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吡柔比星

吡柔比星用途

【用途1】
对头颈部癌、乳癌、尿路上皮癌、卵巢癌、子宫癌、急性白血病、恶性淋巴瘤有缓解作用。

吡柔比星名称

[ CAS 号 ]:
72496-41-4

[ 中文名 ]:
吡柔比星

[ 英文名 ]:
Pirarubicin

[英文别名 ]:

Pinorubicin
Therarubicin
Tepirubicin
4'-O-Tetrahydropyranyl Doxorubicin
Pirabucin
THP-Adriamycin
MFCD00869742
1609rb
(2''R)-4'-O-Tetrahydropyranyladriamycin
Theprubicin

吡柔比星生物活性

[ 描述 ]:

Pirarubicin 是一种蒽环类抗生素,为拓扑异构酶 II (topoisomerase II) 的抑制剂,可用于各种癌症尤其是固体肿瘤的治疗。

[ 相关类别 ]:

信号通路 >> 自噬 >> 自噬

研究领域 >> 癌症

[ 靶点 ]

Topoisomerase II

[体外研究]

吡柔比星是一种拓扑异构酶II抑制剂[1]。吡柔比星显示出对M5076和Ehrlich细胞的抑制活性,IC50分别为0.366和0.078μM。 Pirarubicin对M5076细胞的细胞毒性低于Ehrlich细胞,这是由于M5076细胞中拓扑异构酶II的表达低于Ehrlich细胞[2]。吡柔比星(2.5,5,10μg/ mL)在膀胱癌(T24,EJ,5637,J82和UM-UC-3)细胞中以剂量依赖性方式显着诱导自噬。此外,吡柔比星(5μg/ mL)通过抑制膀胱癌细胞中的mTOR/p70S6K/4E-BP1诱导细胞凋亡,并通过抑制自噬来增强这种作用[3]。

[体内研究]

与急性心脏毒性大鼠对照组相比,吡柔比星(18 mg/kg,iv)显着升高血清BNP,CK-MB,CTnT,LDH和MDA水平。在急性心脏毒性模型中,吡柔比星还可降低心率,抑制R波电压,延长QT间期[4]。

[细胞实验]

MTS用于分析细胞存活。简而言之，将细胞以每孔2×103个细胞一式三份接种在96孔板中，并在生长培养基中培养。然后用不同浓度的吡柔比星（2.5μg/ mL，5μg/ mL，10μg/ mL）处理细胞24小时。加入MTS试剂（5mg / mL）并在37℃下孵育4小时。使用酶标仪在490nm处监测吸光度[3]。

[动物实验]

通过尾静脉注射单次剂量18mg / kg吡柔比星建立急性心脏毒性模型。将36只大鼠随机分成6组：正常对照，心脏损伤（THP）模型，右雷佐生（180 mg / kg），低剂量芦丁（25 mg / kg），中剂量芦丁（50 mg / kg）和高剂量芦丁（100毫克/千克）。在芦丁处理组中的大鼠通过管饲法施用不同剂量的芦丁和CMC-Na 7天，并通过尾静脉注射施用单剂量的18mg / kg吡柔比星。右雷佐生处理组中的大鼠通过管饲法接受羧甲基纤维素钠（CMC-Na）六天。然后通过腹膜内注射给大鼠施用40mg / kg右雷佐生，并且在第7天通过尾静脉注射施用18mg / kg吡柔比星.THP模型组中的大鼠通过管饲法接受CMC-Na七天，然后接着吡柔比星18mg在第7天通过尾静脉注射/ kg。正常对照组中的大鼠通过管饲法接受CMC-Na七天，然后在第7天通过尾静脉注射盐水[4]。

[参考文献]

[1]. Takigawa N, et al. Cytotoxic effect of topoisomerase II inhibitors against adriamycin- and etoposide-resistant small cell lung cancer sublines. Gan To Kagaku Ryoho. 1993 May;20(7):929-35.

[2]. Nagai K, et al. Relationships between the in vitro cytotoxicity and transport characteristics of pirarubicin and doxorubicin in M5076 ovarian sarcoma cells, and comparison with those in Ehrlich ascites carcinoma cells. Cancer Chemother Pharmacol. 2002 Mar;49(3):244-50. Epub 2002 Jan 8.

[3]. Li K, et al. Pirarubicin induces an autophagic cytoprotective response through suppression of the mammalian target of rapamycin signaling pathway in human bladder cancer cells. Biochem Biophys Res Commun. 2015 May 1;460(2):380-5.

[4]. Wang YD, et al. Cardioprotective effects of rutin in rats exposed to pirarubicin toxicity. J Asian Nat Prod Res. 2017 Oct 27:1-13.

[相关活性小分子]

吡柔比星物理化学性质

[ 密度 ]:
1.5±0.1 g/cm3

[ 沸点 ]:
834.7±65.0 °C at 760 mmHg

[ 熔点 ]:
188-192ºC (dec.)

[ 分子式 ]:
C₃₂H₃₇NO₁₂

[ 分子量 ]:
627.636

[ 闪点 ]:
458.6±34.3 °C

[ 精确质量 ]:
627.231567

[ PSA ]:
204.30000

[ LogP ]:
3.85

[ 外观性状 ]:
红色结晶粉末

[ 蒸汽压 ]:
0.0±3.2 mmHg at 25°C

[ 折射率 ]:
1.671

[ 储存条件 ]:
2-8°C

吡柔比星毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QI9296000

CHEMICAL NAME :: 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-4-O-(tetrahydro-2H-pyran- 2-yl)-alpha-L- lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-tr ihydroxy-8-(hydroxyac etyl)-1-methoxy-, (8S-cis)-

CAS REGISTRY NUMBER :: 72496-41-4

LAST UPDATED :: 199512

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C32-H37-N-O12

MOLECULAR WEIGHT :: 627.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 27800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 14 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Lymphocyte

DOSE/DURATION :: 230 ug/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 36,312,1983

吡柔比星安全信息

[ 危害码 (欧洲) ]:
Xi

[ 风险声明 (欧洲) ]:
36/37/38

[ 安全声明 (欧洲) ]:
S26-S37/39

[ 危险品运输编码 ]:
NONH for all modes of transport

[ RTECS号 ]:
QI9296000

吡柔比星制备

由阿霉素和二氢吡喃合成的蒽环类抗肿瘤抗生素。

吡柔比星文献

Synthesis and therapeutic effect of styrene-maleic acid copolymer-conjugated pirarubicin.

Cancer Sci. 106(3) , 270-8, (2015)

Previously, we prepared a pirarubicin (THP)-encapsulated micellar drug using styrene-maleic acid copolymer (SMA) as the drug carrier, in which active THP was non-covalently encapsulated. We have now d...

Co-delivery of Pirarubicin and Paclitaxel by Human Serum Albumin Nanoparticles to Enhance Antitumor Effect and Reduce Systemic Toxicity in Breast Cancers.

Mol. Pharm. 12 , 4085-98, (2015)

In our study, we aimed to develop a codelivery nanoparticulate system of pirarubicin (THP) and paclitaxel (PTX) (Co-AN) using human serum albumin to improve the therapeutic effect and reduce systemic ...

Porphyrin-adsorbed Allograft Bone: A Photoactive, Antibiofilm Surface.

Clin. Orthop. Relat. Res. 473 , 2865-73, (2015)

Allograft bone is commonly used to augment bone stock. Unfortunately, allograft is prone to bacterial contamination and current antimicrobial therapies are inadequate. Photoactivated porphyrins combat...

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