Unraveling the cytotoxicity and metabolic pathways of binary natural deep eutectic solvent systems

Scientific Reports

Volumn 7, Issue , 2017, Pages

  Mbous, Yves Paul ^a   Hayyan, Maan ^a   Wong, Won Fen ^a   Looi, Chung Yeng ^a   Hashim, Mohd Ali ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

[No Author keywords available]

Indexed keywords

ADVANCED GLYCATION END PRODUCT; FRUCTOSE; GLUCOSE; REACTIVE OXYGEN METABOLITE; SOLVENT;

ANIMAL; CELL DEATH; CELL MEMBRANE PERMEABILITY; CELL SURVIVAL; CHEMISTRY; DRUG EFFECT; INSTITUTE FOR CANCER RESEARCH MOUSE; METABOLISM; MOLECULAR MODEL; OXIDATION REDUCTION REACTION; PH; TRANSPORT AT THE CELLULAR LEVEL; TUMOR CELL LINE; VISCOSITY;

ANIMALS; BIOLOGICAL TRANSPORT; CELL DEATH; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; CELL SURVIVAL; FRUCTOSE; GLUCOSE; GLYCATION END PRODUCTS, ADVANCED; HYDROGEN-ION CONCENTRATION; METABOLIC NETWORKS AND PATHWAYS; MICE, INBRED ICR; MODELS, MOLECULAR; OXIDATION-REDUCTION; REACTIVE OXYGEN SPECIES; SOLVENTS; VISCOSITY;

EID: 85011422737     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep41257     Document Type: Article

References (55)

1. Smith, E. L., Abbott, A. P. & Ryder, K. S. Deep eutectic solvents (DES) and their applications. Chem. Rev. 114, 11060-11082 (2014).
2. Zhang, Q., Vigier, K. D. O., Royer, S. & Jerome, F. Deep eutectic solvents: Syntheses, properties and applications. Chem. Soc. Rev. 41, 7108-7146 (2012).
3. Tang, B. & Row, K. H. Recent developments in deep eutectic solvents in chemical sciences. Monatsh. Chem.-Chem. Mon. 144, 1427-1454 (2013).
4. Durand, E. et al. Evaluation of deep eutectic solvents as new media for Candida antarctica B lipase catalyzed reactions. Process Biochem. 47, 2081-2089 (2012).
5. Hayyan, M., Mjalli, F. S., Hashim, M. A. & AlNashef, I. M. A novel technique for separating glycerine from palm oil-based biodiesel using ionic liquids. Fuel Process. Technol. 91, 116-120 (2010).
6. Hayyan, A., Hashim, M. A., Hayyan, M., Mjalli, F. S. & AlNashef, I. M. A new processing route for cleaner production of biodiesel fuel using a choline chloride based deep eutectic solvent. J. Clean. Prod. 65, 246-251 (2014).
7. Wei, Z.-F. et al. Fast and green extraction and separation of main bioactive flavonoids from Radix Scutellariae. Ind. Crop. Prod. 63, 175-181 (2015).
8. Sanchez-Leija, R. J. J., Pojman, A., Luna-Barcenas, G. & Mota-Morales, J. D. Controlled release of lidocaine hydrochloride from polymerized drug-based deep-eutectic solvents. J. Mater. Chem. B 2, 7495-7501 (2014).
9. Wagle, D. V., Zhao, H. & Baker, G. A. Deep eutectic solvents: Sustainable media for nanoscale and functional materials. Acc.Chem. Res. 47, 2299-2308 (2014).
10. Hayyan, M. et al. Assessment of cytotoxicity and toxicity for phosphonium-based deep eutectic solvents. Chemosphere 93, 455-459 (2013).
11. Hayyan, M. et al. Are deep eutectic solvents benign or toxic? Chemosphere 90, 2193-2195 (2013).
12. Hayyan, M., Looi, C. Y., Hayyan, A., Wong, W. F. & Hashim, M. A. In vitro and in vivo toxicity profiling of ammonium-based deep eutectic solvents. PLoS One 10, e0117934 (2015).
13. Radošević, K. et al. Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol. Environ. Saf. 112, 46-53 (2015).
14. Wen, Q., Chen, J.-X., Tang, Y.-L., Wang, J. & Yang, Z. Assessing the toxicity and biodegradability of deep eutectic solvents. Chemosphere 132, 63-69 (2015).
15. Zhao, B.-Y. et al. Biocompatible deep eutectic solvents based on choline chloride: Characterization and application to the extraction of rutin from Sophora japonica. ACS Sustain. Chem. Eng. 3, 2746-2755 (2015).
16. Choi, Y. H. et al. Are natural deep eutectic solvents the missing link in understanding cellular metabolism and physiology? Plant Physiol. 156, 1701-1705 (2011).
17. Dai, Y., van Spronsen, J., Witkamp, G.-J., Verpoorte, R. & Choi, Y. H. Natural deep eutectic solvents as new potential media for green technology. Anal. Chim. Acta 766, 61-68 (2013).
18. Paiva, A. et al. Natural deep eutectic solvents-Solvents for the 21st century. ACS Sustain. Chem. Eng. 2, 1063-1071 (2014).
19. Hayyan, A. et al. Fruit sugar-based deep eutectic solvents and their physical properties. Thermochim. Acta 541, 70-75 (2012).
20. Hayyan, A. et al. Glucose-based deep eutectic solvents: Physical properties. J. Mol. Liq. 178, 137-141 (2013).
21. Juneidi, I., Hayyan, M. & Mohd Ali, O. Toxicity profile of choline chloride-based deep eutectic solvents for fungi and Cyprinus carpio fish. Environ Sci Pollut Res 23, 7648-7659 (2016).
22. Hayyan, M. et al. Natural deep eutectic solvents: Cytotoxic profile. SpringerPlus 5, 913 (2016).
23. Looi, C. et al. Induction of apoptosis in melanoma A375 cells by a chloroform fraction of Centratherum anthelminticum (L.) seeds involves NF-kappaB, p53 and Bcl-2-controlled mitochondrial signaling pathways. BMC Complement Altern Med 13, 1-14 (2013).
24. Liew, S. Y. et al. Subditine, a new monoterpenoid indole alkaloid from bark of Nauclea subdita (Korth.) Steud. induces apoptosis in human prostate cancer cells. PLoS ONE 9, e87286 (2014).
25. Ludwig, D. S. Examining the health effects of fructose. JAMA 310, 33-34 (2013).
26. Helou, C. et al. Microorganisms and Maillard reaction products: A review of the literature and recent findings. Amino Acids 46, 267-277 (2013).
27. Pun, P. B. L. & Murphy, M. P. Pathological significance of mitochondrial glycation. Int. J. Cell Biol. 2012, 1-13 (2012).
28. Bucala, R., Makita, Z., Koschinsky, T., Cerami, A. & Vlassara, H. Lipid advanced glycosylation: Pathway for lipid oxidation in vivo. P. Natl. Acad. Sci. 90, 6434-6438 (1993).
29. Ravandi, A. et al. Isolation and identification of glycated aminophospholipids from red cells and plasma of diabetic blood. FEBS Lett. 381, 77-81 (1996).
30. Requena, J. R. et al. Carboxymethylethanolamine, a biomarker of phospholipid modification during the maillard reaction in vivo. J. Biol. Chem. 272, 17473-17479 (1997).
31. Oak, J.-H., Nakagawa, K. & Miyazawa, T. Synthetically prepared Amadori-glycated phosphatidylethanolamine can trigger lipid peroxidation via free radical reactions. FEBS Lett. 481, 26-30 (2000).
32. Kasai, H., Iwamoto-Tanaka, N. & Fukada, S. DNA modifications by the mutagen glyoxal: Adduction to G and C, deamination of C and GC and GA cross-linking. Carcinogenesis 19, 1459-1465 (1998).
33. Pischetsrieder, M., Seidel, W., Mönch, G. & Schinzel, R. N 2-(1-Carboxyethyl) deoxyguanosine, a nonenzymatic glycation adduct of DNA, induces single-strand breaks and increases mutation frequencies. Biochem. Biophys. Res. Commun. 264, 544-549 (1999).
34. Chen, H.-J. C. & Chen, Y.-C. Analysis of glyoxal-induced DNA cross-links by capillary liquid chromatography nanospray ionization tandem mass spectrometry. Chem. Res. Toxicol. 22, 1334-1341 (2009).
35. Bose, T. & Chakraborti, A. S. Fructose-induced structural and functional modifications of hemoglobin: Implication for oxidative stress in diabetes mellitus. Biochim. Biophys. Acta (BBA)-General Subjects 1780, 800-808 (2008).
36. Bunn, H. F. & Higgins, P. J. Reaction of monosaccharides with proteins: Possible evolutionary significance. Science 213, 222-224 (1981).
37. Liu, H. & Heaney, A. P. Refined fructose and cancer. Expert Opin. Ther. Targets 15, 1049-1059 (2011).
38. Liu, H. et al. Fructose induces transketolase flux to promote pancreatic cancer growth. Cancer Res. 70, 6368-6376 (2010).
39. Charrez, B., Qiao, L. & Hebbard, L. The role of fructose in metabolism and cancer. Horm. Mol. Biol. Clin. Investig. 22, 79-89 (2015).
40. Damaghi, M., Wojtkowiak, J. W. & Gillies, R. J. pH sensing and regulation in cancer. Front. Physiol. 4, 370 (2013).
41. Wu, W. & Zhao, S. Metabolic changes in cancer: Beyond the Warburg effect. Acta Biochim. Biophys. Sinica 45, 18-26 (2013).
42. Wike-Hooley, J. L., Haveman, J. & Reinhold, H. S. The relevance of tumour pH to the treatment of malignant disease. Radiother. Oncol. 2, 343-366 (1984).
43. Riemann, A. et al. Acidic environment leads to ROS-induced MAPK signaling in cancer cells. PLoS One 6, e22445 (2011).
44. Herold, D. A., Keil, K. & Bruns, D. E. Oxidation of polyethylene glycols by alcohol dehydrogenase. Biochem. Pharmacol. 38, 73-76 (1989).
45. McKennis, H. et al. The excretion and metabolism of triethylene glycol. Toxicol. Appl. Pharmacol. 4, 411-431 (1962).
46. Escribá, P. V. et al. Membranes: A meeting point for lipids, proteins and therapies. J. Cell. Mol. Med. 12, 829-875 (2008).
47. Szachowicz-Petelska, B., Dobrzyńska, I., Sulkowski, S. & Figaszewski, Z. A. In Colorectal Cancer Biology-From Genes to Tumor (ed. Dr. Rajun or Ettarh) (InTech, 2012).
48. Michel, V., Yuan, Z., Ramsubir, S. & Bakovic, M. Choline transport for phospholipid synthesis. Exp. Biol. Med. 231, 490-504 (2006).
49. Fagone, P. & Jackowski, S. Phosphatidylcholine and the CDP-choline cycle. BBA-Mol Cell Biol L 1831, 523-532 (2013).
50. Plagemaen, P. G. Choline metabolism and membrane formation in rat hepatoma cells grown in suspension culture. III. Choline transport and uptake by simple diffusion and lack of direct exchange with phosphatidylcholine. J. Lipid Res. 12, 715-724 (1971).
51. Gal, N. et al. Membrane interactions of ionic liquids: Possible determinants for biological activity and toxicity. Biochim. Biophys. Acta 1818, 2967-2974 (2012).
52. Dobrzynska, I., Skrzydlewska, E. & Figaszewski, Z. Parameters characterizing acid-base equilibria between cell membrane and solution and their application to monitoring the effect of various factors on the membrane. Bioelectrochemistry 69, 142-147 (2006).
53. Szachowicz-Petelska, B., Dobrzyńska, I., Sulkowski, S. & Figaszewski, Z. A. in From Genes to Tumor (ed Dr. Rajunor Ettarh) Ch. 11, (InTech, 2012).
54. Owusu-Ansah, E., Yavari, A. & Banerjee, U. A protocol for in vivo detection of Reactive oxygen species. Protocol Exchange doi: 10.1038/nprot.2008.2 (2008).
55. Dai, Y., Witkamp, G.-J., Verpoorte, R. & Choi, Y. H. Tailoring properties of natural deep eutectic solvents with water to facilitate their applications. Food Chem. 187, 14-19 (2015).