CAS |
1397-89-3 |
Chinese Name |
可溶性两性霉素B |
English Name |
Amphotericin B |
Synonyms |
两性霉素B |
Molecular Formula |
C47H73NO17 |
Molecular Weight |
924.08 |
Solubility |
Soluble in Water/DMSO |
Purity |
≥85% |
Appearance |
Light yellow to yellow Solid |
Storage |
Powder:2-8℃,2 years;Insolvent(Mother Liquid):-20℃,6 months;-80℃,1 year |
EC |
EINECS 215-742-2 |
MDL |
MFCD00877763 |
SMILES |
C[C@H]([C@@H](O)[C@@H](C)[C@H](C)OC1=O)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@]2([H])O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@]3([H])[C@H](C(O)=O)[C@@H](O)C[C@](C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)C1)(O)O3 |
InChIKey |
APKFDSVGJQXUKY-INPOYWNPSA-N |
InChI |
InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1 |
PubChem CID |
5280965 |
Target Point |
Fungal |
Passage |
Anti-infection |
Background |
Amphotericin B is a polyene antifungal (fungal) agent against a variety of fungal pathogens. It binds irreversibly to ergosterol, leading to disruption of membrane integrity and eventual cell death. |
Biological Activity |
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。[1-5] |
In Vitro |
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]。 |
In Vivo |
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显著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著延迟宿主死亡的伯氏疟原虫感染的小鼠[5]。 |
Cell Experiment |
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。 |
Kinase Experiment |
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。 |
Data Literature Source |
[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. |
Unit |
Bottle |
Specification |
25mg 50mg 10mM*1mL in DMSO 10mM*1mL in Water 100mg 500mg |