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。

The ability of rat liver microsomes from phenobarbitone pretreated animals to reduce the azo groups of amaranth, sunset yellow, congo red, trypan blue, chloramine sky blue FF and direct black 38 was measured in vitro. The dyes amaranth and sunset yellow acted as positive controls. Of the dyes derived from (the carcinogen) benzidine or its congeners, only direct black 38 was reduced to an appreciable extent; the rate of reduction was 10% of that for amaranth. The dyes were tested for mutagenicity in the Salmonella/microsome assay, the only active compound being direct black 38. Mutagenicity of this dye may be due in part to the mutagen 1,2,4-triaminobenzene. Mutagenic activity and azo-reduction of direct black 38 was independent of the presence of oxygen. Mammalian liver may play only a minor or negligible role in the azo-reduction of dyes derived from benzidine or its congeners.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。有充分的证据表明对动物具有致癌性。总体评估：2B组：该物质可能对人类具有致癌性。

No data are available in humans. Sufficient evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 2B: The agent is possibly carcinogenic to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌剂：台盼蓝

IARC Carcinogenic Agent:Trypan blue

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：2B组：可能对人类致癌

IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专论集：第8卷：（1975年）一些芳香偶氮化合物

IARC Monographs:Volume 8: (1975) Some Aromatic Azo Compounds

来源:International Agency for Research on Cancer (IARC)

毒理性

• 相互作用

L-谷氨酸对曲利本蓝的胚胎毒性和致畸作用的影响在Wistar白化大鼠中进行了研究。L-谷氨酸要么被添加到饮食中，从妊娠第2天到第20天，要么悬浮在芝麻油中并通过灌胃给药，从妊娠第6天到第10天。在妊娠第8天注射了致畸剂量的曲利本蓝，要么腹膜内注射（14 mg/kg母体体重）要么皮下注射（160 mg/kg）。在注射曲利本蓝后，大鼠消耗的谷氨酸量范围从600到1500 mg/鼠/天。在第20天，检查了胎儿。谷氨酸未能一致地保护大鼠胚胎免受曲利本蓝的致死和致畸作用。这些结果与在小鼠中获得的结果相反。发现单独给药芝麻油会导致胚胎死亡，但不会导致畸形。

The effect of L-glutamic acid on the embryolethal and teratogenic action of trypan blue was investigated in Wistar albino rats. L-glutamic acid was either incorporated into the diet, from gestation day 2 to day 20, or suspended in sesame oil and administered by gavage, from gestation day 6 to day 10. A teratogenic dose of trypan blue was injected at day 8 of pregnancy, either intraperitoneally (14 mg/kg maternal body weight) or subcutaneously (160 mg/kg). The amount of glutamic acid consumed, after the injection of trypan blue, ranged from 600 to 1,500 mg/rat/day. At day 20, the fetuses were examined. Glutamic acid failed consistently to protect the rat embryo against the lethal and teratogenic action of trypan blue. These results are in contrast to those obtained in mice. The administration of sesame oil alone was found to cause embryonic death but not malformations.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

锥虫蓝...在动物中被观察到可以从血液通过虹膜和脉络膜的血管壁，但不能通过视网膜血管壁。

Trypan blue ... was observed in animals to pass from bloodstream through walls of vessels of iris & choroid, but not through walls of retinal vessels.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在给小鼠或大鼠进行静脉或腹腔注射后，台盼蓝会迅速被吸收并在全身广泛分布。血清中的最大浓度在2小时内达到；它似乎与血清蛋白结合，并且通过尿液快速排泄以及被网状内皮系统摄取。

Following sc or ip injections into mice or rats, trypan blue is rapidly absorbed & widely distributed throughout the body. Max serum concentrations are ... within 2 hr; it appears bound to serum proteins with ... rapid excretion in urine & uptake by the reticulo-endothelial system.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

锥虫蓝从未到达大鼠胚胎，而是在母体网状内皮系统和胎盘中积累。

Trypan blue never reaches the rat embryo, but accumulates in maternal reticuloendothelial system and in the placenta.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

使用带有环状标记的放射性锥虫蓝进行的实验没有提供任何证据表明有（14）C的胚胎吸收。在绒毛膜尿囊胎盘形成后未出现致畸作用，这也表明卵黄囊功能在病理发生中是重要的。这种染料可以在内脏卵黄囊的细胞中可视化。

Experiments with ring-labelled radioactive trypan blue did not give evidence of any embryonic incorporation of the (14)C. The absence of teratogenic action after the initiation of chorio-allantoic placentation also indicated that yolk sac function was important in pathogenesis. The dye can be visualized in the cells of the visceral yolk sac.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  T
• 安全说明：
  S45,S53
• 危险类别码：
  R45
• WGK Germany：
  3
• 海关编码：
  32041400
• 危险品运输编号：
  2811
• RTECS号：
  QJ6475000
• 危险标志：
  GHS08
• 危险性描述：
  H350
• 危险性防范说明：
  P201,P308 + P313
• 包装等级：
  III
• 危险类别：
  6.1

制备方法与用途

台盼蓝简介

台盼蓝，化学名为3,3'-{[3,3'-二甲基-(1,1'-二苯基)-4,4'-二基]双(偶氮)}-双(5-氨基-4-羟基-2,7-萘二磺酸)四钠盐，是一种细胞活性染料。它常用于检测细胞膜的完整性。正常且活的细胞能够排斥台盼蓝，使其不能进入胞内；而丧失活性或细胞膜不完整的细胞，则会因通透性增加被台盼蓝染成蓝色。通常认为当细胞膜完整性丧失时，即可判断该细胞已经死亡。

应用示例

借助台盼蓝染色可以非常简便、快速地区分活细胞和死细胞。它是组织和细胞培养中最常用的死细胞鉴定染色方法之一。需要注意的是，凋亡小体也有拒染现象。

化学性质

台盼蓝是一种蓝灰色的粉状物，溶于水呈蓝色，微溶于溶纤纱，不溶于其他有机溶剂。遇浓硫酸为暗绿光蓝色，稀释后呈红光蓝色；遇浓硝酸则呈棕光灰色溶液。其水溶液遇10%硫酸为红色，遇氢氧化钠则呈现红光紫色。

用途

台盼蓝主要用于棉、麻、粘胶等纤维素纤维的染色，也可用于蚕丝、锦纶、粘/棉混纺的染色，还可应用于纸张、皮革及生物染色。

生产方法

台盼蓝由3,3'-二甲基联苯胺用亚硝酸钠与盐酸重氮化后，在碱性介质中与H酸进行偶合。随后经盐析、过滤及干燥而得。其生产配方如下：

• 3，3'-二甲基联苯胺（100%）：100克/吨
• H酸（100%）：345克/吨
• 亚硝酸钠（100%）：72克/吨
• 纯碱：380克/吨
• 盐酸（31%）：490毫升/吨
• 精盐：2700克/吨
• 元明粉：33克/吨