铁草胺B | 14836-73-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 铁草胺B
• 英文名称: deferoxamine iron(III) complex
• 英文别名: ferrioxamine B；Fe(desferrioxamine B)；(deferoxamine)Fe；(DFO)Fe；Fe(DFO)；Feroxamine；N-[5-[[4-[5-[acetyl(oxido)amino]pentylamino]-4-oxobutanoyl]-oxidoamino]pentyl]-N'-(5-aminopentyl)-N'-oxidobutanediamide;iron(3+)
• CAS: 14836-73-8
• 化学式: C₂₅H₄₅FeN₆O₈
• 分子量: 613.515
• InChiKey: SRMBQCVUAVULDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  214
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  iron(III) chloride 、 去铁胺 反应 1.0h， 生成 铁草胺B
  参考文献：
  名称：

  铁摄取氧化还原酶（IruO）使用黄素腺嘌呤二核苷酸半醌中间体还原铁-五聚体

  摘要：

  许多致病菌，包括金黄色葡萄球菌，都使用铁螯合铁载体来获取铁。铁摄取氧化还原酶（IruO）是一种来自金黄色葡萄球菌的含黄素腺嘌呤二核苷酸（FAD）的烟酰胺腺嘌呤二核苷酸磷酸（NADPH）依赖性还原酶，可作为IsdG和IsdI的还原酶，这是两种旁系血红素降解酶。而且，显示出编码IruO的基因对于金黄色葡萄球菌在异羟肟酸酯铁载体上作为唯一铁源的生长是必需的。在这里，我们显示IruO以低微摩尔亲和力结合异羟肟酸酯型铁载体去铁胺B和亚铁铬A，并在NADPH存在下释放Fe（II）。Fe（II）释放的稳态动力学提供k cat /K m值在600到7000 M –1 s –1范围内这些铁载体支持IruO作为铁利用中的铁载体还原酶。通过形成分子内二硫键介导的IruO的晶体结构被解析为两个不同的构象状态。一个推定的铁载体结合位点被确定与FAD辅因子相邻。该位点部分地被堵塞在氧化的IruO结构中，这与这种形式的

  DOI：

  10.1021/acschembio.7b00203

文献信息

• Multifunctional Pt(<scp>iv</scp>) prodrug candidates featuring the carboplatin core and deferoxamine
  作者：Sophia Harringer、Michaela Hejl、Éva A. Enyedy、Michael A. Jakupec、Mathea S. Galanski、Bernhard K. Keppler、Paul J. Dyson、Hristo P. Varbanov

  DOI：10.1039/d1dt00214g

  日期：——

  carboplatin and the iron chelator deferoxamine (DFO) served as a foundation for the development of novel multifunctional prodrugs. Hence, five platinum(IV) complexes, featuring the equatorial coordination sphere of carboplatin, and one or two DFO units incorporated at axial positions, were synthesized and characterized using ESI-HRMS, multinuclear (1H, 13C, 15N, 195Pt) NMR spectroscopy and elemental analysis

  抗癌药物卡铂和铁螯合剂去铁胺 (DFO) 的协同组合为开发新型多功能前药奠定了基础。因此，五铂（IV）配合物，具有卡铂的赤道配位球，和一个或两个DFO单位在轴向位置并入，进行合成，并使用ESI-HRMS，多核（其特征1 H，13 C，15 N，195的Pt ) 核磁共振光谱和元素分析。分析研究表明，DFO 部分的螯合特性在与铂（IV） 核。在源自卵巢畸胎癌 (CH1/PA-1)、结肠癌 (SW480) 和非小细胞肺癌 (A549) 的单层 (2D) 和球状 (3D) 癌细胞模型中评估了化合物的细胞毒活性。铂 ( IV )–DFO 前药显示出中等的体外细胞毒性（由于其缓慢的活化动力学），但与临床使用的铂 ( II )相比，固有化学抗性和化学敏感性细胞系之间以及 2D 和 3D 模型之间的差异较小药物卡铂。
• Th^IV–Desferrioxamine: characterization of a fluorescent bacterial probe
  作者：Kelly Elise Aldrich、Maksim Yuryevich Livshits、Loreen Rose Stromberg、Michael Timothy Janicke、Mila Nhu Lam、Benjamin Stein、Gregory Lawerence Wagner、Rebecca J. Abergel、Harshini Mukundan、Stosh Anthony Kozimor、Laura Margaret Lilley

  DOI：10.1039/d1dt02177j

  日期：——

  Here we present the solution state structure of thorium(iv) desferrioxamine (DFO), a bacterial siderophore, and a synthesized fluorescent conjugate amenable for bacterial imaging.

  在这里，我们展示了铥（IV）去铁胺（DFO）的溶液态结构，这是一种细菌铁载体，并且合成了一种适用于细菌成像的荧光共轭物。
• The iron chelating agent, deferoxamine detoxifies Fe(Salen)-induced cytotoxicity
  作者：Masanari Umemura、Jeong-Hwan Kim、Haruki Aoyama、Yujiro Hoshino、Hidenobu Fukumura、Rina Nakakaji、Itaru Sato、Makoto Ohtake、Taisuke Akimoto、Masatoshi Narikawa、Ryo Tanaka、Takayuki Fujita、Utako Yokoyama、Masataka Taguri、Satoshi Okumura、Motohiko Sato、Haruki Eguchi、Yoshihiro Ishikawa

  DOI：10.1016/j.jphs.2017.07.002

  日期：2017.8

  new anti-cancer compound with intrinsic magnetic properties. Chelation therapy has been widely used in management of metallic poisoning, because an administration of agents that bind metals can prevent potential lethal effects of particular metal. In this study, we confirmed the therapeutic effect of deferoxamine mesylate (DFO) chelation against Fe(Salen) as part of the chelator antidote efficacy.

  铁-沙仑，即μ-氧代-N，N'-双（水杨基）乙二胺铁（Fe（Salen））最近被鉴定为具有固有磁性的新型抗癌化合物。螯合疗法已被广泛用于金属中毒的治疗，因为与金属结合的药剂的施用可以防止特定金属的潜在致死作用。在这项研究中，我们确认了甲磺酸去铁胺（DFO）螯合剂对Fe（Salen）的治疗作用，这是螯合剂解毒剂功效的一部分。DFO给药可降低癌细胞中Fe（Salen）的细胞毒性和ROS生成。DFO（25 mg / kg）减少了Fe（Salen）（25 mg / kg）引起的急性肝和肾功能不全的发作。系统注射致命剂量的Fe（Salen）（200 mg / kg）的小鼠后，DFO（300 mg / kg）可以提高存活率。DFO可以使用较高剂量的Fe（Salen）来治疗癌症的进展状态，而且它似乎还可以减少Fe（Salen）的急性副作用。这使得DFO成为基于Fe（Salen）的癌症治疗的潜在解毒剂候选
• Kinetics and Mechanism of Iron(III) Removal from Citrate by Desferrioxamine B and 3-Hydroxy-1,2-Dimethyl-4-Pyridone
  作者：Bernard Faller、Hanspeter Nick

  DOI：10.1021/ja00088a022

  日期：1994.5

  The second-order rate constants for iron removal from citrate by the chelating agents desferrioxamine B (DFO) and 3-hydroxy-1,2-dimethyl-4-pyridone (L1) were determined. The overall rate constant k(on) for the transfer of Fe from citrate to the chelator is 4 M(-1) s(-1) for DFO and 43 M(-1) s(-1) for L1 at pH 7.4 and 37 degrees C. The kinetics of transfer of iron from citrate to the two chelators was examined in detail, and a possible mechanism is proposed. Both DFO and L1 form a mixed complex with citrate-iron prior to the transfer of the metal ion. The dissociation equilibrium constant of this initial complex is 10 and 0.45 mM for DFO and L1, respectively. The first-order rate constant for its dissociation into free citrate and chelator-Fe is 0.04 and 0.02 s(-1) for DFO and L1, respectively. These results indicate that, at concentrations close to what is achieved in vivo during chelation therapy (10-100 mu M), although DFO has a thermodynamic advantage over L1, the latter acts 10 times faster than DFO in mobilizing citrate-bound iron. This large difference in the kinetics of iron removal is mainly due to the difference in the equilibrium dissociation constant of the initial complex between the chelator and Fe-citrate. The ability of a chelating agent to make a transitory complex with the iron bound to its biological carrier seems to be a major determinant in the kinetics of transfer. Our data show that the reaction pathway for the removal of Fe from citrate by DFO and L1 is different from what was observed with transferrin. Unlike transferrin, L1 (and to a lesser extent DFO) is able to directly interact with the polymeric iron-citrate; thus, depolymerization of Fe-citrate is not the rate-limiting step in the kinetics of transfer.