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MedKoo Cat#: 122986 | Name: R-DOTAP chloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

R-DOTAP. also known as 1,2-Dioleoyl-3(R)-trimethylammoniumpropane (chloride), is a cationic lipid and the more immunologically active isomer of DOTAP. R-DOTAP has potential applications as an immune stimulant for next-generation prophylactic recombinant protein-based vaccines. R-DOTAP is seen to generate anti-tumor immunity through the induction of potent cytotoxic CD8 T cells.

Chemical Structure

R-DOTAP chloride
R-DOTAP chloride
CAS#328250-28-8 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 122986

Name: R-DOTAP chloride

CAS#: 328250-28-8 (R-isomer)

Chemical Formula: C42H80ClNO4

Exact Mass: 0.0000

Molecular Weight: 698.56

Elemental Analysis: C, 72.22; H, 11.54; Cl, 5.07; N, 2.01; O, 9.16

Price and Availability

Size Price Availability Quantity
50mg USD 350.00 2 Weeks
100mg USD 650.00 2 Weeks
250mg USD 1,150.00 2 Weeks
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Related CAS #
132172-61-3 (chloride) 113669-21-9 (cation) 428506-51-8 (S-isomer) 328250-28-8 (R-isomer) 144189-73-1 (methylsulfate)
Synonym
R-DOTAP; R-DOTAP chloride; (R)-DOTAP chloride
IUPAC/Chemical Name
(R)-N,N,N-trimethyl-2,3-bis(oleoyloxy)propan-1-aminium chloride
InChi Key
KSXTUUUQYQYKCR-HEXDFCBFSA-M
InChi Code
InChI=1S/C42H80NO4.ClH/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-41(44)46-39-40(38-43(3,4)5)47-42(45)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2;/h20-23,40H,6-19,24-39H2,1-5H3;1H/q+1;/p-1/b22-20-,23-21-;/t40-;/m1./s1
SMILES Code
CCCCCCCC/C=C\CCCCCCCC(O[C@@H](COC(CCCCCCC/C=C\CCCCCCCC)=O)C[N+](C)(C)C)=O.[Cl-]
Appearance
To be determined
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 698.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Henson TR, Richards KA, Gandhapudi SK, Woodward JG, Sant AJ. R-DOTAP Cationic Lipid Nanoparticles Outperform Squalene-Based Adjuvant Systems in Elicitation of CD4 T Cells after Recombinant Influenza Hemagglutinin Vaccination. Viruses. 2023 Feb 15;15(2):538. doi: 10.3390/v15020538. PMID: 36851752; PMCID: PMC9959843. 2: Gandhapudi SK, Shi H, Ward MR, Bush JP, Avdiushko M, Sundarapandiyan K, Wood LV, Dorrani M, Fatima A, Dervan J, Bedu-Addo F, Conn G, Ross TM, Woodward JG. Recombinant Protein Vaccines Formulated with Enantio-Specific Cationic Lipid R-DOTAP Induce Protective Cellular and Antibody-Mediated Immune Responses in Mice. Viruses. 2023 Feb 4;15(2):432. doi: 10.3390/v15020432. PMID: 36851646; PMCID: PMC9965888. 3: Riehl M, Harms M, Hanefeld A, Baleeiro RB, Walden P, Mäder K. Combining R-DOTAP and a particulate antigen delivery platform to trigger dendritic cell activation: Formulation development and in-vitro interaction studies. Int J Pharm. 2017 Oct 30;532(1):37-46. doi: 10.1016/j.ijpharm.2017.08.119. Epub 2017 Sep 1. PMID: 28866132. 4: Vasievich EA, Ramishetti S, Zhang Y, Huang L. Trp2 peptide vaccine adjuvanted with (R)-DOTAP inhibits tumor growth in an advanced melanoma model. Mol Pharm. 2012 Feb 6;9(2):261-8. doi: 10.1021/mp200350n. Epub 2011 Dec 28. PMID: 22142394; PMCID: PMC3273554. 5: White CL, Glover MA, Gandhapudi SK, Richards KA, Sant AJ. Flublok Quadrivalent Vaccine Adjuvanted with R-DOTAP Elicits a Robust and Multifunctional CD4 T Cell Response That Is of Greater Magnitude and Functional Diversity Than Conventional Adjuvant Systems. Vaccines (Basel). 2024 Mar 7;12(3):281. doi: 10.3390/vaccines12030281. PMID: 38543915; PMCID: PMC10975948. 6: Vasievich EA, Chen W, Huang L. Enantiospecific adjuvant activity of cationic lipid DOTAP in cancer vaccine. Cancer Immunol Immunother. 2011 May;60(5):629-38. doi: 10.1007/s00262-011-0970-1. Epub 2011 Jan 26. PMID: 21267720; PMCID: PMC5514367. 7: Terp MC, Bauer F, Sugimoto Y, Yu B, Brueggemeier RW, Lee LJ, Lee RJ. Differential efficacy of DOTAP enantiomers for siRNA delivery in vitro. Int J Pharm. 2012 Jul 1;430(1-2):328-34. doi: 10.1016/j.ijpharm.2012.04.017. Epub 2012 Apr 15. PMID: 22525086; PMCID: PMC3504612. 8: Gandhapudi SK, Ward M, Bush JPC, Bedu-Addo F, Conn G, Woodward JG. Antigen Priming with Enantiospecific Cationic Lipid Nanoparticles Induces Potent Antitumor CTL Responses through Novel Induction of a Type I IFN Response. J Immunol. 2019 Jun 15;202(12):3524-3536. doi: 10.4049/jimmunol.1801634. Epub 2019 May 3. PMID: 31053626; PMCID: PMC9347971. 9: Smalley Rumfield C, Pellom ST, Morillon Ii YM, Schlom J, Jochems C. Immunomodulation to enhance the efficacy of an HPV therapeutic vaccine. J Immunother Cancer. 2020 Jun;8(1):e000612. doi: 10.1136/jitc-2020-000612. PMID: 32554612; PMCID: PMC7304848. 10: Dokka S, Toledo D, Shi X, Ye J, Rojanasakul Y. High-efficiency gene transfection of macrophages by lipoplexes. Int J Pharm. 2000 Sep 25;206(1-2):97-104. doi: 10.1016/s0378-5173(00)00531-7. PMID: 11058814.

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