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Amine-containing transfection reagents and methods for making and using same

A compound, pharmaceutical technology, applied in the field of transfection complexes

Active Publication Date: 2013-10-30
LIFE TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, concerns about possible undesired side effects (such as undesired immune responses) when using viral vectors have led to the development of non-viral alternatives (e.g., polymeric delivery systems, liposomal formulations, and "naked" DNA injections) )s hard work

Method used

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  • Amine-containing transfection reagents and methods for making and using same
  • Amine-containing transfection reagents and methods for making and using same
  • Amine-containing transfection reagents and methods for making and using same

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Embodiment approach

[0104] Amine-containing transfection compounds

[0105] The present invention describes various amine-containing compounds useful as transfection reagents and methods for their synthesis. More specifically, according to some embodiments of the present invention, there is provided a compound having the general structure I or a pharmaceutically acceptable salt thereof:

[0106]

[0107]

[0108] where X 1 and x 2 Each of is a moiety independently selected from O, S, N-A and C-A, wherein A is selected from hydrogen and C 1 -C 20 Hydrocarbon chain; each of Y and Z is a moiety independently selected from CH-OH, C=O, C=S, S=O and SO 2 ; 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 Each of is a moiety independently selected from hydrogen, cyclic or acyclic, substituted or unsubstituted, branched or linear aliphatic group, cyclic or acyclic, substituted Substituted or unsubstituted, branched or straight chain heteroaliphatic, substituted or unsubstituted, branched or st...

Embodiment 1

[0242] The synthesis of embodiment 1.2-bromo-N-dodecylacetamide

[0243] The title intermediate was synthesized according to the following general reaction scheme:

[0244]

[0245] In a round bottom flask with a pressure equilibrating addition funnel, to 200 mL of dichloromethane was added 1.5 g (7.431 mmol, 1.05 equiv) of bromoacetyl bromide and the mixture was stirred under nitrogen. The flask was cooled to about 0°C using an ice bath. 1.31 g (7.077 mmol) of dodecylamine and 0.716 g (983 μL, 7.077 mmol) of triethylamine were dissolved in 100 mL of dichloromethane. Transfer the solution to an addition funnel and slowly add the bromoacetyl solution. reverse the The mixture was stirred at about 0°C for about another 1 hour, slowly warming to room temperature by allowing the ice to melt.

[0246] The resulting reaction mixture was transferred to a separatory funnel and extracted with 100 mL of saturated sodium bicarbonate solution. The aqueous layer was washed with...

Embodiment 2

[0247] Example 2. Synthesis of tetradecyl-2-bromoacetate

[0248] The title intermediate was synthesized according to the following general reaction scheme:

[0249]

[0250] Dissolve 3 g (1.3 mL, 14.862 mmol, 1.05 equiv) of bromoacetyl bromide in 50 mL of dichloromethane. Using an ice bath, the flask was cooled to about 0°C. Dissolve 3.03 g (14.154 mmol) of tetradecyl alcohol in 50 mL of dichloromethane, and slowly add to the above mixture via a pipette, then add about 5 drops of concentrated sulfuric acid, and stir at about 0 ° C for about 30 minutes, then Stir overnight at room temperature.

[0251] Add about 150 mL of saturated sodium bicarbonate solution and stir rapidly for about 30 minutes. The mixture was then transferred to a separatory funnel, and the organic layer was collected. The aqueous layer was washed with about 100 mL of dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 4.095 g (89.7% y...

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Abstract

There are provided for herein novel amine-containing transfection compounds and methods for making and using same. The compounds are generally obtained by reacting a primary amine with an unsaturated compound. Transfection complexes made using the amine-containing transfection compounds in combination with additional compounds to encapsulate biologically active agents such as nucleic acids are also provided for herein. Methods of using the transfection complexes for the in vivo or in vitro delivery of biologically active agents are also described. The transfection complexes of the present invention are highly potent, thereby allowing effective modulation of a biological activity at relatively low doses compared to analogous transfection compounds known in the art.

Description

[0001] Cross References to Related Applications [0002] This application claims under 35 U.S.C. §119 U.S. Provisional Application Serial No. 61 / 543,242 filed October 4, 2011, U.S. Provisional Application Serial No. 61 / 438,903 filed February 2, 2011, January 28, 2011 Priority of U.S. Provisional Application Serial No. 61 / 437,503, filed November 15, 2210, and U.S. Provisional Application Serial No. 61 / 413,905, filed November 15, 2210. The aforementioned applications are commonly owned by the present application and their entire contents are hereby expressly incorporated by reference in their entirety as if fully set forth herein. technical field [0003] The present invention relates generally to the field of transfection reagents for the delivery of biologically active agents in vitro and in vivo. More specifically, the present invention relates to biodegradable and biocompatible lipids and transfection complexes prepared using them, which can be used to introduce nucleic aci...

Claims

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Application Information

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IPC IPC(8): C07D211/58A61K48/00C07C229/16C07C229/24C07C229/26C07C237/06C07D211/28
CPCC07C227/06C12N15/88C07D211/58C07D211/28A61K47/543C07C229/26A61K48/0008C07C229/08C12N15/1137C12N2310/11C12N2310/141A61K47/54
Inventor Z.杨P.安格里什X.德莫勒拉迪热K.维德霍尔特T.吴
Owner LIFE TECH CORP
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