PMID- 27628428
OWN - NLM
STAT- MEDLINE
DCOM- 20180509
LR  - 20180509
IS  - 1521-3765 (Electronic)
IS  - 0947-6539 (Linking)
VI  - 22
IP  - 49
DP  - 2016 Dec 5
TI  - Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors.
PG  - 17514-17525
LID - 10.1002/chem.201602947 [doi]
AB  - In 2001, two years before the disclosure of the CERT-associated Cer transfer 
      machinery, N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)alkanamides (HPAs) were 
      described as the first, and to date unique, family of intracellular Cer 
      trafficking inhibitors. The dodecanamide derivative, HPA-12, turned out to be a 
      benchmark as a cellular inhibitor of CERT-mediated de novo sphingomyelin 
      biosynthesis. In only 15 years after its first disclosure, this compound has 
      prompted a growing number of biological and chemical studies. Its initial 
      chemical development closely paralleled the study of the CERT protein. It was 
      only after its structural revision in 2011 that HPA-12 received broad attention 
      from the synthetic chemistry community, leading to novel analogues with enhanced 
      protein binding. This Minireview aims at presenting an exhaustive report of the 
      syntheses of HPA-12 and analogues. Biological activities of this CERT inhibitor 
      and structure-activity relationships are also presented to afford a comprehensive 
      overview of the chemistry and biology of the HPA series.
CI  - (c) 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
FAU - Berkes, Dusan
AU  - Berkes D
AD  - Department of Organic Chemistry, Slovak University of Technology, Radlinskeho 9, 
      81237, Bratislava, Slovak Republic.
FAU - Daich, Adam
AU  - Daich A
AD  - Normandie Univ, UNIHAVRE, CNRS, URCOM, Universite du Havre, URCOM EA-3221, INC3 M 
      CNRS FR-3038, UFR des Sciences et Techniques, 25 rue Philippe Lebon, B.P. 1123, 
      76063, Le Havre Cedex, France.
FAU - Santos, Cecile
AU  - Santos C
AD  - SPCMIB, UMR5068 CNRS-, Universite Paul Sabatier-Toulouse III, 118 route de 
      Narbonne, 31062, Toulouse, France.
FAU - Ballereau, Stephanie
AU  - Ballereau S
AUID- ORCID: 0000-0002-7250-6188
AD  - SPCMIB, UMR5068 CNRS-, Universite Paul Sabatier-Toulouse III, 118 route de 
      Narbonne, 31062, Toulouse, France.
FAU - Genisson, Yves
AU  - Genisson Y
AD  - SPCMIB, UMR5068 CNRS-, Universite Paul Sabatier-Toulouse III, 118 route de 
      Narbonne, 31062, Toulouse, France.
LA  - eng
PT  - Journal Article
PT  - Review
DEP - 20160915
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
RN  - 0 (Amides)
RN  - 0 (Ceramides)
RN  - 0 (N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide)
SB  - IM
MH  - Amides/*chemistry
MH  - Cell Movement
MH  - Ceramides/*chemistry
MH  - Structure-Activity Relationship
OTO - NOTNLM
OT  - 1,3-amino alcohol
OT  - CERT protein
OT  - HPA-12
OT  - ceramide
OT  - sphingolipids
EDAT- 2016/09/16 06:00
MHDA- 2018/05/10 06:00
CRDT- 2016/09/16 06:00
PHST- 2016/06/20 00:00 [received]
PHST- 2016/09/16 06:00 [pubmed]
PHST- 2018/05/10 06:00 [medline]
PHST- 2016/09/16 06:00 [entrez]
AID - 10.1002/chem.201602947 [doi]
PST - ppublish
SO  - Chemistry. 2016 Dec 5;22(49):17514-17525. doi: 10.1002/chem.201602947. Epub 2016 
      Sep 15.