DODAP

Product NameDODAP
CAS127512-29-2
MFC41H77NO4
MW648.05
EINECS
MOL File127512-29-2.mol

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

Safety Information

WGK Germany	WGK 3
Storage Class	6.1D - Non-combustible acute toxic Cat.3 toxic hazardous materials or hazardous materials causing chronic effects
Hazard Classifications	Acute Tox. 3 Inhalation Acute Tox. 4 Oral Carc. 2 Eye Irrit. 2 Repr. 2 Skin Irrit. 2 STOT RE 1 Oral STOT SE 3

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] Mendona 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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