EVALUATION OF BENZYLIDENE-ACETONE ANALOGUES OF CURCUMIN AS ANTITUBERCULOSIS

  • Cikra Ikhda Nur Hamidah Safitri Department of Pharmaceutical Chemistry, Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta, Indonesia.
  • Ritmaleni Ritmaleni Department of Pharmaceutical Chemistry, Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta, Indonesia.
  • Ning Rintiswati Department of Microbiology, , Faculty of Medicine Universitas Gadjah Mada, Yogyakarta, Indonesia.
  • Sardjiman Sardjiman Department of Pharmaceutical Chemistry, Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta, Indonesia.
  • Takushi Kaneko Tuberculosis Alliance, New York, United State.

Abstract

 Objective: The objective of this research is to evaluate the effect of benzylideneacetone analog of curcumin against Mycobacterium tuberculosis (MTB) H37Rv.

Method: The activity of benzylideneacetone analog of curcumin is evaluated using mycobacteria growth indicator tube (MGIT) method and microplate alamar blue assay (MABA) method. The compound of minimum inhibitory concentration (MIC) is defined as the minimum concentration of drugs which really inhibit the growth of MTB.

Result: The MIC compound of 1,5-bis(3,4-dichlorophenyl)-1,4-pentadiene-3-one (C9) and 1,5-bis(3-chlorophenyl)-1,4-pentadiene-3-one (C10) can inhibit the bacteria of MTB at the concentration of 500 μg/ml using MGIT method. Based on MABA method, it can be obtained similar MIC value of C9 compound and C10 compound that are 187.5 μg/ml.

Conclusion: C9 and C10 have antituberculosis activity. Benzylideneacetone analog of curcumin which has chlor moiety has a better activity in inhibiting MTB, but it still needs further research to make it become a potent antituberculosis drug.

Keywords: Tuberculosis, Curcumin analog, Mycobacteria growth indicator tube, Microplate alamar blue assay.

References

1. World Health Organization. W. H. Bending The Curve-Ending Tb: Annual Report; 2017.
2. Shaji J, Shaikh M. Drug-resistant tuberculosis: Recent approach in polymer based nanomedicine. Int J Pharm Pharm Sci 2016;8:1.
3. Saewan N, Thakam A, Jintaisong A, Kittigowitana K. Anti-tyrosinase and cytotoxicity activities of curcumin-metal complexes. Int J Pharm Pharm Sci 2014;6:270-3.
4. Bisht S, Maitra A. Systemic delivery of curcumin: 21st century solutions for an ancient conundrum. Curr Drug Discov Technol 2009;6:192-9.
5. Supardjan. Chemical content of turmeric ; Curcumin and its derivatives. Indones J Pharm 2005;12(3):115-9.
6. Meng B. Antioxidant and antiinflammatory activities of curcumin on diabetes mellitus and its complications. Curr Pharm Des 2013;19:2101-13.
7. Kumar TV, Manjunatha H, Rajesh KP. Anti-inflammatory activity of curcumin and capsaicin augmented in combination. Int J Pharm Pharm Sci 2017;9:145-9.
8. Sajithlal GB, Chithra P, Chandrakasan G. Effect of curcumin on the advanced glycation and cross-linking of collagen in diabetic rats. Biochem Pharmacol 1998;56:1607-14.
9. Mazumder A, Neamati N, Sunder S, Schulz J, Pertz H, Eich E, et al. Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. J Med Chem 1997;40:3057-63.
10. Bourne KZ, Bourne N, Reising SF, Stanberry LR. Plant products as topical microbicide candidates: Assessment of in vitro and in vivo activity against herpes simplex virus Type 2. Antiviral Res 1999;42:219-26.
11. Nugroho AE, Ikawati Z, Null S, Maeyama K. Effects of benzylidenecyclopentanone analogues of curcumin on histamine release from mast cells. Biol Pharm Bull 2009;32:842-9.
12. Sukardiman S, Suharjono S, Oktaviyanti ND. Immunohistochemical study of Curcuma Xantorrhiza Roxb. and Morinda Citirifolia L. ethanolic extract granules combination in high fat diet induced hyperlipidemia rats. Int J Pharm Pharm Sci 2014;6:142-5.
13. Tyagi P, Singh M, Kumari H, Kumari A, Mukhopadhyay K. Bactericidal activity of curcumin i is associated with damaging of bacterial membrane. PLoS One 2015;10:e0121313.
14. Elgadir MA, Salama M, Adam A. Anti-breast cancer from various natural sources-review. Int J Pharm Pharm Sci 2015;7:44-7.
15. Bhawana, Basniwal RK, Buttar HS, Jain VK, Jain N. Curcumin nanoparticles: Preparation, characterization, and antimicrobial study. J Agric Food Chem 2011;59:2056-61.
16. Baldwin PR, Reeves AZ, Powell KR, Napier RJ, Swimm AI, Sun A, et al. Monocarbonyl analogs of curcumin inhibit growth of antibiotic sensitive and resistant strains of mycobacterium tuberculosis. Eur J Med Chem 2015;92:693-9.
17. Chabib L, Awaluddin R, Ikawati Z, Martien R, Ismail H. Molecular docking, pharmacophore modelling, and adme-toxicity prediction of curcumin analog compounds as inflammatory inhibitor on rheumatoid arthritis. Int J Pharm Pharm Sci 2017;9:16-21.
18. Changtam C, Hongmanee P, Suksamrarn A. Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. Eur J Med Chem 2010;45:4446-57.
19. Nugroho AE, Sardjiman S, Maeyama K. The effects of PGV-1 and PGV-2 on The B-hexosaminidase release from intraceluller calcium ion-induced mast cells. Indones J Pharm 2009;20:207-16.
20. Nugroho AE, Yuniarti N, Estyastono EP, Supardjan, Hakim L. Determination of antioxidant activity of dehydrozingerone through hydroxy radical scavengers using deoxyribosa method. Indones J Pharm 2006;7(3):116-22.
21. Meiyanto E, Da’i M, Supardjan AM, Jenie UA. Geometric isomers and cytotoxic effect on T47d cells of curcumin analogues PGV-0 and PGV- 1. Indones J Pharm 2007;18:40-7.
22. Hadi FT, Sugiyanto, Oetari. Identification of pentagamavunon-0 metabolite in faeces after intravenous injection of white-male sprague dawley-derived rats. Indones J Pharm 2005;12:72-8.
23. Nurrochmad A, Sari IP, Murwanti R, Candraningrum T, Afritasari D, Martina D, et al. Hepatoprotective effect of gamavuton-0 against dË—galactosamine/lipopolysaccharide-induced fulminant hepatic failure. Indones J Pharm 2012;23:18-26.
24. Ritmaleni R, Simbara A. Synthesis of tetrahydro pentagavunon-0. Indones J Pharm 2010;21(2):100-5.
25. Abdel-Aziz HA, Eldehna WM, Fares M, Al-Rashood ST, Al-Rashood KA, Abdel-Aziz MM, et al. Synthesis, biological evaluation and 2d-QSAR study of halophenyl bis-hydrazones as antimicrobial and antitubercular agents. Int J Mol Sci 2015;16:8719-43.
26. Shaikh SI, Zaheer Z, Mokale SN, Lokwani DK. Development of new pyrazole hybrids as antitubercular agents: Synthesis, biological evaluation and molecular docking study. Int J Pharm Pharm Sci 2017;9:50-6.
27. Rathod AS, Godipurge SS, Biradar JS. Synthesis of indole, coumarinyl and pyridinyl derivatives of isoniazid as potent antitubercular and antimicrobial agents and their molecular docking studies. Int J Pharm Pharm Sci 2017;9:233-40.
28. Parumasivam T, Kumar HS, Mohamad S, Ibrahim P, Sadikun A. Effects of a lipophilic isoniazid derivative on the growth and cellular morphogenesis of mycobacterium tuberculosis H37Rv. Int J Pharm Pharm Sci 2013;5:43-50.
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Safitri, C. I. N. H., R. Ritmaleni, N. Rintiswati, S. Sardjiman, and T. Kaneko. “EVALUATION OF BENZYLIDENE-ACETONE ANALOGUES OF CURCUMIN AS ANTITUBERCULOSIS”. Asian Journal of Pharmaceutical and Clinical Research, Vol. 11, no. 4, Apr. 2018, pp. 226-30, doi:10.22159/ajpcr.2018.v11i4.22991.
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