Oxidation-reduction and photophysical properties of isomeric forms of Safranin.

Oxidation-reduction and photophysical properties of isomeric forms of Safranin.
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DOI:
10.1371/journal.pone.0265105
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发表时间:
2022
期刊:
影响因子:
3.7
通讯作者:
--
中科院分区:
综合性期刊3区
文献类型:
--
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藏红O广泛用于生物能量学领域,作为指示染料测定膜电位,并作为电位滴定中的电子传递介质。在这里,我们表明,藏红O的两种不同的商业制剂含有不到百分之六十的标题化合物的重量,其余主要由两个密切相关的藏红异构体。使用反相HPLC分离所有三种主要异构体组分,并使用质谱和二维NMR确定其结构。这些番红的双电子中点电位范围为−272至−315 mV(相对于SHE)。我们还研究了这些化合物的吸收光谱和荧光光谱,发现它们具有独特的光谱和物理性质。虽然这种混合物可能有助于藏红O作为介体化合物的效用,但膜电位测量必须考虑到染料电位的这一范围。
Safranine O is widely used in the bioenergetics community as an indicator dye to determine membrane potentials and as an electron transfer mediator in potentiometric titrations. Here we show that two different commercial preparations of Safranine O contain less than sixty percent by weight of the title compound, with the rest primarily consisting of two closely related safranine isomers. All three major isomer components were isolated using reverse phase HPLC and their structures determined using mass spectrometry and two-dimensional NMR. These Safranines have two-electron midpoint potentials ranging from −272 to −315 mV vs. SHE. We have also investigated the absorption and fluorescence spectra of the compounds and found that they display distinct spectral and photophysical properties. While this mixture may aid in Safranine O’s utility as a mediator compound, membrane potential measurements must take this range of dye potentials into account.
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