Institute of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldstrasse 10, 07743 Jena, Germany.
J Fluoresc. 2011 May;21(3):1195-204. doi: 10.1007/s10895-010-0798-7. Epub 2011 Jan 11.
Due to their optical and electro-conductive attributes, carbazole derivatives are interesting materials for a large range of biosensor applications. In this study, we present the synthesis routes and fluorescence evaluation of newly designed carbazole fluorosensors that, by modification with uracil, have a special affinity for antiretroviral drugs via either Watson-Crick or Hoogsteen base pairing. To an N-octylcarbazole-uracil compound, four different groups were attached, namely thiophene, furane, ethylenedioxythiophene, and another uracil; yielding four different derivatives. Photophysical properties of these newly obtained derivatives are described, as are their interactions with the reverse transcriptase inhibitors such as abacavir, zidovudine, lamivudine and didanosine. The influence of each analyte on biosensor fluorescence was assessed on the basis of the Stern-Volmer equation and represented by Stern-Volmer constants. Consequently we have demonstrated that these structures based on carbazole, with a uracil group, may be successfully incorporated into alternative carbazole derivatives to form biosensors for the molecular recognition of antiretroviral drugs.
由于咔唑衍生物具有光学和导电性，因此它们是一类适用于多种生物传感器应用的有趣材料。在本研究中，我们提出了新设计的咔唑荧光传感器的合成路线和荧光评估，这些传感器通过与尿嘧啶的修饰，通过 Watson-Crick 或 Hoogsteen 碱基配对，对抗逆转录病毒药物具有特殊亲和力。我们将四个不同的基团（噻吩、呋喃、乙撑二氧噻吩和另一个尿嘧啶）连接到一个 N-辛基咔唑-尿嘧啶化合物上，得到了四个不同的衍生物。描述了这些新获得的衍生物的光物理性质及其与逆转录酶抑制剂（如阿巴卡韦、齐多夫定、拉米夫定和去羟肌苷）的相互作用。根据 Stern-Volmer 方程评估了每个分析物对生物传感器荧光的影响，并由 Stern-Volmer 常数表示。因此，我们已经证明，基于咔唑和尿嘧啶基团的这些结构可以成功地纳入替代咔唑衍生物中，以形成用于分子识别抗逆转录病毒药物的生物传感器。
