[Fe2(cysteamine)2(NO)4] | 356041-78-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [Fe2(cysteamine)2(NO)4]
• 英文别名: [Fe₂(cysteamine)₂(NO)₄]；[(NO)₂Fe(μ-SEtNH₂)₂Fe(NO)₂]
• CAS: 356041-78-6
• 化学式: C₄H₁₂Fe₂N₆O₄S₂
• 分子量: 384.003
• InChiKey: JKIAYSHEMRNHNU-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  [Fe2(cysteamine)2(NO)4] 、 2-巯基乙醇 以 四氢呋喃 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Water-Soluble Dinitrosyl Iron Complex (DNIC): a Nitric Oxide Vehicle Triggering Cancer Cell Death via Apoptosis

  摘要：

  Nitric oxide (NO) is an important cellular signaling molecule that modulates various physiological activities. Angiogenesis-promoting activities of NO-donor drugs have been explored in both experimental and clinical studies. In this study, a structurally well characterized and water-soluble neutral {Fe-(NO)(2)}(9) DNIC [(S(CH2)(2)OH)(S(CH2)(2)NH3)Fe(NO)(2)] (DNIC 2) was synthesized to serve as a NO-donor species. The antitumor activity of DNIC 2 was determined by MTT assay, confocal imaging, and Annexin-V/PI staining. The IC50 values of DNIC 2 were 18.8, 42.9, and 38.6 mu M for PC-3, SKBR-3, and CRLS866 tumor cells, respectively. Moreover, DNIC 2 promoted apoptotic cell death via activation of apoptosis-associated proteins and inhibition of survival associated proteins. In particular, DNIC 2 treatment suppressed PC-3 tumor growth by 2.34- and 19.3-fold at 7 and 21 days, in comparison with the control group. These results indicate that water-soluble DNIC 2 may serve as a promising drug for cancer therapy.

  DOI：

  10.1021/acs.inorgchem.6b01562
• 作为产物：
  描述：

  在 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 [Fe2(cysteamine)2(NO)4]
  参考文献：
  名称：

  Formation Pathway of Roussin’s Red Ester (RRE) via the Reaction of a {Fe(NO)₂}¹⁰ Dinitrosyliron Complex (DNIC) and Thiol: Facile Synthetic Route for Synthesizing Cysteine-Containing DNIC

  摘要：

  Transformation of {Fe(NO)(2)}(10) dinitrosyliron complex (DNIC) Fe(CO)(2)(NO)(2) into [{Fe(NO)(2)}(9)](2) Roussin's red ester (RRE) [(mu-S(CH2)(2)NH2)Fe(NO)(2)](2) (3) triggered by cysteamine via the reaction pathway (intermediates) [{Fe-(NO)(2)}(10)]2[(NO)(2)Fe(mu-CO)(mu-S(CH2)(2)NH3)Fe(NO)(2)] (1) -> {Fe(NO)(2)}(9){Fe(NO)(2)}(10)[(NO)(2)Fe(mu-S(CH2)(2)NH2)(mu-S(CH2)(2)-NH3)Fe(NO)(2)] (2) -> RRE 3 is demonstrated. The 1-to-2-to-3 conversion is promoted by proton transfer followed by O-2 oxidation and deprotonation. Additionally, a study on facile conversion of complex 3 to complexes [(SR)(S(CH2)(2)NH3)Fe-(NO)(2)] [SR = 2-aminoethanethiolate (4), benzenethiolate (5)] and [(CysS))(S(CH2)(2)NH3)Fe(NO)(2)] (6) via reaction with thiols and the further utility of complex 5 as a template for synthesizing mixed-thiolate-containing reduced RRE (rRRE)[(mu-SC6H5)(mu-S(CH2)(2)NH3)Fe-2(NO)(4)] (7) provide the methodology for the synthesis and isolation of neutral, pure cysteine-/ mixed-thiolate-containing DNIC/RRE. Compared to the conversion of complex 2 to complex 3 via reaction with O-2, diphenyl disulfide triggers oxidation of complex 2 to lead to formation of the neutral {Fe(NO)(2)}(9) DNIC 5 and RRE 3. S-S bond activation of diphenyl disulfide by rRRE 2 may support the decay (oxidation) of rRRE species in ToMOC via the reduction of adjacent protein residues such as cystins, proposed by Lippard.

  DOI：

  10.1021/ic402364p

文献信息

• Re-examination of the formation of dinitrosyl–iron complexes during reaction of S-nitrosothiols with Fe(II)
  作者：Simona Costanzo、Stephane Ménage、Roberto Purrello、Raffaele P Bonomo*、Marc Fontecave*

  DOI：10.1016/s0020-1693(01)00402-9

  日期：2001.6

  The reaction of S-nitrosothiol compounds with ferrous ions in solution has been investigated and the generated dinitrosyl-iron complexes have been characterized. During the reaction of S-nitrosocysteamine with Fe(II) in water solution in the presence of a twofold excess (with respect to iron) of cysteamine hydrochloride (CSH), an EPR-silent dinuclear iron complex (complex A of formula [Fe-2(RS)(2)(NO)(4)]) was formed as the major species and was characterized by FAB MS+, UV-Vis, NMR and IR spectroscopies. In the presence of a large excess of CSH (CSH/Fe(II) = 20:1), a green paramagnetic mononuclear complex (complex B of formula [Fe(RS)(2)(NO)(2)](-)) was formed. From EPR and UV-Vis data, and also on the basis of the few crystallographic structures known for similar complexes, complex B is proposed to display a distorted tetrahedral geometry (C-2 nu), approaching a trigonal bipyramid with a missing ligand, with the unpaired electron mainly localized on the d(z2), orbital of the iron characterized by a d(9) electronic configuration. (C) 2001 Elsevier Science B.V. All rights reserved.