Comparison between amine-terminated phthalocyanines and their chlorambucil conjugates: Synthesis, spectroscopic properties, and in vitro anticancer activity - Details

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Abstract：

Two　amine-terminated　phthalocyanines,　including　mono-α-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　IC50values　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　μM)　and　SiPc-CLB　7　(IC50=　17.47　μM),　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.　©　2016　Elsevier　Ltd

Keyword：

Anticancer; Chlorambucil; Photodynamic therapy; Phthalocyanine; Structure-activity relationship

Community：

[ 1 ] [Peng, X.-H.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, 350108, China
[ 2 ] [Chen, S.-F.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, 350108, China
[ 3 ] [Zheng, B.-Y.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, 350108, China
[ 4 ] [Zheng, B.-D.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, 350108, China
[ 5 ] [Zheng, Q.-F.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, 350108, China
[ 6 ] [Li, X.-S.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, 350108, China
[ 7 ] [Ke, M.-R.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, 350108, China
[ 8 ] [Huang, J.-D.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, 350108, China

Reprint 's Address：

[Huang, J.-D.]College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou UniversityChina

Email：

jdhuang@fzu.edu.cn

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Source ：

Tetrahedron

ISSN： 0040-4020

Year： 2017

Issue： 4

Volume： 73

Page： 378-384

2 . 3 7 7

JCR@2017

2 . 1 0 0

JCR@2023

ESI HC Threshold：226

JCR Journal Grade：2

CAS Journal Grade：3

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WoS CC Cited Count：

SCOPUS Cited Count： 28

ESI Highly Cited Papers on the List： 0 Unfold All

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Chinese Cited Count：

30 Days PV： 2

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