The Second-Generation Click-to-Sense Probe for Intraoperative Diagnosis of Breast Cancer Tissues Based on Acrolein Targeting
Ambara R. Pradipta, Hiroyuki Michiba, Anna Kubo, Motoko Fujii, Tomonori Tanei, Koji Morimoto, Kenzo Shimazu, Katsunori Tanaka
Abstract
Abstract Recently, we found that a bulky 2,6-diisopropylphenyl azide is more reactive than a simple phenyl azide toward acrolein. Herein, we conjugated tetramethylrhodamine (TAMRA) to the bulky phenyl azide and utilized it as a second-generation click-to-sense (CTS) probe to analyze cancer by targeting the cellular acrolein. Subsequently, we observed that this second-generation CTS probe could distinguish breast cancer tissues with higher sensitivity than the first-generation CTS probe. Moreover, adding Rh2(OAc)4 to the system promotes the formation of a metal carbenoid intermediate that accelerates the covalent attachment of the probe to an organelle in the cancer cells.