The history, chemistry and modes of action of carmine and related dyes
The history, chemistry and modes of action of carmine and related dyes
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DOI：
10.1080/10520290701704188
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发表时间：
2007-08-01
影响因子：
1.6
通讯作者：
Dapson, R. W.
中科院分区：
文献类型：
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作者：
Dapson, R. W.
胭脂红已被用于生物染色，根据配方选择性地显示细胞核、染色体或粘蛋白。纵观其在科学上的历史，人们对染料质量的抱怨和沮丧一直存在。染料质量或特性的不稳定阻碍了对染色机制的彻底理解，并导致许多染色溶液的性能不令人满意。本文的目的是（1）详细说明这些问题的原因，这些问题根源于历史、地理和生产，（2）提供减少问题的方法，（3）提供对污渍行为的现代解释。胭脂红是一种“半合成”染料，即，铝和天然染料胭脂虫红（胭脂红酸）的复合物。胭脂红显示出相当大的批次间变异性。地理，政治，历史，农业实践和图像都有助于胭脂虫的变化。此外，胭脂红的生产方法也各不相同。此外，术语的混乱也导致了贴错标签。来自食品工业的压力，要求为酸性食品提供更令人满意的着色剂，这导致了一种新染料氨基胭脂酸的引入，这种染料可能很快进入生物市场。改进的分析方法应有助于生物染色委员会的认证过程。进一步的标准化可以通过取代大多数的增溶胭脂红的方法来实现。这些方法中的大多数使用热，这可能会损坏染料分子。幸运的是，胭脂红很容易通过将水性溶剂的pH值提高到12以上而溶解，并且现在可商购的一种新形式的染料可溶于水而无需加热或pH值调节。综述了胭脂红酸、胭脂红、氨基胭脂红酸和胭脂红酸的化学结构和物理性质。提出了胭脂红的一种新构型，以及胭脂红酸和胭脂红分子由于加热引起的分解而可能发生的变化。每一个主要类别的胭脂红为基础的染色剂被描述为是可能的机制，附着到特定的基板。糖原通过氢键结合胭脂红，正是在这里，胭脂红被热分解可能产生最大的有害影响。细胞核和染色体通过配位键染色，可能还辅以氢键。最后，酸性粘蛋白与胭脂红发生离子反应。后一种情况下的特异性可能是由于在氯化铝存在下形成的独特聚合胭脂红分子。
Carmine has been used in biological staining to demonstrate selectively nuclei, chromosomes or mucins, depending on the formulation. Throughout its history in science, complaints and frustrations have been expressed about dye quality. Inconsistencies in dye quality or identity have prevented thorough understanding of staining mechanisms and have caused many stain solutions to behave unsatisfactorily. The aim of this review is to (1) detail causes of these problems, which are rooted in history, geography and production, (2) offer ways to minimize problems and (3) provide modern explanations for stain behavior. Carmine is a "semi-synthetic" dye, i.e., a complex of aluminum and the natural dye cochineal (carminic acid). Carmine shows considerable batch-to-batch variability. Geography, politics, history, agricultural practices and iconography all contribute to the variability of cochineal. In addition, widely divergent manufacturing methods are used to produce carmine. Also, confusion in terminology has led to mislabeling. Pressure from the food industry for a more satisfactory colorant for acidic foods led to the introduction of a new dye, aminocarminic acid, which could enter the biological market inadvertantly. Improved methods of analysis should help the certification process by the Biological Stain Commission. Further standardization could be achieved by replacing most of the methods of solubilizing carmine. The majority of these methods use heat, which is likely to damage the dye molecule. Fortunately, carmine is readily dissolved by raising the pH of the aqueous solvent above 12, and a new form of the dye, now available commercially, is soluble in water without the: need for heat or pH adjustment. Chemical structures and physical properties of carminic acid, carmine, aminocarminic acid and kermesic acid are reviewed. A new configuration for carmine is proposed, as well as possible changes to carminic acid and carmine molecules as a result of decomposition caused by heating. Each of the major classes of carmine-based stains is described as are possible mechanisms of attachment to specific substrates. Glycogen binds carmine through hydrogen bonding, and it is here that carmine decomposed by heat could have the greatest detrimental impact. Nuclei and chromosomes are stained via coordination bonds, perhaps supplemented by hydrogen bonds. Finally, acidic mucins react ionically with carmine. Specificity in the latter case may be due to unique polymeric carmine molecules that form in the presence of aluminum chloride.