THE ISOLATION AND IDENTIFICATION OF A NEW MUTAGEN FROM FRIED GROUND-BEEF - 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE(PHIP)
THE ISOLATION AND IDENTIFICATION OF A NEW MUTAGEN FROM FRIED GROUND-BEEF - 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE(PHIP)
复制标题
DOI：
10.1093/carcin/7.7.1081
复制
发表时间：
1986-07-01
期刊：
影响因子：
4.7
通讯作者：
HATCH, FT
中科院分区：
文献类型：
--
作者：
FELTON, JS;KNIZE, MG;HATCH, FT
从300度油炸的碎牛肉中分离出一种新的致突变化合物。每侧5.5分钟。采用酸液萃取、XAD-2吸附-溶剂洗脱、一系列制备和分析h.p.l.c.纯化步骤，并用艾姆斯/沙门氏菌测定监测。这项研究揭示了芳香胺氨基咪唑氮杂芳烃类的一个新致突变剂成员，其分子量为。w为224，通过高分辨率质谱法测定的分子式为C13 H12 N4。N.m.r.光谱分析支持新诱变剂的结构2-氨基-1-甲基-6-苯基-咪唑并[4，5-B]吡啶（PhIP）。将PhIP的1-甲基和3-甲基合成异构体与纯化的诱变剂进行比较。两种异构体的质谱与纯化化合物相同，但仅1-甲基异构体显示出相似的u. v.和n.m.r.。谱两种合成异构体可通过高效液相色谱法分离。并且牛肉衍生组分与1-甲基-PhIP异构体共洗脱。PhIP在1950个回复突变体/μ g的艾姆斯/沙门氏菌测定中具有比活性。虽然它不像从油炸牛肉中分离的其它化合物（例如MeIQx，58000回复突变体/μ g）那样具有致突变性，但它是油炸牛肉中质量最丰富的致突变化合物。PhIP的含量约为15 p.p.b.。生牛肉的致突变性占生牛肉原重的75%（占遗传毒性物质质量的75%），占油炸牛肉总致突变性的18%。
A new mutagenic compound has been isolated from ground beef which was fried at 300.degree. C for 5.5 min on each side. The new mutagen was purified using an aqueous acid extraction, XAD-2 adsorption-solvent elution, a series of preparative and analytical h.p.l.c. purification steps, and monitored with the Ames/Salmonella assay. This study reveals a new mutagen member of the amino-imidazoazaarene class of aromatic amines, having a mol. w of 224, and a formula of C13H12N4 as determined by high-resolution mass spectrometry. N.m.r. spectrometry supports the structure, 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine (PhIP), for the new mutagen. The 1-methyl and 3-methyl synthesized isomers of PhIP were compared to the purified mutagen. The two isomers had identical mass spectra to the purified compound, but only the 1-methyl isomer showed similar u.v. and n.m.r. spectra. The two synthetic isomers were separable by h.p.l.c. and the beef derived component co-eluted with the 1-methyl-PhIP isomer. PhIP has a specific activity in the Ames/Salmonella assay of 1950 revertants/.mu.g. Although it is not as mutagenic as other compounds isolated from fried beef (e.g. MeIQx, 58000 revertants/.mu.g) it is the most abundant mutagenic compound by mass in fried beef. PhIP is present at approximately 15 p.p.b. of the original weight of uncooked beef (accounting for 75% of the mass of genotoxic material) and contributes 18% of the total mutagenicity of the fried beef.