PMID- 30155533
OWN - NLM
STAT- MEDLINE
DCOM- 20190312
LR  - 20190312
IS  - 1477-0539 (Electronic)
IS  - 1477-0520 (Linking)
VI  - 16
IP  - 35
DP  - 2018 Sep 11
TI  - Synthesis and biological activity of a CXCR4-targeting bis(cyclam) lipid.
PG  - 6479-6490
LID - 10.1039/c8ob01439f [doi]
AB  - A bis(cyclam)-capped cholesterol lipid designed to bind C-X-C chemokine receptor 
      type 4 (CXCR4) was synthesised in good overall yield from 4-methoxyphenol through 
      a seven step synthetic route, which also provided a bis(cyclam) intermediate 
      bearing an octaethyleneglycol-primary amine that can be easily derivatised. This 
      bis(cyclam)-capped cholesterol lipid was water soluble and self-assembled into 
      micellar and non-micellar aggregates in water at concentrations above 8 muM. The 
      bioactivity of the bis(cyclam)-capped cholesterol lipid was assessed using 
      primary chronic lymphocytic leukaemia (CLL) cells, first with a competition 
      binding assay then with a chemotaxis assay along a C-X-C motif chemokine ligand 
      12 (CXCL12) concentration gradient. At 20 muM, the bis(cyclam)-capped cholesterol 
      lipid was as effective as the commercial drug AMD3100 for preventing the 
      migration of CLL cells, despite a lower affinity for CXCR4 than AMD3100.
FAU - Peters, Anna D
AU  - Peters AD
AD  - School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, 
      UK.
FAU - McCallion, Catriona
AU  - McCallion C
FAU - Booth, Andrew
AU  - Booth A
FAU - Adams, Julie A
AU  - Adams JA
FAU - Rees-Unwin, Karen
AU  - Rees-Unwin K
FAU - Pluen, Alain
AU  - Pluen A
FAU - Burthem, John
AU  - Burthem J
FAU - Webb, Simon J
AU  - Webb SJ
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - England
TA  - Org Biomol Chem
JT  - Organic & biomolecular chemistry
JID - 101154995
RN  - 0 (Heterocyclic Compounds)
RN  - 0 (Lipids)
RN  - 0 (Receptors, CXCR4)
RN  - 295-37-4 (cyclam)
SB  - IM
MH  - Cell Line, Tumor
MH  - Chemistry Techniques, Synthetic
MH  - Heterocyclic Compounds/*chemistry
MH  - Humans
MH  - Lipids/*chemical synthesis/chemistry/*pharmacology
MH  - Receptors, CXCR4/*metabolism
MH  - Signal Transduction/drug effects
EDAT- 2018/08/30 06:00
MHDA- 2019/03/13 06:00
CRDT- 2018/08/30 06:00
PHST- 2018/08/30 06:00 [pubmed]
PHST- 2019/03/13 06:00 [medline]
PHST- 2018/08/30 06:00 [entrez]
AID - 10.1039/c8ob01439f [doi]
PST - ppublish
SO  - Org Biomol Chem. 2018 Sep 11;16(35):6479-6490. doi: 10.1039/c8ob01439f.