PMID- 20063872
OWN - NLM
STAT- MEDLINE
DCOM- 20100427
LR  - 20100128
IS  - 1520-5207 (Electronic)
IS  - 1520-5207 (Linking)
VI  - 114
IP  - 4
DP  - 2010 Feb 4
TI  - Endogenous nonionic saturated monoethanolamide lipids: solid state, lyotropic 
      liquid crystalline, and solid lipid nanoparticle dispersion behavior.
PG  - 1729-37
LID - 10.1021/jp910578h [doi]
AB  - The n-acylethanolamides (NAEs) are a family of naturally occurring 
      monoethanolamide containing lipids that display a variety of interesting 
      biological properties. In this study, some physicochemical properties of a series 
      of saturated monoethanolamide lipids with increasing hydrocarbon chain length 
      (lauroyl, myristoyl, palmitoyl, and stearoyl) have been investigated. Temperature 
      induced phase transitions for these NAEs indicate that both the monoethanolamide 
      headgroups and the unsaturated hydrophobic tails play a role in the melting 
      behavior of these lipids. All four lipids examined demonstrate the presence of at 
      least three different polymorphic crystal forms. Transitions in crystal structure 
      can be induced via heating and visualized with polarized optical microscopy. At 
      room and physiological temperature, the four NAEs are solid lamellar crystalline 
      materials. All four molecules form lyotropic liquid crystalline phases in water, 
      albeit at relatively high temperatures, including the lamellar liquid crystalline 
      phase and at least two isotropic phases. Lamellar crystalline palmitoyl 
      monoethanolamide was dispersed as solid lipid nanoparticles (SLNs). The 
      cytotoxicity of these SLNs toward human mammary epithelial cells (HMEpiC) and the 
      MCF7 breast cancer cell line was assessed at physiological temperature. The 
      palmitoyl monoethanolamide SLNs showed little to no toxicity to the HMEpiC even 
      at a concentration of 30 microM. At concentrations above 3 microM, the HMEpiC 
      population was reduced by less than 15%, while the MCF7 population was reduced by 
      approximately 20-30%. The endogenous nature and natural medicinal properties make 
      this series of lipids ideal candidates for further investigation as solid lipid 
      nanoparticle drug delivery systems.
FAU - Sagnella, Sharon M
AU  - Sagnella SM
AD  - CSIRO Molecular and Health Technologies, P.O. Box 184, North Ryde, New South 
      Wales 1670, Australia.
FAU - Conn, Charlotte E
AU  - Conn CE
FAU - Krodkiewska, Irena
AU  - Krodkiewska I
FAU - Moghaddam, Minoo
AU  - Moghaddam M
FAU - Drummond, Calum J
AU  - Drummond CJ
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - United States
TA  - J Phys Chem B
JT  - The journal of physical chemistry. B
JID - 101157530
RN  - 0 (Amides)
RN  - 0 (Lipids)
SB  - IM
MH  - Amides/*chemistry
MH  - Calorimetry, Differential Scanning
MH  - Cell Line, Tumor
MH  - Humans
MH  - Lipids/*chemistry
MH  - Liquid Crystals/*chemistry
MH  - Nanoparticles/*chemistry/toxicity
MH  - Phase Transition
MH  - Transition Temperature
EDAT- 2010/01/13 06:00
MHDA- 2010/04/28 06:00
CRDT- 2010/01/13 06:00
PHST- 2010/01/13 06:00 [entrez]
PHST- 2010/01/13 06:00 [pubmed]
PHST- 2010/04/28 06:00 [medline]
AID - 10.1021/jp910578h [doi]
PST - ppublish
SO  - J Phys Chem B. 2010 Feb 4;114(4):1729-37. doi: 10.1021/jp910578h.