DODAP
DODAP Basic information
- Product Name:
- DODAP
- Synonyms:
-
- 18:1 DAP
- 9-Octadecenoic acid(9Z)-1,1'-[1-[(dimethylamino)methyl]-1,2-ethanediyl] ester
- 1,2-DIOLEOYLOXY-3-(DIMETHYLAMINO)PROPANE
- 1,2-DIOLEOYL-3-DIMETHYLAMMONIUM-PROPANE
- DODAP
- (+/-)-N,N-dimethyl-N-[2,3-bis(9-(Z)-octadecanoyloxy)propyl]amine
- 1,2-dioleoyl-3-dimethylammonium-propane (DODAP)
- (Z)-3-(Dimethylamino)propane-1,2-diyl dioleate
- CAS:
- 127512-29-2
- MF:
- C41H77NO4
- MW:
- 648.05
- Product Categories:
-
- Mixed Fatty Acids
- Fatty Acid Derivatives & Lipids
- Glycerols
- Glycerols, Fatty Acid Derivatives & Lipids
- Mol File:
- 127512-29-2.mol
DODAP Chemical Properties
- 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
DODAP Usage And Synthesis
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).
Chemical Properties
Light Yellow Oil
Uses
DODAP is a cationic lipid utilized as the lipid component in liposomes (pKa = 5.59 in TNS binding tests). DODAP is employed for encapsulating siRNA and delivering immunostimulated chemotherapeutic agents both in vitro and in vivo. DODAP holds great promise for research in vaccines and inflammation[1][2][3][4][5].
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
DODAPSupplier
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DODAP(127512-29-2)Related Product Information
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- DODMA
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