7184-60-3

• 常用中文名：抗螺旋體鏈絲菌素
• 常用英文名：(-)-borrelidin
• CAS号：7184-60-3
• 分子式：C₂₈H₄₃NO₆
• 分子量：489.644
• 相关类别： 原料药 抗生素类药物 其它抗生素类药
• 发布时间：2018-08-04 17:05:48
• 更新时间：2024-01-02 20:36:55
• Borrelidin (Treponemycin) 是从 Streptomyces rochei 中分离的一种含氮大环内酯类抗生素,能作为抑制细菌和真核 threonyl-tRNA 合成酶的抑制剂,通过诱导细胞凋亡和介导 G1 期阻滞作用来靶向 ALL 细胞。Borrelidin (Treponemycin) 是一种出芽酵母细胞周期蛋白依赖性激酶 (CDK) Cdc28/Cln2 的抑制剂,其 IC50 值为 24 μM。Borrelidin (Treponemycin) 是一种强效的血管生成抑制剂,其 IC50 值为 0.8 nM,可诱导血管形成细胞凋亡。Borrelidin (Treponemycin) 具有较强的抗疟活性,对恶性疟原虫 K1 株和 FCR3 株作用的 IC50 值分别为 1.9 nM 和 1.8 nM。

名称

• 中文名: 抗螺旋体链丝菌素
• 英文名: borrelidin
• 中文别名: 疏螺体素; 疏螺旋体素; 抗螺旋體鏈絲菌素
• 英文别名: Borrelidin; Cyclopentanecarboxylic acid, 2-[(2S,4Z,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]-, (1R,2R)-; Borrelidine; Quinquangulin K 031; 2-(7-CYANO-8,16-DIHYDROXY-9,11,13,15-TETRAMETHYL-18-OXOOXACYCLOOCTADECA-4,6-DIEN-2-YL)-CYCLOPENTANECARBOXYLIC ACID; Quinquangulin K 182; Cyclopentanecarboxylic acid, 2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]-, (1R,2R)-; (1R,2R)-2-[(2S,4Z,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid; (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid; (-)-borrelidine; TREPONEMYCIN

物化性质

• 密度: 1.1±0.1 g/cm3
• 沸点: 710.3±60.0 °C at 760 mmHg
• 熔点: 143-145℃
• 分子式: C₂₈H₄₃NO₆
• 分子量: 489.644
• 闪点: 383.4±32.9 °C
• 精确质量: 489.309052
• PSA: 127.85000
• LogP: 4.31
• 外观性状: 白色至灰白色粉末
• 蒸汽压: 0.0±5.1 mmHg at 25°C
• 折射率: 1.539
• 储存条件: 库房通风低温干燥,与食品原料分开存放
• 水溶解性: DMSO: 1 mg/mL

生物活性

• 描述: Borrelidin (Treponemycin) 是从 Streptomyces rochei 中分离的一种含氮大环内酯类抗生素,能作为抑制细菌和真核 threonyl-tRNA 合成酶的抑制剂,通过诱导细胞凋亡和介导 G1 期阻滞作用来靶向 ALL 细胞。Borrelidin (Treponemycin) 是一种出芽酵母细胞周期蛋白依赖性激酶 (CDK) Cdc28/Cln2 的抑制剂,其 IC50 值为 24 μM。Borrelidin (Treponemycin) 是一种强效的血管生成抑制剂,其 IC50 值为 0.8 nM,可诱导血管形成细胞凋亡。Borrelidin (Treponemycin) 具有较强的抗疟活性,对恶性疟原虫 K1 株和 FCR3 株作用的 IC50 值分别为 1.9 nM 和 1.8 nM。
• 相关类别:
  信号通路 >> 抗感染 >> 寄生物
  信号通路 >> 细胞凋亡 >> 细胞凋亡
  研究领域 >> 感染
  信号通路 >> 细胞周期/DNA损伤 >> CDK
• 靶点:

  IC50：24μM (Cdc28/Cln2)[2]

• 参考文献:

  [1]. Habibi D, et al. Borrelidin, a small molecule nitrile-containing macrolide inhibitor of threonyl-tRNA synthetase, is a potent inducer of apoptosis in acute lymphoblastic leukemia. Invest New Drugs. 2012 Aug;30(4):1361-70.

  [2]. Tsuchiya E, et al. Borrelidin inhibits a cyclin-dependent kinase (CDK), Cdc28/Cln2, of Saccharomyces cerevisiae. J Antibiot (Tokyo). 2001 Jan;54(1):84-90.

  [3]. Wakabayashi T, et al. Borrelidin is an angiogenesis inhibitor; disruption of angiogenic capillary vessels in a rat aorta matrix culture model. J Antibiot (Tokyo). 1997 Aug;50(8):671-6.

  [4]. Otoguro K, et al. In vitro and in vivo antimalarial activities of a non-glycosidic 18-membered macrolide antibiotic, borrelidin, against drug-resistant strains of Plasmodia. J Antibiot (Tokyo). 2003 Aug;56(8):727-9.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : ED8750000 CHEMICAL NAME : Borrelidin CAS REGISTRY NUMBER : 7184-60-3 BEILSTEIN REFERENCE NO. : 0066270 LAST UPDATED : 199612 DATA ITEMS CITED : 5 MOLECULAR FORMULA : C28-H43-N-O6 MOLECULAR WEIGHT : 489.72 WISWESSER LINE NOTATION : T-18-OV MU OUTJ DQ E1 G1 I1 K1 LQ MCN R- AL5TJ BVQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 1780 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JCINAO Journal of Clinical Investigation. (Rockefeller Univ. Press, 1230 York Ave., New York, NY 10021) V.1- 1924- Volume(issue)/page/year: 28,1047,1949 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 2,1198,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 75 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JCINAO Journal of Clinical Investigation. (Rockefeller Univ. Press, 1230 York Ave., New York, NY 10021) V.1- 1924- Volume(issue)/page/year: 28,1047,1949 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 39 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JCINAO Journal of Clinical Investigation. (Rockefeller Univ. Press, 1230 York Ave., New York, NY 10021) V.1- 1924- Volume(issue)/page/year: 28,1047,1949 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Bird - chicken DOSE/DURATION : 74 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 2,1198,1978

安全

• 个人防护装备: Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
• 危害码 (欧洲): T+
• 安全声明 (欧洲): 24/25
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 3
• RTECS号: ED8750000
• 海关编码: 29419090

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