81480-40-2

Usage

Uses

Used in Pharmaceutical Industry:
Oleic Acid N-Hydroxysuccinimide Ester is used as an inhibitor of CD36/FAT translocase and the mitochondrial respiratory chain for its potential role in modulating cellular processes and developing therapeutic agents.
Used in Cosmetics and Dermatological Applications:
Oleic Acid N-Hydroxysuccinimide Ester is used in the preparation of ceramide analogues as skin permeation enhancers, which can improve the absorption and effectiveness of topically applied drugs and cosmetics.

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 112-80-1 cis-Octadecenoic acid 
• 112-77-6 (Z)-9-octadecenoyl chloride 

Downstream Products

• 108455-80-7 (S,Z)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)octadecan-9-en-1-one 

Relevant academic research and scientific papers

Design and evaluation of clickable gelatin-oleic nanoparticles using fattigation-platform for cancer therapy

The principles of bioorthogonal click chemistry and metabolic glycoengineering were applied to produce targeted anti-cancer drug delivery via fattigation-platform-based gelatin-oleic nanoparticles. A sialic acid precursor (Ac4ManNAz) was introduced to the cell surface. Gelatin and oleic acid were conjugated by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride/N-hydroxysuccinimide (EDC/NHS) chemistry with the subsequent covalent attachment of dibenzocyclooctyne (DBCO) in a click reaction on the cell surface. The physicochemical properties, drug release, in vitro cytotoxicity, and cellular uptake of DBCO-conjugated gelatin oleic nanoparticles (GON-DBCO; particle size, ～240 nm; zeta potential, 6 mV) were evaluated. Doxorubicin (DOX) was used as a model drug and compared with the reference product, Caelyx. A549 and MCF-7 cell lines were used for the in vitro studies. GON-DBCO showed high DOX loading and encapsulation efficiencies. In A549 cells, the IC50 value for GON-DBCO-DOX (1.29 μg/ml) was six times lower than that of Caelyx (10.54 μg/ml); in MCF-7 cells, the IC50 values were 1.78 μg/ml and 2.84 μg/ml, respectively. Confocal microscopy confirmed the click reaction between GON-DBCO and Ac4ManNAz on the cell surface. Flow cytometry data revealed that the intracellular uptake of GON-DBCO-DOX was approximately two times greater than that of GON-DOX and Caelyx. Thus, the newly designed GON-DBCO-DOX provided a safe and efficient drug delivery system to actively target the anticancer agents.

Polymeric micelles based on amphiphilic oleic acid modified carboxymethyl chitosan for oral drug delivery of bcs class iv compound: Intestinal permeability and pharmacokinetic evaluation

Chemical modification of chitosan derivatives with hydrophobic fatty acids to enhance their self-aggregation behavior is well established. Previously our group reported low molecular weight carboxymethyl chitosan (CMCS) which showed enhancement in apparent permeability of hydrophobic drug, tamoxifen. Further extension to this work, herein we synthesize a new polymer of oleic acid grafted low molecular weight carboxymethyl chitosan (OA-CMCS) for maneuvering biopharmaceutical performance of poorly water soluble drugs. This polymer was designed and synthesized via amidation reaction and well characterized by analytical tools like 1H-NMR and FT-IR spectroscopy. OA-CMCS conjugate easily self-organized into micelles like structure in an aqueous medium and showed a low critical micellar concentration of 1 μg/mL. Poorly water-soluble drug, docetaxel (DTX) was used as a model drug in this study. Optimization of variables resulted in the formation of spherical DTX loaded OA-CMCS micelles in the size range of 213.4 ± 9.6 nm with an entrapment efficiency of 57.26 ± 1.25percent. DTX loaded OA-CMCS micelles showed slow and sustained DTX release behavior in simulated body fluid during in vitro release study. The permeability of DTX loaded OA-CMCS micelles across the gastrointestinal tract were investigated by in vitro Caco-2 cells model. The apparent permeability of DTX loaded OA-CMCS micelles improved up to 6.57-fold in comparison to free DTX suspension which indicates the increase in paracellular absorption of DTX. Additionally, in vivo pharmacokinetic study demonstrates an increase in Cmax (1.97-fold) and AUC (2.62-fold) for DTX loaded OA-CMCS micelles compared to free DTX suspension. Hence, we propose OA-CMCS as a promising cargo to incorporate drugs for enhancement of biopharmaceutical performance.

Mucoadjuvant properties of lipo- and glycoconjugated derivatives of oligochitosans

Chitosan, (1-4)-2-amino-2-deoxy-beta-d-glucan, is a deacetylated form of chitin, an abundant biodegradable, positively charged natural polysaccharide. Chitosan is used for antigen delivery through mucosal barrier due to its ability to disrupt tight junctions. Here we produced new water-soluble low-molecular weight chitosan (LMW-Chi) lipid derivatives and compared their ability to stimulate humoral response with the effect of unmodified LMW-Chi or its oligosaccharide derivatives. LMW-Chi effectively penetrated into macrophage-like, lymphoid and epithelial cells. It also stimulated in mice IgG production to model proteins delivered either by subcutaneous or intranasal routes. Adjuvant effect of chitosan derivatives was comparable to or lower than that of unmodified LMW-Chi. Thus, it is possible that adjuvant effect is induced by unmodified glucosamine units of chitosan.

GEMCITABINE AMPHIPHILE PRODRUGS

The present invention relates to improved prodrugs, and compositions thereof. In particular, it relates to amphiphilic gemcitabine prodrugs or amphiphilic prodrugs of other biologically active molecules with the capacity to make liquid crystalline nanostructured nanoparticles, and uses thereof to treat animals, including humans.

Single-stranded nucleic acid molecule for regulating expression of gene having delivering function

The invention provides a single-stranded nucleic acid capable of inhibiting expression of a target gene having a delivery function. The nucleic acid contains, from the 5′-side to the 3′-side, a 5′-side region (Xc), a linker region (Lx), an inner region (Z), a linker region (Ly) and a 3′-side region (Yc) in this order, wherein the inner region (Z) is constituted by linkage of the inner 5′-side region (X) and the inner 3′-side region (Y), the 5′-side region (Xc) is complementary to the inner 5′-side region (X), the 3′-side region (Yc) is complementary to the inner 3′-side region (Y), at least one of the inner region (Z), the 5′-side region (Xc) and the 3′-side region (Yc) comprises an expression inhibitory sequence that inhibits expression of a target gene, and at least one of the 5′-terminus, the 3′-terminus, the linker region (Lx) and the linker region (Ly) is bound to a bio-related substance.

METHODS AND COMPOSITIONS FOR TREATMENT OF PRADER-WILLI SYNDROME

The present invention provides pharmaceutical compositions comprising a fatty acid amide of an amino acid as defined herein, such as oleoyl-α-methyl-serine, or a stereoisomer or salt thereof, for improving, i.e., increasing or preventing loss of, bone mineral density and/or treating osteoporosis in patients suffering from Prader-Willi syndrome; and methods of use.

Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyn

Α - galactose ceramide new isomer and its synthetic method

The invention provides an alpha-galactosyl ceramide new isomer and its synthetic method. Configuration of sphingosine chain is changed to 4,5-cis double bond sphingosine chain. According to the invention, reaction steps are shortened, yield is raised, and aftertreatment and purification steps are omitted. The synthetic method can be used for total synthesis of similar glycosyl ceramide and satisfies wide range of development, research and application of different glycosyl ceramide.

Multiplexed supramolecular assemblies for non-viral delivery of genetic material

The invention provides a composition comprising two or more of a) genetic material; b) a condensing agent; c) a membrane destabilizing agent; d) a targeting/stabilizing agent, and optionally e) an ionic cross-linking agent. The components of the composition can self-assemble to form particles via electrostatic and/or lipophilic interactions. Methods of making and using the composition are also provided. The compositions can be used, for example, to transfer genetic material to cells in vitro or in vivo.

METHODS AND COMPOSITIONS FOR PREVENTING OPIOID ABUSE

Abuse-resistant opioid compounds, drug delivery systems, pharmaceutical compositions comprising an opioid covalently bound to a chemical moiety are provided. Methods of delivering an active ingredient to a subject and methods of preventing opioid abuse are also provided.