Saffron carotenoids (crocin and crocetin) binding to human serum albumin as investigated by different spectroscopic methods and molecular docking

References

• Ajmal, M. R. , Zaidi, N. , Alam, P. , Nusrat, S. , Siddiqi, M. K. , Badr, G. , … Khan, R. H. (2017). Insight into the interaction of antitubercular and anticancer compound clofazimine with human serum albumin: Spectroscopy and molecular modelling. Journal of Biomolecular Structure & Dynamics , 35 , 46–57. doi:10.1080/07391102.2015.1132258
   PubMed Web of Science ®Google Scholar
• Ashrafi, M. , Bathaie, S. , Taghikhani, M. , & Moosavi-Movahedi, A. (2005). The effect of carotenoids obtained from saffron on histone H1 structure and H1–DNA interaction. International Journal of Biological Macromolecules , 36 , 246–252. doi:10.1016/j.ijbiomac.2005.05.008
   PubMed Web of Science ®Google Scholar
• Bathaie, S. Z. , & Mousavi, S. Z. (2010). New applications and mechanisms of action of saffron and its important ingredients. Critical Reviews in Food Science and Nutrition , 50 , 761–786. doi:10.1080/10408390902773003
   PubMed Web of Science ®Google Scholar
• Bathaie, S. Z. , Bolhasani, A. , Hoshyar, R. , Ranjbar, B. , Sabouni, F. , & Moosavi-Movahedi, A. A. (2007). Interaction of saffron carotenoids as anticancer compounds with ctDNA, oligo (dG.dC)(15), and oligo (dA.dT)(15). DNA and Cell Biology , 26 , 533–540. doi:10.1089/dna.2007.0598
   PubMed Web of Science ®Google Scholar
• Beg, M. , Maji, A. , Mandal, A. K. , Das, S. , Jha, P. K. , & Hossain, M. (2017). Spectroscopic investigation on interaction of biogenic, Croton bonplandianum leaves extract mediated potential bactericidal silver nanoparticles with human hemoglobin and human serum albumin. Journal of Biomolecular Structure & Dynamics , 28 , 1–13. doi:10.1080/07391102.2017.1294505
   Web of Science ®Google Scholar
• Berman, H. M. , Westbrook, J. , Feng, Z. , Gilliland, G. , Bhat, T. N. , Weissig, H. , … Bourne, P. E. (2000). The protein data bank. Nucleic Acids Research , 28 , 235–242. doi:10.1093/nar/28.1.235
   PubMed Web of Science ®Google Scholar
• Bolhasani, A. , Bathaie, S. Z. , Yavari, I. , Moosavi-Movahedi, A. A. , & Ghaffari, M. (2005). Separation and purification of some components of iranian saffron. Asian Journal of Chemistry , 17 , 725–729.
   Web of Science ®Google Scholar
• Cohen, S. , & Margalit, R. (1990). Binding of porphyrin to human serum albumin. Structure–activity relationships. Biochemical Journal , 270 , 325–330. doi:10.1042/bj2700325
   PubMed Web of Science ®Google Scholar
• Dewey, T. G. (1991). Biophysical and biochemical aspects of fluorescence spectroscopy . New York, NY : Springer. doi:10.1007/978-1-4757-9513-4
   Google Scholar
• Dezhampanah, H. , & Firouzi, R. (2016). An Investigation on intermolecular interaction between Bis (indolyl) methane and HSA and BSA using multi technique methods. Journal of Biomolecular Structure and Dynamics , 1–37. doi:10.1080/07391102.2016.1264890
   PubMed Web of Science ®Google Scholar
• Fadai, F. , Mousavi, B. , Ashtari, Z. , Farhang, S. , Hashempour, S. , Shahhamzei, N. , & Bathaie, S. Z. (2014). Saffron aqueous extract prevents metabolic syndrome in patients with schizophrenia on olanzapine treatment: A randomized triple blind placebo controlled study. Pharmacopsychiatry , 47 , 156–161. doi:10.1055/s-0034-1382001
   PubMed Web of Science ®Google Scholar
• Fasano, M. , Curry, S. , Terreno, E. , Galliano, M. , Fanali, G. , Narciso, P. , … Ascenzi, P. (2005). The extraordinary ligand binding properties of human serum albumin. IUBMB Life , 57 , 787–796. doi:10.1080/15216540500404093
   PubMed Web of Science ®Google Scholar
• Ghuman, J. , Zunszain, P. A. , Petitpas, I. , Bhattacharya, A. A. , Otagiri, M. , & Curry, S. (2005). Structural basis of the drug-binding specificity of human serum albumin. Journal of Molecular Biology , 353 , 38–52. doi:10.1016/j.jmb.2005.07.075
   PubMed Web of Science ®Google Scholar
• He, X. M. , & Carter, D. C. (1992). Atomic structure and chemistry of human serum albumin. Nature , 358 , 209–215. doi:10.1038/358209a0
   PubMed Web of Science ®Google Scholar
• Hoshyar, R. , Bathaie, S. Z. , & Sadeghizadeh, M. (2013). Crocin triggers the apoptosis through increasing the Bax/Bcl-2 ratio and caspase activation in human gastric adenocarcinoma, AGS, cells. DNA Cell Biology , 32 , 50–57. doi:10.1089/dna.2012.1866
   PubMed Web of Science ®Google Scholar
• Kanakis, C. D. , Tarantilis, P. A. , Tajmir-Riahi, H. A. , & Polissiou, M. G. (2007). Crocetin, dimethylcrocetin, and safranal bind human serum albumin: Stability and antioxidative properties. Journal of Agricultural and Food Chemistry , 55 , 970–977. doi:10.1021/jf062638l
   PubMed Web of Science ®Google Scholar
• Karami, M. , Bathaie, S. Z. , Tiraihi, T. , Habibi-Rezaei, M. , Arabkheradmand, J. , & Faghihzadeh, S. (2013). Crocin improved locomotor function and mechanical behavior in the rat model of contused spinal cord injury through decreasing calcitonin gene related peptide (CGRP). Phytomedicine , 21 , 62–67. doi:10.1016/j.phymed.2013.07.013
   PubMed Web of Science ®Google Scholar
• Kola, I. , & Landis, J. (2004). Can the pharmaceutical industry reduce attrition rates? Nature Reviews Drug Discovery , 3 , 711–716. doi:10.1038/nrd1470
   PubMed Web of Science ®Google Scholar
• Lakowicz, J. R. (2013). Principles of fluorescence spectroscopy . New York, NY : Springer Science & Business Media. doi:10.1007/978-0-387-46312-4
   Google Scholar
• Lakowicz, J. R. , & Weber, G. (1973). Quenching of fluorescence by oxygen. Probe for structural fluctuations in macromolecules. Biochemistry , 12 , 4161–4170. doi:10.1021/bi00745a020
   PubMed Web of Science ®Google Scholar
• Messina, P. V. , Prieto, G. , Ruso, J. M. , & Sarmiento, F. (2005). Conformational changes in human serum albumin induced by sodium perfluorooctanoate in aqueous solutions. The Journal of Physical Chemistry B , 109 , 15566–15573. doi:10.1021/jp051655v
   PubMed Web of Science ®Google Scholar
• Miller, T. L. , Willett, S. L. , Moss, M. E. , Miller, J. , & Belinka, B. A. (1982). Binding of crocetin to plasma albumin. Journal of Pharmaceutical Sciences , 71 , 173–177. doi:10.1002/jps.2600710209
   PubMed Web of Science ®Google Scholar
• Montero, M. T. , Hernández, J. , & Estelrich, J. (1990). Fluorescence quenching of albumin. A spectrofluorimetric experiment. Biochemical Education , 18 , 99–101. doi:10.1016/0307-4412(90)90188-T
   Google Scholar
• Mousavi, S. Z. , & Bathaie, S. Z. (2011). Historical uses of saffron: Identifying potential new avenues for modern research. Avicenna Journal of Phytomedicine , 1 , 57–66.
   Google Scholar
• Nusrat, S. , Siddiqi, M. K. , Zaman, M. , Zaidi, N. , Ajmal, M. R. , Alam, P. , … Khan, R. H. (2016). A comprehensive spectroscopic and computational investigation to probe the interaction of antineoplastic drug nordihydroguaiaretic acid with serum albumins. PLoS ONE , 11 , e0158833. doi:10.1371/journal.pone.0158833
   PubMed Web of Science ®Google Scholar
• Pace, C. N. , Vajdos, F. , Fee, L. , Grimsley, G. , & Gray, T. (1995). How to measure and predict the molar absorption-coefficient of a protein. Protein Science , 4 , 2411–2423. doi:10.1002/pro.5560041120
   PubMed Web of Science ®Google Scholar
• Papadopoulou, A. , Green, R. J. , & Frazier, R. A. (2005). Interaction of flavonoids with bovine serum albumin: A fluorescence quenching study. Journal of Agricultural and Food Chemistry , 53 , 158–163. doi:10.1021/jf048693g
   PubMed Web of Science ®Google Scholar
• Peters Jr, T. (1995). All about Albumin: Biochemistry, Genetics, and Medical Applications . San Diego, CA : Academic Press. doi:10.1016/B978-012552110-9/50005-2
   Google Scholar
• Petitpas, I. , Bhattacharya, A. A. , Twine, S. , East, M. , & Curry, S. (2001). Crystal structure analysis of warfarin binding to human serum albumin anatomy of drug site I. Journal of Biological Chemistry , 276 , 22804–22809. doi:10.1074/jbc.M100575200
   PubMed Web of Science ®Google Scholar
• Prentis, R. , Lis, Y. , & Walker, S. (1988). Pharmaceutical innovation by the seven UK-owned pharmaceutical companies (1964–1985). British Journal of Clinical Pharmacology , 25 , 387–396. doi:10.1111/j.1365-2125.1988.tb03318.x
   PubMed Web of Science ®Google Scholar
• Routledge, P. (1986). The plasma protein binding of basic drugs. British Journal of Clinical Pharmacology , 22 , 499–506. doi:10.1111/j.1365-2125.1986.tb02927.x
   PubMed Web of Science ®Google Scholar
• Scholtz, J. M. , Qian, H. , York, E. J. , Stewart, J. M. , & Baldwin, R. L. (1991). Parameters of helix–coil transition theory for alanine-based peptides of varying chain lengths in water. Biopolymers , 31 , 1463–1470. doi:10.1002/bip.360311304
   PubMed Web of Science ®Google Scholar
• Shirali, S. , Zahra Bathaie, S. , & Nakhjavani, M. (2013). Effect of crocin on the insulin resistance and lipid profile of streptozotocin-induced diabetic rats. Phytotherapy Research , 27 , 1042–1047. doi:10.1002/ptr.4836
   PubMed Web of Science ®Google Scholar
• Sudlow, G. , Birkett, D. , & Wade, D. (1975). The characterization of two specific drug binding sites on human serum albumin. Molecular Pharmacology , 11 , 824–832.
   PubMed Web of Science ®Google Scholar
• Sułkowska, A. (2002). Interaction of drugs with bovine and human serum albumin. Journal of Molecular Structure , 614 , 227–232. doi:10.1016/S0022-2860(02)00256-9
   Web of Science ®Google Scholar
• Sułkowska, A. , Równicka, J. , Bojko, B. , & Sułkowski, W. (2003). Interaction of anticancer drugs with human and bovine serum albumin. Journal of Molecular Structure , 651–653 , 133–140. doi:10.1016/S0022-2860(02)00642-7
   Web of Science ®Google Scholar
• Suryawanshi, V. D. , Walekar, L. S. , Gore, A. H. , Anbhule, P. V. , & Kolekar, G. B. (2016). Spectroscopic analysis on the binding interaction of biologically active pyrimidine derivative with bovine serum albumin. Journal of Pharmaceutical Analysis , 6 , 56–63. doi:10.1016/j.jpha.2015.07.001
   PubMed Web of Science ®Google Scholar
• Tayman, C. , Rayyan, M. , & Allegaert, K. (2011). Neonatal pharmacology: extensive interindividual variability despite limited size. The Journal of Pediatric Pharmacology and Therapeutics : JPPT , 16 , 170–184. doi:10.5863/1551-6776-16.3.170
   PubMedGoogle Scholar
• Ware, W. R. (1962). Oxygen quenching of fluorescence in solution: An experimental study of the diffusion process. The Journal of Physical Chemistry , 66 , 455–458. doi:10.1021/j100809a020
   Web of Science ®Google Scholar
• Wishart, D. S. (2007). Improving early drug discovery through adme modelling. Drugs in R & D , 8 , 349–362. doi:10.2165/00126839-200708060-00003
   Google Scholar
• Yang, F. , Zhang, Y. , & Liang, H. (2014). Interactive association of drugs binding to human serum albumin. International Journal of Molecular Sciences , 15 , 3580–3595. doi:10.3390/ijms15033580
   PubMed Web of Science ®Google Scholar
• Zsila, F. , Bikádi, Z. , & Simonyi, M. (2001). Induced chirality upon crocetin binding to human serum albumin: Origin and nature. Tetrahedron: Asymmetry , 12 : 3125–3137. doi:10.1016/S0957-4166(01)00552-3
   Web of Science ®Google Scholar
• Zsila, F. , Bikádi, Z. , & Simonyi, M. (2002). Further insight into the molecular basis of carotenoid–albumin interactions: circular dichroism and electronic absorption study on different crocetin–albumin complexes. Tetrahedron: Asymmetry , 13 , 273–283. doi:10.1016/S0957-4166(02)00097-6
   Web of Science ®Google Scholar