(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride

• ChemBase编号: 72636
• 分子式: C27H30ClNO10
• 平均质量: 563.9808
• 单一同位素质量: 563.15582385
• SMILES: c1ccc2c(c1OC)C(=O)c1c(C2=O)c(c2c(c1O)[C@H](C[C@](C2)(O)C(=O)C)O[C@H]1C[C@@H]([C@@H]([C@@H](O1)C)O)N)O.Cl
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)C(=O)C.Cl
• InChI: InChI=1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1
• InChIKey: GUGHGUXZJWAIAS-QQYBVWGSSA-N

名称和登记号

名称

• IUPAC标准名: (8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride
• IUPAC传统名: daunorubicin hydrochloride
• 别名: 道诺霉素 盐酸盐; 柔红霉素 盐酸盐; (8S,10S)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride; (8S-cis)-Daunomycin Hydrochloride; 13-Dihydrocarminomycin; Cerubidine; Daunoblastin; Daunomycin Chlorohydrate; NDC 0082-4155; Ondena; RP 13057 Hydrochloride; Daunorubicin Hydrochloride; Daunomycin hydrochloride; Daunorubicin; Rubidomycin hydrochloride; Cerubidine; Daunorubicin hydrochloride; (-)-Daunorubicin; WP900 hydrochloride; Daunorubicin HCl (Daunomycin HCl); Daunorubicinol hydrochloride

登记号

• CAS号: 23541-50-6
• EC号: 245-723-4
• MDL号: MFCD04974507
• Beilstein号: 4229221
• PubChem SID: 24724666; 162037561; 24858374; 24894229
• PubChem CID: 62770

理论计算性质

• Acid pKa: 7.996109
• 质子受体: 11
• 质子供体: 5
• LogD (pH = 5.5): -0.49411148
• LogD (pH = 7.4): 0.9138854
• Log P: 1.3442496
• 摩尔折射率: 132.8915 cm^3
• 极化性: 52.022972 Å^3
• 极化表面积: 185.84 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Methanol; Water
• 外观: Dark Red Solid; solid
• 熔点: >180°C (dec)

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: HB7878000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22-40-42/43
• 安全公开号: 22-36/37-45
• GHS危险品标识: GHS06; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H334-H351; H302-H334-H351
• GHS警示性声明: P261-P281-P301 + P310-P342 + P311; P261-P281-P342 + P311
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: -20°C; 2-8°C

药理学性质

• 作用靶点: Telomerase; Topoisomerase

产品相关信息

• 纯度: ≥90% (HPLC); ≥95% (HPLC); 95+%
• 成盐信息: HCL; Hydrochloride
• 适用性: meets USP testing specifications
• Empirical Formula (Hill Notation): C27H29NO10 · HCl; C27H30NO10Cl

详细说明

Selleck Chemicals - S1216

Biological Activity:
Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is the hydrochloride salt of an anthracycline cytotoxic antibiotic produced by a strain of Streptomyces coeruleorubidus (IC50=0.5μM). On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) has the highest preference for two adjacent G/C base pairs flanked on the 5’ side by an A/T base pair. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) effectively binds to every 3 base pairs and induces a local unwinding angle of 11o, but negligible distortion of helical conformation. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is chemotherapeutic of the anthracycline family that is given as a treatment for some types of cancer. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is most commonly used to treat specific types of leukaemia (acute myeloid leukemia and acute lymphocytic leukemia). Cerubidine (Daunorubicin HCl, Rubidomycin HCl) was initially isolated from Streptomyces peucetius. [1][2][3]

Sigma Aldrich - 30450

Biochem/physiol Actions
Daunorubicin inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent. On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. Daunomycin effectively binds to every 3 base pairs which causes unwinding.
强效抗癌剂，已证明是 DNA 和 RNA 合成的强抑制剂。性质
Application
Daunorubicin hydrochloride is used in photostability 1, antileukemic, 2, and drug metabolism studies 3.

Sigma Aldrich - W4013

Biochem/physiol Actions
Synthetic left-handed enantiomer of (+)-daunorubicin, anti-tumor antibiotic, binds to right-handed B-form DNA under low salt conditions.

Sigma Aldrich - D8809

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
强效抗癌剂，已证明是 DNA 和 RNA 合成的强抑制剂。性质
自发荧光的蒽环类抗生素，抗癌药。Pgp、MRP-1 和 BCRP 的底物。已利用荧光特性来测量药物外排泵活性，以及解决许多重要问题，如多种多药耐药蛋白的胞内定位和亚细胞器（高尔基体和溶酶体）在药物螯合中的作用及其在耐药表型中的含义。根据 pH 分配型机理将柔红霉素螯合进溶酶体。1,2DNA 和 RNA 合成的强抑制剂。

Toronto Research Chemicals - D194500

Anthracycline antibiotic related to the rhodomycins. Antineoplastic.

参考文献

• http://www.cancer.gov/drugdictionary/?CdrID=39779
• Yang, Z., et al.: J. Pharmacol. Experim. Ther., 327, 474 (2008)
• Zhao, Y., et al.: Int. J. Pharm., 379, 90 (2008)
• Bayne, W., et al.: J. Pharm. Sci., 98, 2540 (2008)