We have developed a new strategy of tumor-specific glucose transporter (GLUT)-mediated selective drug delivery using amphiphilic fluorescent monoglycocalix[4]arene in docetaxel (DTX) encapsulated nanoparticles (NPs) that leads to significant improvement in cytotoxic activity against a panel of human cancer cells. The fluorescent tracer conjugation in the calixarene enables the self-probed tumor targeting analysis and makes the system potentially suitable for tumor diagnostic imaging.