An ionizable cationic lipid
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C14-4

Item No. 38942

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,1′-[[2-[2-[4-[2-[[2-[2-[bis(2-hydroxytetradecyl)amino]ethoxy]ethyl](2-hydroxytetradecyl)amino]ethyl]-1-piperazinyl]ethoxy]ethyl]imino]bis-2-tetradecanol
CAS Number
2639634-80-1
Synonyms
  • C14-494
  • Lipid B4
Molecular Formula
C84H173N5O7
Formula Weight
1365.3
Purity
≥95% (mixture of isomers)
Formulation (Request formulation change)
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: 10 mg/ml
SMILES
CCCCCCCCCCCCC(O)CN(CC(O)CCCCCCCCCCCC)CCOCCN(CCN1CCN(CCOCCN(CC(O)CCCCCCCCCCCC)CC(O)CCCCCCCCCCCC)CC1)CC(O)CCCCCCCCCCCC
InChi Code
InChI=1S/C84H173N5O7/c1-6-11-16-21-26-31-36-41-46-51-56-80(90)75-87(68-72-96-74-70-89(78-83(93)59-54-49-44-39-34-29-24-19-14-9-4)79-84(94)60-55-50-45-40-35-30-25-20-15-10-5)66-65-85-61-63-86(64-62-85)67-71-95-73-69-88(76-81(91)57-52-47-42-37-32-27-22-17-12-7-2)77-82(92)58-53-48-43-38-33-28-23-18-13-8-3/h80-84,90-94H,6-79H2,1-5H3
InChi Key
OQALBVGFAKJDAR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    10 mg

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    25 mg

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    Cayman Chemical
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    Product Description

    C14-4 is an ionizable cationic lipid (pKa = 6.5).1,2 It has been used in the generation of lipid nanoparticles (LNPs) for the delivery of mRNA in vitro or in vivo.1,3 LNPs containing C14-4 and encapsulating mRNA encoding chimeric antigen receptor (CAR) induce CAR expression in primary human T cells ex vivo to the same level as expression induced via electroporation, but with reduced cytotoxicity, and induce cytotoxicity in Nalm-6 acute lymphoblastic leukemia (ALL) cells in vitro.1 LNPs containing C14-4 and the secondary bile acid deoxycholic acid (Item Nos. 20756 | 18231) and encapsulating mRNA encoding luciferase accumulate in the uterus when intraperitoneally administered and in the lungs and small intestine when intravenously administered in mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Billingsley, M.M., Singh, N., Ravikumar, P., et al. Ionizable lipid nanoparticle-mediated mRNA delivery for human car T cell engineering. Nano Lett. 20(3), 1578-1589 (2020).

    2. Billingsley, M.M., Hamilton, A.G., Mai, D., et al. Orthogonal design of experiments for optimization of lipid nanoparticles for mRNA engineering of car T cells. Nano Lett. 22(1), 533-542 (2022).

    3. Patel, S.K., Billingsley, M.M., Mukalele, A.J., et al. Bile acid-containing lipid nanoparticles enhance extrahepatic mRNA delivery. Theranostics 14(1), 1-16 (2024).