Nasiri Azadeh, Mokhtari Shaya, Daraei Bahram, Yazdanpanah Hassan, Faizi Mehrdad, Kobarfard Farzad
Department of Pharmacology and Toxicology, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
Food Safety Research Center, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
Iran J Pharm Res. 2022 May 24;21(1):e127036. doi: 10.5812/ijpr-127036. eCollection 2022 Dec.
Aldehydes are compounds that are widely used and popular in organic synthesis due to their high reactivity. This advantage is a disadvantage in medicinal chemistry. Due to the ability of aldehydes to participate in nucleophilic reactions (especially in aqueous biological media) and access to nucleophiles such as amino acids and nucleic acids, drugs with aldehyde functional groups are always used with caution and carefully quantified in biological fluids. Our experience in working on biologically active aldehydes indicates the transformation of these groups of compounds in aqueous or alcoholic solution and thus the failure of analytical methods for their accurate monitoring in such media. Both mass spectrometry and Proton nuclear magnetic resonance spectroscopic findings indicate the reaction of spiramycin with water molecules in an aqueous solution, resulting in the conversion of spiramycin to a new molecule with 18 mass unit difference and thus, the residue amount which is measured and reported based on a mass spectrometries method does not show the correct amount of spiramycin in these samples.
醛类化合物因其高反应活性而在有机合成中被广泛使用且备受关注。然而，这一优势在药物化学领域却成为了劣势。由于醛类能够参与亲核反应（尤其是在水性生物介质中），并且易与氨基酸和核酸等亲核试剂发生反应，所以含有醛官能团的药物在生物流体中使用时总是需要谨慎对待，并要仔细定量。我们在研究生物活性醛类方面的经验表明，这些化合物在水溶液或醇溶液中会发生转化，从而导致在这类介质中对其进行准确监测的分析方法失效。质谱分析和质子核磁共振光谱分析结果均表明，螺旋霉素在水溶液中会与水分子发生反应，导致螺旋霉素转化为一个质量相差18个单位的新分子，因此，基于质谱法测量和报告的残留量并不能准确反映这些样品中螺旋霉素的实际含量。
