145-63-1

• 常用中文名：苏拉明
• 常用英文名：Suramin
• CAS号：145-63-1
• 分子式：C₅₁H₄₀N₆O₂₃S₆
• 分子量：1297.28000
• 相关类别： 信号通路 G 蛋白偶联受体/G 蛋白 P2Y受体
• 发布时间：2017-11-09 10:35:46
• 更新时间：2025-08-22 16:29:37
• Suramin是具有各种生物活性的多磺化萘脲。Suramin是DNA topoisomerase II抑制剂,IC50值为5 μM。

名称

• 中文名: 苏拉明
• 英文名: suramin
• 英文别名: Naphuride; EINECS 205-658-4; Naganin; Farma; Antrypol; Germanin; Fourneau; 8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic acid; Suramine; Belganyl; Naganol

物化性质

• 分子式: C₅₁H₄₀N₆O₂₃S₆
• 分子量: 1297.28000
• 精确质量: 1296.05000
• PSA: 534.03000
• LogP: 13.66600
• 折射率: 1.777
• 储存条件:

  通风低温干燥处

• 计算化学:

  1.疏水参数计算参考值（XlogP）:1.5

  2.氢键供体数量:12

  3.氢键受体数量:23

  4.可旋转化学键数量:16

  5.互变异构体数量:155

  6.拓扑分子极性表面积534

  7.重原子数量:86

  8.表面电荷:0

  9.复杂度:3020

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

生物活性

• 描述: Suramin是具有各种生物活性的多磺化萘脲。Suramin是DNA topoisomerase II抑制剂,IC50值为5 μM。
• 相关类别:
  信号通路 >> G 蛋白偶联受体/G 蛋白 >> P2Y受体
  研究领域 >> 癌症
• 靶点:

  IC50: 5 μM (DNA topoisomerase II)[3]

• 体外研究: 苏拉明抑制培养的HeLa细胞中的细胞增殖和DNA合成。通过40μM苏拉明完全消除SV40 DNA的复制。 DNA聚合酶α对较低浓度的苏拉明敏感(IC50 =8μM)比DNA聚合酶δ(IC50 =36μM)敏感,而DNA聚合酶β对药物相对不敏感(IC50为90μM)[1]。苏拉明是细菌RecA蛋白的DNA链交换和ATP酶活性的有效抑制剂。苏拉明抑制RecA催化的LexA阻遏蛋白水解切割。苏拉明这种抑制作用的机制涉及其拆解RecA-单链DNA细丝的能力[2]。苏拉明是核酶DNA拓扑异构酶II的有效抑制剂。苏拉明抑制纯化的酵母拓扑异构酶II,IC50约为5μM[3]。
• 体内研究: 与对照大鼠相比,苏拉明治疗在第21天显示出较低的肺动脉压,右心室肥大和远端血管肌肉化值。苏拉明治疗抑制PA-SMC增殖并减弱炎症反应和胶原沉积[4]。
• 激酶实验: ATP酶测定在10μL反应混合物中进行，所述反应混合物含有20mM Tris-HCl（pH 7.5），1mM DTT，8mM MgCl2,5μMM13环状ssDNA，来自指定细菌物种的2.5μMRecA和增加浓度的苏拉明。通过加入2mM [α-32P] ATP引发反应，在37℃温育30分钟并通过加入25mM EDTA终止反应[2]。
• 动物实验: 大鼠：为了评估苏拉明的潜在预防和疗效，在MCT注射后将大鼠随机分成4组。在预防策略中，治疗在第一天开始，并且一组每周两次静脉内接受10mg / kg苏拉明，持续3周，而第二组在相同时间点仅接受载体。为了评估苏拉明的潜在疗效，给予大鼠MCT并且不进行处理21天，然后将其随机分成两组，随后从第21天至第42天（包括苏拉明或载体）用苏拉明或载体治疗。从MCT注射的第21天到对应于治疗期的第42天评估苏拉明对存活的影响[4]。
• 参考文献:

  [1]. Jindal HK, et al. Suramin affects DNA synthesis in HeLa cells by inhibition of DNA polymerases. Cancer Res. 1990 Dec 15;50(24):7754-7.

  [2]. Nautiyal A, et al. Suramin is a potent and selective inhibitor of Mycobacterium tuberculosis RecA protein and the SOS response: RecA as a potential target for antibacterial drug discovery. J Antimicrob Chemother. 2014 Jul;69(7):1834-43.

  [3]. Bojanowski K, et al. Suramin is an inhibitor of DNA topoisomerase II in vitro and in Chinese hamster fibrosarcomacells. Proc Natl Acad Sci U S A. 1992 Apr 1;89(7):3025-9.

  [4]. Izikki M, et al. The beneficial effect of suramin on monocrotaline-induced pulmonary hypertension in rats. PLoS One. 2013 Oct 15;8(10):e77073.

毒性和生态

毒理学数据: 静脉-小鼠 LD50: 620 毫克/公斤。 CHEMICAL IDENTIFICATION RTECS NUMBER : QM6900000 CHEMICAL NAME : 1,3,5-Naphthylenetrisulfonic acid, 8,8'-(ureylenebis(m-phenylenecarbonylimino(4-methyl- m-phenylene)carbonylimino))di- CAS REGISTRY NUMBER : 145-63-1 BEILSTEIN REFERENCE NO. : 3230873 LAST UPDATED : 199710 DATA ITEMS CITED : 10 MOLECULAR FORMULA : C51-H40-N6-O23-S6 MOLECULAR WEIGHT : 1297.33 WISWESSER LINE NOTATION : L66J BSWQ DSWQ GSWQ JMVR D1 CMVR CMVMR CVMR B1 EVM- JL66J BSWQ DSWQ GSWQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human - man DOSE/DURATION : 46 mg/kg/5W-I TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - effect, not otherwise specified REFERENCE : NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 314,1455,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 620 mg/kg TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) REFERENCE : AVPCAQ Advances in Pharmacology and Chemotherapy. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.7-20, 1969-84. Volume(issue)/page/year: 15,289,1978 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3 gm/kg/16W-I TOXIC EFFECTS : Liver - other changes Liver - changes in liver weight Endocrine - changes in spleen weight REFERENCE : TOPADD Toxicologic Pathology. (c/o Dr. F.A. de la Iglesia, Warner-Lambert Co., Pharmaceutical Research Div., POB 1047, Ann Arbor, MI 48106) V.6(3/4)- 1978- Volume(issue)/page/year: 19,266,1991 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 300 mg/kg SEX/DURATION : female 7-9 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - abortion REFERENCE : CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 167,1518,1973 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 250 mg/kg SEX/DURATION : female 9 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) REFERENCE : CBINA8 Chemico-Biological Interactions. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1969- Volume(issue)/page/year: 58,149,1986 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 150 mg/kg SEX/DURATION : female 9-11 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 167,1518,1973 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 195 mg/kg SEX/DURATION : female 9-11 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) REFERENCE : CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 167,1518,1973 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported DOSE : 195 mg/kg SEX/DURATION : female 9-11 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) REFERENCE : CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 167,1717,1973