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[ CAS No. 4004-05-1 ] {[proInfo.proName]}

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Chemical Structure| 4004-05-1
Chemical Structure| 4004-05-1
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Xuexiang Han ; Junchao Xu ; Ying Xu , et al. DOI: PubMed ID:

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 [ 4004-05-1 ]

CAS No. :4004-05-1 MDL No. :MFCD00057986
Formula : C41H78NO8P Boiling Point : -
Linear Structure Formula :(C18H33O)2OCH2CHOCH2OPO3CH2CH2NH3 InChI Key :MWRBNPKJOOWZPW-NYVOMTAGSA-N
M.W : 744.03 Pubchem ID :9546757
Synonyms :
dioleoylphosphatidylethanolamine;1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine;1,2-Dioleoyl-sn-glycero-3-Phosphoethanolamine 1,2-DOPE;1,2-DOPE;1,2-Dioleoyl-sn-glycero-3-PE
Chemical Name :(Z)-(2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate

Safety of [ 4004-05-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4004-05-1 ]

* 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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