 MILLARD, JT (WOS:A1990CU14400079) 1990; 112 LAWLEY, PD (WOS:A1989AF65500002) 1989; 213 RINK, SM (WOS:A1993KW98000001) 1993; 115 HAWORTH, IS (WOS:A1992JL89900013) 1992; 10 SAMBROOK J (WOS:A1995RM70000029.20) 1989 SCHNEIDER, HJ (WOS:A1992JR57500016) 1992; 31 HOLLEY, JL (WOS:A1992JF74600020) 1992; 52 PEGG AE (WOS:A1995RM70000029.18) 1988; 44 CULLIS PM (WOS:A1995RM70000029.6) LIQUORI, AM (WOS:A19679214500010) 1967; 24 ALLEY, SC (WOS:A1994NG37800006) 1994; 116 CULLIS PM (WOS:A1995RM70000029.7) SUNTERS, A (WOS:A1992JF16000009) 1992; 44 BANCROFT, D (WOS:A1994MW25700005) 1994; 33 (WOS:A1995RM70000029.1) 1994; 315 (WOS:A1995RM70000029.2) 1992; 13 OJWANG, JO (WOS:A1989CA66300012) 1989; 49 Maxam, A M (MEDLINE:6246368) 1980; 65 FARMER PB (WOS:A1995RM70000029.9) 1994 JANNE, J (WOS:A1991GC57200009) 1991; 23 |
| References_xml | – ident: WOS:A1995RM70000029.7 publication-title: UNPUB contributor: fullname: CULLIS PM – volume: 31 start-page: 1207 year: 1992 ident: WOS:A1992JR57500016 article-title: INTERACTIONS BETWEEN ACYCLIC AND CYCLIC PERALKYLAMMONIUM COMPOUNDS AND DNA .33. publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH contributor: fullname: SCHNEIDER, HJ – volume: 33 start-page: 1073 year: 1994 ident: WOS:A1994MW25700005 article-title: THE LOW-TEMPERATURE CRYSTAL-STRUCTURE OF THE PURE-SPERMINE FORM OF Z-DNA REVEALS BINDING OF A SPERMINE MOLECULE IN THE MINOR-GROOVE publication-title: BIOCHEMISTRY contributor: fullname: BANCROFT, D – volume: 10 start-page: 195 year: 1992 ident: WOS:A1992JL89900013 article-title: A MOLECULAR-DYNAMICS SIMULATION OF A POLYAMINE-INDUCED CONFORMATIONAL CHANGE OF DNA - A POSSIBLE MECHANISM FOR THE B TO Z TRANSITION publication-title: JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS contributor: fullname: HAWORTH, IS – volume: 49 start-page: 6529 year: 1989 ident: WOS:A1989CA66300012 article-title: SYNTHESIS OF A DUPLEX OLIGONUCLEOTIDE CONTAINING A NITROGEN-MUSTARD INTERSTRAND DNA-DNA CROSS-LINK publication-title: CANCER RESEARCH contributor: fullname: OJWANG, JO – start-page: 1 year: 1994 ident: WOS:A1995RM70000029.9 publication-title: INT ENCY PHARM THERA contributor: fullname: FARMER PB – volume: 23 start-page: 241 year: 1991 ident: WOS:A1991GC57200009 article-title: POLYAMINES - FROM MOLECULAR-BIOLOGY TO CLINICAL-APPLICATIONS publication-title: ANNALS OF MEDICINE contributor: fullname: JANNE, J – volume: 52 start-page: 4190 year: 1992 ident: WOS:A1992JF74600020 article-title: TARGETING OF TUMOR-CELLS AND DNA BY A CHLORAMBUCIL-SPERMIDINE CONJUGATE publication-title: CANCER RESEARCH contributor: fullname: HOLLEY, JL – year: 1989 ident: WOS:A1995RM70000029.20 publication-title: MOL CLONING LABORATO contributor: fullname: SAMBROOK J – volume: 213 start-page: 3 year: 1989 ident: WOS:A1989AF65500002 article-title: MUTAGENS AS CARCINOGENS - DEVELOPMENT OF CURRENT CONCEPTS publication-title: MUTATION RESEARCH contributor: fullname: LAWLEY, PD – volume: 24 start-page: 113 year: 1967 ident: WOS:A19679214500010 article-title: COMPLEXES BETWEEN DNA AND POLYAMINES - A MOLECULAR MODEL publication-title: JOURNAL OF MOLECULAR BIOLOGY contributor: fullname: LIQUORI, AM – volume: 112 start-page: 2459 year: 1990 ident: WOS:A1990CU14400079 article-title: MECHLORETHAMINE CROSS-LINKS DEOXYGUANOSINE RESIDUES AT 5'-GNC SEQUENCES IN DUPLEX DNA FRAGMENTS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MILLARD, JT – volume: 115 start-page: 2551 year: 1993 ident: WOS:A1993KW98000001 article-title: COVALENT STRUCTURE OF A NITROGEN MUSTARD-INDUCED DNA INTERSTRAND CROSS-LINK - AN N7-TO-N7 LINKAGE OF DEOXYGUANOSINE RESIDUES AT THE DUPLEX SEQUENCE 5'-D(GNC) publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: RINK, SM – volume: 13 year: 1992 ident: WOS:A1995RM70000029.2 publication-title: USER B APPLIED BIOSY – volume: 315 year: 1994 ident: WOS:A1995RM70000029.1 publication-title: PUBLICATION AMICON L – volume: 22 start-page: 211 year: 1990 ident: WOS:A1990CU88700002 article-title: POLYAMINE TRANSPORT IN MAMMALIAN-CELLS publication-title: INTERNATIONAL JOURNAL OF BIOCHEMISTRY contributor: fullname: SEILER, N – volume: 151 start-page: 535 year: 1981 ident: WOS:A1981MJ92600009 article-title: STRUCTURE OF A B-DNA DODECAMER .3. GEOMETRY OF HYDRATION publication-title: JOURNAL OF MOLECULAR BIOLOGY contributor: fullname: DREW, HR – volume: 44 start-page: 59 year: 1992 ident: WOS:A1992JF16000009 article-title: THE CYTOTOXICITY, DNA CROSS-LINKING ABILITY AND DNA-SEQUENCE SELECTIVITY OF THE ANILINE MUSTARDS MELPHALAN, CHLORAMBUCIL AND 4-[BIS(2-CHLOROETHYL)AMINO] BENZOIC-ACID publication-title: BIOCHEMICAL PHARMACOLOGY contributor: fullname: SUNTERS, A – volume: 44 start-page: 759 year: 1988 ident: WOS:A1995RM70000029.18 publication-title: CANCER RES contributor: fullname: PEGG AE – ident: WOS:A1995RM70000029.6 publication-title: IN PRESS J CHEM S P2 contributor: fullname: CULLIS PM – start-page: 298 year: 1992 ident: WOS:A1992HH97100006 article-title: TARGETING OF CYTOTOXIC AGENTS BY POLYAMINES - SYNTHESIS OF A CHLORAMBUCIL SPERMIDINE CONJUGATE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: COHEN, GM – volume: 116 start-page: 2734 year: 1994 ident: WOS:A1994NG37800006 article-title: DNA INTERSTRAND CROSS-LINKING BY 2,5-BIS(1-AZIRIDINYL)-1,6-BENZOQUINONE - NUCLEOTIDE-SEQUENCE PREFERENCES AND COVALENT STRUCTURE OF THE DG-TO-DG CROSS-LINKS AT 5'-D(GN(N)C) IN SYNTHETIC OLIGONUCLEOTIDE DUPLEXES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: ALLEY, SC – volume: 65 start-page: 499 year: 1980 ident: MEDLINE:6246368 article-title: Sequencing end-labeled DNA with base-specific chemical cleavages. publication-title: Methods in enzymology contributor: fullname: Maxam, A M |
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| Snippet | We report here that chlorambucil introduces interstrand cross-links preferentially between two guanine residues in the sequence 5'-GNC, as has been observed... |
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| Title | CONJUGATION OF A POLYAMINE TO THE BIFUNCTIONAL ALKYLATING AGENT CHLORAMBUCIL DOES NOT ALTER THE PREFERRED CROSS-LINKING SITE IN DUPLEX DNA |
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