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Chemical Structure| 4004-05-1 Chemical Structure| 4004-05-1

Structure of DOPE
CAS No.: 4004-05-1

Chemical Structure| 4004-05-1

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1,2-DOPE can be used in combination with cationic phospholipids to increase efficiency during DNA transfection.

Synonyms: dioleoylphosphatidylethanolamine; 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine; 1,2-DOPE

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Product Citations      Show More

Patterson, Leah A ; Coppage, David A ; Figueroa, Sydney M ; Cobo, Angel A ; O’Geen, Henriette ; Segal, David J , et al.

Abstract: The design of amphiphilic lipid structures can be used to modulate key properties for diverse applications in biology and nanomaterials. We have engineered a structurally diverse class of amphiphilic silyl lipids using a hydrosilylation reaction as the key step to access lipids that vary the silyldimethyl position, branching, length, and substituents in the lipid tail. We demonstrate that the size, zeta potential, rRNA encapsulation, stability, bilayer fluidity, and mRNA transfection are controlled by varying the structure of the silyl lipid tail. Five silyl lipids exhibit high encapsulation, and three feature enhanced stability and transfection in HEK293T cells relative to DOTAP as a classic reference lipid. Incorporation of a branching silyldimethyl group (in place of a cis alkene or methylene) increases bilayer fluidity in liposomes.These results support the idea that incorporating a silyldimethyl group and accessing diverse lipid structures can control liposome properties and mRNA delivery, showing promise for using silyl lipid structures in other biology and biomaterial applications.

Keywords: lipids ; silanes ; hydrosilylation ; nanoparticles ; RNA

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Xuexiang Han ; Junchao Xu ; Ying Xu ; Mohamad-Gabriel Alameh ; Lulu Xue ; Ningqiang Gong , et al.

Abstract: The ionizable lipidoid is a key component of nanoparticles (LNPs). Degradable lipidoids containing extended alkyl branches have received tremendous attention, yet their optimization and investigation are underappreciated. Here, we devise an in situ construction method for the combinatorial synthesis of degradable branched (DB) lipidoids. We find that appending branch tails to inefficacious lipidoids via degradable linkers boosts mRNA delivery efficiency up to three orders of magnitude. Combinatorial screening and systematic investigation of two libraries of DB-lipidoids reveal important structural criteria that govern their in vivo potency. The DB-LNP demonstrates robust delivery of mRNA therapeutics and gene editors into the liver. In a diet-induced obese mouse model, we show that repeated administration of DB-LNP encapsulating mRNA encoding human fibroblast growth factor 21 alleviates obesity and fatty liver. Together, we offer a construction strategy for high-throughput and cost-efficient synthesis of DB-lipidoids. This study provides insights into branched lipidoids for efficient mRNA delivery.

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Product Details of DOPE

CAS No. :4004-05-1
Formula : C41H78NO8P
M.W : 744.03
SMILES Code : CCCCCCCC/C=C\CCCCCCCC(O[C@@H](COP(O)(OCCN)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)=O
Synonyms :
dioleoylphosphatidylethanolamine; 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine; 1,2-DOPE
MDL No. :MFCD00057986
InChI Key :MWRBNPKJOOWZPW-NYVOMTAGSA-N
Pubchem ID :9546757

Safety of DOPE

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Primary cortical neurons 12 μg 24 hours Significantly improved transfection efficiency in primary cortical neurons, approximately 80% of neurons expressed EGFP Nucleic Acids Res. 2017 Apr 7;45(6):e38
Mesenchymal stem cells (MSC) 12 μg 24 hours Significantly improved transfection efficiency in MSC, approximately 70% of MSC expressed EGFP Nucleic Acids Res. 2017 Apr 7;45(6):e38
Neuro2A cells 12 μg 24 hours Enhanced transfection efficiency, significantly improved transfection efficiency in differentiated neuronal cells Nucleic Acids Res. 2017 Apr 7;45(6):e38

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.34mL

0.27mL

0.13mL

6.72mL

1.34mL

0.67mL

13.44mL

2.69mL

1.34mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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