Paul.xu at 13:43, 18 July 2014

2014-07-18T13:43:31Z

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[[Image:PHP structure.jpg]]

[[Image:PHP.jpg]]

 

[[Image:Diamines.jpg|400px|Diamines.jpg]]

[[Image:PHP mw.jpg|400px|PHP mw.jpg]]

 

[[Image:PHP NMR.jpg|400px|PHP NMR.jpg]]

[[Image:PHP pKa.jpg|400px|PHP pKa.jpg]]

 

[[Image:PHP size.jpg|400px|PHP size.jpg]]

 

pHP: poly(2-hydroxypropylene imine)

pHPE: poly(2-hydroxypropylene imine ethylene imine)

pHPP: poly(hydroxypropylene imine propylene imine) 

[[Image:Comparison_PHP_pHPE_pHPP.png|400px]]

Synthesis

== Synthesis of pHP ==

In a three-neck 50 mL round-bottom reaction flask, fitted with a stirrer, dropping funnel and a thermometer, '''1,3-diamino-2-propanol''' ('''1.5 g''') was dissolved in methanol (3 mL). Resulting solution was preheated 50° C. and upon vigorous stirring '''1,3-dibromo-2-propanol''' ('''3.63 g''', '''1.7 mL''') was added. Reaction mixture was stirred for '''48 hours at 50° C'''. Upon completion the viscous polycondensation reaction mixture was diluted with distilled water (10 mL) and dialyzed against water for 5 days with SERVA Membra-Cel visking dialysis tubing MWCO '''4 kDa'''. Dialysis solution was concentrated under reduced pressure until ca 25% of starting volume and then freeze-dried to furnish pHP poly(2-hydroxypropylene imine) ('''0.78 g''', 32%).

== Synthesis of pHPE ==

To the stirred solution of '''1,3-diamino-2-propanol''' ('''3.00 g''') in methanol ('''4 mL)''' in a three-neck 50 mL round-bottom reaction flask, equipped with a stirrer, dropping funnel and a thermometer, '''1,2-dibromoethane''' ('''6.25 g, 2.87 mL''') was added drop-wise. The resulting solution was stirred for 48 hours at 50° C. Resulting viscous polycondensation reaction mixture was diluted with distilled water (10 mL) and dialyzed against water for 5 days with SERVA Membra-Cel dialysis tubing MWCO 4 kDa. Dialysis solution was concentrated under reduced pressure and resulting polymer was further dried using oil pump to give pHPE (poly(2-hydroxypropylene imine ethyleneimine) ('''0.81 g''', 21%).

== Synthesis of pHPP ==

To the stirred preheated (50° C.) solution of '''1,3-diamino-2-propanol (3.00 g) '''in methanol ('''4 mL''') in a three-neck 50 mL round-bottom flask, equipped with a stirrer, dropping funnel and a thermometer '''1,3-dibromopropane (6.72 g, 3.38 mL)''' was added drop-wise. Resulting solution was stirred for '''24 hours at 50° C'''. Upon completion the viscous polycondensation reaction mixture was diluted with distilled water (10 mL) and dialyzed against water for 5 days with SERVA Membra-Cel visking dialysis tubing MWCO 4 kDa. Dialysis solution was concentrated under reduced pressure until ca 25% of starting volume and then freeze-dried to yield pHPP (poly(2-hydroxypropylene imine propylene imine) ('''1.2 g, '''28%). 

 

1.5 g 1,3-DA-2-P 16.6 mmole, + 3 ml MeOH to dissolve, + 3.63 g 1,3-DB-2-P (16.6 mmole), 50 oc for 48 hours

add 6X1ml MeOH to wash, spin, remove soluble material, collect pellet (~3.5 g wet weight).

Add 5 ml h2O to insoluble polymer to dissolve

add 15 ml EtOH, --> precipitate, votex, spin decant EtOH

Wash 2 more times with EtOH

dry at 50 oC, got 1.6 g white powder

dissolve 0.6 g powder in 2 ml H2O~>2200 ul.

dissolve 0.7 g PEI18 in 3.1 ml H2O-->3.6 ml

suspend 0.3 g CBA in 10% MeOH 

{| width="200" cellspacing="1" cellpadding="1" border="1"
|-
| 
| PHP 
| PEI18 
| CBA 
|-
| TR1 
| 0.2 
| 0.05 
| 0.05 
|-
| TR2 
| 0.2 
| 0.1 
| 0.05 
|-
| TR3 
| 0.2 
| 0.2 
| 0.05 
|-
| TR4 
| 0 
| 0.05 
| 0.05 
|-
| TR5 
| 0 
| 0.1 
| 0.05 
|-
| TR6 
| 0 
| 0.2 
| 0.05 
|}

 

 

50 oC O/N.

 

TR2+: mix TR1+TR2 reaction solution, add 0.15 g PEI18 and 0.1 g CBA, reaction at 50 oC O/N

TR6+: add 0.2 g PHP to TR6 reaction solution, add 0.05g CBA, react at 50 oC O/N

--[[User:Paul.xu|Paul.xu]] 17:45, 25 April 2011 (EST)

[[Category:Transfection]] [[Category:Paul]]

Synthesis of pHP - Revision history

Paul.xu at 13:43, 18 July 2014