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4449-51-8

4449-51-8结构式
4449-51-8结构式

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中文名 环巴胺
英文名 Cyclopamine
中文别名 环杷明
英文别名 11-DEOXYJERVINE
alkaloidv
Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-, (3S,3'R,3a'S,6'S,6aS,6bS,7a'R,9R,11aS,11bR)-
deoxojervine
11-Desoxo-jervin
Veratraman-3-ol, 17,23-epoxy-, (3β,23β)-
Cyclopamine
(3β,22S,23R)-17,23-Epoxyveratraman-3-ol
Spiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)pyridin)-3-ol, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-, (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
11-deoxojervine
MFCD01735266
(3β,17β,22S,23R)-17,23-Epoxyveratraman-3-ol
11-deoxo-jervin
描述 Cyclopamine 是 Hedgehog 通路的拮抗剂,在细胞实验中的 IC50 为 46 nM。
相关类别
靶点

IC50: 46 nM (Hedgehog, in Hh cell assay)[1]

体外研究 用小分子Hh抑制剂如HhAntag和天然产物Cyclopamine(均与Smo结合)治疗可诱导成神经管细胞瘤基因小鼠模型的肿瘤缓解[1]。环巴胺是一种Hedgehog(Hh)通路拮抗剂。环巴胺抑制细胞生长。环巴胺(3μM)抑制Hh通路活性和消化道肿瘤细胞系的生长与PTCHmRNA的表达相关[2]。 Cyclopamine是一种甾体生物碱,通过与Smo的直接相互作用抑制Hh信号传导[3]。
体内研究 环巴胺导致异种移植肿瘤持续消退。环巴胺治疗动物的肿瘤完全消退12天[2]。环巴胺(1.2 mg)治疗在移植入裸鼠后阻断人胰腺癌细胞的肿瘤形成[3]。
细胞实验 将细胞在96孔板中一式三份培养在测定培养基中,在0h以正文中指出的浓度加入5E1单克隆抗体,ShhNp和/或环巴胺(3μM)。使用CellTiter96比色测定,通过在490nm(OD490)在2天和4天的光密度测量来确定活细胞质量。相对生长计算为OD(第4天)-OD(第2天)/ OD(第2天)[2]。
动物实验 小鼠[3]将总共0.1mL Hanks'平衡盐溶液和含有2×106个细胞的基质胶(1:1)皮下注射到CD-1裸鼠中。使肿瘤生长4天至最小体积125mm 3;对所有受试者同时开始治疗。每天皮下注射小鼠皮下注射载体(三油酸甘油酯:乙醇4:1v / v)或环巴胺悬浮液(每小鼠1.2mg三油酸甘油酯:乙醇4:1v / v),持续7天。在治疗期结束时,从小鼠切下肿瘤,称重,然后在4℃下用4%多聚甲醛固定3小时,包埋在石蜡中并切片(6μm)。使用重组Tdt通过TUNEL鉴定凋亡细胞。然后将切片用曙红复染。从随机选择对应于两个对照和两个环巴胺处理的肿瘤的外部,中间和内部的区域的8×20-放大的视野。我们手动计算了TUNEL阳性细胞核的数量。进行苏木精/伊红染色。
参考文献

[1]. Peukert S, et al. Identification and structure-activity relationships of ortho-biphenyl carboxamides as potent Smoothened antagonists inhibiting the Hedgehog signaling pathway. Bioorg Med Chem Lett, 2009, 19(2), 328-331.

[2]. Berman DM, et al. Widespread requirement for Hedgehog ligand stimulation in growth of digestive tract tumours. Nature, 2003, 425(6960), 846-851.

[3]. Thayer SP, et al. Hedgehog is an early and late mediator of pancreatic cancer tumorigenesis. Nature, 2003, 425(6960), 851-856.

[4]. Ma W, et al. Reduced Smoothened level rescued Aβ-induced memory deficits and neuronal inflammation in animal models of Alzheimer's disease. J Genet Genomics. 2018 May 20;45(5):237-246.

密度 1.1±0.1 g/cm3
沸点 550.8±50.0 °C at 760 mmHg
熔点 236-238ºC
分子式 C27H41NO2
分子量 411.620
闪点 286.9±30.1 °C
精确质量 411.313721
PSA 41.49000
LogP 5.44
外观性状 白色结晶固体
蒸汽压 0.0±3.4 mmHg at 25°C
折射率 1.583
储存条件

避光,通风干燥处,密封保存

稳定性

常温常压下稳定

水溶解性 DMSO: soluble
分子结构

1、 摩尔折射率:120.66

2、 摩尔体积(m3/mol):361.7

3、 等张比容(90.2K):940.2

4、 表面张力(dyne/cm):45.6

5、 极化率(10 -24cm 3):47.83

计算化学

1、 疏水参数计算参考值(XlogP):3.5

2、 氢键供体数量:2

3、 氢键受体数量:3

4、 可旋转化学键数量:0

5、 拓扑分子极性表面积(TPSA):41.5

6、 重原子数量:30

7、 表面电荷:0

8、 复杂度:801

9、 同位素原子数量:0

10、 确定原子立构中心数量:0

11、 不确定原子立构中心数量:0

12、 确定化学键立构中心数量:0

13、 不确定化学键立构中心数量:0

14、 共价键单元数量:1

更多

1. 性状:不确定

2. 密度:不确定

3. 相对蒸汽密度(g/mL,空气=1):不确定

4. 熔点(ºC):不确定

5. 沸点(ºC,常压):不确定

6. 沸点(ºC,35mmHg):不确定

7. 折射率:不确定

8. 闪点(ºC):不确定

9. 比旋光度(º):不确定

10. 自燃点或引燃温度(ºC):不确定

11. 蒸气压(kPa,25ºC):不确定

12. 饱和蒸气压(kPa,60ºC):不确定

13. 燃烧热(KJ/mol):不确定

14. 临界温度(ºC):不确定

15. 临界压力(KPa):不确定

16. 油水(辛醇/水)分配系数的对数值:不确定

17. 爆炸上限(%,V/V):不确定

18. 爆炸下限(%,V/V):不确定

19. 溶解性:不确定

毒理学数据:

1、急性毒性:小鼠口径LDLo: 180 mg/kg;仓鼠口径LDLo:170 mg/kg

2、 繁殖性:大鼠(120毫克/ kgSEX /时间:女性6-9天后受孕)口径TDLo;小鼠TDLo:300 mg/kgSEX/DURATION : female 10 day(s) after conception;兔子口径TDLo:44500 ug/kgSEX/DURATION : female 7 day(s) after conception;

生态学数据:

该物质对环境可能有危害,对水体应给予特别注意

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GY0750000
CHEMICAL NAME :
Cyclopamine
CAS REGISTRY NUMBER :
4449-51-8
LAST UPDATED :
199712
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C27-H41-N-O2
MOLECULAR WEIGHT :
411.69
WISWESSER LINE NOTATION :
L D6 B566 FX DU LUTJ A1 E1 OQ F-& CT56 BOX FMTJ D1 H1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
180 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
170 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
120 mg/kg
SEX/DURATION :
female 6-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,1187,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
300 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 29(2),22A,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
44500 ug/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 136,1174,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
116 mg/kg
SEX/DURATION :
female 7-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 136,1174,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
250 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
170 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
54546 ug/kg
SEX/DURATION :
female 30-31 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 142,1287,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
30 mg/kg
SEX/DURATION :
female 14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 192,153,1989 *** REVIEWS *** TOXICOLOGY REVIEW AEMBAP Advances in Experimental Medicine and Biology. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.1- 1967- Volume(issue)/page/year: 27,107,1972

危害码 (欧洲) Xi: Irritant;
安全声明 (欧洲) 22-24/25
WGK德国 3
RTECS号 GY0750000
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