PMID- 6161706
OWN - NLM
STAT- MEDLINE
DCOM- 19810424
LR  - 20190825
IS  - 0009-2797 (Print)
IS  - 0009-2797 (Linking)
VI  - 34
IP  - 1
DP  - 1981 Feb
TI  - Arylhydroxylamine-induced ribonucleic acid chain cleavage and chromatographic 
      analysis of arylamine-ribonucleic acid adducts.
PG  - 109-24
AB  - Reaction of N-hydroxy-2-aminofluorene (N-OH-AF) with rRNA at pH 5.0 decreased the 
      molecular weight of the polynucleotide. Toluene-soluble aryl derivatives were 
      released on hydrolysis of fluorenylamine- and biphenylamine-substituted RNA by 
      treatment with venom phosphodiesterase and alkaline phosphatase. These data 
      suggested that arylhydroxylamines, activated by incubation at pH 5.0 or by 
      enzymatic O-acetylation, might react with the phosphate group of RNA to give 
      unstable phosphate triesters. Spontaneous hydrolysis of these triesters would 
      result in cleavage of the polynucleotide chain. Further enzymatic hydrolysis of 
      the phosphate esters would yield nonpolar arylamine derivatives. Enzymatically 
      degraded 4-aminobiphenyl(ABP)-RNA adducts were examined by high performance 
      liquid chromatography (HPLC) for the presence of a putative phosphorylated 
      adduct. Synthetic standards of the C-8-guanosine monophosphate-ABP adduct 
      (ABP-GMP) and o-aminobiphenyl-O-phosphate were used as markers in the analysis of 
      the digested RNA. A phosphate adduct of ABP was undetectable by these methods. 
      The data also indicated that the ABP-GMP formed in the acyltransferase-mediated 
      binding of N-hydroxy-4-acetylaminobiphenyl (N-OH-AABP) to RNA is readily degraded 
      during the enzymatic digestion of the RNA adduct.
FAU - Vaught, J B
AU  - Vaught JB
FAU - Lee, M S
AU  - Lee MS
FAU - Shayman, M A
AU  - Shayman MA
FAU - Thissen, M R
AU  - Thissen MR
FAU - King, C M
AU  - King CM
LA  - eng
GR  - CA23386/CA/NCI NIH HHS/United States
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - Ireland
TA  - Chem Biol Interact
JT  - Chemico-biological interactions
JID - 0227276
RN  - 0 (Amines)
RN  - 0 (Aminobiphenyl Compounds)
RN  - 0 (Fluorenes)
RN  - 0 (Hydroxylamines)
RN  - 63231-63-0 (RNA)
RN  - 85-32-5 (Guanosine Monophosphate)
SB  - IM
MH  - Amines/*metabolism
MH  - Aminobiphenyl Compounds/metabolism
MH  - Centrifugation, Density Gradient
MH  - Chromatography, High Pressure Liquid
MH  - Fluorenes/metabolism
MH  - Guanosine Monophosphate/metabolism
MH  - Hydroxylamines/*metabolism
MH  - RNA/*metabolism
EDAT- 1981/02/01 00:00
MHDA- 1981/02/01 00:01
CRDT- 1981/02/01 00:00
PHST- 1981/02/01 00:00 [pubmed]
PHST- 1981/02/01 00:01 [medline]
PHST- 1981/02/01 00:00 [entrez]
AID - 0009-2797(81)90095-8 [pii]
AID - 10.1016/0009-2797(81)90095-8 [doi]
PST - ppublish
SO  - Chem Biol Interact. 1981 Feb;34(1):109-24. doi: 10.1016/0009-2797(81)90095-8.