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Novel flourescent spiroborate esters: potential therapeutic agents in in vitro cancer models

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The current treatment system in cancer therapy, which includes chemotherapy/radiotherapy is expensive and often deleterious to surrounding healthy tissue. Presently, several medicinal plants and their constituents are in use to manage the development and progression of these diseases.They have been found effective, safe, and less expensive. In the present study, we are proposing the utility of a new class of curcumin derivative, Rubrocurcumin, the spiroborate ester of curcumin with boric acid and oxalic acid (1:1:1), which have enhanced biostability for therapeutic applications. In vitro cytocompatibility of this drug complex was analysed using MTT assay, neutral red assay, lactate dehydrogenase assay in 3T3L1 adipocytes. Anti tumour activity of this drug complex on MCF7 and A431 human cancer cell line was studied by morphological analysis using phase contrast microscopy, Hoechst staining and cell cycle analysis by FACS. To explore the chemotherapeutic effect, the cytotoxic effect of this compound was also carried out. Rubrocurcumin is more biostable than natural curcumin in physiological medium. Our results prove that this curcumin derivative drug complex possess more efficacy and anti-cancer activity compared with curcumin. The findings out of this study suggests this novel compound as potential candidate for site targeted drug delivery.

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  1. Siegel RL, Miller KD, Jemal A (2017) Cancer statistics, 2017. CA Cancer J Clin 67:7–30

    Article  PubMed  Google Scholar 

  2. Tang L, Wang K (2016) Chronic inflammation in skin malignancies. J Mol Signal 11:2

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Torre LA, Bray F, Siegel RL, Ferlay J, Lortet-Tieulent J, A. Jemal (2015) Global cancer statistics, 2012. CA Cancer J Clin 65:87–108

    Article  PubMed  Google Scholar 

  4. Phillips JM, Clark C, Herman-Ferdinandez L, Moore-Medlin T, Rong X, Gill JR, Clifford JL, Nathan AF (2011) Curcumin inhibits skin squamous cell carcinoma tumor growth in vivo. Otolaryngol Head Neck Surg 145:58–63

    Article  PubMed  Google Scholar 

  5. Sonavane K, Phillips J, Ekshyyan O, Moore-Medlin T, Gill JR, Rong X, Lakshmaiah RR, Abreo F, Boudreaux D, Clifford JL, Nathan CAO (2012) Topical curcuminbased cream is equivalent to dietary curcumin in a skin cancer model. J Skin Cancer.

    Article  PubMed  PubMed Central  Google Scholar 

  6. Ravindran J, Prasad S, Aggarwal BB (2009) Curcumin and cancer cells: how many ways can curry kill tumor cells selectively? AAPS J 11:495–510

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Park W, Amin AR, Chen ZG, Shin DM (2013) New perspectives of curcumin in cancer prevention. Cancer Prev Res 6:387–400

    Article  CAS  Google Scholar 

  8. Hodges RE, Minich DM (2015) Modulation of metabolic detoxification pathways using foods and food-derived components: a scientific review with clinical application. J Nutr Metab.

    Article  PubMed  PubMed Central  Google Scholar 

  9. Lee WH, Loo CY, Bebawy M, Luk F, Mason RS, Rohanizadeh R (2013) Curcumin and its derivatives: their application in neuropharmacology and neuroscience in the 21st century. Curr Neuropharmacol 11:338–378

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Wanninger S, Lorenz V, Subhan A, Edelmann FT (2015) Metal complexes of curcumin—synthetic strategies, structures and medicinal applications. Chem Soc Rev 7:4986–5002

    Article  Google Scholar 

  11. Jeena J, Sudha Devi J, Balachandran SN (2017) Kinetic analysis of thermal and hydrolytic decomposition of spiroborate ester of curcumin with salicylic acid. Orient J Chem 33:849–858

    Article  CAS  Google Scholar 

  12. Jeena J, Sudha Devi R, Balachandran S (2016) Kinetic analysis of thermal decomposition of rubrocurcumin. Acta Clienta Indica XLII C 2:121

    Google Scholar 

  13. Kornhauser A, Coelho SG, Hearing VJ (2010) Applications of hydroxy acids: classification, mechanisms, and photoactivity. Clin Cosmet Investig Dermatol CCID 3:135–142

    Article  CAS  PubMed  Google Scholar 

  14. Sui Z, Salto R, Li J, Craik C, Ortiz de Montellano PR (1993) Inhibition of the HIV-1 and HIV-2 proteases by curcumin and curcumin boron complexes. Bioorg Med Chem 1:415–422

    Article  CAS  PubMed  Google Scholar 

  15. Asha R, Devi RS, Priya RS, Balachandran S, Mohanan PV, Abraham A (2012) Bioactive derivatives of curcumin attenuate cataract formation in vitro. Chem Biol Drug Des 80:887–892

    Article  CAS  Google Scholar 

  16. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65(1–2):55–63

    Article  CAS  PubMed  Google Scholar 

  17. Lasarow RM, Isseroff RR, Gomez EC (1992) Quantitative in vitro assessment of phototoxicity by a fibroblast-neutral red assay. J Invest Dermatol 98(5):725–9

    Article  CAS  PubMed  Google Scholar 

  18. Wolterbeek HT, van der Meer AJ (2005) Optimization, application, and interpretation of lactate dehydrogenase measurements in microwell determination of cell number and toxicity. Assay Drug Dev Technol 3(6):675–682

    Article  CAS  PubMed  Google Scholar 

  19. Vijayalaksmi R, Sathyanarayana MN, Rao MVL (1981) Rubrocurcumin reaction and its use in microdetermination of certain organic acids. Indian J Chem 20B:907

    Google Scholar 

  20. Amin A, Gali-Muhtasib H, Ocker M, Schneider-Stock R (2009) Overview of major classes of plant-derived anticancer drugs. Int J Biomed Sci 5:1–11

    CAS  PubMed  PubMed Central  Google Scholar 

  21. Ji HF, Li XJ, Zhang HY (2009) Can thousands of years of ancient medical knowledge lead us to new and powerful drug combinations in the fight against cancer and dementia EMBO. Nat Prod Rep 10:194–200

    CAS  Google Scholar 

  22. Huang XH, Jain PK, El Sayed IH, El Sayed MA (2007) Gold nanoparticles: interesting optical properties and recent applications in cancer diagnostic and therapy. Nanomedicine 2:681–693

    Article  CAS  PubMed  Google Scholar 

  23. Venu Gopal Y, Ravindranath A, Kalpana G, Rajkapoor B, Sreenivas S (2012) Antitumor and antioxidant activity of Diospyros peregrina against Dalton’s ascites lymphoma in rodents. Ann Biol Res 3:4985–4992

    Google Scholar 

  24. Bose S, Panda AK, Mukherjee S (2015) Curcumin and tumor immune-editing: resurrecting the immune system. Cell Div.

    Article  PubMed  PubMed Central  Google Scholar 

  25. Bernabé Pineda M, Ramírez-Silva MT, Romero-Romo M, González-Vergara E, Rojas-Hernández A (2004) Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition. Spectrochim Acta 0(5):1091–1097

    Article  CAS  Google Scholar 

  26. Souza CRA, Osme SF, Gloria MBA (1997) Stability of curcuminoid pigments in model systems. J Food Process Preserv 21(5):353–363

    Article  CAS  Google Scholar 

  27. Wang YJ, Pan MH, Cheng AL, Lin LI, Ho YS, Hsieh CY, Lin JK (1997) Stability of curcumin in buffer solutions and characterization of its degradation products. J Pharm Biomed Anal 15(12):1867–1876

    Article  CAS  PubMed  Google Scholar 

  28. Germain CS, Niknejad N, Ma L, Garbuio K, Hai T, Dimitroulakos J (2010) Cisplatin induces cytotoxicity through the mitogen-activated protein kinase pathways and activating transcription factor 3. Neoplasia 12(7): 527–538

    Article  CAS  Google Scholar 

  29. Kovács AF, Cinatl J (2002) In vitro cytotoxic dose-relation of cisplatin and sodium thiosulphate in human tongue and oesophageal squamous carcinoma cell lines. J Craniomaxillofac Surg 30(1):54–58

    Article  PubMed  Google Scholar 

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The first author acknowledges Indian Council for Medical Research (ICMR) for the award of Senior Research fellowship to carry out this work.

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Correspondence to Annie Abraham.

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Anjana, S., Joseph, J., John, J. et al. Novel flourescent spiroborate esters: potential therapeutic agents in in vitro cancer models. Mol Biol Rep 46, 727–740 (2019).

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