| Identification | Back Directory | [Name]
DODAP | [CAS]
127512-29-2 | [Synonyms]
DODAP
18:1 DAP
1,2-DIOLEOYL-3-DIMETHYLAMMONIUM-PROPANE
1,2-DIOLEOYLOXY-3-(DIMETHYLAMINO)PROPANE
9-Octadecenoic acid(9Z)-1,1'-[1-[(dimethylamino)methyl]-1,2-ethanediyl] ester | [Molecular Formula]
C41H77NO4 | [MDL Number]
MFCD01321074 | [MOL File]
127512-29-2.mol | [Molecular Weight]
648.05 |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Oil | [Boiling point ]
670.1±55.0 °C(Predicted) | [density ]
0.916±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer, Under Inert Atmosphere | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Oil | [pka]
8.02±0.28(Predicted) | [color ]
Colourless to Light Yellow | [Stability:]
Light Sensitive; Hydroscopic; Store at -15 to -25°C | [InChIKey]
NYDLOCKCVISJKK-WRBBJXAJSA-N | [SMILES]
C(OC(=O)CCCCCCC/C=C\CCCCCCCC)(CN(C)C)COC(=O)CCCCCCC/C=C\CCCCCCCC |
| Hazard Information | Back Directory | [Chemical Properties]
Light Yellow Oil | [Uses]
Cationic amphiphiles are being studied for their potential role in preparing liposomes for interaction with artificial and biological membranes and cellular transfection techniques. Cationic species with ester linkages to the hydrophobic portion are more easily degraded by recipient cells and more efficiently metabolized. | [Description]
DODAP (18:1) is an ionizable cationic lipid with lower cytotoxicity and high transfection efficiency. DODAP is neutral at physiological pH, but acquires a positive charge inside the endosome due to the protonation of free amines when pH is lower than its pKa (<7). | [in vivo]
In vitro potency of DODAP (100 μg/mL, i.v., i.m., 4h) strongly predicts in vivo potency for intramuscular administration but not for intravascular administration in female Balb/c mice[1]. | Animal Model: | female Balb/c mice[1] | | Dosage: | 100 μg/mL | | Administration: | Intravenous injection (i.v.), Intramuscular injection (i.m.),4 h | | Result: | Treatment resulted that a less negatively charged DODAP was more efficient in vitro and in vivo intramuscular injection, while for Intravenous injection administration, a more negative DODAP that was passively targeted through Apo-E absorption was more efficient for hepatocyte targeting. |
| [References]
[1] Carrasco MJ, et al. Ionization and structural properties of mRNA lipid nanoparticles influence expression in intramuscular and intravascular administration. Commun Biol. 2021 Aug 11;4(1):956. DOI:10.1038/s42003-021-02441-2
[2] Dabbas S, et al. Importance of the liposomal cationic lipid content and type in tumor vascular targeting: physicochemical characterization and in vitro studies using human primary and transformed endothelial cells. Endothelium. 2008;15(4):189-201. DOI:10.1080/10623320802228583
[3] Hamzah J, et al. Targeted liposomal delivery of TLR9 ligands activates spontaneous antitumor immunity in an autochthonous cancer model. J Immunol. 2009;183(2):1091-1098. DOI:10.4049/jimmunol.0900736
[4] Liu Q, et al. Biotinylated cyclen-contained cationic lipids as non-viral gene delivery vectors. Chem Biol Drug Des. 2013;82(4):376-383. DOI:10.1111/cbdd.12159
[5] Mendon?a LS, et al. Transferrin receptor-targeted liposomes encapsulating anti-BCR-ABL siRNA or asODN for chronic myeloid leukemia treatment. Bioconjug Chem. 2010 Jan;21(1):157-68. DOI:10.1021/bc9004365 |
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