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两性霉素B

两性霉素B用途

Amphotericin B是针对多种真菌病原体的多烯抗真菌 (fungal) 剂。 它与麦角甾醇不可逆地结合,导致膜完整性破坏并最终导致细胞死亡。
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两性霉素B名称

[ CAS 号 ]:
1397-89-3

[ 中文名 ]:
两性霉素B

[ 英文名 ]:
Amphotericin B

[中文别名 ]:

[英文别名 ]:

两性霉素B生物活性

[ 描述 ]:

Amphotericin B是针对多种真菌病原体的多烯抗真菌 (fungal) 剂。 它与麦角甾醇不可逆地结合,导致膜完整性破坏并最终导致细胞死亡。

[ 相关类别 ]:

信号通路 >> 抗感染 >> 真菌
研究领域 >> 感染

[ 靶点 ]

Fungal[1]


[体外研究]

两性霉素B给药受到输注相关毒性的限制,包括发烧和寒战,这是由先天免疫细胞产生促炎性细胞因子引起的效应。两性霉素B诱导表达TLR2和CD14的细胞的信号转导和炎性细胞因子释放[1]。两性霉素B与哺乳动物膜的主要甾醇胆固醇相互作用,因此限制了两性霉素B的有效性,因为它具有相对高的毒性。两性霉素B作为前胶束或高度聚集状态分散在亚相中[2]。当可形成小阳离子和阴离子的水性孔时,两性霉素B仅杀死单细胞利什曼原虫前鞭毛体(LP)。两性霉素B(0.1mM)诱导极化电位,表明悬浮在等渗蔗糖溶液中的载有KCl的脂质体中的K +泄漏。两性霉素B(0.05 mM)表现出负膜电位几乎完全崩溃,表明Na +进入细胞[3]。

[体内研究]

两性霉素B导致延长孵育时间并降低仓鼠瘙痒病模型中的PrPSc积累。两性霉素B显着降低传染性亚急性海绵状脑病(TSSE)小鼠的PrPSc水平[4]。两性霉素B对恶性疟原虫发挥直接作用,并影响感染的红细胞,寄生虫血症和小鼠疟疾中的宿主生存。两性霉素B倾向于延迟寄生虫血症的增加并显着延迟宿主死亡的伯氏疟原虫感染的小鼠[5]。

[激酶实验]

分别使用DEAE-葡聚糖和Polyfect试剂瞬时转染THP-1和HEK293细胞。转染的质粒含有编码NF-κB依赖性pELAM-luc荧光素酶报告基因，TLR2，TLR4，CD14和MD2的基因。将细胞（5×105 THP-1或1×105HEK293）加入到12孔板中，18小时后洗涤，并刺激5小时。然后按照指导用报道裂解缓冲液裂解细胞，用Promega荧光素酶底物和Monolight 3010发光计分析裂解物的发光。

[细胞实验]

AmB对利什曼原虫前鞭毛体诱导的细胞死亡的动力学之后是使用DNA结合化合物溴化乙锭（EB）的荧光测定法。荧光测量在SPEX Fluorolog II分光光度计上在365-580nm激发发射波长下进行。将终浓度为25×10 6个细胞/ mL的前鞭毛体在荧光比色杯中与2mL不同的缓冲溶液温和搅拌孵育5分钟，但总是含有10mM葡萄糖和EB（50mM）。在实现信号稳定后，加入AmB并溶解在二甲基亚砜中。通过添加洋地黄皂苷（50mg / mL）总是获得最大EB掺入。所用的所有溶液均用75mM TRIS（pH4.66）缓冲，含有150mM NaCl（BNa +），150mM KCl（BK +），150mM氯化胆碱和100mM蔗糖，100mM NaCl。使用先进的仪器SW2渗透压计，所有溶液的渗透压总是调整到390±5mOsm。

[参考文献]

[1]. Sau K, et al. The antifungal drug amphotericin B promotes inflammatory cytokine release by a Toll-like receptor- and CD14-dependent mechanism. J Biol Chem. 2003 Sep 26;278(39):37561-8. Epub 2003 Jul 14.

[2]. Barwicz J, et al. The effect of aggregation state of amphotericin-B on its interactions with cholesterol- or ergosterol-containing phosphatidylcholine monolayers. Chem Phys Lipids. 1997 Feb 28;85(2):145-55.

[3]. Ramos H, et al. Amphotericin B kills unicellular leishmanias by forming aqueous pores permeable to small cations and anions. J Membr Biol. 1996 Jul;152(1):65-75.

[4]. Demaimay R, et al. Pharmacological studies of a new derivative of amphotericin B, MS-8209, in mouse and hamster scrapie. J Gen Virol. 1994 Sep;75 (Pt 9):2499-503.

[5]. Adams ML, et al. Amphotericin B encapsulated in micelles based on poly(ethylene oxide)-block-poly(L-amino acid) derivatives exerts reduced in vitro hemolysis but maintains potent in vivo antifungal activity. Biomacromolecules. 2003 May-Jun;4(3):750-7.


[相关活性小分子]

放线菌酮 | 潮霉素B | 醋酸卡泊芬净 | 5-氟胞嘧啶 | 泊沙康唑 | 特比萘芬 | 环吡酮胺 | 艾沙康唑 | 阿尼芬净 | 克霉唑 | 5-氯-8-羟基-7-碘喹啉 | 硝酸咪康唑 | 纳他霉素 | 长川霉素 | 硝酸益康唑

两性霉素B物理化学性质

[ 密度 ]:
1.3±0.1 g/cm3

[ 沸点 ]:
1140.4±65.0 °C at 760 mmHg

[ 熔点 ]:
>170°C

[ 分子式 ]:
C47H73NO17

[ 分子量 ]:
924.079

[ 闪点 ]:
643.5±34.3 °C

[ 精确质量 ]:
923.487854

[ PSA ]:
319.61000

[ LogP ]:
1.16

[ 外观性状 ]:
结晶黄色固体

[ 蒸汽压 ]:
0.0±0.6 mmHg at 25°C

[ 折射率 ]:
1.614

[ 储存条件 ]:
库房通风低温干燥

[ 稳定性 ]:
Stable, but may be light sensitive. Incompatible with strong oxidizing agents.

[ 水溶解性 ]:
sterile water: 20 mg/mL as a stock solution. Stock solutions should be stored at −20?#x00b0;C. Stable at 37?#x00b0;C for 3 days. | <0.1 g/100 mL at 21 ºC

两性霉素BMSDS

详细MSDS(安全技术说明书)

两性霉素B毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BU2625000
CHEMICAL NAME :
Amphotericin B
CAS REGISTRY NUMBER :
1397-89-3
BEILSTEIN REFERENCE NO. :
0078342
LAST UPDATED :
199612
DATA ITEMS CITED :
33
MOLECULAR FORMULA :
C47-H73-N-O17
MOLECULAR WEIGHT :
924.21
WISWESSER LINE NOTATION :
T6-36- A AO RVO A&U C&U E&U G&U I&U K&U M&UTJ CVQ DQ FQ HQ JQ KQ NQ PQ T1 U1 VQ W1 O&O- BT6OT

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
22 mg/kg/4D-I
TOXIC EFFECTS :
Blood - leukopenia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
20 ug/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
164 ug/kg/5H-I
TOXIC EFFECTS :
Cardiac - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
15 mg/kg/4D-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - changes in potassium Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1 mg/kg/1H-C
TOXIC EFFECTS :
Cardiac - pulse rate
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/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 :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/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 :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1600 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 :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/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 :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>8 gm/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 :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
27740 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 :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1200 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 :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>50 mg/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 :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
6 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
490 mg/kg/14W-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
55 mg/kg/13W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in erythrocyte (RBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
37 mg/kg/30D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
5500 ug/kg
SEX/DURATION :
female 6-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
600 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
20 mg/kg
SEX/DURATION :
male 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

MUTATION DATA

TEST SYSTEM :
Rodent - rabbit
DOSE/DURATION :
20 mg/kg/11D
REFERENCE :
JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 7,13,1964 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84491 No. of Facilities: 561 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 6392 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84491 No. of Facilities: 386 (estimated) No. of Industries: 2 No. of Occupations: 10 No. of Employees: 15048 (estimated) No. of Female Employees: 12218 (estimated)
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两性霉素B安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H335

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S26-S36/37/39-S45-S36

[ 危险品运输编码 ]:
UN 1759 8/PG 3

[ WGK德国 ]:
3

[ RTECS号 ]:
BU2625000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1(b)

两性霉素B合成路线

详细合成路线

两性霉素B上下游产品

两性霉素B上游产品

两性霉素B下游产品

两性霉素B制备

用节链霉菌菌株为菌种，在含有碳水化合物和有机氮源的液体培养基中进行通气深层发酵，当达到相当效价单位后，由发酵液中提取两性霉素。两性霉素含有A、B两种成分，A成分毒性小，抗真菌作用微弱，不用于临床，B成分的作用强，称两性霉素B。

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两性霉素B文献

The influence of surface charge and photo-reactivity on skin-permeation enhancer property of nano-TiO₂ in ex vivo pig skin model under indoor light.

Int. J. Pharm. 467(1-2) , 90-9, (2014)

Several topical products contain nanometric TiO2 (nano-TiO2), which is a useful and safe component that absorbs UV light and does not cross skin barrier. However, nano-TiO2 may impregnate the first la...

The use of chitosan-dextran gel shows anti-inflammatory, antibiofilm, and antiproliferative properties in fibroblast cell culture.

Am. J. Rhinol. Allergy 28(5) , 361-5, (2014)

Chitosan-dextran gel has been used as an antihemostatic agent and antiadhesive agent after endoscopic sinus surgery. Because Staphylococcus aureus biofilms have been implicated in recalcitrant chronic...

Flow perfusion co-culture of human mesenchymal stem cells and endothelial cells on biodegradable polymer scaffolds.

Ann. Biomed. Eng. 42(7) , 1381-90, (2014)

In this study, we investigated the effect of flow perfusion culture on the mineralization of co-cultures of human umbilical vein endothelial cells (HUVECs) and human mesenchymal stem cells (hMSCs). Os...


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相关化合物

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