The Second-Generation Click-to-Sense Probe for Intraoperative Diagnosis of Breast Cancer Tissues Based on Acrolein Targeting

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.