Two　amine-terminated　phthalocyanines,　including　mono-alpha-substituted　zinc　phthalocyanine　(ZnPc)　4　and　axially　di-substituted　silicon　phthalocyanine　(SiPc)　6,　as　well　as　their　chlorambucil　(CLB)　conjugates　(5　and　7)　have　been　prepared.　Both　4　and　6　show　very　high　photocytotoxicities　against　HepG2　cells　with　IC50　values　down　to　31　nM　and　9　nM,　respectively.　However,　after　conjugating　with　CLB,　the　anticancer　activities　of　both　conjugates,　ZnPc-CLB　5　(IC50　=　0.20　mu　M)　and　SiPc-CLB　7　(IC50　=　17.47　mu　M),　are　greatly　reduced　as　a　result　of　their　lower　efficiency　in　fluorescence　emission　and　singlet　oxygen　generation　in　aqueous　solution.　Moreover,　both　conjugates　show　significantly　lower　cellular　uptake　than　their　precursors,　4　and　6.　Synergetic　chemo-photodynamic　therapy　could　not　be　observed　on　the　two　conjugates.　(C)　2016　Elsevier　Ltd.　All　rights　reserved.