Studies on α-, β-, and γ-cyclodextrin inclusion complexes of isoquinoline alkaloids berberine, palmatine and coralyne

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 78, Issue 1-4, 2014, Pages 311-323

  Hazra, Soumitra ^a   Hossain, Maidul ^a,b   Kumar, Gopinatha Suresh ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b VIDYASAGAR UNIVERSITY   (India)

Author keywords

1H NMR and NOESY; Calorimetry; Cyclodextrin inclusion complexes; Inclusion geometry; Inclusion thermodynamics; Isoquinoline alkaloids; Spectroscopy

Indexed keywords

EID: 84893742700     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-013-0301-6     Document Type: Article

References (70)

1. Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J.: Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 46, 3-26 (2001)
2. Dahan, A.; Hoffman, A.: Rationalizing the selection of oral lipid based drug delivery systems by an in vitro dynamic lipolysis model for improved oral bioavailability of poorly water soluble drugs. J. Control Release 129, 1-10 (2008)
3. Van De Waterbeemd, H.; Smith, D.A.; Beaumont, K.; Walker, D.K.: Property-based design: optimization of drug absorption and pharmacokinetics. J. Med. Chem. 44, 1313-1333 (2001)
4. 2 (M = Mo, Ti) with cucurbit[n]urils. Dalton Trans. 17, 2328-2334 (2008)
5. Suvitha, A.; Venkataramanan, N.S.; Mizuseki, H.; Kawazoe, Y.; Ohuchi, N.: Theoretical insights into the formation, structure, and electronic properties of anticancer oxaliplatin drug and cucurbit[n]urils n = 5 to 8. J. Inclusion Phenom. Macrocycl. Chem. 66, 213-218 (2010)
6. Fan, Z.-F.; Wang, J.; Huang, Y.; Xue, S.-F.; Xiao, X.; Zhang, Y.-Q.; Zhu, Q.-J.; Tao, Z.: Host-guest complexes of various cucurbit[n]urils with the hydrochloride salt of 2,4-diaminoazobenzene. J. Inclusion Phenom. Macrocycl. Chem. 72, 213-220 (2012)
7. Ma, D.; Hettiarachchi, G.; Nguyen, D.; Zhang, B.; Wittenberg, J.B.; Zavalij, P.Y.; Briken, V.; Isaacs, L.: Acyclic cucurbit[n]uril molecular containers enhance the solubility and bioactivity of poorly soluble pharmaceuticals. Nat. Chem. 4, 503-510 (2012)
8. Svec, J.; Sindelar, V.; Kaifer, A.E.: Effects of cucurbituril size on the binding of a lutidine guest. New J. Chem. 36, 1721-1724 (2012)
9. Stancu, A.D.; Buschmann, H.-J.; Mutihac, L.: Survey on thermodynamic properties for the complexation behaviour of some calixarene and cucurbituril receptors. J. Inclusion Phenom. Macrocycl. Chem. 75, 1-10 (2013)
10. Yang, R.; Chen, J.-B.; Dai, X.-Y.; Huang, R.; Xiao, C.-F.; Gao, Z.-Y.; Yang, B.; Yang, L.-J.; Yan, S.-J.; Zhang, H.-B.; Qing, C.; Lin, J.: Inclusion complex of GA-13315 with cyclodextrins: preparation, characterization, inclusion mode and properties. Carbohydr. Polym. 89, 89-97 (2012)
11. Dandawate, P.R.; Vyas, A.; Ahmad, A.; Banerjee, S.; Deshpande, J.; Swamy, K.V.; Jamadar, A.; Dumhe-Klaire, A.C.; Padhye, S.; Sarkar, F.H.: Inclusion complex of novel curcumin analogue CDF and β-cyclodextrin (1:2) and its enhanced in vivo anticancer activity against pancreatic cancer. Pharm. Res. 29, 1775-1786 (2012)
12. Kostadinova, E.; Kaloyanova, S.; Stoyanov, S.; Petkov, I.: Spectroscopic elucidation of the interaction of native cyclodextrins and their acetylated derivatives with asymmetric monomethyne cyanine dye. J. Inclusion Phenom. Macrocycl. Chem. 72, 63-69 (2012)
13. Liu, B.; Li, W.; Nguyen, T.A.; Zhao, J.: Empirical, thermodynamic and quantum-chemical investigations of inclusion complexation between flavanones and (2-hydroxypropyl)-cyclodextrins. Food Chem. 134, 926-932 (2012)
14. 1H NMR and molecular modeling studies. Carbohydr. Polym. 89, 492-496 (2012)
15. Nguyen, T.A.; Liu, B.; Zhao, J.; Thomas, D.S.; Hook, J.M.: An investigation into the supramolecular structure, solubility, stability and antioxidant activity of rutin/cyclodextrin inclusion complex. Food Chem. 136, 186-192 (2013)
16. Takacs, Z.; Brotin, T.; Dutasta, J.-P.; Lang, J.; Todde, G.; Kowalewski, J.: Inclusion of chloromethane guests affects conformation and internal dynamics of cryptophane-D host. J. Phys. Chem. B 116, 7898-7913 (2012)
17. Shi, Y.; Li, X.; Yang, J.; Gao, F.; Tao, C.: Efficient encapsulation of chloroform with cryptophane-M and the formation of exciplex studied by fluorescence spectroscopy. J. Fluoresc. 21, 531-538 (2011)
18. 3. Spectrochim. Acta Part A 75, 157-161 (2010)
19. Taratula, O.; Hill, P.A.; Khan, N.S.; Carrol, P.J.; Dmochowski, I.J.: Crystallographic observation of 'induced fit' in a cryptophane host-guest model system. Nat. Commun. 1, 148 (2010)
20. Connors, K.A.: The stability of cyclodextrin complexes in solution. Chem. Rev. 97, 1325-1357 (1997)
21. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743-1754 (1998)
22. Liu, L.; Guo, Q.-X.: The driving forces in the inclusion complexation of cyclodextrins. J. Inclusion Phenom. Macrocycl. Chem. 42, 1-14 (2002)
23. Rekharsky, M.V.; Inoue, Y.: Complexation thermodynamics of cyclodextrins. Chem. Rev. 98, 1875-1918 (1998)
24. Eli, W.; Chen, W.; Xue, Q.: The association of triton-X surfactants with β-cyclodextrin: an isothermal titration calorimetry study. J. Inclusion Phenom. Macrocycl. Chem. 36, 439-445 (2000)
25. Yu, J.-S.; Wei, F.-D.; Gao, W.; Zhao, C.-C.: Thermodynamic study on the effects of β-cyclodextrin inclusion with berberine. Spectrochim. Acta Part A 58, 249-256 (2002)
26. Qiu, X.-M.; Sun, D.-Z.; Wei, X.-L.; Yin, B.-L.: Thermodynamic study of the inclusion interaction between gemini surfactants and cyclodextrins by isothermal titration microcalorimetry. J. Solut. Chem. 36, 303-312 (2007)
27. Othman, M.; Bouchemal, K.; Couvreur, P.; Desmaële, D.; Morvan, E.; Pouget, T.; Gref, R.: A comprehensive study of the spontaneous formation of nanoassemblies in water by a 'lock-and-key' interaction between two associative polymers. J. Colloid Interface Sci. 354, 517-527 (2011)
28. Lin, C.-C.; Lin, S.-Y.; Chung, J.-G.; Lin, J.-P.; Chen, G.-W.; Kao, S.-T.: Down-regulation of cyclin B1 and up-regulation of Wee1 by berberine promotes entry of leukemia cells into the G2/M-phase of the cell cycle. Anticancer Res. 26, 1097-1104 (2006)
29. Sun, Y.; Xun, K.; Wang, Y.; Chen, X.: A systematic review of the anticancer properties of berberine, a natural product from Chinese herbs. Anticancer Drugs 20, 757-769 (2009)
30. Satyavathi, G.V.; Gupta, A.K.; Tandon, N.: Medicinal Plants of India. Indian Council of Medical Research, New Delhi (1987)
31. Letasiova, S.; Jantova, S.; Cipak, L.; Muckova, M.: Berberine- antiproliferative activity in vitro and induction of apoptosis/necrosis of the U937 and B16 cells. Cancer Lett. 239, 254-262 (2006)
32. Mantena, S.K.; Sharma, S.D.; Katiyar, S.K.: Berberine inhibits growth, induces G1 arrest and apoptosis in human epidermoid carcinoma A431 cells by regulating Cdki-Cdk-cyclin cascade, disruption of mitochondrial membrane potential and cleavage of caspase 3 and PARP. Carcinogenesis 27, 2018-2027 (2006)
33. Kuo, C.L.; Chi, C.W.; Liu, T.Y.: The anti-inflammatory potential of berberine in vitro and in vivo. Cancer Lett. 203, 127-137 (2004)
34. Hwang, J.M.; Kuo, H.C.; Tseng, T.H.; Liu, J.Y.; Chu, C.Y.: Berberine induces apoptosis through a mitochondria/caspases pathway in human hepatoma cells. Arch. Toxicol. 80, 62-73 (2006)
35. Eom, K.S.; Hong, J.M.; Youn, M.J.; So, H.S.; Park, R.; Kim, J.M.; Kim, T.Y.: Berberine induces G1 arrest and apoptosis in human glioblastoma T98G cells through mitochondrial/caspases pathway. Biol. Pharm. Bull. 31, 558-562 (2008)
36. Peng, P.L.; Hsieh, Y.S.; Wang, C.J.; Hsu, J.L.; Chou, F.P.: Inhibitory effect of berberine on the invasion of human lung cancer cells via decreased productions of urokinase-plasminogen activator and matrix metalloproteinase-2. Toxicol. Appl. Pharmacol. 214, 8-15 (2006)
37. Mantena, S.K.; Sharma, S.D.; Katiyar, S.K.: Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells. Mol. Cancer Ther. 5, 296-308 (2006)
38. Lin, J.P.; Yang, J.S.; Lee, J.H.; Hsieh, W.T.; Chung, J.G.: Berberine induces cell cycle arrest and apoptosis in human gastric carcinoma SNU-5 cell line. World J. Gastroenterol. 12, 21-28 (2006)
39. Katiyar, S.K.; Meeran, S.M.; Katiyar, N.; Akhtar, S.: p53 cooperates berberine-induced growth inhibition and apoptosis of non-small cell human lung cancer cells in vitro and tumor xenograft growth in vivo. Mol. Carcinog. 48, 24-37 (2009)
40. Kluza, J.; Baldeyrou, B.; Colson, P.; Rasoanaivo, P.; Mambu, L.; Frappier, F.; Bailly, C.: Cytotoxicity and DNA binding properties of the plant alkaloid burasaine. Eur. J. Pharm. Sci. 20, 383-391 (2003)
41. Chang, Y.L.; Usami, S.; Hsieh, M.T.; Jiang, M.J.: Effects of palmatine on isometric force and intracellular calcium levels of arterial smooth muscle. Life Sci. 64, 597-606 (1999)
42. Bhadra, K.; Suresh Kumar, G.: Therapeutic potential of nucleic acid binding isoquinoline alkaloids: binding aspects and implications for drug design. Med. Res. Rev. 31, 821-862 (2011)
43. Maiti, M.; Suresh Kumar, G.: Protoberberine alkaloids: physicochemical and nucleic acid binding properties. Top. Heterocycl. Chem. 10, 155-209 (2007)
44. Bhadra, K.; Maiti, M.; Suresh Kumar, G.: DNA-Binding cytotoxic alkaloids: comparative study of the energetics of binding of berberine, palmatine, and coralyne. DNA Cell Biol. 27, 675-685 (2008)
45. Bhadra, K.; Suresh Kumar, G.: Interaction of berberine, palmatine, coralyne, and sanguinarine to quadruplex DNA: a comparative spectroscopic and calorimetric study. Biochim. Biophys. Acta 1810, 485-496 (2011)
46. Islam, M.M.; Sinha, R.; Suresh Kumar, G.: RNA binding small molecules: studies on t-RNA binding by cytotoxic plant alkaloids berberine, palmatine and the comparison to ethidium. Biophys. Chem. 125, 508-520 (2007)
47. Islam, M.M.; Roy Chowdhury, S.; Suresh Kumar, G.: Spectroscopic and calorimetric studies on the binding of alkaloids berberine, palmatine and coralyne to double stranded RNA polynucleotides. J. Phys. Chem. B 113, 1210-1224 (2009)
48. Sinha, R.; Suresh Kumar, G.: Interaction of isoquinoline alkaloids with an RNA triplex: structural and thermodynamic studies of berberine, palmatine, and coralyne binding to poly(U).poly(A)poly(U). J. Phys. Chem. B 113, 13410-13420 (2009)
49. Giri, P.; Suresh Kumar, G.: Molecular recognition of poly(A) targeting by protoberberine alkaloids: in vitro biophysical studies and biological perspectives. Mol. BioSyst. 6, 81-88 (2010)
50. Giri, P.; Suresh Kumar, G.: Isoquinoline alkaloids and their binding with polyadenylic acid: potential basis of therapeutic action. Mini-Rev. Med. Chem. 10, 568-577 (2010)
51. Hu, Y.-J.; Liu, Y.; Xiao, X.-H.: Investigation of the interaction between berberine and human serum albumin. Biomacromolecules 10, 517-521 (2009)
52. Hu, Y.-J.; Yu, O.-Y.; Dai, C.-M.; Liu, Y.; Xiao, X.-H.: Site-selective binding of human serum albumin by palmatine: spectroscopic approach. Biomacromolecules 11, 106-112 (2010)
53. Khan, A.Y.; Hossain, M.; Suresh Kumar, G.: Investigations on the interaction of the phototoxic alkaloid coralyne with serum albumins. Chemosphere 87, 775-781 (2012)
54. Khan, A.Y.; Hossain, M.; Suresh Kumar, G.: Binding of plant alkaloids berberine and palmatine to serum albumins: a thermodynamic investigation. Mol. Biol. Rep. 40, 553-566 (2013)
55. Hazra, S.; Hossain, M.; Suresh Kumar, G.: Binding of isoquinoline alkaloids berberine, palmatine and coralyne to hemoglobin: structural and thermodynamic characterization studies. Mol. BioSyst. 9, 143-153 (2013)
56. Pilch, D.S.; Yu, C.; Makhey, D.; LaVoie, E.J.; Srinivasan, A.R.; Olson, W.K.; Sauers, R.R.; Breslauer, K.J.; Geacintov, N.E.; Liu, L.F.: Minor groove-directed and intercalative ligand-DNA interactions in the poisoning of human DNA topoisomerase I by protoberberine analogs. Biochemistry 36, 12542-12553 (1997)
57. Li, T.-K.; Bathory, E.; LaVoie, E.J.; Srinivasan, A.R.; Olson, W.K.; Sauers, R.R.; Liu, L.F.; Pilch, D.S.: Human topoisomerase I poisoning by protoberberines: potential roles for both drug-DNA and drug-enzyme interactions. Biochemistry 39, 7107-7116 (2000)
58. Megyesi, M.; Biczók, L.: Considerable fluorescence enhancement upon supramolecular complex formation between berberine and p-sulfonated calixarenes. Chem. Phys. Lett. 424, 71-76 (2006)
59. Miskolczy, Z.; Biczók, L.: Inclusion complex formation of ionic liquids with 4-sulfonatocalixarenes studied by competitive binding of berberine alkaloid fluorescent probe. Chem. Phys. Lett. 477, 80-84 (2009)
60. Megyesi, M.; Biczók, L.; Jablonkai, I.: Highly sensitive fluorescence response to inclusion complex formation of berberine alkaloid with cucurbit[7]uril. J. Phys. Chem. C 112, 3410-3416 (2008)
61. Freyer, M.W.; Lewis, E.A.: Isothermal titration calorimetry: experimental design, data analysis, and probing macromolecule/ligand binding and kinetic interactions. Methods Cell Biol. 84, 79-113 (2008)
62. Chaires, J.B.: Calorimetry and thermodynamics in drug design. Annu. Rev. Biophys. 37, 135-151 (2008)
63. Benesi, H.A.; Hildebrand, J.H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703-2707 (1949)
64. Connors, K.A.: Binding Constants: the measurement of molecular complex stability, pp. 28-261. John Wiley & Sons, Inc.; New York, USA (1987)
65. Del Martin Valle, E.M.: Cyclodextrins and their uses: a review. Process Biochem. 39, 1033-1047 (2004)
66. Suresh Kumar, G.: RNA targeting by small molecules: binding of protoberberine, benzophenanthridine and aristolochia alkaloids to various RNA structures. J. Biosci. 37, 539-552 (2012)
67. Harata, K.; Uedaira, H.: The circular dichroism spectra of the β-cyclodextrin complex with naphthalene derivatives. Bull. Chem. Soc. Jpn. 48, 375-378 (1975)
68. Biedermann, F.; Uzunova, V.D.; Scherman, O.A.; Nau, W.M.; Simone, A.D.: Release of high-energy water as an essential driving force for the high-affinity binding of cucurbit[n]urils. J. Am. Chem. Soc. 134, 15318-15323 (2012)
69. Demarco, P.V.; Thakkar, A.L.: Cyclohepta-amylose inclusion complexes: a proton magnetic resonance study. J. Chem. Soc. Chem. Commun. 1, 2-4 (1970)
70. Correia, I.; Bezzenine, N.; Ronzani, N.; Platzer, N.; Beloeil, J.-C.; Doan, B.-T.: Study of inclusion complexes of acridine with β-, and (2,6-di-O-methyl)-β-cyclodextrin by use of solubility diagrams and NMR spectroscopy. J. Phys. Org. Chem. 15, 647-659 (2002)