Fumagillin from Aspergillus fumigatus, >=90%, powder | 23110-15-8

• 物质功能分类: 原料药 - 抗生素类药物 - 其它抗生素类药
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Fumagillin from Aspergillus fumigatus, >=90%, powder
• 英文别名: (2E,4E,6E,8E)-10-[[5-methoxy-4-[2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy]-10-oxodeca-2,4,6,8-tetraenoic acid
• CAS: 23110-15-8
• 化学式: C₂₆H₃₄O₇
• 分子量: 458.5
• InChiKey: NGGMYCMLYOUNGM-HCNIIHBUSA-N

物化性质

• 熔点：
  194-195℃
• 比旋光度：
  D25 -26.6° (c = 1 in 95% ethanol)
• 沸点：
  484.03°C (rough estimate)
• 密度：
  1.1368 (rough estimate)
• 闪点：
  2℃
• 溶解度：
  乙醇：1 mg/mL
• LogP：
  3.260 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36
• 危险类别码：
  R22
• WGK Germany：
  2,3
• 海关编码：
  29419090

制备方法与用途

烟曲霉素简介

烟曲霉素是由烟曲霉（Aspergillus fumigatus）的发酵培养液中分离得到的一种抗生素。

理化性质

烟曲霉素是一种黄色针状结晶，熔点为194～195℃。其旋光度在25℃时为-26.6°（c=1, 乙醇）。该物质几乎不溶于水和稀酸类溶液，但易溶于有机溶剂如乙醇。

用途

烟曲霉素不仅具有抗生素活性，还具备抑制血管生成的作用，因此在治疗肿瘤生长方面具有潜在的应用价值。

生物活性

Fumagillin 是一种选择性且高效的甲硫氨酸胺基肽酶2（MetAP2）不可逆抑制剂，并被用作抗微孢子虫病的抗生素。

靶点

• 靶点：MetAP2

体外研究

Fumagillin 能够特异性地抑制Δmap1菌株的生长，但对野生型或缺乏 MetAP-2 的酿酒酵母菌株没有影响。在出芽酵母细胞中，它不仅逆转了 Vpr 对生长的抑制作用，还抑制了基于人巨噬细胞感染的Vpr依赖性病毒基因表达。尽管 fumagillin 因其毒性限制了对人类的应用，但它的类似物可能因为与血管生成性能相关的结构活性关系而进一步用于探索治疗血管生成依赖性疾病。

体内研究

在经过 DEN 处理的大鼠中，fumagillin（30 mg/kg, i.p.）能有效抑制肝细胞癌的肝脏恶化及其全身性转移。

文献信息

• Methods of treating an overweight subject
  申请人：Zafgen, Inc.

  公开号：US10406134B2

  公开（公告）日：2019-09-10

  The invention generally relates in part to methods of effecting weight loss and/or improving glucose tolerance in a patient in need thereof, comprising administering a MetAP2 inhibitor.

  本发明总体上部分涉及对有需要的患者进行减肥和/或改善葡萄糖耐量的方法，包括给药 MetAP2 抑制剂。
• Use Of Fumagillin And The Derivatives Thereof To Increase The Bioavilability Of The Macrocyclic Lactones
  申请人：Alvinerie Michel

  公开号：US20080200402A1

  公开（公告）日：2008-08-21

  The invention relates to the use of fumagillin and the analog derivatives thereof, as inhibitors of cellular transporters, such as ABC transporters, and especially of P-glycoprotein, in order to increase the bioavailability of active ingredients that can be used in the treatment of pathologies such as cancers or parasitic diseases, and especially in order to increase the bioavailability of the macrocyclic lactones.
• METHODS OF TREATING AN OVERWEIGHT OR OBESE SUBJECT
  申请人：Vath James

  公开号：US20100016425A1

  公开（公告）日：2010-01-21

  The invention herein generally relates to pharmaceutical formulations and methods of treating an overweight or obese subject, and overweight- or obesity-related conditions.
• TERPENES WITH ANTIFUNGAL ACTIVITY AGAINST MALASSEZIA YEASTS
  申请人：Canedo Hernandez Librada Maria

  公开号：US20100184853A1

  公开（公告）日：2010-07-22

  The present invention relates to the use of some terpenes, for example chlovalicin, ovalicin or fumagillin, as antifungal against Malassezia species and to their use in the manufacture of medicaments for the treatment of human skin diseases caused by these Malassezia species, such as pityriasis versicolor, seborrheic dermatitis, dandruff, atopic dermatitis, psoriasis, confluent and reticulated papillomatosis, onychomycosis, and transient acantholytic dermatosis.
• USE OF FUMAGILLIN AND THE DERIVATIVES THEREOF TO INCREASE THE BIOAVAILABILITY OF THE MACROCYCLIC LACTONES
  申请人：ALVINERIE Michel

  公开号：US20110144045A1

  公开（公告）日：2011-06-16

  A method for increasing the bioavailability of antiparasitic active ingredients, and therefore to potentiate the effects thereof, including combining antiparasitic active ingredients with an adjuvant, wherein, the antiparasitic active ingredients are capable of being recognized and binding to cellular transporters in order to be transported out of cells without being able to reach an intracellular therapeutic target, the transporters being present in the cells of the human or animal organism to which the antiparasitic active ingredients are administered, and, optionally, in the cells of parasites against which the antiparasitic active ingredients are administered, the adjuvant is a compound corresponding to fumagillin of the following formula (II):