Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. synthesis and identification of N2-(2'-deoxyguanosin-8-yl) - PhIP

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Standard

Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. synthesis and identification of N2-(2'-deoxyguanosin-8-yl) - PhIP. / Frandsen, Henrik; Grivas, Spiros; Andersson, Rolf; Dragsted, Lars Ove; Larsen, John Christian.

I: Carcinogenesis, Bind 13, Nr. 4, 1992, s. 629-635.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Frandsen, H, Grivas, S, Andersson, R, Dragsted, LO & Larsen, JC 1992, 'Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. synthesis and identification of N2-(2'-deoxyguanosin-8-yl) - PhIP', Carcinogenesis, bind 13, nr. 4, s. 629-635. https://doi.org/10.1093/carcin/13.4.629

APA

Frandsen, H., Grivas, S., Andersson, R., Dragsted, L. O., & Larsen, J. C. (1992). Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. synthesis and identification of N2-(2'-deoxyguanosin-8-yl) - PhIP. Carcinogenesis, 13(4), 629-635. https://doi.org/10.1093/carcin/13.4.629

Vancouver

Frandsen H, Grivas S, Andersson R, Dragsted LO, Larsen JC. Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. synthesis and identification of N2-(2'-deoxyguanosin-8-yl) - PhIP. Carcinogenesis. 1992;13(4):629-635. https://doi.org/10.1093/carcin/13.4.629

Author

Frandsen, Henrik ; Grivas, Spiros ; Andersson, Rolf ; Dragsted, Lars Ove ; Larsen, John Christian. / Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. synthesis and identification of N2-(2'-deoxyguanosin-8-yl) - PhIP. I: Carcinogenesis. 1992 ; Bind 13, Nr. 4. s. 629-635.

Bibtex

@article{da9b715dba20499690bd199f1db35fd7,
title = "Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. synthesis and identification of N2-(2'-deoxyguanosin-8-yl) - PhIP",
abstract = "The direct acting mutagenic N2-hydroxylated metabolite of the food mutagen 2-amino-1-methyl-6-phenylimidazo-[4, 5-b]pyridine (PhIP) does not react with DNA. Upon acetylation of the N2-hydroxy-PhIP with acetic anhydride two products could be detected. Mass spectrometric analysis showed that both products were monoacetyl derivatives of N2-hydroxy-PhIP. One of the products did not show any reactivity towards DNA and is probably the N-acetyl derivative of N2-hydroxy-PhIP. The other product which is most likely to be N2-acetoxy-PhIP reacted with DNA and 2'-deoxyguanosine but not with 2'-deoxycytidine, 2'-deoxy-adenosine or 2'-deoxythymidine. The PhIP-2'-deoxyguanosine adduct was purified and characterized by mass spectral, 1H and [13C]NMR analysis, showing that PhIP like the other cooked food mutagen 2-amino-3-memytiniidazo[4, 5-f]quinoline, had reacted with C-8 of guanine forming N(2'-deoxy-guanosin-8-yl) - PhIP. HPLC analysis of enzymatically hydrolyzed calf thymus DNA which had been reacted with N2-acetoxy-PhIP showed one adduct which was chromato-graphically and spectroscopkally identical to N2-(2'-deoxy-guanosin-8-yl)-PhIP. HPLC separation followed by liquid scintillation counting of hydrolyzed liver DNA from a rat dosed with [3H]PhlP showed that radioactivity coehited with the hydrolysis product of the synthetic PhIP-2-deoxyguanosine adduct, indicating that PhIP in vivo also forms an N2-(2'-deoxyguanosin-8-yl)-PhIP adduct.",
author = "Henrik Frandsen and Spiros Grivas and Rolf Andersson and Dragsted, {Lars Ove} and Larsen, {John Christian}",
note = "(Ekstern)",
year = "1992",
doi = "10.1093/carcin/13.4.629",
language = "English",
volume = "13",
pages = "629--635",
journal = "Carcinogenesis",
issn = "0143-3334",
publisher = "Oxford University Press",
number = "4",

}

RIS

TY - JOUR

T1 - Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. synthesis and identification of N2-(2'-deoxyguanosin-8-yl) - PhIP

AU - Frandsen, Henrik

AU - Grivas, Spiros

AU - Andersson, Rolf

AU - Dragsted, Lars Ove

AU - Larsen, John Christian

N1 - (Ekstern)

PY - 1992

Y1 - 1992

N2 - The direct acting mutagenic N2-hydroxylated metabolite of the food mutagen 2-amino-1-methyl-6-phenylimidazo-[4, 5-b]pyridine (PhIP) does not react with DNA. Upon acetylation of the N2-hydroxy-PhIP with acetic anhydride two products could be detected. Mass spectrometric analysis showed that both products were monoacetyl derivatives of N2-hydroxy-PhIP. One of the products did not show any reactivity towards DNA and is probably the N-acetyl derivative of N2-hydroxy-PhIP. The other product which is most likely to be N2-acetoxy-PhIP reacted with DNA and 2'-deoxyguanosine but not with 2'-deoxycytidine, 2'-deoxy-adenosine or 2'-deoxythymidine. The PhIP-2'-deoxyguanosine adduct was purified and characterized by mass spectral, 1H and [13C]NMR analysis, showing that PhIP like the other cooked food mutagen 2-amino-3-memytiniidazo[4, 5-f]quinoline, had reacted with C-8 of guanine forming N(2'-deoxy-guanosin-8-yl) - PhIP. HPLC analysis of enzymatically hydrolyzed calf thymus DNA which had been reacted with N2-acetoxy-PhIP showed one adduct which was chromato-graphically and spectroscopkally identical to N2-(2'-deoxy-guanosin-8-yl)-PhIP. HPLC separation followed by liquid scintillation counting of hydrolyzed liver DNA from a rat dosed with [3H]PhlP showed that radioactivity coehited with the hydrolysis product of the synthetic PhIP-2-deoxyguanosine adduct, indicating that PhIP in vivo also forms an N2-(2'-deoxyguanosin-8-yl)-PhIP adduct.

AB - The direct acting mutagenic N2-hydroxylated metabolite of the food mutagen 2-amino-1-methyl-6-phenylimidazo-[4, 5-b]pyridine (PhIP) does not react with DNA. Upon acetylation of the N2-hydroxy-PhIP with acetic anhydride two products could be detected. Mass spectrometric analysis showed that both products were monoacetyl derivatives of N2-hydroxy-PhIP. One of the products did not show any reactivity towards DNA and is probably the N-acetyl derivative of N2-hydroxy-PhIP. The other product which is most likely to be N2-acetoxy-PhIP reacted with DNA and 2'-deoxyguanosine but not with 2'-deoxycytidine, 2'-deoxy-adenosine or 2'-deoxythymidine. The PhIP-2'-deoxyguanosine adduct was purified and characterized by mass spectral, 1H and [13C]NMR analysis, showing that PhIP like the other cooked food mutagen 2-amino-3-memytiniidazo[4, 5-f]quinoline, had reacted with C-8 of guanine forming N(2'-deoxy-guanosin-8-yl) - PhIP. HPLC analysis of enzymatically hydrolyzed calf thymus DNA which had been reacted with N2-acetoxy-PhIP showed one adduct which was chromato-graphically and spectroscopkally identical to N2-(2'-deoxy-guanosin-8-yl)-PhIP. HPLC separation followed by liquid scintillation counting of hydrolyzed liver DNA from a rat dosed with [3H]PhlP showed that radioactivity coehited with the hydrolysis product of the synthetic PhIP-2-deoxyguanosine adduct, indicating that PhIP in vivo also forms an N2-(2'-deoxyguanosin-8-yl)-PhIP adduct.

UR - http://www.scopus.com/inward/record.url?scp=0026612317&partnerID=8YFLogxK

U2 - 10.1093/carcin/13.4.629

DO - 10.1093/carcin/13.4.629

M3 - Journal article

C2 - 1576716

AN - SCOPUS:0026612317

VL - 13

SP - 629

EP - 635

JO - Carcinogenesis

JF - Carcinogenesis

SN - 0143-3334

IS - 4

ER -

ID: 254779905