台盼蓝

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 台盼蓝
• 中文别名: 曲利苯兰；直接蓝14；曲利苯蓝；锥虫兰；锥虫蓝；曲利本蓝；直接蓝3B；3,3"-{[3,3"-二甲基-(1,1"-二苯基)-4,4"-二基]双(偶氮)}-双(5-氨基-4-；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；台盼兰
• 英文名称: Diphenyl Blue
• 英文别名: tetrasodium;5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate
• 化学式: C34H24N6Na4O14S4
• 分子量: 960.8
• InChiKey: GLNADSQYFUSGOU-UHFFFAOYSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -6.68
• 重原子数：
  62
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  404
• 氢给体数：
  4
• 氢受体数：
  20

ADMET

代谢

/锥虫蓝/ 在大鼠肝脏酶的作用下还原为邻联甲苯胺和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

六种偶氮染料，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

代谢实验在大鼠身上进行，大鼠服用基于二甲苯、二甲氧基或二氯联苯胺的9种偶氮染料，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。服用2毫克的剂量，并在给药后至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个实例中的7个，48小时后在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或更少。所有9种染料在大鼠体内都转化为了可以测量的基于联苯胺同类物的代谢物水平。

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

被苯巴比妥预处理的大鼠肝微粒体还原苋菜红、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小的或可忽略的作用。

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著：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

• 副作用

国际癌症研究机构致癌物-第3类：化学品无法被国际癌症研究机构分类。

IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

吸收、分配和排泄

锥虫蓝...在动物中被观察到从血液流通过虹膜和脉络膜血管壁，但并未通过视网膜血管壁。

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。血清中的最高浓度在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台盼蓝进行的实验没有显示出有任何（14）C的胚胎吸收证据。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看到。

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)

吸收、分配和排泄

锥虫蓝...在动物中被观察到从血液流通过虹膜和脉络膜血管壁，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)

表征谱图