Page last updated: 2024-11-11

1,2-dioleoyloxy-3-(trimethylammonium)propane

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1,2-dioleoyloxy-3-(trimethylammonium)propane: fluorescent probe for phospholipids; RN & structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6437371
CHEMBL ID1180576
SCHEMBL ID138218
MeSH IDM0190949

Synonyms (23)

Synonym
dotap
1,2-dotap
n,n,n-trimethyl-2,3-bis((-1-oxo-octadecenyl)oxy)-(z,z)-1-propanaminium
n-(1-(2,3-dioleoyloxy)propyl)-n,n,n-trimethylammonium methylsulfate
113669-21-9
1,2-dioleoyloxy-3-(trimethylammonium)propane
2,3-bis[[(z)-octadec-9-enoyl]oxy]propyl-trimethylazanium
CHEMBL1180576
unii-mr86k0xrqp
mr86k0xrqp ,
1-propanaminium, n,n,n-trimethyl-2,3-bis(((9z)-1-oxo-9-octadecenyl)oxy)-
1-propanaminium, n,n,n-trimethyl-2,3-bis((1-oxo-9-octadecenyl)oxy)-, (z,z)-
SCHEMBL138218
1,2-dioleoyl-3-trimethylammonium propane
1-propanaminium, n,n,n-trimethyl-2,3-bis(((9z)-1-oxo-9-octadecen-1-yl)oxy)-
dotap, (+/-)-
KWVJHCQQUFDPLU-YEUCEMRASA-N
n,n,n-trimethyl-2,3-bis(oleoyloxy)propan-1-aminium
Q27284189
STARBLD0005610
18:1 tap (dotap, ms salt)
DTXSID501029587
BP-28291

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Also, cell morphology showed early toxic changes, such as cytoplasmic vacuolization and cell shrinking, and it should be included with such toxicity evaluations."( Comparison of cell proliferation and toxicity assays using two cationic liposomes.
Jääskeläinen, I; Lappalainen, K; Syrjänen, K; Syrjänen, S; Urtti, A, 1994
)
0.29
" There was no evidence for excess nasal inflammation, circulating inflammatory markers or other adverse events ascribable to active treatment."( Evidence for safety and efficacy of DOTAP cationic liposome mediated CFTR gene transfer to the nasal epithelium of patients with cystic fibrosis.
Carothers, AD; Davidson, H; Davidson-Smith, H; Dorin, JR; Greening, AP; Ho, LP; Hoenes, C; Imrie, M; Innes, JA; Kallmeyer, G; McLachlan, G; Michaelis, U; Moralee, S; Naujoks, K; Porteous, DJ; Samways, JM; Stevenson, BJ; Wallace, WA, 1997
)
0.3
" Moreover, we demonstrate that although intravenous administration of lipid-DNA complexes does not induce toxic effects in the lung, high transgene expression in lung correlates with histopathological lesions in liver, this fact being documented by high transaminase levels in serum of treated mice."( Contribution of plasmid DNA to hepatotoxicity after systemic administration of lipoplexes.
Doucet, L; Ferec, C; Floch, V; Le Gall, C; Loisel, S, 2001
)
0.31
" The cationic liposomes showed a dose-dependent toxicity and were found to be most toxic for cells of macrophage origin."( Transfection efficiency and cytotoxicity of cationic liposomes in salmonid cell lines of hepatocyte and macrophage origin.
Bols, NC; Evensen, Ø; Romøren, K; Thu, BJ, 2004
)
0.32
"The safe and efficient delivery of nucleic acids into haematopoietic stem cells (HSCs) has a wide range of therapeutic applications."( KLN-5: a safe monocationic lipophosphoramide to transfect efficiently haematopoietic cell lines and human CD34+ cells.
Clément, JC; Delépine, P; Férec, C; Fichou, Y; Hardy, E; Le Bris, M; Le Ny, K; Montier, T; Picquet, E; Yaouanc, JJ, 2004
)
0.32
" Cationic lipids alone were not toxic to these cells."( Lipoplexes prepared from cationic liposomes and mammalian DNA induce CpG-independent, direct cytotoxic effects in cell cultures and in mice.
Barenholz, Y; Khazanov, E; Simberg, D, 2006
)
0.33
" When considering possible clinical applications of siRNA for humans, the adverse immunostimulatory effects must also be taken into account."( Atelocollagen-mediated systemic delivery prevents immunostimulatory adverse effects of siRNA in mammals.
Inaba, S; Ishimoto, T; Kadomatsu, K; Makita, N; Matsuo, S; Nagahara, S; Takei, Y; Tarumi, Y, 2012
)
0.38
" A screening battery was established for assessment of a broad range of parameters related to adverse effects."( In vitro toxicity of cationic micelles and liposomes in cultured human hepatocyte (HepG2) and lung epithelial (A549) cell lines.
Andresen, TL; Christensen, T; Gjetting, T; Knudsen, KB; Kumar, PEK; Loft, S; Lykkesfeldt, J; Møller, P; Northeved, H; Permin, A; Persson, M; Roursgaard, M; Vesterdal, LK, 2016
)
0.43
" We investigated the hypothesis that commonly used and poorly tolerated cationic lipids might be replaced with more efficacious and safe lipidoids as the lipid component of siRNA-loaded lipid-polymer hybrid nanoparticles (LPNs) for achieving more efficient gene silencing at lower and safer doses."( Engineering of small interfering RNA-loaded lipidoid-poly(DL-lactic-co-glycolic acid) hybrid nanoparticles for highly efficient and safe gene silencing: A quality by design-based approach.
Falkenberg, E; Foged, C; Franzyk, H; Justesen, S; Mørck Nielsen, H; Tejlmann, S; Thanki, K; Van Driessche, E; Zeng, X, 2017
)
0.46

Pharmacokinetics

ExcerptReferenceRelevance
"In the present work we set out to apply pharmacodynamic concepts derived from dose-response curves (Potency and Efficacy) to characterize the gene transfer efficiency of a vector:DNA complex."( Pharmacodynamic approach to study the gene transfer process employing non-viral vectors.
Aliño, SF; Crespo, A; Escrig, E; Guillem, VM; Revert, F, 2000
)
0.31
"Here, we developed a novel ELISA-based assay for quantifying double-stranded intact siRNAs for in vivo pharmacokinetic analysis."( Assessment of siRNA pharmacokinetics using ELISA-based quantification.
Kim, EJ; Oh, YK; Park, TG; Shim, CK, 2010
)
0.36

Compound-Compound Interactions

ExcerptReferenceRelevance
" Intranasal vaccination with ovalbumin (OVA) in combination with DOTAP/DC-chol liposomes induced the production of OVA-specific IgA in nasal tissues and increased serum IgG1 levels, suggesting that the cationic DOTAP/DC-chol liposome leads to the induction of a Th2 immune response."( Intranasal Immunization with DOTAP Cationic Liposomes Combined with DC-Cholesterol Induces Potent Antigen-Specific Mucosal and Systemic Immune Responses in Mice.
Aramaki, Y; Hidaka, A; Honjo, E; Iwase, N; Iwata, T; Kiyono, H; Kunisawa, J; Muto, S; Sato, E; Tada, R; Takahashi, S; Takayama, N; Yamakita, Y, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
" In vivo pharmacokinetic study revealed noticeable enhancement of bioavailability and plasma circulation time of the drugs when encapsulated in the carrier system."( Folate receptor-targeted hybrid lipid-core nanocapsules for sequential delivery of doxorubicin and tanespimycin.
Choi, HG; Gautam, M; Gupta, B; Jeong, JH; Kim, JO; Lee, JS; Pathak, S; Poudel, BK; Regmi, S; Ruttala, HB; Yong, CS, 2017
)
0.46
"The molecular targeted drug ATRA demands a suitable carrier that delivers to the cancer site due to its poor bioavailability and drug resistance."( Liposome nano-formulation with cationic polar lipid DOTAP and cholesterol as a suitable pH-responsive carrier for molecular therapeutic drug (all-trans retinoic acid) delivery to lung cancer cells.
Bonati, L; Danisha, JP; Grace, VMB; Guruvayoorappan, C; Wilson, DD, 2021
)
0.62
" In this study, we constructed ATV-loaded nanoemulsions (ATV-NEs) containing multivalent intestinal transporter-targeting lipids to improve the oral bioavailability of ATV."( Enhancement of the anticancer effect of atorvastatin-loaded nanoemulsions by improving oral absorption via multivalent intestinal transporter-targeting lipids.
Byun, Y; Cho, SS; Khadka, B; Kim, KT; Kweon, S; Pandey, P; Park, JW; Shim, JH; Subedi, L, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" Two routes of administration and a dose-response study of bV-CEA were used in BALB/c mice to define the magnitude of the immune response as well as the most effective route of immunization."( The use of a cationic liposome formulation (DOTAP) mixed with a recombinant tumor-associated antigen to induce immune responses and protective immunity in mice.
Bei, R; Frati, L; Guptill, V; Kantor, J; Kashmiri, SV; Masuelli, L; Muraro, R; Schlom, J, 1998
)
0.3
"In the present work we set out to apply pharmacodynamic concepts derived from dose-response curves (Potency and Efficacy) to characterize the gene transfer efficiency of a vector:DNA complex."( Pharmacodynamic approach to study the gene transfer process employing non-viral vectors.
Aliño, SF; Crespo, A; Escrig, E; Guillem, VM; Revert, F, 2000
)
0.31
" Subcutaneous liposome-mediated DNA immunisation employing two DRV(DNA) formulations as well as naked DNA revealed that humoural responses (immunoglobulin total IgG, and subclasses IgG1 and 1gG2a) engendered by the plasmid encoded NP were substantially higher after dosing twice, 28 days apart with 10 microg liposome-entrapped DNA compared to naked DNA."( Liposome-mediated DNA immunisation via the subcutaneous route.
McNeil, S; Perrie, Y; Vangala, A, 2003
)
0.32
"Liposomes as drug delivery systems--in comparison to the traditional dosage forms--offer the advantage of the targeted drug delivery and as a consequence, reduction of the side effects."( [Methods to increase the encapsulation efficiency for liposomal drugs].
Budai, L; Budai, M; Gróf, P; Kaszás, N; Klebovich, I; Zimmer, A, 2008
)
0.35
" In addition, proper siRNA dosing seems to be important for a positive therapeutic outcome in vivo."( MRI-assessed therapeutic effects of locally administered PLGA nanoparticles loaded with anti-inflammatory siRNA in a murine arthritis model.
Colombo, S; Foged, C; Jensen, LB; Lammers, T; Nicolay, K; Nielsen, HM; Schiffelers, RM; Storm, G; Strijkers, GJ; te Boekhorst, BC; Varkouhi, AK, 2012
)
0.38
" Luminescence returned to baseline by 24-48 hours after drug injection and was reinducible over two additional rounds of drug dosing in pxr(+/+) mice."( Bioimaging real-time PXR-dependent mdr1a gene regulation in mdr1a.fLUC reporter mice.
Chen, J; Forman, BM; Gu, L; Kane, SE; Synold, TW, 2013
)
0.39
" An optimized formulation of purified lipo-complex LNPs (DOTAP/Chol/DNA, 45 nm) showed significantly higher (5-fold in the lungs and 4-fold in the liver) transgene expression activity upon oral dosage than lipo-polyplex LNPs (DPPC/Chol/lPEI/DNA, 75 nm) or lPEI/DNA nanoparticles (43 nm)."( Size-controlled lipid nanoparticle production using turbulent mixing to enhance oral DNA delivery.
Chen, K; Chen, Y; He, Z; Hu, Y; Leong, KW; Liu, L; Mao, HQ; Nie, T; Tang, H; Zhu, J, 2018
)
0.48
" saRNA has been shown to induce protein expression for up to 60 days and elicit immune responses with lower dosing than messenger RNA (mRNA)."( Inside out: optimization of lipid nanoparticle formulations for exterior complexation and in vivo delivery of saRNA.
Aldon, Y; Blakney, AK; McKay, PF; Shattock, RJ; Yus, BI, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (688)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's92 (13.37)18.2507
2000's292 (42.44)29.6817
2010's252 (36.63)24.3611
2020's52 (7.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.15

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index8.15 (24.57)
Research Supply Index6.56 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.28%)5.53%
Reviews5 (0.71%)6.00%
Case Studies1 (0.14%)4.05%
Observational0 (0.00%)0.25%
Other695 (98.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]