References

pharmjournal

Разработка и регистрация лекарственных средств

Drug development & registration

2305-20662658-5049

LLC «CPHA»

pharmjournal-605

Research Article

ФАРМАЦЕВТИЧЕСКАЯ ТЕХНОЛОГИЯ И НАНОТЕХНОЛОГИИ

PHARMACEUTICAL TECHNOLOGY AND NANOTECHNOLOGY

БИОДОСТУПНОСТЬ КУРКУМИНА И МЕТОДЫ ЕЕ ПОВЫШЕНИЯ (ОБЗОР)

BIOAVAILABILITY OF CURCUMIN AND METHODS OF ITS ENHANCING

Соловьёва

Н. Л.

Soloveva

N. L.

noemail@neicon.ru

Сокуренко

М. С.

Sokurenkova

M. S.

noemail@neicon.ru

Зырянов

О. А.

Zypyanov

O. A.

noemail@neicon.ru

ФГАОУ ВО Первый Московский государственный медицинский университет им. И. М. Сеченова Минздрава РоссииSechenov First State Medical University

ФГБУН «Федеральный исследовательский центр питания и биотехнологии»Sechenov First State Medical University; Federal Research of Nutrition, Biotechnology and Food Safety

2018

09012019

034653

2019

Соловьёва Н.Л., Сокуренко М.С., Зырянов О.А.

Soloveva N.L., Sokurenkova M.S., Zypyanov O.A.

Данная работа распространяется под лицензией Creative Commons Attribution 4.0.

This work is licensed under a Creative Commons Attribution 4.0 License.

https://www.pharmjournal.ru/jour/article/view/605

Куркумин - гидрофобное полифенольное соединение природного происхождения. Куркумин обладает широким спектром фармакологического действия. По своей природе полифенол плохо всасывается при пероральном приеме и обладает низкой биодоступностью, частично за счет низкой скорости всасывания в кишечнике и частично за счет быстрого метаболизма (глюкуронирования), что ограничивает его клиническое использование. Одной из важных задач является разработка эффективных форм куркумина с целью повышения биодоступности этого соединения. Это достигается за счет включения куркумина в такие системы, как липосомы, наночастицы, мицеллы и др., образования комплексов с циклодекстринами, а также использования биоэнхансеров. В частности, применение комплекса куркумина с пиперином, известным ингибитором процесса глюкуронизации в печени и кишечнике, увеличивало биодоступность куркумина в несколько раз. Сочетание куркумина с фосфолипидами за счет встраивания его в липофильные мембраны увеличивало его максимальную концентрацию по сравнению с отдельно взятым куркумином. Куркумин в виде наночастиц оказывал фармакологический эффект в более низкой - в 15 раз - концентрации, чем обычный куркумин.

Curcumin is a hydrophobic polyphenolic compound of natural origin. Curcumin has a wide range of pharmacological effects. Curcumin is inherently poorly absorbed when ingested and has low bioavailability, in part due to a low rate of absorption in the intestine and, in part, due to rapid metabolism (glucuronidation), which limits its clinical use. One of the important tasks is the development of effective forms of curcumin with the aim of increasing the bioavailability of this compound. This is achieved by including curcumin in such systems as liposomes, nanoparticles, micelles, etc., formation of complexes with cyclodextrins, and the use of bio-enhancers. In particular, the use of a complex of curcumin with piperine, a known inhibitor of the glucuronization process in the liver and intestine, increased the bioavailability of curcumin several times. Combination of curcumin with phospholipids due to its incorporation into lipophilic membranes, increased its maximum concentration in comparison with an individual curcumin. Curcumin in the form of nanoparticles had a pharmacological effect at a 15-fold lower concentration than conventional curcumin.

куркуминбиодоступностьбиоэнхансерыпиперинлипосомынаночастицыциклодекстрины

curcuminbioavailabilitybio-enhancerspiperineliposomesnanoparticlescyclodextrins

References1

Kunwar B., Barik A., Pandey R., Priyadarsini K. I. Transport of liposomal and albumin loaded curcumin to living cells: An absorption and fluorescence spectroscopic study // Biochim. Biophys. Acta (Gen.). 2006. V. 1760. P. 1513-1522.

Bharti A. C., Donato N., Aggarwal B. B. Curcumin (diferuloylmethane) inhibits constitutive and IL-6-inducible STAT3 phosphorylation in human multiple myeloma cells // J Immunol. 2003. V. 171(7). P. 3863-3871.

Dinda A. K., Prashant C. K., Naqvi S. Curcumin loaded organically modified silica (ORMOSIL) nanoparticle; A novel agent for cancer therapy // Int. J. Nanotechnol. 2012. V. 9. P. 862-871.

Cheng A. L., Hsu C. H., Lin J. K., Hsu M. M., Ho Y. F., Shen T. S., Ko J. Y., Lin J. T., Lin B. R., Ming-Shiang W., Yu H. S., Jee S. H., Chen G. S., Chen T. M., Chen C. A., Lai M. K., Pu Y. S., Pan M. H., Wang Y. J., Tsai C. C., Hsieh C. Y. Phase I Clinical Trial of Curcumin, a Chemopreventive Agent, in Patients with High-Risk or Pre-Ma-lignant Lesions // Anticancer Research. 2001. V. 21. P. 2895-2900.

Liu A., Lou H., Zhao L., Fan P. Validated LC/MS/MS assay for curcumin and tetrahydrocurcumin in rat plasma and applicationto pharmacokinetic study of phospholipid complex of curcumin // J. Pharm. Biomed. Anal. 2006. V. 40 (3). P. 720-727.

Chandran C., Goel A. A randomized, pilot study to assess the efficacy and safety of curcumin in patients with active rheumatoid arthritis // Phytother Res PTR. 2012. V. 26(11). P. 1719-1725

Wahlstrom C., Blennow G. A study on the fate of curcumin in the rat // ActaPharmacolToxicol (Copenh). 1978. V. 43(2). P. 86-92.

Millington C., Sonego S., Karunaweera N., Rangel A., Aldrich-Wright J. R., Campbell I. L., Gyengesi E., Munch G. Chronic neuroinflammation in Alzheimer’s disease: new perspectives on animal models and promising candidate drugs // Biomed Res Int. 2014. V. 2014. P. 32-34.

Sreelakshmi C., Goel N., Datta K. K. R., Addlagatta A., Ummani R., Reddy B. V. S. Green synthesis of curcumin capped gold nanoparticles and evaluation of their cytotoxicity // Nanosci. Nanotechnol. Lett. 2013. V. 5. P. 1258-1265.

Lao C. D., Demierre M. F., Sondak V. K. Targeting Events Inmelanoma Carcinogenesis for the Prevention of Melanoma // Expert Review of Anticancer Therapy. 2006. V. 6. P. 1559-1568.

Lao C. D., Ruffin M. T., Normolle D., Heath D. D., Murray S. I., Bailey J. M., Boggs M. E., Crowell J., Rock C. L., Brenner D. E. Dose Escalation of a Curcuminoid Formulation // BMC Complementary and Alternative Medicine. 2006. V. 6. P. 10.

Atal C. K., Dubey R. K., Singh J. Biochemical basis of enhanced drug bioavailability by piperine: Evidence that piperine is a potent inhibitor of drug metabolism // J PharmacolExpTher. 1985. V. 232. P. 258-262.

Jin D., Lee J., Seo M. L., Jaworski J., Jung J. H. Controlled drug delivery from mesoporous silica using a pH response release // New J. Chem. 2012. V. 36. P. 1616-1620.

Jin D., Park K.-W., Lee J. H., Song K., Kim J.-G., Seo M. L., Jung J.H. The selective immobilization of curcumin onto the internal surface of mesoporous hollow silica particles by covalent bonding and its controlled release // J. Mat. Chem. 2011. V. 21. P. 3641-3645.

Singh D. K., Jagannathan R., Khandelwal P., Abraham P. M., Poddar P. In situ synthesis and surface functionalization of gold nanoparticles with curcumin and their antioxidant properties: An experimental and density functional theory investigation // Nanoscale. 2013. V. 5. P. 1882-1893.

Patra D., Sleem F. A new method for pH triggered curcumin release by applying poly(l-lysine) mediated nanoparticlecongregation // Anal. Chim. Acta. 2013. V. 795. P. 60-68.

Ratnam D. V., Ankola D. D., Bhardwaj V., Sahana D. K., M. N. V. Ravi. Kumar. Role of antioxidants in prophylaxis and therapy: A pharmaceutical perspective // J. Control. Rel. 2006. V. 113. P. 189-207.

Hansen, M. Krautwald, Maczurek A. E., Stuchbury G., Fromm P., Steele M., Schulz O., Garcia O. B., Castillo J., Korner H., Munch G. A versatile high throughput screening system for the simultaneous identification of anti-inflammatory and neuroprotective compounds // J Alzheimer’s Dis. 2010. V. 19(2). P. 438-441.

Liliemark E., Liliemark J., Kållberg N., Björkholm M., Sjöström B., Peterson C. Studies of the organ distribution in mice of teniposide liposomes designed for treatment of diseases in the mononuclear phagocytic system // Pediatr Res. 1995. V. 38(1). P. 7-10.

Kazemi-Lomedasht, Rami A., Zarghami N. Comparison of Inhibitory Effect of Curcumin Nanoparticles and Free Curcumin in Human Telomerase Reverse Transcriptase Gene Expression in Breast Cancer // Advanced Pharmaceutical Bulletin. 2013. V. 3(1). P. 127-130.

Shoba, Joy D., Joseph T., Majeed M., Rajendran R., Srinivas P. S. Influence of Piperine on the Pharmacokinetics of Curcuminin Animals and Human Volunteers // Planta Medica. 1998. V. 64(4). P. 353-356.

Dudhatra G. B., Mody S. K., Awale M. M., Patel H. B., Modi C. M., Kumar A. et al. A comprehensive review on pharmacotherapeutics of herbal bioenhancers // Scientific World Journal. 2012. V. 2012. P. 24-26.

Jagetia G.C., Aggarwal B.B. «Spicing up» of the immune system by curcumin // J ClinImmunol. 2007. V. 27(1). P. 19-35.

Shin G. H., Chung S. K., Kim J. T., Joung H. J., Park H. J. Preparation of chitosan-coated nanoliposomes for improving the mucoadhesive property of curcumin using the ethanol injection method // J Agric Food Chem. 2013. V. 61(46). P. 111-119.

Asher G. N., Spelman K. Clinical utility of curcumin extract // Altern Ther Health Med. 2013. V. 19(2). P. 20-22.

Chen, Wu J., Sun M. et al. N-trimethyl chitosan chloride-coated liposomes for the oral delivery of curcumin // J Liposome Res. 2012. V. 22(22). P. 100-109.

Hatcher H., Planalp R., Cho J., Torti F. M., Torti S. V. Curcumin: from ancient medicine to current clinical trials // CellMol Life Sci CMLS. 2008. V. 65(11). P. 1632, 1642-1644.

Yan H., The C., Sreejit S., Zhu L., Kwok A., Fang W., Ma X., Nguyen K. T., Korzh V., Zhao Y. Functional mesoporous silica nanoparticles for phootthermal-controlled drug delivery // Angew. Chem. Int. Ed. 2012. V. 51. P. 8373-8377.

Bharat, Somdatt G. Bio-potentiation using herbs: Novel Technique for poor bioavailable drugs // Int J PharmTech Res. 2014. V. 6. P. 443-541.

Sun, Han M. Preparation of novel curcumin liposomes and associated preliminary stability study // World Sci Technol. 2008. V. 10(4). P. 66-72.

Gu J. J., Deng Y. J. Preparation of curcumin liposomes and its oral pharmacokinetics in rats // J Chengdu Med Coll. 2010. V. 5(2). P. 97-100.

Jurenka J. S. Anti-inflammatory properties of curcumin, а major constituent of Curcuma Longa: A review of preclinical and clinical research // Alternative Medicine Review. 2009. V. 14 (2). P. 141-153.

Berginc, Trontelj J., Basnet N. S., Kristl A. Physiological barriers to the oral delivery of curcumin // Pharmazie. 2012. V. 67(6). P. 518-524.

Priyadarsini K. I. The Chemistry of Curcumin: From Extraction to Therapeutic Agent // Molecules. 2014. V. 19. P. 291-212.

Sindhu K., Rajaram A., Sreeram K. J., Rajaram R. Curcumin conjugated gold nanoparticle synthesis and its bioavailability // RSC Adv. 2014. V. 4. P. 1808-1814.

Li, Braiteh F.S., Kurzrock R. Liposome-encapsulated curcumin: in vitro and in vivo effects on proliferation, apoptosis, signaling, and angiogenesis // Cancer. 2005. V. 104. P. 1322-1331.

Ma’Mani L., Nikzad S., Kheiri-Manjili H., Al-Musawi S., Saeedi M., Askaralou S. Curcumin-loaded guanidine functionalized PEGylated mesoporous silica nanoparticles KIT-6: Practical strategy for the breast cancer therapy // Eur. J. Med. Chem. 2014. V. 83. P. 646-654.

Purpura, Lowery R. P., Wilson J. M., Mannan H., Münch G., Razmovski-Naumovski. V. Analysis of different innovative formulations of curcumin for improved relative oral bioavailability in human subjects // Eur J Nutr. 2017. P. 19.

Venigalla M., Gyengesi E., Munch G. Curcumin and Apigenin-novel and promising therapeutics against chronic neuroinflammation in Alzheimer’s disease // Neural Regen Res. 2015. V. 10(8). Р. 1182-1183.

Venigalla M., Sonego S., Gyengesi E., Sharman M.J., Munch G. Novel promising therapeutics against chronic neuroinflammation and neurodegeneration in Alzheimer’s disease // Neurochem Int. 2016. V. 95. P. 70-77.

Yallapu M. M., Ebeling M. C., Khan S., Sundram V., Chauhan N., Gupta B. K., Puumala S. E., Jaggi M., Chauhan S. C. Novel curcumin-loaded magnetic nanoparticles for pancreatic cancer treatment // Mol. Cancer Ther. 2013. V. 12. P. 1471-1480.

Yallapu M. M., Othman S. F., Curtis E. T., Bauer N. A., Chauhan N., Kumar D., Jaggi M., Chauhan S.C. Curucmin loaded magnetic nanoparticles for breast cancer therapeutics and imaging applications // Int. J. Nanomed. 2012. V. 7.

Yellapu M. M., Shadi F. O., Curtis E. T. Multifunctional magnetic nanoparticles for magnetic resonance imaging and cancer therapy // Biomaterials. 2011. V. 32. P. 1890-1905.

Mozafari M. R. Nanoliposomes: preparation and analysis // Methods Mol Biol. 2010. V. 605(605). P. 29-50.

Wojcik M., Krawczyk М., Wojcik Р., Cypryk К., Wozniak L. A. Molecular Mechanisms Underlying Curcumin-Mediated Therapeutic Effects in Type 2 Diabetes and Cancer // Oxidative Medicine and Cellular Longevity. V. 2018, Article ID 9698258. P. 14.

Karunaweera, Raju R., Gyengesi E., Munch G. Plant polyphenols as inhibitors of NF-kappaB induced cytokine production-a potential anti-inflammatory treatment for Alzheimer’s disease? // Front. Mol. Neurosci. 2015. V. 8. P. 3-4, 11.

Muddineti O. S., Kumari P., Ajjarapu S., Lakhani P. M., Bahl R., Ghosh B., Biswas S. Xanthan gum stabilized PEGylated gold nanoparticles for improved delivery of curcumin in cancer // Nanotechnology. 2016. V. 27. P. 32-51.

Anand, Kunnumakkara A. B., Newman R. A., Aggarwal B. B. Bioavailability of curcumin: problems and promises // MolPharm. 2007. V. 4(6). P. 807-818

Ravichandran. Pharmacokinetic study of nanoparticulate curcumin: oral formulationfor enhanced bioavailability // Journal of Biomaterials and Nanobiotechnology. 2013.V. 4. P. 291-299.

Sakey, Bafubiandi-Mulaba A. F., Rajnikanth V., Varaprasad K., Reddy N. N., Raju K. M. Development and characterization of curcumin loaded silver nanoparticle hydrogels for antibacterial. and drug delivery applications // J. Inorg. Organomet. Polym. Mat. 2012. V. 22. P. 1254-1262.

DiSilvestro R. A., Joseph E., Zhao S., Bomser J. Diverse effects of a low dose supplement of lipidated curcumin in healthy middle aged people // Nutr J. 2012. V. 11. P. 80.

Bhardwaj R. K., Glaeser H., Becquemont L., Klotz U., Gupta S. K., Fromm M. F. Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4 // J PharmacolExpTher. 2002. V. 302. P. 645-700.

Gangwar R. K., Tomar G. B., Dhumale V. A., Zinjarde S., Sharma R. B., Datar S. Curcumin conjugated silica nanoparticles for improving bioavailability and its anticancer applications // J. Agric. Food Chem. 2013. V. 61. P. 9632-9637.

Gangwar R. K., Dhumale V. A., Kumari D., Nakate U. T., Gosavi S. W., Sharma R. B., Kale S. N., Datar S. Conjugation of curcumin with PVP capped gold nanoparticles for improving bioavailability // Mater. Sci. Eng. C. 2012. V. 32. P. 2659-2663.

Johri R. K., Thusu N., Khajuria A., Zutshi U. Piperine mediated changes in the permeability of rat intestinal epithelial cells: Status of gamma glutamyltranspeptidase activity, uptake of amino acid and lipid peroxidation // Biochem Pharmacol. 1992. V. 43. P. 1401-1407.

Bhattacharyya R. J., Mandal D., Saha B., Sen G. S., Das T., Sa G. Curcumin prevents tumor-induced T-cell apoptosis through Stat-5a-mediated Bcl-2 induction // J BiolChem. 2007. V. 282(22). P. 15954-15964.

Hatamie, Nouri M., Karandikar S. K., Kulkarni A., Dhole S. D., Phase D. M., Kale S. N. Complexes of cobalt nanoparticles and polyfunctional curcumin as antimicrobial agents // Mat. Sci. Eng. C. 2012. V. 32. P. 92-97.

Ikeda S., Uchida T., Ichikawa T., Watanabe T., Uekaji Y., Nakata D., Terao K., Yano T. Complexation of tocotrienol with gamma-cyclodextrin enhances intestinal absorption of tocotrienol in rats // Biosci. Biotechnol. Biochem. 2010. V. 74(7). P. 1452-1457.

Lev-Ari S., Maimon Y., Strier L., Kazanov D., Arber N. Down-regulation of prostaglandin E2 by curcumin is correlated with inhibition of cell growth and induction of apoptosis in human colon carcinoma cell lines // J Soc Integr Oncol. 2006. V. 4(1). P. 21-26.

Prasad S., Tyagi A. K., Aggarwal B. Recent developments in delivery, bioavailability, absorption and metabolism of curcumin: The golden pigment from golden spice // Cancer Res. Treat. 2014. V. 46. P. 2-18.

Qureshi S., Shah A. H., Ageel A. M. Toxicity Studies on Alpiniagalanga and Curcuma longa // Planta Medica. 1992. V. 58. P. 124-127.

Singh S., Tripathi J. S., Rai N. P. An appraisal of the bioavailability enhancers in Ayurveda in the light of recent pharmacological advances. // Ayu. 2016. 37(1). P. 3-10.

Chin S. F., Iyer K. S., Saunders M., Tim G., Buckley C., Paskevicious M., aston C. L. Encapsulation and sustained release of curcumin using superparamagnetic silica reservoirs // Chemistry. 2009. V. 15. P. 5661-5665.

Johnson S. M., Bangham A. D., Hill M. W. et al. Single bilayer liposomes // Biochim Biophys Acta. 1971. V. 233(233). P. 820-826.

Singh S. P., Sharma M., Gupta P. K. Enhancement of phototoxicity of curcumin in human oral cancer cells using silica nanoparticles as delivery vehicle // Lasers Med. Sci. 2014. V. 29. P. 645-652.

Feng, Wei Y., Lee R.J., Zhao L. Liposomal curcumin and its application in cancer // International Journal of Nanomedicine. 2017. V. 12. P. 602-604.

Shankar T. N., Shantha N. V., Ramesh H. P., Murthy I. A., Murthy V. S. Toxicity Studies on Turmeric (Curcuma longa): Acutetoxicity Studies in Rats, Guineapigs& Monkeys // Indian Journal of Experimental Biology. 1980. V. 18. P. 73-75.

Balakrishnan V., Varma S., Chatterji D. Piperine augments transcription inhibitory activity of rifampicin by several fold in Mycobacterium smegmatis // Curr Sci. 2001. V. 80. P. 1302-1305.

Menon V. P., Sudheer A. R. Antioxidant and anti-inflammatory properties of curcumin // Adv Exp Med Biol. 2007. V. 595. P. 105-125.

Chen W. S., Xu N., Xu L., Wang L., Li Z., Ma W., Zhu Y., Xu C., Kotov N. A. Multifunctional magnetoplasmonic nanoparticle assemblies for cancer therapy and diagnostics (Theranostics) // Macromol. Rapid Comm. 2010. V. 31. P. 228-236.

Sun W. T., Zou Y., Guo Y.P. et al. Construction and characterization of curcumin nanoparticles system // J Nanopart Res. 2014. V. 16(3). P.173-178.

Wang X. Y., Ishida T., Ichihara M., Kiwada H. Influence of the physicochemical properties of liposomes on the accelerated blood clearance phenomenon in rats // J Control Release. 2005. V. 104(1). P. 91-102.

WAbe X. X., Hashimoto S., Horie T. Curcumin inhibition of inflammatory cytokine production by human peripheral blood monocytes and alveolar macrophages // Pharmacol Res Off J Italian Pharmacol Soc. 1999. V. 39(1). P. 41-47.

Бычковский П. М., Кладиев А. А., Соломевич С. О., Щеголев С. Ю. Золотые наночастицы: синтез, свойства, биомедицинское применение // Российский биотерапевтический журнал. 2011. № 3. С. 37-46.

Bychkovskii P. M., Kladiev A. A., Solomevich S.O., Shchegolev S. Yu. Gold nanoparticles: synthesis, properties, biomedical applications // Russian biotherapeutic journal. 2011. № 3. S. 37-46.

The authors declare that there are no conflicts of interest present.