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Constrained Photophysics of 5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one in the Bioenvironment of Serum Albumins: A Spectroscopic Endeavour Supported by Molecular Docking Analysis

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Abstract

This paper vividly indicates that steady state as well as time-resolved fluorescence techniques can serve as highly sensitive monitors to explore the interactions of 5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one with model transport proteins, bovine serum albumin (BSA) and human serum albumin (HSA). Besides these, we have used fluorescence anisotropy study to assess the degree of restrictions imparted by the micro-environments of serum albumins. Again, to speculate the triplet excited state interaction between such fluorophore and albumin proteins (BSA& HSA), laser flash-photolysis experiments have been carried out. Molecular docking experiments have also been performed to support the conclusions obtained from steady state experiments.

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References

  1. Brown JR, Rosenoer VM, Oratz M, Rothschild MA (1977) Albumin structure, function and uses. Pergamon Press, Oxford

    Google Scholar 

  2. Sharma RN, Pancholi SS (2014) Int J Pharm Pharm Sci 6:726

    CAS  Google Scholar 

  3. Carter DC, Ho JX (1994) Adv Protein Chem 45:153

    Article  CAS  PubMed  Google Scholar 

  4. Bojesen E, Bojesen IN (1996) J Phys Chem 100:17981

    Article  CAS  Google Scholar 

  5. Karachentsev AN, Melchenko IA (1997) Eksp Klin Farmakol 60:68

    CAS  PubMed  Google Scholar 

  6. Ali MS, Al Lohedan HA (2014) J Mol Liq 197:124

    Article  CAS  Google Scholar 

  7. Kandagal PB, Ashoka S, Seetharamappa J, Shaikh SMT, Jadegoud Y, Ijare OB (2006) J Pharm Biomed Anal 41:393

    Article  CAS  PubMed  Google Scholar 

  8. Ali MS, Al Lohedan HA (2013) Mol Biol Rep 40:6081

    Article  CAS  Google Scholar 

  9. Sengupta B, Sengupta PK (2002) Biochem Biophys Res Commun 299:400

    Article  CAS  PubMed  Google Scholar 

  10. Yang GD, Li C, Zeng AG, Zhao Y, Yang R, Brian XL (2013) J Pharm Anal 3:200

    Article  CAS  Google Scholar 

  11. Klopfenstein WE (1969) Biochim Biophys Acta 187:272

    Article  CAS  PubMed  Google Scholar 

  12. Khan SN, Islam B, Yennamalli R, Sultan A, Subbarao N, Khan AU (2008) Eur J Pharm Sci 35:371

    Article  CAS  PubMed  Google Scholar 

  13. Mathew MK, Balaram P (1980) FEBS Lett 115:91

    Article  CAS  PubMed  Google Scholar 

  14. Makino S, Reynolds JA, Tanford C (1973) J Biol Chem 248:4926

    CAS  PubMed  Google Scholar 

  15. Lin H, Lan J, Guan M, Sheng F, Zhang H (2009) Spectrochim Acta A Mol Biomol Spectrosc 73:936

    Article  PubMed  Google Scholar 

  16. Bal W, Christodoulou J, Sadler PJ, Tucker A (1998) J Inorg Biochem 70:33

    Article  CAS  PubMed  Google Scholar 

  17. Khan AB, Khan JM, Ali MS, Khan RH, Din KU (2012) Spectrochim Acta A Mol Biomol Spectrosc 97:119

    Article  CAS  PubMed  Google Scholar 

  18. Gelamo EL, Tabak M (2000) Spectrochim Acta A 56:2255

    Article  Google Scholar 

  19. Gelamo EL, Silva CH, Imasato H, Tabak M (2002) Biochim Biophys Acta 84:1594

    Google Scholar 

  20. Yang L, Lv J, Wang X, Zhang J, Qi L, Zhang T, Zhang Z, Zhang L (2015) J Mol Recognit 28:459

    Article  CAS  PubMed  Google Scholar 

  21. Rawel HM, Meidtner K, Kroll J (2005) J Agric Food Chem 53:4228

    Article  CAS  PubMed  Google Scholar 

  22. Hu YJ, Liu Y, Zhang LX, Zhao RM, Qu SS (2005) J Mol Struct 750:174

    Article  CAS  Google Scholar 

  23. Jayabharathi J, Thanikachalam V, Perumal MV (2012) J Lumin 132:707

    Article  CAS  Google Scholar 

  24. Shen L, Yang Z, Tang R (2012) Spectrochim Acta A Mol Biomol Spectrosc 98:170

    Article  CAS  PubMed  Google Scholar 

  25. Zhu Y, Zhang R, Wang Y, Ma J, Li K, Li Z (2014) J Photochem Photobiol B Biol 140:381

    Article  CAS  Google Scholar 

  26. Shahabadi N, Hadidi S, Feizi F (2015) Spectrochim Acta A Mol Biomol Spectrosc 138:169

    Article  CAS  PubMed  Google Scholar 

  27. Dufour C, Dangles O (2005, 1721) Biochim Biophys Acta Gen Subj:164

  28. Sijmons PC, Dekker BMM, Schrammeijer B, Verwoerd TC, Van den Elzen PJM, Hoekema A (1990) BioTechniques 8:217

    CAS  Google Scholar 

  29. Moriyama Y, Ohta D, Hadiya K, Mitsui Y, Takeda K (1996) J Protein Chem 15:265

    Article  CAS  PubMed  Google Scholar 

  30. Mikusinska-Planner A, Surma M (2000) Spectrochim Acta A 56:1835

    Article  Google Scholar 

  31. Kumar CV, Buranaprapuk A (1997) Angew Chem Int Ed England 36:2085

    Article  CAS  Google Scholar 

  32. Hu YJ, Liu Y, Xiao XH (2009) Biomacromolecules 10:517

    Article  CAS  PubMed  Google Scholar 

  33. Lhiaubet-Vallet V, Sarabia Z, Bosca F, Miranda MA (2004) J Am Chem Soc 126:9538

    Article  CAS  PubMed  Google Scholar 

  34. He XM, Carter DC (1992) Nature 358:209

    Article  CAS  PubMed  Google Scholar 

  35. Jimenez MC, Miranda MA, Vaya I (2005) J Am Chem Soc 127:10134

    Article  CAS  PubMed  Google Scholar 

  36. Szacilowski K, Macyk W, Drzewiecka-Matuszek A, Brindell M, Stochel G (2005) Chem Rev 105:2647

    Article  CAS  PubMed  Google Scholar 

  37. Pandey RK, Constantine S, Tsuchida T, Zheng G, Medforth CJ, Aoudia M, Kozyrev AN, Rogers MAJ, Kato H, Smith KM, Dougherty TJ (1997) J Med Chem 40:2770

    Article  CAS  PubMed  Google Scholar 

  38. Patrice T (2004) Photodynamic therapy, Royal Society of Chemistry (GB)

    Google Scholar 

  39. Peters T (1985) Serum albumin, advances in protein chemistry, vol 37. Academic Press, New York

    Google Scholar 

  40. Kar C, Ojha B, Das G (2013) J Lumin 28:339

    Article  CAS  Google Scholar 

  41. Helms MK, Peterson CE, Bhagavan NV, Jameson DM (1997) FEBS Lett 408:67

    Article  CAS  PubMed  Google Scholar 

  42. Pavdridge W, Am M (1987) J Physiol 252:157

    Google Scholar 

  43. Gonzalez-Jimenez J, Cortijo M (2002) J Protein Chem 21:75

    Article  CAS  PubMed  Google Scholar 

  44. Sulkowska A, Bojko B, Rownicka J, Pentak D, Sulkowska W (2003) J Mol Struct 651:237

    Article  Google Scholar 

  45. Tayyab S, Sharma N, Khan MM (2000) Biochem Biophys Res Commun 277:83

    Article  CAS  PubMed  Google Scholar 

  46. Ahmad B, Khan MKA, Haq SK, Khan RH (2004) Biochem Biophys Res Commun 314:166

    Article  CAS  PubMed  Google Scholar 

  47. Cohen BE, Pralle A, Yao XJ, Swaminath G, Gandhi CS, Jan YN, Kobilka BK, Isacoff EY, Jan LY (2005) Proc Natl Acad Sci U S A 102:965

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. Banerjee M, Pal U, Subudhhi A, Chakrabarti A, Basu S (2012) J Photochem Photobiol B Biol 108:23

    Article  CAS  Google Scholar 

  49. Mitra AK, Ghosh S, Sau A, Saha C, Basu S (2015) J Lumin 167:233

    Article  CAS  Google Scholar 

  50. Tetko IV, Gasteiger J, Todeschini R, Mauri A, Livingstone D, Ertl P, Palyulin VA, Radchenko EV, Zefirov NS, Makarenko AS (2005) J Comput Aided Mol Des 19:453

    Article  CAS  PubMed  Google Scholar 

  51. Trott O, Olson AJ (2010) J Comput Chem 31:455

    CAS  PubMed  PubMed Central  Google Scholar 

  52. Pal U, Pramanik SK, Bhattacharya B, Banerji B, Maiti NC (2015) SpringerPlus 4:548

    Article  PubMed  PubMed Central  Google Scholar 

  53. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ (2009) J Comput Chem 30:2785

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  54. Majorek KA, Porebski PJ, Dayal A, Zimmerman MD, Jablonska K, Stewart AJ, Chruszcz M, Minor W (2012) Structural and immunologic characterization of bovine, horse, and rabbit serum albumins. Mol Immunol 52:174

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. Bhattacharya AA, Curry S, Franks NP (2000) J Biol Chem 275:38731

    Article  CAS  PubMed  Google Scholar 

  56. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) Nucleic Acids Res 28:235

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  57. Hanwell MD, Curtis DE, Lonie DC, Vandermeersch T, Zurek E, Hutchison GR (2012) J Cheminformatics 4:17

    Article  CAS  Google Scholar 

  58. Lakowicz JR (1999) Principles of fluorescence spectroscopy; Plenum: New York

  59. Krishnakumar SS, Panda D (2002) Biochemistry 41:7443

    Article  CAS  PubMed  Google Scholar 

  60. Macgregor RB, Weber G (1986) Nature 319:70

    Article  CAS  PubMed  Google Scholar 

  61. Mallick A, Haldar B, Maiti S, Bera SC, Chattopadhyay N (2005) J Phys Chem B 109:14675

    Article  CAS  PubMed  Google Scholar 

  62. Chakrabarty A, Mallick A, Haldar B, Das P, Chattopadhyay N (2007) Biomacromolecules 8:920

    Article  CAS  PubMed  Google Scholar 

  63. Stern O, Volmer M (1919) Über die Abklingungszeit der Fluoreszenz. Phys Z 20:183

    CAS  Google Scholar 

  64. Bickerton GR, Paolini GV, Besnard J, Muresan S, Hopkins AL (2012) Nat Chem 4:90

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  65. Alam A, Pal C, Goyal M, Kundu MK, Kumar R, Iqbal MS, Dey S, Bindu S, Sarkar S, Pal U (2011) Bioorg Med Chem 19:7365

    Article  CAS  PubMed  Google Scholar 

  66. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Adv Drug Deliv Rev 23:3

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work has been funded by Chemical and Biophysical Approaches for Understanding of Natural Processes (CBAUNP) project, SINP of the Department of Atomic Energy (DAE), Government of India. Thanks to CSIR, New Delhi for providing financial help in the form of fellowships. Special thanks to Mr. Amartya Krishna Mitra for being a constant source of inspiration. We also want to thank Mrs. Sayantani Mitra for her sincere support in perusing the paper and making suitable modifications in language.

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Correspondence to Samita Basu.

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Mitra, A.K., Sau, A., Pal, U. et al. Constrained Photophysics of 5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one in the Bioenvironment of Serum Albumins: A Spectroscopic Endeavour Supported by Molecular Docking Analysis. J Fluoresc 27, 1547–1558 (2017). https://doi.org/10.1007/s10895-017-2094-2

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