Why is lecithin a good molecule for the formation of micelles

The Journal of Physical Chemistry B , 33 , The Journal of Physical Chemistry B , 26 , The Journal of Physical Chemistry B , 24 , The Journal of Physical Chemistry B , 21 , The Journal of Physical Chemistry B , 10 , The Journal of Physical Chemistry B , 43 , Mariano Correa and, Nancy E. Rosenfeld and, Charles A. The Journal of Physical Chemistry B , 29 , Stevenson and, G.

Langmuir , 22 14 , Chemical Reviews , 4 , Piletic,, David E. Moilanen,, D. Spry,, Nancy E. Levinger, and, M. The Journal of Physical Chemistry A , 15 , Grant,, Karen E. Steege,, Michelle R. Bunagan, and, Edward W. Castner, Jr. The Journal of Physical Chemistry A , 43 , Piletic,, Howe-Siang Tan, and, M. The Journal of Physical Chemistry B , 45 , Chemical Reviews , 9 , Sollenberger,, Lijuan Wang, and, Dongping Zhong. Harpham,, Branka M. Ladanyi, and, Nancy E. The Journal of Physical Chemistry A , 33 , The Journal of Physical Chemistry B , 14 , Langmuir , 21 9 , The Journal of Physical Chemistry B , 8 , Grant,, Michelle R.

DeRitter,, Karen E. Steege,, Tatiana A. Fadeeva, and, Edward W. Langmuir , 21 5 , Jaye,, Neil T. Hunt, and, Stephen R. Langmuir , 21 4 , Vishal,, K. Gandhi, and, K. Ion Exchange in Reverse Micelles. Langmuir , 21 2 , The Journal of Physical Chemistry B , 50 , Corbeil,, Ruth E. Riter, and, Nancy E. The Journal of Physical Chemistry A , 16 , Hunt,, Andrew A.

Jaye,, Alexander Hellman, and, Stephen R. The Journal of Physical Chemistry B , 1 , Langmuir , 20 2 , Effect of Sodium Salicylate and Sodium Cholate. The Journal of Physical Chemistry B , 39 , DelaCruz and, G. Aoudia and, M. The Journal of Physical Chemistry B , 25 , The Journal of Physical Chemistry A , 19 , Jaye, and, Stephen R.

The Journal of Physical Chemistry B , 15 , The Journal of Physical Chemistry A , 14 , Liu,, A. Miller,, K. Gaffney,, P. Szymanski,, S. Garrett-Roe,, I. Bezel, and, C. Zhong,, D. Steinhurst,, E.

Carpenter, and, J. Langmuir , 18 20 , Chemical Reviews , 8 , Solvation Dynamics in Bile Salt Aggregates. The Journal of Physical Chemistry B , 32 , Grainger, and, Christian Salesse. Langmuir , 18 14 , Journal of the American Chemical Society , 25 , The Journal of Physical Chemistry A , 25 , Slow Solvation Dynamics of Dimethylformamide in a Nanocavity. The Journal of Physical Chemistry A , 47 , The Journal of Physical Chemistry B , 7 , Langmuir , 16 26 , The Journal of Physical Chemistry A , 46 , Choma,, Edward F.

Gooding,, William F. DeGrado, and, Robin M. Chemical Reviews , 6 , Bardo,, Cruz Martinez, and, Daniel A. The Journal of Physical Chemistry B , 2 , The polydispersity index P. Tables 1 and 2 and Fig. The optimal formulation ratio for curcumin:lecithin:NaDOC was found to be However, adding lecithin increased the particle size and reduced the EE. Moreover, the F87 and F micelles were more stable and formed at a lower concentration; but adding lecithin increased the particle size.

These two optimal formulations were selected for further evaluation. The MPMs reduced the elimination rate and increased the retention time of curcumin. The potential efficacy of curcumin in treating various diseases is a valuable research topic, and several clinical trials have determined its therapeutic effect.

The pharmacological efficacy and safety make curcumin a prospective compound for treating and preventing various human diseases; however, curcumin has limited clinical applications because of its extremely low aqueous solubility, fast systemic elimination, insufficient tissue absorption, and degradation at an alkaline pH, severely curtailing the BA and limiting its clinical use.

Therefore, the relative low solubility and BA of curcumin constitute a major problem, hindering its clinical use in exerting the maximum therapeutic activity against various diseases. To investigate the potential of using micelles as a drug delivery system for enhancing solubility and BA, the present study used amphiphilic polymers for developing curcumin micelles.

Lecithin, a natural mixture of phospholipids, is a major constituent of cell membranes, nervous tissues, and brain substances. Phospholipids possess a positively or negatively charged head group and a hydrocarbon tail, which has a zwitterionic head group at a physiological pH.

Lecithin is a typical amphiphilic phospholipid with favorable biocompatibility and facilitates encapsulated drug absorption. However, the hydrophobic part alone is too short for forming a micelle. The major factors affecting the particle size, D. Combining TPGS and lecithin also caused precipitation. Furthermore, a small particle size is beneficial for passive targeting to tumor tissues through the EPR effect, cellular uptake, and intracellular trafficking.

Hence, we infer that the small size of the formulated curcumin micelles improved the circulation half-life and enabled avoiding the RES. A major challenge in delivering curcumin to cancerous tissue is its instability and biodegradation at a physiological pH.

Curcumin is stable in the stomach and small intestine but unstable in neutral and basic environments 42 , In PBS and FBS, the micelle formulation increased curcumin stability by protecting the encapsulated curcumin against hydrolysis.

Hence, the formulated system efficiently increased curcumin stability. Curcumin-loaded micelles are designed for improving the BA of the delivered curcumin. Therefore, curcumin-loaded sa MPMs and free curcumin were intravenously injected or orally administered in rats for monitoring the BA.

Our results suggested the slow release of curcumin from micelles, reduced degradation, and prolonged duration increased the BA. The degradation possibly resulted from rapid hydrolysis and biotransformation of curcumin into its glucuronide and sulfate conjugates within a short period. For oral administration, the maximum plasma concentration of curcumin was observed after 0.

The micelle biodistribution mainly depends on components of the hydrophilic shell causing the micelles to stabilize and interact with plasma proteins and cell membranes. Moreover, because of their amphiphilic characteristics, the encapsulated polymers used here have surfactant properties and offer stability and biocompatibility to micelles. For intravenous administration, the aforementioned surface-coated hydrophilic polymers are required for minimizing opsonization and for prolonging the in vivo micelle circulation.

Conclusively, we reported a simple and cost effective formulation composed of lecithin-based MPMs that was able to achieve the same degree of improvement in PK profiles and BA of curcumin as those reported PLGA formulations which was an expensive material 13 , 14 , 44 , The current sa MPMs system for curcumin demonstrated that when curcumin-loaded sa MPMs were orally administrated, the time to achieve maximum plasma concentration of curcumin Tmax was shortened from 1.

It indicates that sa MPMs is able to not only improve the solubility of curcumin but also enhance its permeability through intestinal epithelial cells resulting in a significantly shorter Tmax, higher Cmax and larger BA. Ultimately, the process to produce lecithin-based sa MPMs is also simple and easily reproducible and preparable on a large scale.

Considering the potential of micelles as a drug delivery system, the present study involved developing and characterizing lecithin-based curcumin sa MPMs for improving the curcumin BA. For intravenous administration, the absolute BA increased 2. Thus, the slow release of curcumin from micelles, reduced degradation, and prolonged duration possibly increased the BA.

Lecithin-based sa MPMs improve the solubility, stability, and BA of curcumin, representing an efficient delivery system. Therefore, increasing the curcumin BA by using lecithin-based sa MPMs can make curcumin a prominent therapeutic agent for treating human disorders.

Curcumin-loaded sa MPMs were prepared using a thin film method, as previously described The unincorporated curcumin aggregates were removed by passing the solution through a 0. The characteristics of the curcumin-loaded sa MPMs, namely the average particle size and size distribution, E. The average diameter and size distribution Polydispersity index, P. The mobile phase was a mixture of methanol and 0. On determining the curcumin concentration from the validated calibration curve, the E.

At a predetermined time-point, the particle size of the curcumin-loaded sa MPMs was analyzed for evaluating the stability of their product. At a predetermined time-point, the particle size of the curcumin-loaded sa MPMs was analyzed for evaluating their stability in plasma. Drug release from the curcumin-loaded sa MPMs was assessed using the dialysis bag method, in which 0.

One milliliter of curcumin-loaded sa MPMs or a free curcumin solution i. All measurements were conducted in triplicate. For comparison, curcumin release from a free solution under the same conditions was assessed. Blood samples were collected in heparinized tubes from the jugular vein at 0. Separation was achieved using a BEH C 18 column 2.

The system delivered a constant flow at 0. During analyses, the ESI parameters were set as follows: capillary voltage, 3. PK parameters were represented as the mean and standard deviation SD from individual rats from each group and were estimated through noncompartmental analysis. The terminal elimination rate constant K e was estimated from the slope of the log—linear phase of a graph of the declining plasma concentration of curcumin versus time. A 2-tailed p value less than 0. How to cite this article : Chen, L.

Sharma, R. Curcumin: The story so far. Cancer 41, — Strimpakos, A. Curcumin: Preventive and therapeutic properties in laboratory studies and clinical trials. Wahlang, B. Identification of permeability-related hurdles in oral delivery of curcumin using the Caco-2 cell model. Chen, A. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. PubMed Google Scholar. Aggarwal, B. Curcumin: The Indian solid gold.

Kaminaga, Y. Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett. Anand, P. Bioavailability of curcumin: Problems and promises. CAS Google Scholar. Pan, M. Biotransformation of curcumin through reduction and glucuronidation in mice.

Drug Metab. Suresh, D. Studies on the in vitro absorption of spice principles - Curcumin, capsaicin and piperine in rat intestines. Food Chem. Takahashi, M. Evaluation of an oral carrier system in rats: Bioavailability and antioxidant properties of liposome-encapsulated curcumin. Maiti, K. Curcumin-phospholipid complex: Preparation, therapeutic evaluation and pharmacokinetic study in rats. Bisht, S. Nanobiotechnology 5, 3 p Design of curcumin-loaded PLGA nanoparticles formulation with enhanced cellular uptake, and increased bioactivity in vitro and superior bioavailability in vivo.

Shaikh, J. Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Mohanty, C. The in vitro stability and in vivo pharmacokinetics of curcumin prepared as an aqueous nanoparticulate formulation.

Biomaterials 31, — Gou, M. Curcumin-loaded biodegradable polymeric micelles for colon cancer therapy in vitro and in vivo. Nanoscale 3, — Gong, J. Polymeric micelles drug delivery system in oncology. Release , — Lu, Y.

Polymeric micelles and alternative nanonized delivery vehicles for poorly soluble drugs. Jones, M. Polymeric micelles - a new generation of colloidal drug carriers. Yokoyama, M. Polymeric micelles as a new drug carrier system and their required considerations for clinical trials. Expert Opin. Drug Del. Maeda, H. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: A review.

Release 65, — Release 74, 47—61 Wei, Z. Krishnadas, A. Sterically stabilized phospholipid mixed micelles: in vitro evaluation as a novel carrier for water-insoluble drugs. Jin, X. A novel drug-phospholipid complex loaded micelle for baohuoside I enhanced oral absorption: in vivo and in vivo evaluations.

Drug Dev. Marczylo, T. Comparison of systemic availability of curcumin with that of curcumin formulated with phosphatidylcholine. Cancer Chemother. Yanasarn, N. Nanoparticles engineered from lecithin-in-water emulsions as a potential delivery system for docetaxel. Hu, K. Enhanced oral bioavailability of docetaxel by lecithin nanoparticles: Preparation, in vitro , and in vivo evaluation.

Yanyu, X. The preparation of silybin-phospholipid complex and the study on its pharmacokinetics in rats. Cuomo, J.