Diamineblue | 72-57-1

• 物质功能分类: 有机原料 - 氨基化合物 - 磺酸类氨基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Diamineblue
• 英文别名: sodium;5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonic acid
• CAS: 72-57-1
• 化学式: C34H28N6NaO14S4+
• 分子量: 895.9
• InChiKey: YNEQSKYLHXEFTL-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (lit.)
• 密度：
  1.007 g/mL at 20 °C
• 溶解度：
  H2O：可溶，10mg/mL
• 物理描述：
  Trypan blue is a bluish-gray to dark blue powder. (NTP, 1992)
• 颜色/状态：
  Bluish-grey powder
• 分解：
  When heated to decomposition it emits very toxic fumes of /nitric oxides/, /sodium oxide/, and /sulfur oxides/.

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  59
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  393
• 氢给体数：
  8
• 氢受体数：
  20

ADMET

代谢

锥虫蓝在大鼠肝酶的作用下被还原成邻联甲苯胺和2,8-二氨基-1-萘酚-3,6-二磺酸。

/Trypan blue/ is reduced in vitro by a rat liver enzyme to ortho-tolidine & 2,8-diamino-1-naphthol-3,6-disulfonic acid.

来源:Hazardous Substances Data Bank (HSDB)

代谢

六个偶氮染料，包括台盼蓝，被还原、N-乙酰化和N-结合。在大鼠尿液中未检测到N,N'-二乙酰化代谢物。

Six azo dyes, including trypan blue, were reduced, N-acetylated, and N-conjugated. No N,N'-diacetylated metabolites were detected in rat urine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

基于β-二酮偶联组分的偶氮染料主要存在为互变异构的腙类。已经制备了一系列基于联苯胺和联苯胺同系物的腙染料……腙染料对由FMN补充的大鼠肝脏线粒体后上清液（S-9）的酶促还原具有抗性；在相同条件下，诸如台盼蓝的偶氮染料被迅速还原。

Azo dyes based on beta-diketone coupling components exist preferentially as the tautomeric hydrazones. A series of hydrazone dyes based on benzidine and benzidine congeners ... was prepared. The hydrazone dyes were resistant to enzymatic reduction by FMN supplemented hamster liver post-mitochondrial supernatant (S-9); under identical conditions, azo dyes such as trypan blue were rapidly reduced.

来源:Hazardous Substances Data Bank (HSDB)

代谢

对大鼠进行9种偶氮染料的代谢实验，这些染料基于二甲基、二甲氧基或二氯偶氮苯，以确定是否在尿液中排出了自由的氨基同类物、它们的单乙酰或二乙酰代谢物，或者是可被碱性水解的结合物。以2毫克的剂量给药，并在给药后长达96小时的时间间隔内收集尿液样本。代谢物的高峰水平在给药后0-12小时或12-24小时内排出，在9个实例中有7个在48小时后尿液中没有检测到代谢物。所有代谢物的最小可检测水平为12 ppb或更低。在大鼠体内，所有9种染料都转化为了可测量的基于偶氮苯同类物的代谢物。

Metabolism experiments were conducted with rats dosed with 9 azo dyes based on dimethyl-, dimethoxy-, or dichlorobenzidine to determine whether the free amine congeners, their monoacetyl or diacetyl metabolites, or alkaline hydrolyzable conjugates were excreted in the urine. 2-mg doses were administered and urine samples were collected at intervals up to 96 hr. Peak levels of metabolites were excreted either 0-12 or 12-24 hr after administration and, in 7 of 9 instances, no metabolites persisted in the urine after 48 hr. Minimum detectable levels of all metabolites were 12 ppb or less. All 9 dyes were converted to measurable levels of their benzidine-congener-based metabolites in rats.

来源:Hazardous Substances Data Bank (HSDB)

代谢

使用对苯巴比妥预处理的大鼠肝脏微粒体还原苋菜红、日落黄、刚果红、台盼蓝、氯胺天青FF和直接黑38偶氮基团的能力在体外进行了测量。苋菜红和日落黄作为阳性对照。在源自（致癌物）联苯胺或其同类物的染料中，只有直接黑38被显著还原；其还原速率是苋菜红的10%。在鼠伤寒沙门氏菌/微粒体试验中检测了这些染料的致突变性，唯一活跃的化合物是直接黑38。这种染料的致突变性可能部分归因于致突变剂1,2,4-三氨基苯。直接黑38的致突变活性和偶氮还原与氧气的存在无关。哺乳动物肝脏在还原源自联苯胺或其同类物的染料的偶氮基团中可能只起微不足道或可忽略的作用。