Optical spectroscopic and morphological characterizations of curcuminized silk biomaterials: A perspective from drug stabilization

ACS Omega

Volumn 2, Issue 10, 2017, Pages 6755-6767

  Panja, Sudipta ^a   Behera, Sibaram ^a   Kundu, Subhas C ^a,b   Halder, Mintu ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b UNIVERSITY OF MINHO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85032644538     PISSN: None     EISSN: 24701343     Source Type: Journal    
DOI: 10.1021/acsomega.7b00809     Document Type: Article

References (73)

1. Pa-mies, P.; Stoddart, A. Materials for drug delivery. Nat. Mater. 2013, 12, 957.
2. Lohcharoenkal, W.; Wang, L.; Chen, Y. C.; Rojanasakul, Y. Protein nanoparticles as drug delivery carriers for cancer therapy. BioMed Res. Int. 2014, 2014, 1-12.
3. Zhang, W.; Jiang, P.; Chen, Y.; Luo, P.; Li, G.; Zheng, B.; Chen, W.; Mao, Z.; Gao, C. Suppressing the cytotoxicity of CuO nanoparticles by uptake of curcumin/BSA particles. Nanoscale 2016, 8, 9572-9582.
4. Numata, K.; Kaplan, D. L. Silk-based delivery systems of bioactive molecules. Adv. Drug Delivery Rev. 2010, 62, 1497-1508.
5. Raja, W. K.; MacCorkle, S.; Diwan, I. M.; Abdurrob, A.; Lu, J.; Omenetto, F. G.; Kaplan, D. L. Transdermal delivery devices: Fabrication, mechanics and drug release from silk. Small 2013, 9, 3704-3713.
6. Tsioris, K.; Raja, W. K.; Pritchard, E. M.; Panilaitis, B.; Kaplan, D. L.; Omenetto, F. G. Fabrication of silk microneedles for controlledrelease drug delivery. Adv. Funct. Mater. 2012, 22, 330-335.
7. Kundu, S. C.; Kundu, B.; Talukdar, S.; Bano, S.; Nayak, S.; Kundu, J.; Mandal, B. B.; Bhardwaj, N.; Botlagunta, M.; Dash, B. C.; Acharya, C.; Ghosh, A. K. Nonmulberry silk biopolymers. Biopolymers 2012, 97, 455-467.
8. Kurland, N. E.; Kundu, J.; Pal, S.; Kundu, S. C.; Yadavalli, V. K. Self-Assembly mechanisms of silk protein nanostructures on twodimensional surfaces. Soft Matter 2012, 8, 4952-4959.
9. Aramwit, P.; Siritientong, T.; Srichana, T. Potential applications of silk sericin, a natural protein from textile industry by-products. Waste Manage. Res. 2012, 30, 217-224.
10. Frandsen, J. L.; Ghandehari, H. Recombinant protein-based polymers for advanced drug delivery. Chem. Soc. Rev. 2012, 41, 2696-2706.
11. Mottaghitalab, F.; Farokhi, M.; Shokrgozar, M. A.; Atyabi, F.; Hosseinkhani, H. Silk fibroin nanoparticle as a novel drug delivery system. J. Controlled Release 2015, 206, 161-176.
12. Subia, B.; Dey, T.; Sharma, S.; Kundu, S. C. Target specific delivery of anticancer drug in silk fibroin based 3D distribution model of bone-breast cancer cells. ACS Appl. Mater. Interfaces 2015, 7, 2269-2279.
13. Zhou, J.; Zhang, B.; Shi, L.; Zhong, J.; Zhu, J.; Yan, J.; Wang, P.; Cao, C.; He, D. Regenerated silk fibroin films with controllable nanostructure size and secondary structure for drug delivery. ACS Appl. Mater. Interfaces 2014, 6, 21813-21821.
14. Fatima, M. T.; Chanchal, A.; Yavvari, P. S.; Bhagat, S. D.; Gujrati, M.; Mishra, R. K.; Srivastava, A. Cell permeating nanocomplexes of amphiphilic polyelectrolytes enhance solubility, stability, and anti-cancer efficacy of curcumin. Biomacromolecules 2016, 17, 2375-2383.
15. Mishra, S.; Palanivelu, K. The effect of curcumin (turmeric) on Alzheimer's disease: An overview. Ann. Indian Acad. Neurol. 2008, 11, 13-19.
16. Prasad, S.; Aggarwal, B. B. Turmeric, the golden spice: from traditional medicine to modern medicine. In Herbal Medicine: Biomolecular and Clinical Aspects; Benzie, I. F. F., Wachtel-Galor, S., Eds.; CRC Press: Boca Raton, FL, 2011.
17. Chattopadhyay, I.; Biswas, K.; Bandyopadhyay, U.; Banerjee, R. K. Turmeric and curcumin: Biological actions and medicinal applications. Curr. Sci. 2004, 87, 44-53.
18. Yanagisawa, D.; Shirai, N.; Amatsubo, T.; Taguchi, H.; Hirao, K.; Urushitani, M.; Morikawa, S.; Inubushi, T.; Kato, M.; Kato, F.; Morino, K.; Kimura, H.; Nakano, I.; Yoshida, C.; Okada, T.; Sano, M.; Wada, Y.; Wada, K.-n.; Yamamoto, A.; Tooyama, I. Relationship between the tautomeric structures of curcumin derivatives and their áǎ-binding activities in the context of therapies for Alzheimer's disease. Biomaterials 2010, 31, 4179-4185.
19. Lee, W.-H.; Loo, C.-Y.; Bebawy, M.; Luk, F.; Mason, R.; Rohanizadeh, R. Curcumin and its derivatives: Their application in neuropharmacology and neuroscience in the 21st century. Curr. Neuropharmacol. 2013, 11, 338-378.
20. Rao, C. V. Regulation of COX and LOX by curcumin. The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease; Advances In Experimental Medicine And Biology; Springer, 2007; Vol. 595, pp 213-226.
21. Kepp, K. P. Bioinorganic Chemistry of Alzheimer's Disease. Chem. Rev. 2012, 112, 5193-5239.
22. Prasad, S.; Tyagi, A. K. Curcumin and its analogues: a potential natural compound against HIV infection and AIDS. Food Funct. 2015, 6, 3412-3419.
23. Egan, M. E.; Pearson, M.; Weiner, S. A.; Rajendran, V.; Rubin, D.; Glo-ckner-Pagel, J.; Canny, S.; Du, K.; Lukacs, G. L.; Caplan, M. J. Curcumin, a major constituent of turmeric, corrects cystic fibrosis defects. Science 2004, 304, 600-602.
24. Daniel, S.; Limson, J. L.; Dairam, A.; Watkins, G. M.; Daya, S. Through metal binding, curcumin protects against lead-And cadmiuminduced lipid peroxidation in rat brain homogenates and against leadinduced tissue damage in rat brain. J. Inorg. Biochem. 2004, 98, 266-275.
25. Salem, M.; Rohani, S.; Gillies, E. R. Curcumin, a promising anticancer therapeutic: a review of its chemical properties, bioactivity and approaches to cancer cell delivery. RSC Adv. 2014, 4, 10815-10829.
26. Wilken, R.; Veena, M. S.; Wang, M. B.; Srivatsan, E. S. Curcumin: A review of anti-cancer properties and therapeutic activity in head and neck squamous cell carcinoma. Mol. Cancer 2011, 10, 1-19.
27. Kaminaga, Y.; Nagatsu, A.; Akiyama, T.; Sugimoto, N.; Yamazaki, T.; Maitani, T.; Mizukami, H. Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett. 2003, 555, 311-316.
28. Leung, M. H. M.; Colangelo, H.; Kee, T. W. Encapsulation of curcumin in cationic micelles suppresses alkaline hydrolysis. Langmuir 2008, 24, 5672-5675.
29. Chignell, C. F.; Bilskj, P.; Reszka, K. J.; Motten, A. G.; Sik, R. H.; Dahl, T. A. Spectral and photochemical properties of curcumin. Photochem. Photobiol. 1994, 59, 295-302.
30. Iwunze, M. O. Binding and distribution characteristics of curcumin solubilized in CTAB micelle. J. Mol. Liq. 2004, 111, 161-165.
31. Banerjee, C.; Ghatak, C.; Mandal, S.; Ghosh, S.; Kuchlyan, J.; Sarkar, N. Curcumin in reverse micelle: An example to control excitedstate intramolecular proton transfer (ESIPT) in confined media. J. Phys. Chem. B 2013, 117, 6906-6916.
32. Mandal, S.; Banerjee, C.; Ghosh, S.; Kuchlyan, J.; Sarkar, N. Modulation of the photophysical properties of curcumin in nonionic surfactant (Tween-20) forming micelles and niosomes: A comparative study of different microenvironments. J. Phys. Chem. B 2013, 117, 6957-6968.
33. Mandal, S.; Ghosh, S.; Banik, D.; Banerjee, C.; Kuchlyan, J.; Sarkar, N. An investigation into the effect of the structure of bile salt aggregates on the binding interactions and ESIHT dynamics of curcumin: A photophysical approach to probe bile salt aggregates as a potential drug carrier. J. Phys. Chem. B 2013, 117, 13795-13807.
34. Ghosh, S.; Kuchlyan, J.; Banik, D.; Kundu, N.; Roy, A.; Banerjee, C.; Sarkar, N. Organic additive, 5-methylsalicylic acid induces spontaneous structural transformation of aqueous pluronic triblock copolymer solution: A spectroscopic investigation of interaction of curcumin with pluronic micellar and vesicular aggregates. J. Phys. Chem. B 2014, 118, 11437-11448.
35. Priyadarsini, K. I. Photophysics, photochemistry and photobiology of curcumin: Studies from organic solutions, bio-mimetics and living cells. J. Photochem. Photobiol., C 2009, 10, 81-95.
36. Pan, K.; Zhong, Q.; Baek, S. J. Enhanced dispersibility and bioactivity of curcumin by encapsulation in casein nanocapsules. J. Agric. Food Chem. 2013, 61, 6036-6043.
37. Leung, M. H. M.; Harada, T.; Dai, S.; Kee, T. W. Nanoprecipitation and spectroscopic characterization of curcuminencapsulated polyester nanoparticles. Langmuir 2015, 31, 11419-11427.
38. Banerjee, C.; Maiti, S.; Mustafi, M.; Kuchlyan, J.; Banik, D.; Kundu, N.; Dhara, D.; Sarkar, N. Effect of encapsulation of curcumin in polymeric nanoparticles: How efficient to control ESIPT process-Langmuir 2014, 30, 10834-10844.
39. Guo, G.; Fu, S.; Zhou, L.; Liang, H.; Fan, M.; Luo, F.; Qian, Z.; Wei, Y. Preparation of curcumin loaded poly(-caprolactone)-poly(ethylene glycol)-poly(-caprolactone) nanofibers and their in vitro antitumor activity against Glioma 9L cells. Nanoscale 2011, 3, 3825-3832.
40. Bagchi, D.; Chaudhuri, S.; Sardar, S.; Choudhury, S.; Polley, N.; Lemmens, P.; Pal, S. K. Modulation of stability and functionality of a phyto-Antioxidant by weakly interacting metal ions: curcumin in aqueous solution. RSC Adv. 2015, 5, 102516-102524.
41. Harada, T.; Lincoln, S. F.; Kee, T. W. Excited-State dynamics of the medicinal pigment curcumin in a hydrogel. Phys. Chem. Chem. Phys. 2016, 18, 28125-28133.
42. Leung, M. H. M.; Kee, T. W. Effective stabilization of curcumin by association to plasma proteins: Human serum albumin and fibrinogen. Langmuir 2009, 25, 5773-5777.
43. Dhar, G.; Chakravarty, D.; Hazra, J.; Dhar, J.; Poddar, A.; Pal, M.; Chakrabarti, P.; Surolia, A.; Bhattacharyya, B. Actin-curcumin interaction: Insights into the mechanism of actin polymerization inhibition. Biochemistry 2015, 54, 1132-1143.
44. Li, C.; Luo, T.; Zheng, Z.; Murphy, A. R.; Wang, X.; Kaplan, D. L. Curcumin-functionalized silk materials for enhancing adipogenic differentiation of bone marrow-derived human mesenchymal stem cells. Acta Biomater. 2015, 11, 222-232.
45. Li, X.; Qin, J.; Ma, J. Silk fibroin/poly (vinyl alcohol) blend scaffolds for controlled delivery of curcumin. Regener. Biomater. 2015, 2, 97-105.
46. Nardo, L.; Andreoni, A.; Bondani, M.; Maísson, M.; Tønnesen, H. H. Studies on curcumin and curcuminoids. XXXIV. Photophysical properties of a symmetrical, non-substituted curcumin analogue. J. Photochem. Photobiol., B 2009, 97, 77-86.
47. Banerjee, S.; Prasad, P.; Hussain, A.; Khan, I.; Kondaiah, P.; Chakravarty, A. R. Remarkable photocytotoxicity of curcumin in HeLa cells in visible light and arresting its degradation on oxovanadium(IV) complex formation. Chem. Commun. 2012, 48, 7702-7704.
48. Panja, S.; Halder, M. Exploration of electrostatic interaction in the hydrophobic pocket of lysozyme: Importance of ligand-induced perturbation of the secondary structure on the mode of binding of exogenous ligand and possible consequences. J. Photochem. Photobiol., B 2016, 161, 253-265.
49. He, Y.-X.; Zhang, N.-N.; Li, W.-F.; Jia, N.; Chen, B.-Y.; Zhou, K.; Zhang, J.; Chen, Y.; Zhou, C.-Z. N-Terminal domain of Bombyx mori fibroin mediates the assembly of silk in response to pH decrease. J. Mol. Biol. 2012, 418, 197-207.
50. Yang, Y.; Shao, Z.; Chen, X.; Zhou, P. Optical spectroscopy to investigate the structure of regenerated Bombyx mori silk fibroin in solution. Biomacromolecules 2004, 5, 773-779.
51. Teague, S. J. Implications of protein flexibility for drug discovery. Nat. Rev. Drug Discovery 2003, 2, 527-541.
52. De Jong, W. H.; Borm, P. J. A. Drug delivery and nanoparticles: Applications and hazards. Int. J. Nanomed. 2008, 3, 133-149.
53. Mandal, B. B.; Kundu, S. C. Non-bioengineered silk fibroin protein 3D scaffolds for potential biotechnological and tissue engineering applications. Macromol. Biosci. 2008, 8, 807-818.
54. Facchiano, A.; Ragone, R. Modification of Job's method for determining the stoichiometry of protein-protein complexes. Anal. Biochem. 2003, 313, 170-172.
55. Datta, S.; Halder, M. Effect of encapsulation in the anion receptor pocket of sub-domain IIA of human serum albumin on the modulation of pKa of warfarin and structurally similar acidic guests: A possible implication on biological activity. J. Photochem. Photobiol., B 2014, 130, 76-85.
56. Meier, M.; Seelig, J. Length dependence of the coil-sheet transition in a membrane environment. J. Am. Chem. Soc. 2008, 130, 1017-1024.
57. Honig, B.; Nicholls, A. Classical electrostatics in biology and chemistry. Science 1995, 268, 1144-1149.
58. Ghatak, C.; Rao, V. G.; Mandal, S.; Ghosh, S.; Sarkar, N. An understanding of the modulation of photophysical properties of curcumin inside a micelle formed by an ionic liquid: A new possibility of tunable drug delivery system. J. Phys. Chem. B 2012, 116, 3369-3379.
59. Ross, P. D.; Subramanian, S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 1981, 20, 3096-3102.
60. Wang, Y.-J.; Pan, M.-H.; Cheng, A.-L.; Lin, L.-I.; Ho, Y.-S.; Hsieh, C.-Y.; Lin, J.-K. Stability of curcumin in buffer solutions and characterization of its degradation products. J. Pharm. Biomed. Anal. 1997, 15, 1867-1876.
61. Harada, T.; Pham, D.-T.; Leung, M. H. M.; Ngo, H. T.; Lincoln, S. F.; Easton, C. J.; Kee, T. W. Cooperative binding and stabilization of the medicinal pigment curcumin by diamide linked ã-cyclodextrin dimers: A spectroscopic characterization. J. Phys. Chem. B 2011, 115, 1268-1274.
62. Hevus, I.; Modgil, A.; Daniels, J.; Kohut, A.; Sun, C.; Stafslien, S.; Voronov, A. Invertible micellar polymer assemblies for delivery of poorly water-soluble drugs. Biomacromolecules 2012, 13, 2537-2545.
63. Gupta, N. K.; Dixit, V. K. Development and evaluation of vesicular system for curcumin delivery. Arch. Dermatol. Res. 2011, 303, 89-101.
64. Datta, S.; Panja, S.; Halder, M. Detailed scenario of the acid-base behavior of prototropic molecules in the subdomain-IIA pocket of serum albumin: Results and prospects in drug delivery. J. Phys. Chem. B 2014, 118, 12153-12167.
65. Ghosh, R.; Mondal, J. A.; Palit, D. K. Ultrafast dynamics of the excited states of curcumin in solution. J. Phys. Chem. B 2010, 114, 12129-12143.
66. Adhikary, R.; Mukherjee, P.; Kee, T. W.; Petrich, J. W. Excitedstate intramolecular hydrogen atom transfer and solvation dynamics of the medicinal pigment curcumin. J. Phys. Chem. B 2009, 113, 5255-5261.
67. Saini, R. K.; Das, K. Picosecond spectral relaxation of curcumin excited state in toluene-Alcohol mixtures. J. Lumin. 2013, 144, 169-175.
68. Saini, R. K.; Das, K. Picosecond spectral relaxation of curcumin excited state in a binary solvent mixture of toluene and methanol. J. Phys. Chem. B 2012, 116, 10357-10363.
69. Adhikary, R.; Carlson, P. J.; Kee, T. W.; Petrich, J. W. Excitedstate intramolecular hydrogen atom transfer of curcumin in surfactant micelles. J. Phys. Chem. B 2010, 114, 2997-3004.
70. Barik, A.; Priyadarsini, K. I.; Mohan, H. Photophysical studies on binding of curcumin to bovine serum albumin. Photochem. Photobiol. 2003, 77, 597-603.
71. Naskar, D.; Nayak, S.; Dey, T.; Kundu, S. C. Non-mulberry silk fibroin influence osteogenesis and osteoblast-macrophage cross talk on titanium based surface. Sci. Rep. 2014, 4, 4745.
72. Kim, U.-J.; Park, J.; Li, C.; Jin, H.-J.; Valluzzi, R.; Kaplan, D. L. Structure and properties of silk hydrogels. Biomacromolecules 2004, 5, 786-792.
73. Jones, G.; Jackson, W. R.; Choi, C. Y.; Bergmark, W. R. Solvent Effects on Emission Yield and Lifetime for Coumarin Laser-Dyes. Requirements for a Rotatory Decay Mechanism. J. Phys. Chem. 1985, 89, 294-300.