Analysis of the DNA adducts of phenyl glycidyl ether in a calf thymus DNA hydrolysate by capillary zone electrophoresis-electrospray mass spectrometry : evidence for phosphate alkylation
Calf thymus DNA was reacted in vitro with phenyl glycidyl ether (PGE) and was hydrolysed enzymatically, to the 5'-monophosphate nucleotides using deoxyribonuclease I (DNA-ase I) and nuclease P1. The adducts were concentrated using solid phase extraction (SPE), on a polystyrene divinylbenzene co...
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| Veröffentlicht in: | Carcinogenesis (New York) 1998-06, Vol.19 (6), p.1077-1086 |
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| container_title | Carcinogenesis (New York) |
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| creator | DEFORCE, D. L. D LEMIERE, F HOES, I MILLECAMPS, R. E. M ESMANS, E. L DE LEENHEER, A VAN DEN EECKHOUT, E. G |
| description | Calf thymus DNA was reacted in vitro with phenyl glycidyl ether (PGE) and was hydrolysed enzymatically, to the 5'-monophosphate nucleotides using deoxyribonuclease I (DNA-ase I) and nuclease P1. The adducts were concentrated using solid phase extraction (SPE), on a polystyrene divinylbenzene copolymer in order to remove the unmodified nucleotides. The adducts could be identified using capillary zone electrophoresis-electrospray tandem mass spectrometry (CZE ES-MS/MS), using sample stacking. In addition to the base alkylated 2'-deoxynucleotides present in the DNA-hydrolysate, also phosphate alkylated 2'-deoxynucleotide adducts were identified for TMP and dAMP. An additional adduct, dUMP alkylated on the uridine moiety was found originating from the hydrolytic deamination of dCMP alkylated on N3 of the cytosine moiety. Enzymatic hydrolysis using nuclease P1 was incomplete as shown by the presence of dinucleotides alkylated on the base moiety. They were successfully hydrolysed to the corresponding 2'-deoxynucleotides by snake venom phosphodiesterase (SVP). Data are shown indicating that alkylations on the pyrimidine bases were more resistant to enzymatic hydrolysis with nuclease P1 than the purine alkylated products. |
| doi_str_mv | 10.1093/carcin/19.6.1077 |
| format | Article |
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L. D ; LEMIERE, F ; HOES, I ; MILLECAMPS, R. E. M ; ESMANS, E. L ; DE LEENHEER, A ; VAN DEN EECKHOUT, E. G</creator><creatorcontrib>DEFORCE, D. L. D ; LEMIERE, F ; HOES, I ; MILLECAMPS, R. E. M ; ESMANS, E. L ; DE LEENHEER, A ; VAN DEN EECKHOUT, E. G</creatorcontrib><description>Calf thymus DNA was reacted in vitro with phenyl glycidyl ether (PGE) and was hydrolysed enzymatically, to the 5'-monophosphate nucleotides using deoxyribonuclease I (DNA-ase I) and nuclease P1. The adducts were concentrated using solid phase extraction (SPE), on a polystyrene divinylbenzene copolymer in order to remove the unmodified nucleotides. The adducts could be identified using capillary zone electrophoresis-electrospray tandem mass spectrometry (CZE ES-MS/MS), using sample stacking. In addition to the base alkylated 2'-deoxynucleotides present in the DNA-hydrolysate, also phosphate alkylated 2'-deoxynucleotide adducts were identified for TMP and dAMP. An additional adduct, dUMP alkylated on the uridine moiety was found originating from the hydrolytic deamination of dCMP alkylated on N3 of the cytosine moiety. Enzymatic hydrolysis using nuclease P1 was incomplete as shown by the presence of dinucleotides alkylated on the base moiety. They were successfully hydrolysed to the corresponding 2'-deoxynucleotides by snake venom phosphodiesterase (SVP). 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L. D</creatorcontrib><creatorcontrib>LEMIERE, F</creatorcontrib><creatorcontrib>HOES, I</creatorcontrib><creatorcontrib>MILLECAMPS, R. E. M</creatorcontrib><creatorcontrib>ESMANS, E. L</creatorcontrib><creatorcontrib>DE LEENHEER, A</creatorcontrib><creatorcontrib>VAN DEN EECKHOUT, E. G</creatorcontrib><title>Analysis of the DNA adducts of phenyl glycidyl ether in a calf thymus DNA hydrolysate by capillary zone electrophoresis-electrospray mass spectrometry : evidence for phosphate alkylation</title><title>Carcinogenesis (New York)</title><addtitle>Carcinogenesis</addtitle><description>Calf thymus DNA was reacted in vitro with phenyl glycidyl ether (PGE) and was hydrolysed enzymatically, to the 5'-monophosphate nucleotides using deoxyribonuclease I (DNA-ase I) and nuclease P1. The adducts were concentrated using solid phase extraction (SPE), on a polystyrene divinylbenzene copolymer in order to remove the unmodified nucleotides. The adducts could be identified using capillary zone electrophoresis-electrospray tandem mass spectrometry (CZE ES-MS/MS), using sample stacking. In addition to the base alkylated 2'-deoxynucleotides present in the DNA-hydrolysate, also phosphate alkylated 2'-deoxynucleotide adducts were identified for TMP and dAMP. An additional adduct, dUMP alkylated on the uridine moiety was found originating from the hydrolytic deamination of dCMP alkylated on N3 of the cytosine moiety. Enzymatic hydrolysis using nuclease P1 was incomplete as shown by the presence of dinucleotides alkylated on the base moiety. They were successfully hydrolysed to the corresponding 2'-deoxynucleotides by snake venom phosphodiesterase (SVP). Data are shown indicating that alkylations on the pyrimidine bases were more resistant to enzymatic hydrolysis with nuclease P1 than the purine alkylated products.</description><subject>Alkylation</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Carcinogenesis, carcinogens and anticarcinogens</subject><subject>Cattle</subject><subject>Chemical agents</subject><subject>DNA - drug effects</subject><subject>DNA Adducts - analysis</subject><subject>Electrophoresis, Capillary - methods</subject><subject>Mass Spectrometry - methods</subject><subject>Medical sciences</subject><subject>Phenyl Ethers - pharmacology</subject><subject>Phosphates - metabolism</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Thymus Gland - drug effects</subject><subject>Thymus Gland - metabolism</subject><subject>Tumors</subject><issn>0143-3334</issn><issn>1460-2180</issn><issn>1460-2180</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdUU2P1SAUJUYzPkf3bkyIMe46wy0UHu5exs9kohtdEwrUMtJSoZ2k_jR_nfS9l1m4As4951zuPQi9BHIFRNJro5Px4zXIK14AIR6hHTBOqhr25DHaEWC0opSyp-hZzneEAKeNvEAXknMhmNihv4dRhzX7jGOH597h918PWFu7mPkITb0b14B_htV4Wy6ucBL2I9bY6LBJ1mHJR1W_2hSLl54dbtdSnnwIOq34TxwddsGZOcWpj8mVdtX5naekVzzonHGejsjg5qJ5h929t240DncxlW8UZr856_BrDXr2cXyOnnQ6ZPfifF6iHx8_fL_5XN1--_Tl5nBbGVbTudo3DKShEojhVpBWUiopEy0IzXgHEljN6rZhtmk5tUxwvq-7PdNdV1vGmoZeorcn3ynF34vLsxp8Nq7MNrq4ZAW8aSQXUIiv_yPexSWV_WZVQ2nbMCYLiZxIpgyfk-vUlPxQ1qSAqC1TdcpUgVRcbZkWyauz79IOzj4IziGW-ptzXectlKRH4_MDraZAQNT0HwcDrdA</recordid><startdate>19980601</startdate><enddate>19980601</enddate><creator>DEFORCE, D. L. D</creator><creator>LEMIERE, F</creator><creator>HOES, I</creator><creator>MILLECAMPS, R. E. M</creator><creator>ESMANS, E. L</creator><creator>DE LEENHEER, A</creator><creator>VAN DEN EECKHOUT, E. G</creator><general>Oxford University Press</general><general>Oxford Publishing Limited (England)</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7T5</scope><scope>7TM</scope><scope>7TO</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>K9.</scope><scope>P64</scope><scope>RC3</scope></search><sort><creationdate>19980601</creationdate><title>Analysis of the DNA adducts of phenyl glycidyl ether in a calf thymus DNA hydrolysate by capillary zone electrophoresis-electrospray mass spectrometry : evidence for phosphate alkylation</title><author>DEFORCE, D. L. D ; LEMIERE, F ; HOES, I ; MILLECAMPS, R. E. 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L. D</creatorcontrib><creatorcontrib>LEMIERE, F</creatorcontrib><creatorcontrib>HOES, I</creatorcontrib><creatorcontrib>MILLECAMPS, R. E. M</creatorcontrib><creatorcontrib>ESMANS, E. L</creatorcontrib><creatorcontrib>DE LEENHEER, A</creatorcontrib><creatorcontrib>VAN DEN EECKHOUT, E. 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L. D</au><au>LEMIERE, F</au><au>HOES, I</au><au>MILLECAMPS, R. E. M</au><au>ESMANS, E. L</au><au>DE LEENHEER, A</au><au>VAN DEN EECKHOUT, E. G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Analysis of the DNA adducts of phenyl glycidyl ether in a calf thymus DNA hydrolysate by capillary zone electrophoresis-electrospray mass spectrometry : evidence for phosphate alkylation</atitle><jtitle>Carcinogenesis (New York)</jtitle><addtitle>Carcinogenesis</addtitle><date>1998-06-01</date><risdate>1998</risdate><volume>19</volume><issue>6</issue><spage>1077</spage><epage>1086</epage><pages>1077-1086</pages><issn>0143-3334</issn><issn>1460-2180</issn><eissn>1460-2180</eissn><coden>CRNGDP</coden><abstract>Calf thymus DNA was reacted in vitro with phenyl glycidyl ether (PGE) and was hydrolysed enzymatically, to the 5'-monophosphate nucleotides using deoxyribonuclease I (DNA-ase I) and nuclease P1. The adducts were concentrated using solid phase extraction (SPE), on a polystyrene divinylbenzene copolymer in order to remove the unmodified nucleotides. The adducts could be identified using capillary zone electrophoresis-electrospray tandem mass spectrometry (CZE ES-MS/MS), using sample stacking. In addition to the base alkylated 2'-deoxynucleotides present in the DNA-hydrolysate, also phosphate alkylated 2'-deoxynucleotide adducts were identified for TMP and dAMP. An additional adduct, dUMP alkylated on the uridine moiety was found originating from the hydrolytic deamination of dCMP alkylated on N3 of the cytosine moiety. Enzymatic hydrolysis using nuclease P1 was incomplete as shown by the presence of dinucleotides alkylated on the base moiety. They were successfully hydrolysed to the corresponding 2'-deoxynucleotides by snake venom phosphodiesterase (SVP). 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| identifier | ISSN: 0143-3334 |
| ispartof | Carcinogenesis (New York), 1998-06, Vol.19 (6), p.1077-1086 |
| issn | 0143-3334 1460-2180 1460-2180 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_16559671 |
| source | MEDLINE; Oxford University Press Journals All Titles (1996-Current); EZB-FREE-00999 freely available EZB journals; Alma/SFX Local Collection |
| subjects | Alkylation Animals Biological and medical sciences Carcinogenesis, carcinogens and anticarcinogens Cattle Chemical agents DNA - drug effects DNA Adducts - analysis Electrophoresis, Capillary - methods Mass Spectrometry - methods Medical sciences Phenyl Ethers - pharmacology Phosphates - metabolism Spectrophotometry, Ultraviolet Thymus Gland - drug effects Thymus Gland - metabolism Tumors |
| title | Analysis of the DNA adducts of phenyl glycidyl ether in a calf thymus DNA hydrolysate by capillary zone electrophoresis-electrospray mass spectrometry : evidence for phosphate alkylation |
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