DODAC | CAS#7212-69-3 | Cationic lipid

MedKoo Cat#: 465240 | Name: DODAC

Description:

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

DODAC is a cationic lipid for DNA, RNA and vaccine delivery. Cationic lipid, added in monomer or micellar form, bind to DNA, resulting in the formation of a hydrophobic complex. This complex can serve as a well-defined intermediate in the preparation of DNA-lipid particles (DLPs) with many potential applications for delivery of polynucleotides in vitro and in vivo.

Chemical Structure

DODAC

CAS#7212-69-3 (chloride)

Theoretical Analysis

MedKoo Cat#: 465240

Name: DODAC

CAS#: 7212-69-3 (chloride)

Chemical Formula: C38H76ClN

Exact Mass: 0.0000

Molecular Weight: 582.48

Elemental Analysis: C, 78.36; H, 13.15; Cl, 6.09; N, 2.40

Price and Availability

Size	Price	Availability
5mg	USD 150.00	Ready to Ship
10mg	USD 250.00	Ready to Ship
25mg	USD 450.00	Ready to Ship
50mg	USD 750.00	Ready to Ship
100mg	USD 1,250.00	Ready to Ship
200mg	USD 1,950.00	Ready to Ship

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Related CAS #

7212-69-3 (chloride) 45315-43-3 (cation)

Synonym

DODAC; Dioleyldimethylammonium chloride; Dimethyldioleylammonium chloride; dioleyldimonium chloride; Dioleyldimethylammonium (chloride)

IUPAC/Chemical Name

(Z)-N,N-dimethyl-N-((Z)-octadec-9-en-1-yl)octadec-9-en-1-aminium chloride

InChi Key

UAKOZKUVZRMOFN-JDVCJPALSA-M

InChi Code

InChI=1S/C38H76N.ClH/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39(3,4)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-2;/h19-22H,5-18,23-38H2,1-4H3;1H/q+1;/p-1/b21-19-,22-20-;

SMILES Code

CCCCCCCC/C=C\CCCCCCCC[N+](C)(C)CCCCCCCC/C=C\CCCCCCCC.[Cl-]

Appearance

Light yellow to yellow viscouse liquid

Purity

>98% (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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#Y22X10M29

QC Data

View QC data: current batch, Lot#Y22X10M29

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

DODAC is a cationic lipid for DNA, RNA and vaccine delivery.

In vitro activity:

The treatment with DODAC/PHO-S (0.3 and 2.0 mM) significantly increased the number of necrotic cells, with values of 9.6 ± 0.14% (0.3 mM) and 12.3 ± 0.3% (2.0 mM). There was also an increase in late apoptosis, with a percentage of 30.4 ± 0.4% (0.3 mM) and 31.0 ± 1.3% (2.0 mM). The treatment with DODAC (0.3 mM) increased the number of necrotic cells to a lesser extent when compared to the other treatments, with a percentage of 6.7 ± 0.9% (Fig. 2b). Reference: BMC Pharmacol Toxicol. 2018 Jul 11;19(1):44. https://pubmed.ncbi.nlm.nih.gov/29996919/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 582.48 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.

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

Formulation protocol:

1. Luna ACL, Saraiva GKV, Chierice GO, Hesse H, Maria DA. Antiproliferative and proapoptotic effects of DODAC/synthetic phosphoethanolamine on hepatocellular carcinoma cells. BMC Pharmacol Toxicol. 2018 Jul 11;19(1):44. doi: 10.1186/s40360-018-0225-2. PMID: 29996919; PMCID: PMC6042440. 2. Luna ACL, Santos Filho JRA, Hesse H, Neto SC, Chierice GO, Maria DA. Modulation of pro-apoptotic effects and mitochondrial potential on B16F10 cells by DODAC/PHO-S liposomes. BMC Res Notes. 2018 Feb 14;11(1):126. doi: 10.1186/s13104-018-3170-7. PMID: 29444697; PMCID: PMC5813323.

In vitro protocol:

In vivo protocol:

TBD

1: Havlíková M, Jugl A, Krouská J, Szabová J, Mravcová L, Venerová T, Chang CH, Pekař M, Mravec F. Interactions between Cationic Ion Pair Amphiphile Vesicles and Hyaluronan-A Physicochemical Study. Langmuir. 2021 Jul 20;37(28):8525-8533. doi: 10.1021/acs.langmuir.1c00993. Epub 2021 Jul 2. PMID: 34214390. 2: Gonçalves RA, Lam YM, Lindman B. Double-Chain Cationic Surfactants: Swelling, Structure, Phase Transitions and Additive Effects. Molecules. 2021 Jun 28;26(13):3946. doi: 10.3390/molecules26133946. PMID: 34203337; PMCID: PMC8271693. 3: Rusli W, van Herk AM. Effect of salts on size and morphology of extruded dimethyldioctadecylammonium bromide or chloride vesicle for polymeric nanocapsules synthesis via templating emulsion polymerization. J Colloid Interface Sci. 2021 Apr;587:393-401. doi: 10.1016/j.jcis.2020.11.116. Epub 2020 Dec 25. PMID: 33370661. 4: Hishida M, Shimokawa N, Okubo Y, Taguchi S, Yamamura Y, Saito K. Phase Transition from the Interdigitated to Bilayer Membrane of a Cationic Surfactant Induced by Addition of Hydrophobic Molecules. Langmuir. 2020 Dec 8;36(48):14699-14709. doi: 10.1021/acs.langmuir.0c02609. Epub 2020 Nov 24. PMID: 33232164. 5: Khattab MH, Weaver M, Cook C, Kinder N, Vassar M. Public Speaker Characteristics at Meetings of the Dermatologic and Ophthalmic Drug Advisory Committee and the Ophthalmic Devices Panel. Am J Ophthalmol. 2021 Mar;223:28-32. doi: 10.1016/j.ajo.2020.09.043. Epub 2020 Nov 6. PMID: 33166500. 6: Luna ACL, Saraiva GKV, Chierice GO, Hesse H, Maria DA. Antiproliferative and proapoptotic effects of DODAC/synthetic phosphoethanolamine on hepatocellular carcinoma cells. BMC Pharmacol Toxicol. 2018 Jul 11;19(1):44. doi: 10.1186/s40360-018-0225-2. PMID: 29996919; PMCID: PMC6042440. 7: Oliveira ACN, Fernandes J, Gonçalves A, Gomes AC, Oliveira MECDR. Lipid-based Nanocarriers for siRNA Delivery: Challenges, Strategies and the Lessons Learned from the DODAX: MO Liposomal System. Curr Drug Targets. 2019;20(1):29-50. doi: 10.2174/1389450119666180703145410. PMID: 29968536. 8: Gonçalves RA, Lindman B, Miguel MG, Iwata T, Lam YM. Elucidating the effect of additives on the alkyl chain packing of a double tail cationic surfactant. J Colloid Interface Sci. 2018 Oct 15;528:400-409. doi: 10.1016/j.jcis.2018.05.092. Epub 2018 May 26. PMID: 29879617. 9: Luna ACL, Santos Filho JRA, Hesse H, Neto SC, Chierice GO, Maria DA. Modulation of pro-apoptotic effects and mitochondrial potential on B16F10 cells by DODAC/PHO-S liposomes. BMC Res Notes. 2018 Feb 14;11(1):126. doi: 10.1186/s13104-018-3170-7. PMID: 29444697; PMCID: PMC5813323. 10: Wang G, Miao Y, Sun Z, Zheng S. Simultaneous adsorption of aflatoxin B1 and zearalenone by mono- and di-alkyl cationic surfactants modified montmorillonites. J Colloid Interface Sci. 2018 Feb 1;511:67-76. doi: 10.1016/j.jcis.2017.09.074. Epub 2017 Sep 25. PMID: 28972897. 11: Rezaee M, Oskuee RK, Nassirli H, Malaekeh-Nikouei B. Progress in the development of lipopolyplexes as efficient non-viral gene delivery systems. J Control Release. 2016 Aug 28;236:1-14. doi: 10.1016/j.jconrel.2016.06.023. Epub 2016 Jun 15. PMID: 27317365. 12: Oliveira ACN, Sárria MP, Moreira P, Fernandes J, Castro L, Lopes I, Côrte- Real M, Cavaco-Paulo A, Real Oliveira MECD, Gomes AC. Counter ions and constituents combination affect DODAX : MO nanocarriers toxicity in vitro and in vivo. Toxicol Res (Camb). 2016 Jun 13;5(4):1244-1255. doi: 10.1039/c6tx00074f. PMID: 30090429; PMCID: PMC6062248. 13: Luna AC, Saraiva GK, Filho OM, Chierice GO, Neto SC, Cuccovia IM, Maria DA. Potential antitumor activity of novel DODAC/PHO-S liposomes. Int J Nanomedicine. 2016 Apr 18;11:1577-91. doi: 10.2147/IJN.S90850. PMID: 27143880; PMCID: PMC4841408. 14: Lopes I, C N Oliveira A, P Sárria M, P Neves Silva J, Gonçalves O, Gomes AC, Real Oliveira ME. Monoolein-based nanocarriers for enhanced folate receptor- mediated RNA delivery to cancer cells. J Liposome Res. 2016 Sep;26(3):199-210. doi: 10.3109/08982104.2015.1076463. Epub 2015 Aug 17. PMID: 26340109. 15: Shin MJ, Kim YJ, Kim JD. Chromatic response of polydiacetylene vesicle induced by the permeation of methotrexate. Soft Matter. 2015 Jul 7;11(25):5037-43. doi: 10.1039/c5sm00925a. Erratum in: Soft Matter. 2015 Sep 14;11(34):6903-4. PMID: 26016992. 16: Park CY, Kim MW. Dynamic mechanical properties of a polyelectrolyte adsorbed insoluble lipid monolayer at the air-water interface. J Phys Chem B. 2015 Apr 23;119(16):5315-20. doi: 10.1021/jp5123773. Epub 2015 Apr 14. PMID: 25826703. 17: Nakamura A, Endo H, Yamashita T, Kawai T. Sodium dodecylsulfate bilayer formation under a cationic surfactant Langmuir monolayer at the air-water interface. J Nanosci Nanotechnol. 2014 Mar;14(3):2198-203. doi: 10.1166/jnn.2014.8522. PMID: 24745212. 18: Oliveira AC, Martens TF, Raemdonck K, Adati RD, Feitosa E, Botelho C, Gomes AC, Braeckmans K, Real Oliveira ME. Dioctadecyldimethylammonium:monoolein nanocarriers for efficient in vitro gene silencing. ACS Appl Mater Interfaces. 2014 May 14;6(9):6977-89. doi: 10.1021/am500793y. Epub 2014 Apr 18. PMID: 24712543. 19: Sabatino P, Choudhury RP, Schönhoff M, Van der Meeren P, Martins JC. NMR investigation of exchange dynamics and binding of phenol and phenolate in DODAC vesicular dispersions. J Phys Chem B. 2012 Aug 2;116(30):9269-76. doi: 10.1021/jp304749g. Epub 2012 Jul 12. PMID: 22731738. 20: Woiterski L, Britt DW, Käs JA, Selle C. Oriented confined water induced by cationic lipids. Langmuir. 2012 Mar 13;28(10):4712-22. doi: 10.1021/la205043x. Epub 2012 Mar 1. PMID: 22339557.