Combination　treatments　are　more　effective　than　conventional　monotherapy　in　combating　cancer.　Herein,　a　multifunctional　prodrug　BDP-L-CPT　was　rationally　engineered　and　prepared　by　the　conjugation　of　a　boron　dipyrromethene　(BDP)-based　photosensitizer　(PS)　to　the　active　site　of　the　chemotherapeutic　drug　camptothecin　(CPT)　via　a　phenyl　benzoate　group.　After　modification,　the　cytotoxicity　of　CPT　was　locked.　Moreover,　the　fluorescence　emission　at　430　nm　from　the　CPT　component　in　the　prodrug　was　substantially　inhibited　through　the　intramolecular　fluorescence　resonance　energy　transfer　process.　The　phenyl　benzoate　linker　in　BDP-L-CPT　could　be　selectively　cleaved　by　exogenous　carboxylesterase　in　phosphate-buffered　saline　solution　and　endogenous　carboxylesterase　overexpressed　in　cancer　cells,　which　was　followed　by　self-immolation　to　release　free　CPT.　The　drug　release　process　could　be　monitored　by　the　turn-on　of　CPT　fluorescence　in　solution　and　cells.　Owing　to　the　combination　of　site-specific　chemotherapy　with　light-driven　photodynamic　therapy,　the　IC50　values　of　the　prodrug　BDP-L-CPT　against　HepG2　human　hepatocellular　carcinoma　and　HeLa　human　cervical　carcinoma　cells　were　lower　than　those　of　the　controls,　BDP-COOH　and　CPT.　The　combined　antitumor　effects　of　the　prodrug　BDP-L-CPT　were　also　observed　in　the　mice　bearing　H22　tumors.　Furthermore,　BDP-L-CPT　had　a　more　prolonged　blood　circulation　time　in　mice　than　CPT,　which　is　beneficial　to　persistent　therapy.　This　study　may　provide　a　promising　strategy　for　a　selective　combination　cancer　treatment　by　conjugating　a　prodrug　to　a　PS.