PMID- 27235981
OWN - NLM
STAT- MEDLINE
DCOM- 20171225
LR  - 20180108
IS  - 1873-4995 (Electronic)
IS  - 0168-3659 (Linking)
VI  - 235
DP  - 2016 Aug 10
TI  - Tunable phosphatase-sensitive stable prodrugs of 5-aminolevulinic acid for tumor 
      fluorescence photodetection.
PG  - 155-164
LID - S0168-3659(16)30326-1 [pii]
LID - 10.1016/j.jconrel.2016.05.047 [doi]
AB  - 5-Aminolevulinic acid (5-ALA) has been at the forefront of small molecule based 
      fluorescence-guided tumor resection and photodynamic therapy. 5-ALA and two of 
      its esters received marketing authorization but suffer from several major 
      limitations, namely low stability and poor pharmacokinetic profile. Here, we 
      present a new class of 5-ALA derivatives aiming at the stabilization of 5-ALA by 
      incorporating a phosphatase sensitive group, with or without self-cleavable 
      linker. Compared to 5-ALA hexyl ester (5-ALA-Hex), these compounds display an 
      excellent stability under acidic, basic and physiological conditions. The 
      activation and conversion into the 5-ALA is controlled and can be 
      structure-tailored. The prodrugs display reduced acute toxicity compared to 
      5-ALA-Hex with superior dose response profiles of protoporphyrin IX synthesis and 
      fluorescence intensity in human glioblastoma cells in vitro. Clinically relevant 
      fluorescence kinetics in vivo shown in U87MG glioblastoma spheroid tumor model in 
      chick embryos provide a solid basis for their further development and translation 
      to clinical fluorescence guided tumor resection and photodynamic therapy.
CI  - Copyright (c) 2016. Published by Elsevier B.V.
FAU - Babic, Andrej
AU  - Babic A
AD  - School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, 
      1211 Geneva, Switzerland. Electronic address: andrej.babic@unige.ch.
FAU - Herceg, Viktorija
AU  - Herceg V
AD  - School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, 
      1211 Geneva, Switzerland.
FAU - Ateb, Imene
AU  - Ateb I
AD  - School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, 
      1211 Geneva, Switzerland.
FAU - Allemann, Eric
AU  - Allemann E
AD  - School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, 
      1211 Geneva, Switzerland.
FAU - Lange, Norbert
AU  - Lange N
AD  - School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, 
      1211 Geneva, Switzerland.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20160525
PL  - Netherlands
TA  - J Control Release
JT  - Journal of controlled release : official journal of the Controlled Release 
      Society
JID - 8607908
RN  - 0 (Prodrugs)
RN  - 0 (Protoporphyrins)
RN  - 88755TAZ87 (Aminolevulinic Acid)
RN  - C2K325S808 (protoporphyrin IX)
RN  - EC 3.1.3.1 (Alkaline Phosphatase)
SB  - IM
MH  - Alkaline Phosphatase/metabolism
MH  - Aminolevulinic Acid/*analogs & derivatives/pharmacology/therapeutic use
MH  - Animals
MH  - Brain Neoplasms/drug therapy
MH  - Cell Line, Tumor
MH  - Chick Embryo
MH  - Chorioallantoic Membrane/pathology
MH  - Fluorescence
MH  - Glioblastoma/drug therapy
MH  - Humans
MH  - *Photochemotherapy
MH  - *Prodrugs/pharmacology/therapeutic use
MH  - Protoporphyrins/metabolism
MH  - Spheroids, Cellular/drug effects/metabolism
OTO - NOTNLM
OT  - 5-Aminolevulinic acid
OT  - Alkaline phosphatase
OT  - Photodynamic therapy
OT  - Prodrugs
OT  - Tumor photodetection
EDAT- 2016/05/29 06:00
MHDA- 2017/12/26 06:00
CRDT- 2016/05/29 06:00
PHST- 2016/03/10 00:00 [received]
PHST- 2016/05/20 00:00 [revised]
PHST- 2016/05/21 00:00 [accepted]
PHST- 2016/05/29 06:00 [entrez]
PHST- 2016/05/29 06:00 [pubmed]
PHST- 2017/12/26 06:00 [medline]
AID - S0168-3659(16)30326-1 [pii]
AID - 10.1016/j.jconrel.2016.05.047 [doi]
PST - ppublish
SO  - J Control Release. 2016 Aug 10;235:155-164. doi: 10.1016/j.jconrel.2016.05.047. 
      Epub 2016 May 25.