A　series　of　novel　phthalocyanine-doxorubicin　(Pc-DOX)　conjugates　have　been　prepared　with　a　fibroblast　activation　protein　(FAP)-sensitive　linker　of　glycine-proline　(Gly-Pro)　dipeptide.　Meanwhile,　two　Pc-DOX　conjugates　(1　c　and　3　c)　without　FAP-sensitive　linker　have　also　been　prepared　for　comparison.　For　Pc-DOX　conjugates,　the　photosensitizing　properties　of　the　phthalocyanines　are　partly　quenched　after　being　conjugated　with　DOX.　The　aggregation　behavior　of　these　conjugates　is　less　affected　by　the　surfactant　of　Cremophor　EL　compared　with　that　of　corresponding　precursors　in　aqueous　media.　The　FAP-responsive　properties　have　been　demonstrated　by　HPLC　analysis　and　fluorescence　spectroscopy　in　phosphate　buffered　saline.　The　Pc-Gly-Pro-DOX　conjugate　2　b　with　longer　linker　is　more　sensitive　to　FAP　than　the　other　two　Pc-Gly-Pro-DOX　conjugates　(1　b　and　3　b).　The　results　suggest　that　the　longer　linker　and　smaller　steric　hindrance　between　phthalocyanine　and　Dox　units　are　beneficial　for　the　cleavage　of　Gly-Pro　linker　induced　by　FAP,　while　the　axial　or　peripheral　substituted　positions　hardly　allow　the　enzymolysis　of　FAP.　This　work　can　thus　provide　a　valuable　reference　for　the　targeted　chemo-photodynamic　therapy　of　cancer.　©　2018　Wiley-VCH　Verlag　GmbH　&　Co.　KGaA,　Weinheim