Small angle X-ray scattering (SAXS) and differential scanning calorimetry (DSC) studies of amide phospholipids

Zhai, Xiuhong; Bartel, Markus; Brezesinski, Gerald; Rattay, Bernd; Möhwald, Helmuth; Li, Junbai

doi:10.1016/j.chemphyslip.2004.09.013

Cited by 8 publications

(9 citation statements)

References 30 publications

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“…For T-ester-amide-PC, the T c value (39.1 °C) was also similar to the T m value (39.7 °C). However, in the case of T-ether-amide-PC, T m (47 °C) 24 is considerably higher than T c indicating distinct differences in packing properties between mono-and bilayers.…”

Section: Resultsmentioning

confidence: 87%

“…Materials. 1- O -Hexadecyl-2- N -palmitoyl-2-amino-2-deoxy- sn - glycero -3-phosphocholine ( l -ether-amide-PC) and 1-palmitoyl-2- N -palmitoyl-2-amino-2-deoxy- sn - glycero -3-phosphocholine ( l -ester-amide-PC) were synthesized based on the procedures described previously , and have been characterized by NMR. The relevant chemical structures are shown in Scheme .…”

Section: Methodsmentioning

confidence: 99%

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Thermodynamics and Structures of Amide Phospholipid Monolayers

et al. 2004

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Monolayers of newly synthesized amide phospholipids, 1-O-hexadecyl-2-N-palmitoyl-2-amino-2-deoxy-snglycero-3-phosphocholine (L-ether-amide-PC) and 1-palmitoyl-2-N-palmitoyl-2-amino-2-deoxy-sn-glycero-3-phosphocholine (L-ester-amide-PC) were investigated at the air/subphase interface by Brewster angle microscopy combined with a conventional LB trough and Grazing incidence X-ray diffraction (GIXD). Both systems investigated exhibit two-dimensional domains with characteristic shape in the coexistence region between liquid-expanded (LE) and liquid-condensed (LC) phases. Especially L-ether-amide-PC shows highly chiral domains depending on temperature. The largest chiral domains (400 µm) growing in a clockwise direction are obtained at 25 °C. Such large domains have rarely been observed for phospholipids before. Thermodynamic data derived from π-A isotherms provide information about critical temperature (T c ) and phase transition enthalpy (∆H) for both amide phospholipids. The amide group leads to pronounced differences in the thermodynamic parameters compared with DPPC. The two-dimensional structures of the monolayers were investigated by GIXD. The results show that both amide phospholipids exhibit chiral in-plane structures. In the case of L-ether-amide-PC, the tilt angle of the aliphatic chains decreases only slightly with increasing pressure. On the contrary, the tilt angle of the aliphatic chains of L-ester-amide-PC shows strong dependence on surface pressure similar to DPPC. Possible hydrogen bonds involving the amide group seem to enhance the chiral interaction and play therefore a key role in the formation of extremely large chiral domains. The affects of substitution in the sn-1 position on structure formation are discussed in detail.

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Section: Resultsmentioning

confidence: 87%

Section: Methodsmentioning

confidence: 99%

Thermodynamics and Structures of Amide Phospholipid Monolayers

et al. 2004

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“…Addition of the surfactant also extended the range of the main phase transition and The SAXS and FTIR studies were supported by DSC results. It is well documented that phase transitions observed in DPPC systems can be visualized by dierential scanning calorimetry [38,39]. DSC thermograms obtained for the reference DPPC and DPPC/surfactant systems are shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Structural Changes of DPPC Bilayers Induced by Gemini Surfactant

Kida

Kozak

2012

Acta Phys. Pol. A

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The phospholipidgemini surfactant systems are promising agents for construction of lipoplexes for DNA delivery systems in gene therapy. In this work the inuence of a gemini surfactant 1,1 ′ -(1,6-hexan)bis3-octyloxymethylimidazolium di-chloride) (IMI_Cl_C6_C8) on the structure and phase behaviour of aqueous suspensions of the fully hydrated phospholipid 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) were characterised using small angle scattering of synchrotron radiation (SAXS), dierential scanning calorimetry (DSC) and Fourier transform infrared spectroscopy (FTIR). The surfactant studied caused a destabilisation of the lamellar phase typical of DPPC. Addition of the surfactant also shifted to lower temperatures and extended the range of the main phase transition

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“…Diacylation with palmitoyl chloride and DMAP in chloroform 29 afforded 23 (Scheme 2). Hydrogenolysis of 23 over Pearlman’s catalyst proceeded smoothly to give the desired alcohol 24 .…”

Section: Synthesis Of 6-mannosylated-myo-inositol 15mentioning

confidence: 99%

“…The commercially available (R)-(+)-2-amino-3-benzyloxy-1-propanol (22) was used as a starting material for the synthesis of the 2-amido containing phosphoramidite 18. Diacylation with palmitoyl chloride and DMAP in chloroform 29 afforded 23 (Scheme 2). Hydrogenolysis of 23 over Pearlman's catalyst proceeded smoothly to give the desired alcohol 24.…”

Section: T H Imentioning

confidence: 99%

Synthesis and Toll-like Receptor 4 (TLR4) Activity of Phosphatidylinositol Dimannoside Analogues

Ainge¹,

Martin

Compton³

et al. 2011

J. Med. Chem.

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A series of five PIM2 analogues were synthesized and tested for their ability to activate primary macrophages and modulate LPS signaling. Structural changes included replacement of the fatty acid esters of the phosphatidyl moiety of PIM2 with the corresponding ether or amide. An AcPIM2 analogue possessing an ether linkage was also prepared. The synthetic methodology utilized an orthogonally protected chiral myo-inositol starting material that was conveniently prepared from myo-inositol in just two steps. Important steps in the synthetic protocols included the regio- and α-selective glycosylation of inositol O-6 and introduction of the phosphodiester utilizing phosphoramidite chemistry. Replacement of the inositol core with a glycerol moiety gave compounds described as phosphatidylglycerol dimannosides (PGM2). Biological testing of these PIM compounds indicated that the agonist activity was TLR4 dependent. An ether linkage increased agonist activity, removal of the inositol ring enhanced antagonist activity and the presence of an additional lipid chain enhanced LPS-induced cytokine production in primary macrophages. Furthermore, the interruption of the LPS-induced TLR4/MD-2 2:2 signaling complex formation by PIM2 represents a previously unidentified mechanism involved in the bioactivity of PIM molecules.

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Small angle X-ray scattering (SAXS) and differential scanning calorimetry (DSC) studies of amide phospholipids

Cited by 8 publications

References 30 publications

Thermodynamics and Structures of Amide Phospholipid Monolayers

Thermodynamics and Structures of Amide Phospholipid Monolayers

Structural Changes of DPPC Bilayers Induced by Gemini Surfactant

Synthesis and Toll-like Receptor 4 (TLR4) Activity of Phosphatidylinositol Dimannoside Analogues

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