2-Amino-5-phenylpyridine
(Synonyms: 2-氨基-5-苯基吡啶) 目录号 : GC60470
2-Amino-5-phenylpyridine是一种诱变的杂环芳族胺，是通过蛋白质中的苯丙氨酸热解形成的。2-Amino-5-phenylpyridine存在于烤沙丁鱼等食品中，并且具有潜在的致癌性。
Cas No.:33421-40-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Amino-5-phenylpyridine is a mutagenic heterocyclic aromatic amine that is formed by pyrolysis of phenylalanine in proteins. 2-Amino-5-phenylpyridine is in broiled sardines and is considered as potentially carcinogenic[1][2].
On the other hand, the chemical structure of 5-phenyl-2-pyridinamine (PPA) shows a great resemblance to the aminobiphenyls, another well known class of carcinogenic aromatic amines[2].
[1]. Dooley KL, et al. Comparative carcinogenicity of the food pyrolysis product, 2-amino-5-phenylpyridine, and the known human carcinogen, 4-aminobiphenyl, in the neonatal B6C3F1 mouse. Cancer Lett. 1988 Jul;41(1):99-103. [2]. Stavenuiter JF, et al. Syntheses of 5-phenyl-2-pyridinamine, a possibly carcinogenic pyrolysis product of phenylalanine, and some of its putative metabolites. Carcinogenesis. 1985 Jan;6(1):13-9.
| Cas No. | 33421-40-8 | SDF | |
| 别名 | 2-氨基-5-苯基吡啶 | ||
| Canonical SMILES | NC1=NC=C(C2=CC=CC=C2)C=C1 | ||
| 分子式 | C11H10N2 | 分子量 | 170.21 |
| 溶解度 | 储存条件 | 4°C, protect from light | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.8751 mL | 29.3755 mL | 58.751 mL |
| 5 mM | 1.175 mL | 5.8751 mL | 11.7502 mL |
| 10 mM | 0.5875 mL | 2.9375 mL | 5.8751 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Chemical properties of the ultimate metabolites of 2-Amino-5-phenylpyridine (PHE-P-1) and its ortho-methyl derivative
Chem Biol Interact 1995 Mar 30;95(1-2):29-40.PMID:7697752DOI:10.1016/0009-2797(94)03342-0.
The reactivity of the N-acetoxy metabolite of 2-Amino-5-phenylpyridine (Phe-P-1), a pyrolysis product of phenylalanine, towards 2'-deoxyguanosine (dG), 2'-deoxyguanosine-3'-monophosphate (dGMP) and DNA was studied and compared with that of the ortho-methyl derivative. Reaction of 2-acetoxyamino-5-phenylpyridine (N-OAc-APP) with dG resulted in substitution at the 8-position of this nucleoside by the ortho carbon of the amine. The major reaction, however, was acetylation of dG. In contrast, 2-acetoxyamino-3-methyl-5-phenyl-pyridine (N-OAc-MeAPP) mainly attacked the 8-position of dG by the exocyclic nitrogen and hardly any acetylation of the nucleoside occurred. The adducts were chromatographically isolated and characterized by their mass and NMR spectra. Upon reaction of N-acetoxy compounds with DNA and dGMP, formation of the same adducts was observed, besides the formation of minor amounts of unidentified compounds, as was established by 32P-postlabelling analysis. The amount of DNA-bound amine, formed by the interaction of N-OAc-APP with DNA, was approximately 15 times smaller than that observed after the reaction with the corresponding ortho-methyl derivative under the same conditions.
Asymmetric tetranuclear nickel chains with unidirectionally ordered 2-(α-(5-phenyl)pyridylamino)-1,8-naphthyridine ligands
Dalton Trans 2016 Nov 1;45(43):17281-17289.PMID:27722491DOI:10.1039/c6dt03223k.
The new ligand, 2-(α-(5-phenyl)pyridylamino)-1,8-naphthyridine (Hphpyany), was synthesised by a palladium(0)-catalysed reaction of 2-chloro-1,8-naphthyridine with 2-Amino-5-phenylpyridine in the presence of potassium tert-butoxide. Linear tetranickel metal complexes, [Ni4(phpyany)4Cl2](CF3SO3) 1, [Ni4(phpyany)4Cl2](BF4)22, [Ni4(phpyany)4(NCS)2](ClO4) 3 and [Ni4(phpyany)4(NCS)2](CF3SO3)24 were prepared and crystallographically characterised. Complexes 1-4 demonstrate that, for the first time, four asymmetric ligands align unidirectionally and thus configure (4,0)-form tetranickel strings, specifically, with the phenyl groups of the four phpyany- pointing to one side of the Ni4 chain and naphthyridyl to the other. The remarkably short Ni-Ni distances (ca. 2.33 Å) for 1 and 3 indicate partial metal-metal bonding, which can be viewed as both complexes containing one mixed-valence Ni23+ unit. The measurements of the magnetic susceptibility reveal that Ni47+ complexes 1 and 3 exhibit antiferromagnetic interactions (J = -42 cm-1 for 1 and -46 cm-1 for 3) between the terminal Ni2+ ion and the Ni23+ unit, while Ni48+ complexes 2 and 4 exhibit antiferromagnetic interactions (J = -33 cm-1 for 2 and -35 cm-1 for 4) between the two terminal Ni2+ ions. The results of the cyclic voltammetry indicate the presence of two reversible redox couples at E1/2(1) = 0.12 V, E1/2(2) = -0.65 V for 1, and at E1/2(1) = 0.12 V, E1/2(2) = -0.72 V for 3. The products of the first oxidation for 1 and 3 are the oxidised species 2 and 4, respectively. The values of single-molecule resistance (15.4 (±3.46) MΩ for 3 and 16.2 (±5.04) MΩ for 4) were determined by STM-based break-junction methods. The results represent the first conductance measurements of linear tetranickel chains.
Comparative carcinogenicity of the food pyrolysis product, 2-Amino-5-phenylpyridine, and the known human carcinogen, 4-aminobiphenyl, in the neonatal B6C3F1 mouse
Cancer Lett 1988 Jul;41(1):99-103.PMID:3390806DOI:10.1016/0304-3835(88)90060-2.
2-Amino-5-phenylpyridine (2-APP) is a mutagenic heterocyclic aromatic amine that is formed by pyrolysis of phenylalanine in proteins. Since this mutagen is structurally similar to the multipotent carcinogen, 4-aminobiphenyl (4-ABP), we compared their relative tumorigenic activity in the neonatal male B6C3F1 mouse. After determinations of the maximum tolerated dose (MTD), both aromatic amines were administered i.p. at 2 dose levels (MTD and MTD/2) on days 1, 8, 15 and 22 after birth. Groups were killed at 9 and 12 months and examined for histopathologic changes. No treatment-related neoplastic lesions were observed for 2-APP. In contrast, 4-ABP was strongly carcinogenic and induced a high incidence of multiple hepatocellular adenomas and carcinomas.
Binding of mutagens by fractions of the cell wall skeleton of lactic acid bacteria on mutagens
J Dairy Sci 1991 May;74(5):1477-81.PMID:1908865DOI:10.3168/jds.S0022-0302(91)78306-9.
The binding effect of cells and cell fractions, cell wall skeleton, cytoplasm, whole cells, and cell wall skeleton treated by lysozyme and alpha-amylase at 37 degrees C for 5 h, on Trp-P-1 (3-amino-1,4-dimethyl-[5H]pyrido [4,3-b]indole) and Trp-P-2 (3-amino-1-methyl-[5H]-pyrido[4,3-b]indole) were investigated. The cell and cell wall skeleton of Streptococcus cremoris Z-25 had greater binding activity, but cytoplasm and extract of cell wall skeleton did not bind Trp-P-1 and Trp-P-2. When the cells or cell wall skeleton were treated with lysozyme and alpha-amylase, unbound Trp-P-1 and Trp-P-2 concentrations were greater than that of the untreated control. It is possible that cell walls may be involved in the binding of mutagenic pyrolyzates to lactic acid bacteria. The cell wall skeleton of S. cremoris Z-25, Lactobacillus acidophilus IFO 13951, and Bifidobacterium bifidum IFO 14252 showed binding of Trp-P-1, 2-amino-6-methyldipyrido(1,2-a:3',2'- d)imidazole, 2-Amino-5-phenylpyridine, 2-amino-3-methylimidazo(4,5-f)quinoline, 2-amino-3,4-dimethylimidazo(4,5-f) quinoline, and 2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline. The cell wall skeleton of S. cremoris group and Streptococcus lactis also showed the binding activity with A N-nitrosodimethylamine. The binding of Trp-P-1 to cell walls was very high, and the binding of mutagenic pyrolyzates was variable with different bacterial species. The peptidoglycan complex and polysaccharides liberated from cell wall skeleton of S. cremoris Z-25 showed strong binding of Trp-P-2. Peptidoglycans has a binding effect of about 19.86 micrograms/mg; polysaccharides had a binding effect of 14 micrograms/mg.
Synthesis of heterocyclic N-acetoxyarylamines and their reactivity with DNA
Carcinogenesis 1989 Oct;10(10):1957-60.PMID:2791211DOI:10.1093/carcin/10.10.1957.
2-Acetoxyamino-5-phenylpyridine and 2-acetoxyamino-3-methyl-5-phenylpyridine, being proposed ultimate carcinogens of the heterocyclic aromatic amines 2-Amino-5-phenylpyridine (APP) and 2-amino-3-methyl-5-phenylpyridine (AMPP), respectively, were synthesized, crystallized and characterized. Using the 32P-postlabelling technique, we show that the total amount of adducts found in DNA after reaction with these N-acetoxyarylamines is at least 30- and 450-fold higher than in DNA reacted with equimolar amounts of the proposed proximate carcinogens 2-hydroxyamino-5-phenylpyridine and 2-hydroxyamino-3-methyl-5-phenylpyridine, respectively. These results support a postulated activation mechanism, in which N-acetoxyarylamines are the ultimate reactive species responsible for DNA modification by carcinogenic aromatic amines in vivo. The possibility to obtain the reactive 0-acetyl derivatives of APP and AMPP in crystalline form makes them unique model compounds for studies on the interaction of ultimate carcinogens of aromatic amines with DNA.