Disodium;2-sulfo-4-[4,5,6,7-tetrabromo-1-(4-oxido-3-sulfophenyl)-3-oxo-2-benzofuran-1-yl]phenolate | 71-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: Disodium;2-sulfo-4-[4,5,6,7-tetrabromo-1-(4-oxido-3-sulfophenyl)-3-oxo-2-benzofuran-1-yl]phenolate
• 英文别名: disodium;2-sulfo-4-[4,5,6,7-tetrabromo-1-(4-oxido-3-sulfophenyl)-3-oxo-2-benzofuran-1-yl]phenolate
• CAS: 71-67-0
• 化学式: C20H8Br4Na2O10S2
• 分子量: 838.0
• InChiKey: GHAFORRTMVIXHS-UHFFFAOYSA-L

物化性质

• 溶解度：
  DMF：5 mg/ml； DMSO：5 mg/ml；乙醇：微溶； PBS（pH 7.2）：1 mg/ml
• 颜色/状态：
  CRYSTALS
• 气味：
  ODORLESS
• 味道：
  BITTER

计算性质

• 辛醇/水分配系数(LogP)：
  -1.57
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  198
• 氢给体数：
  2
• 氢受体数：
  10

ADMET

代谢

S-芳基转移酶被认为参与了对磺溴酚的代谢...

S-ARYLTRANSFERASE IS THOUGHT TO BE INVOLVED IN METABOLISM OF SULFOBROMOPHTHALEIN...

来源:Hazardous Substances Data Bank (HSDB)

代谢

它以BSP-谷胱甘肽和其他氨基酸酰结合物的形式被大鼠排出在胆汁中，这些结合物是通过BSP与谷胱甘肽的缩合形成的，可能没有消除任何溴原子。

IT IS EXCRETED IN BILE OF RATS AS BSP-GLUTATHIONE & OTHER AMINOACYL CONJUGATES, FORMED BY CONDENSATION OF BSP WITH GLUTATHIONE, PROBABLY WITHOUT ELIMINATION OF ANY OF BROMINE ATOMS.

来源:Hazardous Substances Data Bank (HSDB)

代谢

磺溴酚酞在狗体内代谢为以下物质：S-(3,3-双(4-羟基-3-磺基苯基)三溴酞酰)谷胱甘肽；Javitt NB等，临床研究杂志，39，1570 (1960)。在肝脏中为磺溴酚酞-β-D-葡萄糖苷酸；Hirayama C等，最新医学，17，2520 (1962)。

SULFOBROMOPHTHALEIN /WAS METABOLIZED TO THE FOLLOWING/ S-(3,3-BIS(4-HYDROXY-3-SULFOPHENYL) TRIBROMOPHTHALIDYL)GLUTATHIONE IN DOG; JAVITT NB, ET AL, J CLIN INVEST, 39, 1570 (1960). SULFOBROMOPHTHALEIN-BETA-D-GLUCURONIDE IN LIVER; HIRAYAMA C, ET AL, SAISHIN IGAKU, 17, 2520 (1962).

来源:Hazardous Substances Data Bank (HSDB)

代谢

S-芳基转移酶被认为参与磺溴酚的代谢...

S-ARYLTRANSFERASE IS THOUGHT TO BE INVOLVED IN METABOLISM OF SULFOBROMOPHTHALEIN...

来源:Hazardous Substances Data Bank (HSDB)

代谢

它以BSP-谷胱甘肽和其他氨基酸酰结合物的形式被大鼠排泄在胆汁中，这些结合物是通过BSP与谷胱甘肽的缩合形成的，可能没有排除任何溴原子。

IT IS EXCRETED IN BILE OF RATS AS BSP-GLUTATHIONE & OTHER AMINOACYL CONJUGATES, FORMED BY CONDENSATION OF BSP WITH GLUTATHIONE, PROBABLY WITHOUT ELIMINATION OF ANY OF BROMINE ATOMS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

去氢胆酸、氯四环素、磺胺类药物、新生霉素和单胺氧化酶抑制剂也可能增加磺溴酚钠的潴留，尽管在实际接受氯四环素、磺胺类药物或新生霉素的患者中应考虑实际肝脏损伤的可能性。

DEHYDROCHOLIC ACID, CHLORTETRACYCLINE, SULFONAMIDES, NOVOBIOCIN, & MONOAMINE OXIDASE INHIBITORS MAY ALSO INCR SULFOBROMOPHTHALEIN RETENTION, ALTHOUGH POSSIBILITY OF ACTUAL LIVER DAMAGE SHOULD BE CONSIDERED IN PT RECEIVING CHLORTETRACYCLINE, SULFONAMIDES, OR NOVOBIOCIN.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

同时给予吲哚菁绿...可能会导致肝排泄功能受损...

SIMULTANEOUS ADMIN OF INDOCYANINE GREEN...MAY RESULT IN IMPAIRMENT OF HEPATIC EXCRETION...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

胆囊造影剂...据报道会与磺溴酚竞争性地干扰其清除与排泄...乙氧氮杂环己烷、非那吡啶、酚酞和酚磺酞（PSP）可能会通过干扰比色测量，导致磺溴酚的排泄量看似减少...

CHOLECYSTOGRAPHIC AGENTS...REPORTED TO COMPETITIVELY INTERFERE WITH SULFOBROMOPHTHALEIN CLEARANCE & EXCRETION... ETHOXAZENE, PHENAZOPYRIDINE, PHENOLPHTHALEIN, & PHENOLSULFONPHTHALEIN (PSP) MAY PRODUCE APPARENT DECR EXCRETION OF SULFOBROMOPHTHALEIN BY INTERFERING WITH COLORIMETRIC MEASUREMENT...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

胆汁排泄速率和磺溴酚血浆消失速率...在用苯巴比妥和其他微粒体酶诱导剂预处理的大鼠中显示出增加，增加的排泄与胆汁流量增加密切相关。

BILIARY EXCRETION RATE & RATE OF PLASMA DISAPPEARANCE OF SULFOBROMOPHTHALEIN... WERE SHOWN...TO INCR AFTER PRE-TREATMENT WITH PHENOBARBITAL & OTHER MICROSOMAL-ENZYME INDUCERS IN RATS, & INCR EXCRETION CORRELATED WELL WITH INCR IN BILE FLOW RATES.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

如果发生外渗，应抬高患肢并使用冷敷或冰袋，直到急性疼痛减轻。皮下注射1%的水合普鲁卡因盐酸可以止痛并减少血管痉挛的可能性。

/IF EXTRAVASATION OCCURS/ EXTREMITY SHOULD BE ELEVATED & COLD COMPRESSES OR ICE PACKS APPLIED UNTIL ACUTE PAIN SUBSIDES. SC INJECTION OF 1% AQ PROCAINE HYDROCHLORIDE WILL STOP PAIN & REDUCE LIKELIHOOD OF VASOSPASM.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当肝功能严重受损时，多达10-25%...可能会通过尿液排出。正常情况下...不到2%的剂量会以这种方式排出，并且可以忽略磺溴酚的肝外清除。

WHEN HEPATIC FUNCTION IS SEVERELY IMPAIRED, UP TO 10-25%...MAY BE EXCRETED IN URINE. NORMALLY...LESS THAN 2% OF DOSE IS EXCRETED IN THIS WAY, & EXTRAHEPATIC REMOVAL OF SULFOBROMOPTHALEIN CAN BE DISREGARDED.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

正常代谢和胆溴酚磺酞排泄取决于肝血流量、肝细胞摄取和浓缩染料的能力以及胆汁排泄的摄入。

NORMAL METABOLISM & EXCRETION OF SULFOBROMOPHTHALEIN DEPEND ON HEPATIC BLOOD FLOW, ABILITY OF LIVER CELLS TO TAKE UP & CONCN THE DYE, & INTAKE BILIARY EXCRETION.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在肝脏通过谷胱甘肽结合代谢，自由态和结合态都排入胆汁中。染料不会经历肠肝循环，并且主要通过粪便排出。染料的排泄通常在24小时内完成。

...METABOLIZED IN LIVER BY CONJUGATION WITH GLUTATHIONE, & BOTH FREE & CONJUGATED...ARE EXCRETED INTO BILE. ... DYE DOES NOT UNDERGO ENTEROHEPATIC CIRCULATION...& IS EXCRETED PRIMARILY IN FECES. ... EXCRETION OF DYE IS USUALLY COMPLETE WITHIN 24 HR.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

静脉给药后...几乎完全与血液中的血浆蛋白结合，主要是白蛋白和α1-脂蛋白。染料被肝脏实质细胞迅速吸收并短暂储存。...少量...可能被骨骼肌吸收，但肝外组织的吸收量最小。...不穿过胎盘。

FOLLOWING IV ADMIN...ALMOST COMPLETELY BOUND TO PLASMA PROTEINS IN BLOOD, MAINLY ALBUMIN & ALPHA1 LIPOPROTEINS. DYE IS RAPIDLY TAKEN UP & BRIEFLY STORED BY HEPATIC PARENCHYMAL CELLS. ... SMALL AMT...MAY BE TAKEN UP BY SKELETAL MUSCLE, BUT EXTRA-HEPATIC TISSUE UPTAKE IS MINIMAL. ...DOES NOT CROSS PLACENTA.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当肝功能严重受损时，多达10-25%...可能会通过尿液排出。正常情况下...剂量中少于2%以这种方式排出，可以忽略磺溴酚的肝外清除。

WHEN HEPATIC FUNCTION IS SEVERELY IMPAIRED, UP TO 10-25%...MAY BE EXCRETED IN URINE. NORMALLY...LESS THAN 2% OF DOSE IS EXCRETED IN THIS WAY, & EXTRAHEPATIC REMOVAL OF SULFOBROMOPTHALEIN CAN BE DISREGARDED.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R42/43
• WGK Germany：
  3
• RTECS号：
  SM8395000

制备方法与用途

生物活性

Sulfobromophthalein（Bromosulfophthalein） disodium盐是一种有机阴离子染料，用于研究动物组织中表达的各种蛋白质，并参与药物和代谢物的运输。

体外研究

1925年，Sulfobromophthalein disodium盐作为一种临床工具被引入，旨在评估肝功能。

• Sulfobromophthalein（BSP） 是一种pH指示染料，具有快速(17)、依赖质子的喹唑啉–酚酮异构体(pK = 8.5)特性。
• 溴化硫酚红常被用作有机阴离子转运多肽1B1 (OATP1B1)、OATP1B3、OATP1A2 和 OATP2B1，以及多重耐药蛋白2 (MDR2) 的底物和抑制剂。

生产方法

将四溴邻苯二甲酸酐与苯酚缩合后再进行磺化，制得Sulfobromophthalein disodium盐。

反应信息

• 作为反应物：
  描述：

  methyl (3S)-<3-(2)H>-2-O-benzoyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside 、 Disodium;2-sulfo-4-[4,5,6,7-tetrabromo-1-(4-oxido-3-sulfophenyl)-3-oxo-2-benzofuran-1-yl]phenolate 以57%的产率得到
  参考文献：
  名称：

  RUSSELL, RAYMOND N.;LIU, HUNG-WEN, TETRAHEDRON LETT., 30,(1989) N2, C. 5729-5732

  摘要：

  DOI：

文献信息

• Reagents and methods for direct labeling of nucleotides
  申请人：Naleway John J.

  公开号：US20130150254A1

  公开（公告）日：2013-06-13

  The present invention provides systems and methods for production of activatable diazo-derivatives for use in labeling nucleotides. Labeling nucleotides is accomplished by contacting a stable hydrazide derivative of a detectable moiety with an activating polymer reagent which is used to directly label the nucleotide sample. Labeling occurs on the phosphate backbone of the nucleotide which does not perturb hybridization of the labeled nucleotide with its anti-sense strand. Since the method involves direct labeling, all types of nucleotides can be labeled without prior amplification or alteration.

  本发明提供了用于生产可激活重氮衍生物以用于标记核苷酸的系统和方法。通过将可检测基团的稳定的肼酰肼衍生物与用于直接标记核苷酸样品的活化聚合物试剂接触来完成核苷酸的标记。标记发生在核苷酸的磷酸骨架上，不会干扰标记核苷酸与其反义链的杂交。由于该方法涉及直接标记，所有类型的核苷酸都可以在不经过扩增或改变的情况下进行标记。
• [EN] ORGANIC ANION TRANSPORTING PEPTIDE-BASED CANCER IMAGING AND THERAPY<br/>[FR] IMAGERIE ET THÉRAPIE CANCÉREUSE BASÉES SUR DES PEPTIDES TRANSPORTANT DES ANIONS ORGANIQUES
  申请人：DA ZEN GROUP LLC

  公开号：WO2016106324A1

  公开（公告）日：2016-06-30

  A dye-drug conjugate for preventing, treating, or imaging cancer having the formular: (I) [Formula (I)] wherein R1 and R2 are independently selected from the group consisting of -H, alkyl, alkyl- sulphonate, alkylcarboxylic, alkylamino, aryl,-SO3H, -PO3H, -OH, -NH2, and - halogen; wherein Υ1 and Y2 is independently selected from the group consisting of alkyl, aryl, aralkyl, alkylsulphonate, alkylcarboxylic, alkylamino, ω-alkylaminium, ω-alkynyl, PEGyl, PEGylcarboxylate, ω-PEGylaminium, ω-acyl-NH, ω- acyl-lysinyl-, ω -acyl-triazole, ω- PEGylcarboxyl-ΝΗ-, ω-PEGylcarboxyl-lysinyl, and ω- PEGylcarboxyl-triazole; wherein X is selected from the group consisting of a hydrogen, halogen, CN, Me, NH2, SH and OH; and R3 and R4 are independently a hydrogen, a therapeutic agent, or an imaging moiety, wherein the therapeutic agent is selected from the group consisting of a platinum-based therapeutic agent, a small molecule therapeutic agent, a peptide, a protein, a polymer, an siRNA, a microRNA, and a nanoparticle, wherein the imaging is a radio- isotope selected from the group consisting of F18, I-125, I-124 I-123, I-131, and small molecule labeled with any of these isotopes, or wherein the imaging moiety is a chelator- complexed radioactive isotope, wherein the radioactive isotope is selected from the group consisting of Cu-64, In-1 1 1, Tc-99m, Ga-68, Lu-177, Zo-89, Th-227 and Gd-157.

  一种用于预防、治疗或成像癌症的染料-药物结合物，其化学式为：(I) [化学式(I)]，其中R1和R2分别从-H、烷基、烷基磺酸酯、烷基羧酸、烷基氨基、芳基、-SO3H、-PO3H、-OH、-NH2和卤素组成的群体中独立选择；其中Υ1和Y2分别从烷基、芳基、芳基烷基、烷基磺酸酯、烷基羧酸、烷基氨基、ω-烷基胺盐、ω-炔基、PEG基、PEG基羧酸酯、ω-PEG基胺盐、ω-酰基-NH、ω-酰基-赖氨酸、ω-酰基-三唑、ω-PEG基羧酸-ΝΗ-、ω-PEG基羧酸-赖氨酸和ω-PEG基羧酸-三唑组成的群体中独立选择；其中X从氢、卤素、CN、Me、NH2、SH和OH组成的群体中选择；R3和R4分别为氢、治疗剂或成像基团，其中治疗剂从基于铂的治疗剂、小分子治疗剂、肽、蛋白质、聚合物、siRNA、microRNA和纳米颗粒组成的群体中选择，成像为从F18、I-125、I-124、I-123、I-131和标记有这些同位素中任何一种的小分子组成的群体中选择的放射同位素，或成像基团为螯合物-络合放射性同位素，其中放射性同位素从Cu-64、In-111、Tc-99m、Ga-68、Lu-177、Zr-89、Th-227和Gd-157组成的群体中选择。
• DRUG WITH HEPATOPROTECTIVE ACTIVITY
  申请人：Tets Viktor Veniaminovich

  公开号：US20180338975A1

  公开（公告）日：2018-11-29

  The invention relates to pharmacology and can be used for treating liver diseases of various etiologies, inter alia, in combination with other preparations. Claimed is a drug with hepatoprotective activity comprised of 3-(4-bromophenyl)-6,6-dihydroxy-5-hydroxyiminohexahydro-2,4-pyrimidinedione and salts thereof of general formula (I), where X is selected from the group: H, Na, K, or from the group of hydroxyalkylammonia derivatives of general formula (II), where R1, R2 are selected from the group: H, CH 3 , CH 2 CH 3 , CH 2 CH 2 OH; R3 is selected from the group: H, CH 2 OH; and n=1, 2; the drug can be prepared in the form of tablets or capsules for enteral administration; or in the form of a liquid or lyophilized substance for parenteral administration; or in the form of rectal suppositories; or in the form of capsules or tablets, or sweets for sucking; and may additionally contain the hepatoprotector Heptral; or the hepatoprotector Essentiale; or the hepatoprotector ursodeoxycholic acid. This increases the effectiveness of a drug with hepatoprotective activity.

  该发明涉及药理学，可用于治疗各种病因的肝病，包括与其他制剂联合使用。所述药物具有肝保护活性，包括3-(4-溴苯基)-6,6-二羟基-5-羟亚胺己氢-2,4-嘧啶二酮及其盐，其一般式为(I)，其中X选自组：H、Na、K，或羟基烷胺衍生物组的一般式(II)，其中R1、R2选自组：H、CH3、CH2 、CH2CH2OH；R3选自组：H、CH2OH；n=1、2；该药物可制备成片剂或胶囊形式用于肠道给药；或以液体或冻干物质形式用于静脉给药；或以直肠栓剂形式；或以胶囊或片剂，或含吸入片剂；并且还可以额外含有肝保护剂Heptral；或肝保护剂Essentiale；或肝保护剂熊去氧胆酸。这增加了具有肝保护活性的药物的有效性。
• CYANINE-CONTAINING COMPOUNDS FOR CANCER IMAGING AND TREATMENT
  申请人：Emory University

  公开号：US20150335765A1

  公开（公告）日：2015-11-26

  This invention relates generally to cyanine-containing compounds; pharmaceutical compositions comprising cyanine-containing compounds; and methods of using cyanine-containing compounds for cancer cell imaging, cancer cell growth inhibition, and detecting cancer cells, for example. Compounds of the invention are preferentially taken up by cancer cells as compared to normal cells. This allows many uses in the cancer treatment, diagnosis, tracking and imaging fields.

  这项发明通常涉及含有青霉素的化合物；包含青霉素化合物的药物组合物；以及使用青霉素化合物进行癌细胞成像、癌细胞生长抑制和检测癌细胞等方法。该发明的化合物相对于正常细胞更容易被癌细胞吸收。这使得在癌症治疗、诊断、跟踪和成像领域有许多用途。
• CONJUGATES OF KINASE INHIBITORS AND CYANINE DYES
  申请人：Small Molecule PPI Mimics LLC

  公开号：US20190343958A1

  公开（公告）日：2019-11-14

  The present disclosure provides conjugates of kinase inhibitors and cyanine dyes, as well as related compositions, methods and uses.

  本公开提供了激酶抑制剂和青霉素染料的结合物，以及相关的组合物、方法和用途。

表征谱图