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通过基质辅助激光解吸电离飞行时间质谱法表征胍衍生物与单链DNA之间的特定非共价复合物

Characterization of specific noncovalent complexes between guanidinium derivatives and single-stranded DNA by MALDI.

作者信息

Ohara Keiichiro, Smietana Michael, Vasseur Jean-Jacques

机构信息

Laboratoire de Chimie Organique Biomoléculaire de Synthèse, CNRS-Université Montpellier II, Montpellier, France.

出版信息

J Am Soc Mass Spectrom. 2006 Mar;17(3):283-91. doi: 10.1016/j.jasms.2005.11.005. Epub 2006 Jan 27.

Abstract

Noncovalently bound complexes between highly basic sites of 12 guanidinium compounds and single-stranded DNA were studied using matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. 6-Aza-2-thiothymine (ATT) was used as the matrix in the presence of ammonium citrate, and spectra were recorded in the positive ion mode. Detailed control experiments confirmed unambiguously the high selectivity and specificity of the guanidinium moiety for phosphate groups of DNA. The results verify the binding stoichiometry and show preferential binding of hydrophobic binders (pyrene and anthracene guanidinium derivatives) to all sequences examined. In addition, we demonstrate that electrostatic noncovalent interactions are strengthened with phosphorothioate analogs of DNA. These results clearly highlight the structure-directing role of the self-assembling organic species and strongly emphasize the significance of concentration, hydrophobicity, hydrogen-bonding, and pi-pi interactions of the artificial receptor in the formation of these noncovalent complexes. Because of the ability of DNA-binding compounds to influence gene expression, and therefore cell proliferation and differentiation, the interactions described above could be important in providing a better understanding of the mechanism of action of these noncovalent genetic regulators.

摘要

利用基质辅助激光解吸/电离(MALDI)质谱法研究了12种胍化合物的高碱性位点与单链DNA之间的非共价结合复合物。在柠檬酸铵存在的情况下,使用6-氮杂-2-硫代胸腺嘧啶(ATT)作为基质,并在正离子模式下记录光谱。详细的对照实验明确证实了胍基部分对DNA磷酸基团具有高选择性和特异性。结果验证了结合化学计量,并表明疏水性结合剂(芘和蒽胍衍生物)对所有检测序列具有优先结合性。此外,我们证明了DNA的硫代磷酸酯类似物会增强静电非共价相互作用。这些结果清楚地突出了自组装有机物种的结构导向作用,并强烈强调了人工受体的浓度、疏水性、氢键和π-π相互作用在形成这些非共价复合物中的重要性。由于DNA结合化合物能够影响基因表达,进而影响细胞增殖和分化,上述相互作用对于更好地理解这些非共价基因调节剂的作用机制可能具有重要意义。

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