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In this study, we synthesized a series of molecules derived from the traditional nucleic acid probe thiazole orange (TO), by incorporating alkyl chains of varying lengths and hydrophilic functional groups. Among them, the specific lipophilicity of TO\u2010Ac (a derivative of TO) enables its penetration into cancer cells, where it binds to nucleic acids and generates intense fluorescence, while being effectively excluded by normal cell membranes. The differential cholesterol content in cell plasma membranes was confirmed to influence the selective uptake of molecules in cancer cells. Accordingly, we established a quantitative design criterion (LogP\u00a0=\u00a01.48\u20131.62) that predicts cancer cell specificity based on oil\u2010water partition coefficients. Finally, TO\u2010Ac was successfully applied for detection of early\u2010stage colon cancer, enabling complete tumor resection via fluorescence imaging while identifying lesions that would otherwise remain undetected. 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