DOTAP chloride | CAS# 132172-61-3 | Cationic lipid

MedKoo Cat#: 555665 | Name: DOTAP chloride

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Description:

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

DOTAP chloride (1,2-dioleoyl-3-trimethylammonium-propane chloride) is a cationic lipid commonly used as a transfection reagent to deliver nucleic acids such as DNA, RNA, or siRNA into cells. It forms lipoplexes with negatively charged nucleic acids, facilitating their uptake via endocytosis and promoting intracellular release. DOTAP chloride is widely utilized in gene delivery research due to its high transfection efficiency and relatively low cytotoxicity in many cell lines.

Chemical Structure

DOTAP chloride

CAS#132172-61-3 (chloride)

Theoretical Analysis

MedKoo Cat#: 555665

Name: DOTAP chloride

CAS#: 132172-61-3 (chloride)

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
100mg	USD 350.00	Ready to ship
250mg	USD 650.00	2 Weeks
500mg	USD 1,050.00	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

DOTAP; DOTAP chloride; (+/-)-Dotap chloride; DOTAP-Cl

IUPAC/Chemical Name

N,N,N-trimethyl-2,3-bis(oleoyloxy)propan-1-aminium chloride

InChi Key

KSXTUUUQYQYKCR-LQDDAWAPSA-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-;

SMILES Code

CCCCCCCC/C=C\CCCCCCCC(OC(C[N+](C)(C)C)COC(CCCCCCC/C=C\CCCCCCCC)=O)=O.[Cl-]

Appearance

Solid powder

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

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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#C22M04C15

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

DOTAP chloride is a useful and effective cationic lipid for transient and stable transfection DNA (plasmids, bacmids) and modified nucleic acids (antisense oligonucleotides) with out the use of helper lipid.

In vitro activity:

This study further found that DOTAP/chol LNPs were able to transfect pDNA and oligonucleotides, demonstrating the ability of these LNPs to transport the cargo into the cell nucleus. The influence of various factors in the formulation of DOTAP/chol cationic LNPs is thus described and will help improve drug delivery of nucleic acid-based vaccines and therapies. Reference: AAPS PharmSciTech. 2022 May 9;23(5):135. https://pubmed.ncbi.nlm.nih.gov/35534697/

In vivo activity:

In CAR-deficient CT26 colon carcinoma murine models, replication-competent TAV255-Df treatment of subcutaneous tumors by intratumoral injection of DOTAP-folate liposome resulted in 67% full tumor remission, prolonged survival, and anti-cancer immunity when mice were rechallenged with cancer cells with no further treatment. Reference: ACS Biomater Sci Eng. 2022 Nov 17. https://pubmed.ncbi.nlm.nih.gov/36395425/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	0.29
	DMSO	12.8	18.25
	Ethanol	81.5	116.67
	Ethanol:PBS (pH 7.2) (1:1)	0.5	0.72

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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. Sun M, Dang UJ, Yuan Y, Psaras AM, Osipitan O, Brooks TA, Lu F, Di Pasqua AJ. Optimization of DOTAP/chol Cationic Lipid Nanoparticles for mRNA, pDNA, and Oligonucleotide Delivery. AAPS PharmSciTech. 2022 May 9;23(5):135. doi: 10.1208/s12249-022-02294-w. PMID: 35534697; PMCID: PMC9084260. 2. Tu ATT, Hoshi K, Shobo M, Yamazaki T. G-quadruplex-based CpG oligodeoxynucleotide/DOTAP complex strongly stimulates immunity in CpG motif-specific and loop-length-dependent manners. Nanomedicine. 2022 Feb;40:102508. doi: 10.1016/j.nano.2021.102508. Epub 2021 Dec 11. PMID: 34906721. 3. Huang CH, Dong T, Phung AT, Shah JR, Larson C, Sanchez AB, Blair SL, Oronsky B, Trogler WC, Reid T, Kummel AC. Full Remission of CAR-Deficient Tumors by DOTAP-Folate Liposome Encapsulation of Adenovirus. ACS Biomater Sci Eng. 2022 Nov 17. doi: 10.1021/acsbiomaterials.2c00966. Epub ahead of print. PMID: 36395425. 4. Buck J, Mueller D, Mettal U, Ackermann M, Grisch-Chan HM, Thöny B, Zumbuehl A, Huwyler J, Witzigmann D. Improvement of DNA Vector Delivery of DOTAP Lipoplexes by Short-Chain Aminolipids. ACS Omega. 2020 Sep 15;5(38):24724-24732. doi: 10.1021/acsomega.0c03303. PMID: 33015490; PMCID: PMC7528285.

In vitro protocol:

In vivo protocol:

1. Huang CH, Dong T, Phung AT, Shah JR, Larson C, Sanchez AB, Blair SL, Oronsky B, Trogler WC, Reid T, Kummel AC. Full Remission of CAR-Deficient Tumors by DOTAP-Folate Liposome Encapsulation of Adenovirus. ACS Biomater Sci Eng. 2022 Nov 17. doi: 10.1021/acsbiomaterials.2c00966. Epub ahead of print. PMID: 36395425. 2. Buck J, Mueller D, Mettal U, Ackermann M, Grisch-Chan HM, Thöny B, Zumbuehl A, Huwyler J, Witzigmann D. Improvement of DNA Vector Delivery of DOTAP Lipoplexes by Short-Chain Aminolipids. ACS Omega. 2020 Sep 15;5(38):24724-24732. doi: 10.1021/acsomega.0c03303. PMID: 33015490; PMCID: PMC7528285.

1: Divya KP, Karthikeyan R, Sinduja B, Anancia Grace A, John SA, Hahn JH, Dharuman V. Carbon dots stabilized silver-lipid nano hybrids for sensitive label free DNA detection. Biosens Bioelectron. 2019 May 15;133:48-54. doi: 10.1016/j.bios.2019.03.027. Epub 2019 Mar 15. PubMed PMID: 30909012. 2: Yuan BO, Zhao Y, Dong S, Sun Y, Hao F, Xie J, Teng L, Lee RJ, Fu Y, Bi YE. Cell-penetrating Peptide-coated Liposomes for Drug Delivery Across the Blood-Brain Barrier. Anticancer Res. 2019 Jan;39(1):237-243. doi: 10.21873/anticanres.13103. PubMed PMID: 30591464. 3: Xiao Y, Wang C, Xiong M, Yang Y, Zhang Q, Liu X, Zou B, Gou M. Self-Assembled Nanoparticle Mediated Survivin-T34A for Ovarian Cancer Therapy. J Biomed Nanotechnol. 2018 Dec 1;14(12):2092-2101. doi: 10.1166/jbn.2018.2641. PubMed PMID: 30305216. 4: Pawar VA, Manjappa AS, Murumkar PR, Gajaria TK, Devkar RV, Mishra AK, Yadav MR. Drug-fortified liposomes as carriers for sustained release of NSAIDs: The concept and its validation in the animal model for the treatment of arthritis. Eur J Pharm Sci. 2018 Dec 1;125:11-22. doi: 10.1016/j.ejps.2018.09.009. Epub 2018 Sep 13. PubMed PMID: 30219410. 5: Maity P, Saha B, Suresh Kumar G, Karmakar S. Effect of Zwitterionic Phospholipid on the Interaction of Cationic Membranes with Monovalent Sodium Salts. Langmuir. 2018 Aug 21;34(33):9810-9817. doi: 10.1021/acs.langmuir.8b01792. Epub 2018 Aug 13. PubMed PMID: 30056708. 6: Hattori Y, Nakamura M, Takeuchi N, Tamaki K, Shimizu S, Yoshiike Y, Taguchi M, Ohno H, Ozaki KI, Onishi H. Effect of cationic lipid in cationic liposomes on siRNA delivery into the lung by intravenous injection of cationic lipoplex. J Drug Target. 2019 Feb;27(2):217-227. doi: 10.1080/1061186X.2018.1502775. Epub 2018 Sep 7. PubMed PMID: 30024300. 7: Zhao W, Yang Y, Song L, Kang T, Du T, Wu Y, Xiong M, Luo L, Long J, Men K, Zhang L, Chen X, Huang M, Gou M. A Vesicular Stomatitis Virus-Inspired DNA Nanocomplex for Ovarian Cancer Therapy. Adv Sci (Weinh). 2017 Dec 29;5(3):1700263. doi: 10.1002/advs.201700263. eCollection 2018 Mar. PubMed PMID: 29593949; PubMed Central PMCID: PMC5867128. 8: Chang SF, Yeh CC, Chen PJ, Chang HI. The Impact of Lipid Types and Liposomal Formulations on Osteoblast Adiposity and Mineralization. Molecules. 2018 Jan 2;23(1). pii: E95. doi: 10.3390/molecules23010095. PubMed PMID: 29301300; PubMed Central PMCID: PMC6017718. 9: Astolfi P, Giorgini E, Gambini V, Rossi B, Vaccari L, Vita F, Francescangeli O, Marchini C, Pisani M. Lyotropic Liquid-Crystalline Nanosystems as Drug Delivery Agents for 5-Fluorouracil: Structure and Cytotoxicity. Langmuir. 2017 Oct 31;33(43):12369-12378. doi: 10.1021/acs.langmuir.7b03173. Epub 2017 Oct 23. PubMed PMID: 29023126. 10: Temprana CF, Prieto MJ, Igartúa DE, Femia AL, Amor MS, Alonso SDV. Diacetylenic lipids in the design of stable lipopolymers able to complex and protect plasmid DNA. PLoS One. 2017 Oct 11;12(10):e0186194. doi: 10.1371/journal.pone.0186194. eCollection 2017. PubMed PMID: 29020107; PubMed Central PMCID: PMC5636127. 11: Steffes VM, Murali MM, Park Y, Fletcher BJ, Ewert KK, Safinya CR. Distinct solubility and cytotoxicity regimes of paclitaxel-loaded cationic liposomes at low and high drug content revealed by kinetic phase behavior and cancer cell viability studies. Biomaterials. 2017 Nov;145:242-255. doi: 10.1016/j.biomaterials.2017.08.026. Epub 2017 Aug 17. PubMed PMID: 28889081; PubMed Central PMCID: PMC5610109. 12: West JD, Zhu Y, Saem S, Moran-Mirabal J, Hitchcock AP. X-ray Absorption Spectroscopy and Spectromicroscopy of Supported Lipid Bilayers. J Phys Chem B. 2017 May 4;121(17):4492-4501. doi: 10.1021/acs.jpcb.7b02646. Epub 2017 Apr 19. PubMed PMID: 28398060. 13: Bochicchio S, Dapas B, Russo I, Ciacci C, Piazza O, De Smedt S, Pottie E, Barba AA, Grassi G. In vitro and ex vivo delivery of tailored siRNA-nanoliposomes for E2F1 silencing as a potential therapy for colorectal cancer. Int J Pharm. 2017 Jun 20;525(2):377-387. doi: 10.1016/j.ijpharm.2017.02.020. Epub 2017 Feb 9. PubMed PMID: 28189855. 14: Yun CH, Bae CS, Ahn T. Cargo-Free Nanoparticles Containing Cationic Lipids Induce Reactive Oxygen Species and Cell Death in HepG2 Cells. Biol Pharm Bull. 2016;39(8):1338-46. doi: 10.1248/bpb.b16-00264. Erratum in: Biol Pharm Bull. 2018;41(2):285. PubMed PMID: 27476941. 15: 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. Review. PubMed PMID: 27317365. 16: Wan N, Jia YY, Hou YL, Ma XX, He YS, Li C, Zhou SY, Zhang BL. Preparation, Physicochemical Properties, and Transfection Activities of Tartaric Acid-Based Cationic Lipids as Effective Nonviral Gene Delivery Vectors. Biol Pharm Bull. 2016 Jul 1;39(7):1112-20. doi: 10.1248/bpb.b16-00007. Epub 2016 Apr 26. PubMed PMID: 27118165. 17: Tao J, Ding WF, Che XH, Chen YC, Chen F, Chen XD, Ye XL, Xiong SB. Optimization of a cationic liposome-based gene delivery system for the application of miR-145 in anticancer therapeutics. Int J Mol Med. 2016 May;37(5):1345-54. doi: 10.3892/ijmm.2016.2530. Epub 2016 Mar 17. PubMed PMID: 26986502. 18: Ohno M, Toyota T, Nomoto T, Fujinami M. Changes in Interfacial Tension of a Lipid Membrane Formed at the Water/Chloroform Interface upon DNA Complex Formation. Anal Sci. 2015;31(10):979-86. doi: 10.2116/analsci.31.979. PubMed PMID: 26460361. 19: Wang S, Cai J, Ding W, Xu Z, Wang Z. Bio-Inspired Aquaporinz Containing Double-Skinned Forward Osmosis Membrane Synthesized through Layer-by-Layer Assembly. Membranes (Basel). 2015 Aug 10;5(3):369-84. doi: 10.3390/membranes5030369. PubMed PMID: 26266426; PubMed Central PMCID: PMC4584286. 20: Hasan AA, Sabry SA, Abdallah MH, El-Damasy DA. Formulation and in vitro characterization of poly(dl-lactide-co-glycolide)/Eudragit RLPO or RS30D nanoparticles as an oral carrier of levofloxacin hemihydrate. Pharm Dev Technol. 2016 Sep;21(6):655-63. doi: 10.3109/10837450.2015.1041044. Epub 2015 Apr 27. PubMed PMID: 25915180.