870016 | 23:2 Diyne PC [DC(8,9)PC]

1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine


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25mg 870016P-25mg 870016P-25mg 1 x 25mg $76.00
200mg 870016P-200mg 870016P-200mg 1 x 200mg $148.00
500mg 870016P-500mg 870016P-500mg 1 x 500mg $290.00
1g 870016P-1g 870016P-1g 1 x 1g $450.00
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23:2 Diyne PC [DC(8,9)PC]

23:2 Diyne PC [DC(8,9)PC]

1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine

Phospholipid containing photo-polymerizable diacetylene fatty acids. These phospholipids produce structures with characteristics of both biomembranes and synthetic polymers.
Notes:
  • The UV wavelength for efficient polymerization of diacetylene-containing lipids is 254nm.
  • Protect diacetylene phospholipids from light, especially in solution.
  • Diacetylene phospholipids will spontaneously polymerize in solution. Store the lipid as a powder for maximum stability.
  • Recommend storage at -20° C or less.
The photopolymerization of diacetylenic lipids is topotactic, thus the rate of polymerization depends strongly upon the correct alignment of the acetylenic monomer units. Efficient photopolymerization can only be achieved if the diacetylenic hydrocarbon chains are in a crystal-like lattice that is present at a temperatures well below the lipid transition temperature (40°C). Diacetylenic lipids are photopolymerized using a low pressure mercury arc lamp, where the photoproduct is initially blue in color and then relaxes to form a red polymer.
Experimental Procedures for the Polymerization of Sonicated Vesicles
Always protect diacetylenic lipids from UV light, thus prepare photopolymerizable membranes in yellow or red light. Prepare sonicated vesicles using a probe sonicator, following typical experimental protocols to prepare small unilamellar vesicles. (In the referenced paper, sonicated vesicles were the only photopolymerized structures obtained, presumably large unilamellar vesicles prepared by extrusion are also polymerizable and membrane curvature does not affect the efficiency of photopolymerization). An aliquot of the vesicles is irradiated at 20°C in a 1-mm quartz cell using a low-pressure Hg arc lamp (253.7 nm) 6-13 cm from the sample. Just prior to irradiation the aqueous suspension of vesicles is purged of oxygen by first flushing the photocell with argon and then capping it under an argon atmosphere.
Notes:
  • It has been found that the photosensitivity of diacetylenic containing membranes is dependent upon its thermal history. Membranes composed of diacetylenic lipids are light sensitive when prepared below the phase trasition but become insensitive to light after the membranes are heated above the transition temperature (40°C). The membranes remain insensitive to light even after they are cooled to 25°C, and only when they are cooled to near 0°C is light sensitivity regained.
  • Photopolymerization of diacetylenic and non-polymerizable lipid (DOPC, DSPC etc.) mixtures depends upon lipid miscibility. High degrees of polymerization cannot be achieved in lipid mixtures where the diacetylenic groups are diluted by other non-polymerizable lipids.
Hygroscopic
No
Light Sensitive
Yes
Molecular Formula
C54H92NO8P
Percent Composition
C 70.94%, H 10.14%, N 1.53%, O 14.00%, P 3.39%
Purity
>99%
Stability
3 Months
Storage Temperature
-20°C
CAS Number
76078-28-9
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
914.284
Exact Mass
913.656
Synonyms
<p>DC(8,9)PCDC8,9PC</p>

Hindley JW, Elani Y, McGilvery CM, Ali S, Bevan CL, Law RV, Ces O. Light-triggered enzymatic reactions in nested vesicle reactors. Nat Commun. 2018 Mar 15;9(1):1093. doi: 10.1038/s41467-018-03491-7.

PubMed ID: 29545566

Punnamaraju S, You H, Steckl AJ. (2012) Triggered Release of Molecules across Droplet Interface Bilayer Lipid Membranes using Photopolymerizable Lipids. Langmuir. 2012 May 22;28(20):7657-64. doi: 10.1021/la3011663. Epub 2012 May 10.

PubMed ID: 22548362

Colantonio S1, Simpson JT, Fisher RJ, Yavlovich A, Belanger JM, Puri A, Blumenthal R. Quantitative analysis of phospholipids using nanostructured laser desorption ionization targets. Lipids. 2011 May;46(5):469-77. doi: 10.1007/s11745-010-3493-1. Epub 2011 Feb 15.

PubMed ID: 21327726

Yavlovich, A., Singh, A., Blumenthal, R., Puri, A. (2011) A novel class of photo-triggerable liposomes containing DPPC:DC(8,9)PC as vehicles for delivery of doxorubicin to cells. Biochim Biophys Acta. 1808:117-26.

PubMed ID: 20691151

Yavlovich, A., Singh, A., Tarasov, S., Capala, J., Blumenthal, R., Puri, A. (2009) Design of liposomes containing photopolymerizable phospholipids for triggered release of contents. J Therm Anal Calorim. 98:97-104.

PubMed ID: 20160877

Hayward, J.A., Chapman, D. (1984) Biomembrane surfaces as models for polymer design: the potential for haemocompatibility. Biomaterials. 5:135-142.

PubMed ID: 6375749

Johnston, D.S., Sanghera, S., Pons, M. Chapman, D. (1980) Phospholipid Polymers-Synthesis and Spectral Characteristics. Biochim Biophys Acta. 602:57-69.

PubMed ID: 6893417

Colantonio, S., Simpson, J.T., Fisher, R.J., Yavlovich, A., Belanger, J.M., Puri, A., Blumenthal, R. (2011) Quantitative analysis of phospholipids using nanostructured laser desorption ionization targets. Lipids. 2011 May;46(5):469-77. doi: 10.1007/s11745-010-3493-1. Epub 2011 Feb 15.

PubMed ID: 21327726