the Formulation and Characterization of Curcumin 12-Hydroxystearic Acid in Triacetin Organogel for Topical Administration

duaa razaq; Masar Basim Mohsin Mohamed; Lina A. Dahabiyeh

doi:10.32947/ajps.v24i2.1011

Authors

duaa razaq Department of Pharmaceutics , College of Pharmacy , Mustansiriyah University, Baghdad, Iraq
Masar Basim Mohsin Mohamed Department of Pharmaceutics, College of Pharmacy, Mustansiriyah University
Lina A. Dahabiyeh Department of Pharmaceutical sciences, School of pharmacy, The University of Amman، Jordan

DOI:

https://doi.org/10.32947/ajps.v24i2.1011

Keywords:

Antibacterial, Curcumin, 12-hydroxystearic acid, Organogels, rheology, topical

Abstract

Background: Curcumin (CUR) and its derivatives have shown a wide variety of biological activities, such as anti-oxidant, anti-inflammatory, anti-tumor, antimicrobial and antiparasitic effects as well as for the treatment of skin diseases. Due to its physico-chemical limitations such as low aqueous solubility and low bioavailability,

we developed curcumin organogel as a topical delivery system to overcome those limitations. The12-hydroxystearic acid (12-HSA) is well known as a low-molecular-weight organogelators (LMOGs) capable of gelling an organic liquid phase. Different concentrations of (12-HSA) in triacetin with 50 mg CUR were gelled and applied for various examinations: tabletop rheology, oil binding capacity, pH measurement, spreadability, in vitro drug release, antibacterial activity and oscillatory rheology studies. The results revealed that the organogels transition temperatures from solid to liquid were greater than the normal body temperature, this helped the organogels keep their shape; they had good spreadability,and the organogels pH levels were within the safe range for the skin . In vitro release data showed that 4% 12HSA+5%CUR +TA (4TA) gave us 100% release after 6 hours. The selected 4TA illustrated good viscoelastic properties in the amplitude sweep test and a frequency-independent as seen in the frequency sweep test. CUR has good antibacterial action against Staphylococcus aureus; Streptococcus pyrogen, Proteus mirabilis, and Escherichia coli, which prevail at the site of wound injury as this pointed out that 4TA organogel can be used for topical wound healing.

References

- Dall'Acqua, S., et al., New findings on the in vivo antioxidant activity of Curcuma longa extract by an integrated 1H NMR and HPLC–MS metabolomic approach. Fitoterapia, 2016. 109: p. 125-131. DOI: https://doi.org/10.1016/j.fitote.2015.12.013

- Zhu, H., et al., Synthesis and optimization of novel allylated mono-carbonyl analogs of curcumin (MACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI) in rats. European Journal of Medicinal Chemistry, 2016. 121: p. 181-193. DOI: https://doi.org/10.1016/j.ejmech.2016.05.041

- Han, Y.-M., et al., 2-Hydroxycurcuminoid induces apoptosis of human tumor cells through the reactive oxygen species–mitochondria pathway. Bioorganic & medicinal chemistry letters, 2011. 21(2): p. 747-751. DOI: https://doi.org/10.1016/j.bmcl.2010.11.114

- Cetin-Karaca, H. and M.C. Newman, Antimicrobial efficacy of plant phenolic compounds against Salmonella and Escherichia Coli. Food bioscience, 2015. 11: p. 8-16. DOI: https://doi.org/10.1016/j.fbio.2015.03.002

- Morais, E.R., et al., Effects of curcumin on the parasite Schistosoma mansoni: a transcriptomic approach. Molecular and biochemical parasitology, 2013. 187(2): p. 91-97. DOI: https://doi.org/10.1016/j.molbiopara.2012.11.006

- Patel, N.A., N.J. Patel, and R.P. Patel, Design and evaluation of transdermal drug delivery system for curcumin as an anti-inflammatory drug. Drug development and industrial pharmacy, 2009. 35(2): p. 234-242. DOI: https://doi.org/10.1080/03639040802266782

- Anand, P., et al., Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature. Biochemical pharmacology, 2008. 76(11): p. 1590-1611. DOI: https://doi.org/10.1016/j.bcp.2008.08.008

- Gholibegloo, E., et al., Improved curcumin loading, release, solubility and toxicity by tuning the molar ratio of cross-linker to β-cyclodextrin. Carbohydrate polymers, 2019. 213: p. 70-78. DOI: https://doi.org/10.1016/j.carbpol.2019.02.075

- Esposito, C.L., P. Kirilov, and V.G. Roullin, Organogels, promising drug delivery systems: An update of state-of-the-art and recent applications. Journal of controlled release, 2018. 271: p. 1-20. DOI: https://doi.org/10.1016/j.jconrel.2017.12.019

- Kaddoori, Z.S., et al., To Consider The Organogel Of Span 40 And Span 60 In Sesame Oil As A New Member In The Gastro Retentive Drug Delivery Systems. Systematic Reviews in Pharmacy, 2020. 11(5): p. 850-861.

- Kaddoori, Z.S., M.B.M. Mohamed, and N.A. Numan, Organogel investigations as a floating oral system with depot property. Al Mustansiriyah Journal of Pharmaceutical Sciences, 2020. 20(4): p. 132-146. DOI: https://doi.org/10.32947/ajps.v20i4.783

- Nser, S.M. and A.D.H. Al-Shohani, Effect of modification of formulation variables on physical characterization of superporouse hydrogel. Al Mustansiriyah Journal of Pharmaceutical Sciences, 2023. 23(3): p. 285-296. DOI: https://doi.org/10.32947/ajps.v23i3.1046

- Iriventi, P., et al., Design & development of nanosponge loaded topical gel of curcumin and caffeine mixture for augmented treatment of psoriasis. DARU Journal of Pharmaceutical Sciences, 2020. 28: p. 489-506. DOI: https://doi.org/10.1007/s40199-020-00352-x

- Rapalli, V.K., et al., Curcumin loaded nanostructured lipid carriers for enhanced skin retained topical delivery: optimization, scale-up, in-vitro characterization and assessment of ex-vivo skin deposition. European Journal of Pharmaceutical Sciences, 2020. 152: p. 105438. DOI: https://doi.org/10.1016/j.ejps.2020.105438

- Kotian, V., M. Koland, and S. Mutalik, Nanocrystal-Based Topical Gels for Improving Wound Healing Efficacy of Curcumin. Crystals, 2022. 12(11): p. 1565. DOI: https://doi.org/10.3390/cryst12111565

- Vigato, A.A., et al., Physico-chemical characterization and biopharmaceutical evaluation of lipid-poloxamer-based organogels for curcumin skin delivery. Frontiers in Pharmacology, 2019. 10: p. 1006. DOI: https://doi.org/10.3389/fphar.2019.01006

- Vintiloiu, A. and J.-C. Leroux, Organogels and their use in drug delivery—A review. Journal of controlled release, 2008. 125(3): p. 179-192. DOI: https://doi.org/10.1016/j.jconrel.2007.09.014

- Jamali, N., M. Adib-Hajbaghery, and A. Soleimani, The effect of curcumin ointment on knee pain in older adults with osteoarthritis: a randomized placebo trial. BMC Complementary Medicine and Therapies, 2020. 20(1): p. 1-10. DOI: https://doi.org/10.1186/s12906-020-03105-0

- Batool, A., et al., Formulation and evaluation of hyaluronic acid-based mucoadhesive self nanoemulsifying drug delivery system (SNEDDS) of tamoxifen for targeting breast cancer. International journal of biological macromolecules, 2020. 152: p. 503-515. DOI: https://doi.org/10.1016/j.ijbiomac.2020.02.275

- Laupheimer, M., N. Preisig, and C. Stubenrauch, The molecular organogel n-decane/12-hydroxyoctadecanoic acid: Sol–gel transition, rheology, and microstructure. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2015. 469: p. 315-325. DOI: https://doi.org/10.1016/j.colsurfa.2015.01.039

- Zeng, C., et al., Structure and properties of organogels developed by diosgenin in canola oil. Food Biophysics, 2020. 15: p. 452-462. DOI: https://doi.org/10.1007/s11483-020-09643-x

- Fonseca, V.R., P.J. Bhide, and M.P. Joshi, Formulation, development and evaluation of etoricoxib nanosize microemulsion based gel for topical drug delivery. Indian J. Pharm. Educ. Res, 2019. 53(4s). DOI: https://doi.org/10.5530/ijper.53.4s.152

- Mao, K.-L., et al., Skin-penetrating polymeric nanoparticles incorporated in silk fibroin hydrogel for topical delivery of curcumin to improve its therapeutic effect on psoriasis mouse model. Colloids and Surfaces B: Biointerfaces, 2017. 160: p. 704-714. DOI: https://doi.org/10.1016/j.colsurfb.2017.10.029

- Klein, S., Influence of different test parameters on in vitro drug release from topical diclofenac formulations in a vertical diffusion cell setup. Die Pharmazie-An International Journal of Pharmaceutical Sciences, 2013. 68(7): p. 565-571.

- Shahani, K. and J. Panyam, Highly loaded, sustained-release microparticles of curcumin for chemoprevention. Journal of pharmaceutical sciences, 2011. 100(7): p. 2599-2609. DOI: https://doi.org/10.1002/jps.22475

- Mohamed, M.I., Optimization of chlorphenesin emulgel formulation. The AAPS journal, 2004. 6: p. 81-87. DOI: https://doi.org/10.1208/aapsj060326

- Singh, A.R. and K. Kalirajan, Anti-microbial activity of turmeric natural dyeagainst different bacterial strains. Journal of Applied Pharmaceutical Science, 2012(Issue): p. 210-212.

- Kali, A., et al., Antibacterial synergy of curcumin with antibiotics against biofilm producing clinical bacterial isolates. Journal of basic and clinical pharmacy, 2016. 7(3): p. 93. DOI: https://doi.org/10.4103/0976-0105.183265

- Alves, T.M.d.A., et al., Biological screening of Brazilian medicinal plants. Memórias do Instituto Oswaldo Cruz, 2000. 95: p. 367-373. DOI: https://doi.org/10.1590/S0074-02762000000300012

- Tomaiuolo, G., et al., Blood linear viscoelasticity by small amplitude oscillatory flow. Rheologica Acta, 2016. 55: p. 485-495. DOI: https://doi.org/10.1007/s00397-015-0894-3

- Mohamed, M.B.M., Z.S. Qaddoori, and G.S. Hameed, Study the Effect of 12-Hydroxyoctadecanoic Acid Concentration on Preparation and Characterization of Floating Organogels using Cinnarizin as Modeling Drug. Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512), 2022. 31(2): p. 169-176. DOI: https://doi.org/10.31351/vol31iss2pp169-176

- Mengiste, B., et al., Safety evaluation of Eucalyptus globulus essential oils through acute and sub-acute toxicity and skin irritation in mice and rats. Current Chemical Biology, 2020. 14(3): p. 187-195. DOI: https://doi.org/10.2174/2212796814999200818095036

- Oxley, J.A., et al., A survey of rabbit handling methods within the United Kingdom and the Republic of Ireland. Journal of Applied Animal Welfare Science, 2019. 22(3): p. 207-218. DOI: https://doi.org/10.1080/10888705.2018.1459192

- Kim, M.J., S.C. Park, and S.-O. Choi, Dual-nozzle spray deposition process for improving the stability of proteins in polymer microneedles. Rsc Advances, 2017. 7(87): p. 55350-55359. DOI: https://doi.org/10.1039/C7RA10928H

- Yan, Y.-D., et al., Enhanced oral bioavailability of curcumin via a solid lipid-based self-emulsifying drug delivery system using a spray-drying technique. Biological and Pharmaceutical Bulletin, 2011. 34(8): p. 1179-1186. DOI: https://doi.org/10.1248/bpb.34.1179

- Thomas, L., et al., Development of Curcumin loaded chitosan polymer based nanoemulsion gel: In vitro, ex vivo evaluation and in vivo wound healing studies. International journal of biological macromolecules, 2017. 101: p. 569-579. DOI: https://doi.org/10.1016/j.ijbiomac.2017.03.066

- Esposito, C.L., et al., Preparation and characterization of 12-HSA-based organogels as injectable implants for the controlled delivery of hydrophilic and lipophilic therapeutic agents. Materials Science and Engineering: C, 2020. 114: p. 110999. DOI: https://doi.org/10.1016/j.msec.2020.110999

- Rogers, M.A., A.J. Wright, and A.G. Marangoni, Engineering the oil binding capacity and crystallinity of self-assembled fibrillar networks of 12-hydroxystearic acid in edible oils. Soft Matter, 2008. 4(7): p. 1483-1490. DOI: https://doi.org/10.1039/b803299h

- Agrawal, V., et al., Preparation and evaluation of tubular micelles of pluronic lecithin organogel for transdermal delivery of sumatriptan. Aaps PharmSciTech, 2010. 11(4): p. 1718-1725. DOI: https://doi.org/10.1208/s12249-010-9540-7

- Dantas, M.G.B., et al., Development and evaluation of stability of a gel formulation containing the monoterpene borneol. The Scientific World Journal, 2016. 2016. DOI: https://doi.org/10.1155/2016/7394685

- Tebcharani, L., et al., Emulsions of hydrolyzable oils for the zero-order release of hydrophobic drugs. Journal of Controlled Release, 2021. 339: p. 498-505. DOI: https://doi.org/10.1016/j.jconrel.2021.10.014

- Mirnejad, R., et al., Curcumin-loaded chitosan tripolyphosphate nanoparticles as a safe, natural and effective antibiotic inhibits the infection of Staphylococcus aureus and Pseudomonas aeruginosa in vivo. Iranian Journal of Biotechnology, 2014. 12(3): p. 1-8. DOI: https://doi.org/10.15171/ijb.1012

- Sharifi, S., et al., Anti‐microbial activity of curcumin nanoformulations: New trends and future perspectives. Phytotherapy Research, 2020. 34(8): p. 1926-1946. DOI: https://doi.org/10.1002/ptr.6658

- Alves, C., et al., Exploring Z-Tyr-Phe-OH-based hydrogels loaded with curcumin for the development of dressings for wound healing. Journal of Drug Delivery Science and Technology, 2022. 73: p. 103484. DOI: https://doi.org/10.1016/j.jddst.2022.103484

- Yan, N., et al., How do liquid mixtures solubilize insoluble gelators? Self-assembly properties of pyrenyl-linker-glucono gelators in tetrahydrofuran–water mixtures. Journal of the American Chemical Society, 2013. 135(24): p. 8989-8999. DOI: https://doi.org/10.1021/ja402560n

- Rogers, M.A., A.J. Wright, and A.G. Marangoni, Crystalline stability of self-assembled fibrillar networks of 12-hydroxystearic acid in edible oils. Food Research International, 2008. 41(10): p. 1026-1034. DOI: https://doi.org/10.1016/j.foodres.2008.07.012

- Terech, P., et al., Rheological properties and structural correlations in molecular organogels. Langmuir, 2000. 16(10): p. 4485-4494. DOI: https://doi.org/10.1021/la991545d

- Mohamed, M.B.M., L.A. Dahabiyeh, and M.N. Sahib, Design and evaluation of molecular organogel based on folic acid as a potential green drug carrier for oral route. Drug Development and Industrial Pharmacy, 2022. 48(8): p. 367-373. DOI: https://doi.org/10.1080/03639045.2022.2118316