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Bio-orthogonal Phosphatidylserine Conjugates for Delivery and Imaging Applications.

  作者 Lampkins, Andrew J.;O'Neil, Edward J.;Smith, Bradley D.;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-16;  页码  6053-6058  
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[摘要]The syntheses of phosphatidylserine (PS) conjugates are described, including fluorescent derivs. for potential cellular delivery and bioimaging applications. Installation of terminal functional groups (amine, thiol, or alkyne) onto the sn-2 chain provides reactive sites for bio-orthogonal conjugation of cargo with suitably protected PS derivs. An amine-contg. PS forms amide bonds with peptidic cargo, a thiol deriv. is designed for conjugation to cargo that contain a-halo carbonyls or Michael acceptors, and the terminal alkyne PS analog permits "click" conjugation with any azide-tagged mol. This latter conjugation method is quite versatile as it can be performed without PS headgroup protection, in aq. media, and with acid-labile cargo.

 
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