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Chemical Structure| 4004-05-1 Chemical Structure| 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

4.5 *For Research Use Only !

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Product Citations

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

Application In Synthesis of DOPE

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4004-05-1 ]

[ 4004-05-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 4004-05-1 ]
  • [ 1426827-79-3 ]
  • (2R)-3-(((2-(((((1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-yl)methoxy)carbonyl)amino)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine; In dichloromethane; (1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethyl succinimidyl carbonate (50 mg, 0.17 mmol) was dissolved in 6 ml dry CH2Cl2 which was then added to a solution of 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) (127 mg, 0.17 mmol) in 4 ml dry CH2Cl2. NEt3 (78 μl, 0.55 mmol) was added and the solution was left stirring overnight.The product was purified directly by column chromatography (95:5CH2Cl2/MeOH) to yield the product as a colorless oil (114 mg, 73%). Analytical data:1H NMR (400 MHz, CDCl3) δ 9.35 (bs, 2H), 5.82 (s, 1H), 5.31 (m, 3H), 5.18 (m, 1H), 4.36 (dd, 2H), 4.11 (m, 3H), 3.92 (m, 4H), 3.57 (m, 1H), 3.38 (d, 2H), 3.07 (q, 6H), 2.62 (s, 4H), 2.23 (m, 8H), 1.97 (q,6H), 1.26 (m, 38H, should be 40H), 0.84 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 173.57, 130.00, 129.62, 129.59, 98.74, 62.68, 34.19, 34.01, 31.89, 29.75, 29.53, 29.31, 29.24, 29.22, 29.18, 29.15, 27.22, 24.90, 24.83, 22.67, 21.41, 20.15, 14.11; HRMS (ESI) calcd for C52H89NO10P[M-H]- 918.6224 found 918.6198.
 

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