Effect of curcumin on the diffusion kinetics of a hemicyanine dye, LDS-698, across a lipid bilayer probed by second harmonic spectroscopy

Langmuir

Volumn 29, Issue 9, 2013, Pages 2912-2918

  Varshney, G K ^a   Saini, R K ^a   Gupta, P K ^a   Das, K ^a  

^a RAJA RAMANNA CENTRE FOR ADVANCED TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BI-LAYER; CONTROL EXPERIMENTS; CURCUMIN; DIFFUSION KINETICS; DIFFUSION PROCESS; DIFFUSION TIME; ELECTROSTATIC ADSORPTION; HEAD GROUPS; HEMICYANINE DYE; MEMBRANE PERMEABILITY; MODEL MEMBRANES; MOLE RATIO; NEGATIVELY CHARGED; NILE RED; ORGANIC CATIONS; OUTER SURFACE; POLAR HEADGROUPS; POSITIVELY CHARGED; REAL TIME; SECOND HARMONIC TECHNIQUE; SECOND-HARMONIC SPECTROSCOPY; TIME CONSTANTS;

LIPID BILAYERS; LIPOSOMES; MOLECULES; RIGIDITY;

DIFFUSION;

ALKENE; COLORING AGENT; CURCUMIN; LDS 698; LDS-698; PYRIDINIUM DERIVATIVE;

ARTICLE; CHEMISTRY; DIFFUSION; DRUG EFFECT; KINETICS; LIPID BILAYER; SPECTROSCOPY;

ALKENES; COLORING AGENTS; CURCUMIN; DIFFUSION; KINETICS; LIPID BILAYERS; PYRIDINIUM COMPOUNDS; SPECTRUM ANALYSIS;

EID: 84874592458     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la304778d     Document Type: Article

References (43)

1. Aggarwal, B. B.; Sundaram, C.; Malini, N.; Ichikawa, H. In Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease; Aggarwal, B. B., Surth, Y. J., Eds.; Springer: New York, 2007.
2. Ruby, A. J.; Kuttan, G.; Babu, K. D.; Rajasekharan, K. N.; Kuttan, R. Anti-tumour and antioxidant activity of natural curcuminoids Cancer Lett. 1995, 94, 79-83
3. Lantz, R. C.; Chen, G. J.; Solyom, A. M.; Jolad, S. D.; Timmermann, B. N. The effect of turmeric extracts on inflammatory mediator production Phytomedicine 2005, 12, 445-452
4. Goel, A.; Kannumakkara, A. B.; Aggarwal, B. B. Curcumin as "Curecumin": From kitchen to clinic Biochem. Pharamacol. 2008, 75, 787-809
5. Shi, M.; Cai, Q.; Yao, L.; Mao, Y.; Ming, Y.; Ouyang, G. Antiproliferation and apoptosis induced by curcumin in human ovarian cancer cells Cell Biol. Int. 2006, 30, 221-226
6. Surh, Y.-J. Anti-tumor promoting potential of selected spice ingredients with antioxidative and anti-inflammatory activities: a short review Food Chem. Toxicol. 2002, 40, 1091-1097
7. Joe, B.; Vijaykumar, M.; Lokesh, B. R. Biological Properties of Curcumin-Cellular and Molecular Mechanisms of Action Crit. Rev. Food Sci. Nutr. 2004, 44, 97-111
8. Maheshwari, R. K.; Singh, A. K.; Gaddipati, J.; Srimal, R. C. Multiple biological activities of curcumin: A short review Life Sci. 2006, 78, 2081-2087
9. Anand, P.; Thomas, S. G.; Kunnumakkara, A. B.; Sundaram, C.; Harikumar, K. B.; Sung, B.; Tharakan, S. T.; Misra, K.; Priyadarsini, I. K.; Rajasekharan, K. N.; Aggarwal, B. B. Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature Biochem. Pharmacol. 2008, 76, 1590-1611
10. Ingolfsson, H. I.; Koeppe, R. E.; Andersen, O. S. Curcumin is a Modulator of Bilayer Material Properties Biochemistry 2007, 46, 10384-10391
11. Jaruga, E.; Salvioli, S.; Dobrucki, J.; Chrul, S.; Bandorowicz- Pikuła, J.; Sikora, E.; Franceschi, C.; Cossarizza, A.; Bartosz, G. Apoptosis-like, reversible changes in plasma membrane asymmetry and permeability, and transient modifications in mitochondrial membrane potential induced by curcumin in rat thymocytes FEBS Lett. 1998, 433, 287-293
12. Jarugaa, E.; Sokala, A.; Chrulb, S.; Bartosza, G. Apoptosis-Independent Alterations in Membrane Dynamics Induced by Curcumin Exp. Cell Res. 1998, 245, 303
13. Hung, W. C.; Chen, F. Y.; Lee, C. C.; Sun, Y.; Lee, M. T.; Huang, H. W. Membrane-Thinning Effect of Curcumin Biophys. J. 2008, 94, 4331-4338
14. Barry, J.; Fritz, M.; Brender, J. R.; Smith, P. E.; Lee, D. K.; Ramamoorthy, A. Determining the Effects of Lipophilic Drugs on Membrane Structure by Solid-State NMR Spectroscopy: The Case of the Antioxidant Curcumin J. Am. Chem. Soc. 2009, 131, 4490-4498
15. Perez-Lara, A.; Ausili, A.; Aranda, F. J.; Godos, A.; Torrecillas, A.; Corbalan-Garcia, S.; Gomez-Fernandez, J. C. Curcumin Disorders 1,2-Dipalmitoyl- sn -glycero-3-phosphocholine Membranes and Favors the Formation of Nonlamellar Structures by 1,2-Dielaidoyl- sn -glycero-3-phosphoethanolamine J. Phys. Chem. B 2010, 114, 9778-9786
16. Eisenthal, K. B. Second Harmonic Spectroscopy of Aqueous Nano- and Microparticle Interfaces Chem. Rev. 2006, 106, 1462-1477
17. Srivastava, A.; Eisenthal, K. B. Kinetics of molecular transport across a liposome bilayer Chem. Phys. Lett. 1998, 292, 345-351
18. Yan, E. C. Y.; Eisenthal, K. B. Effect of Cholesterol on Molecular Transport of Organic Cations across Liposome Bilayer Probed by Second Harmonic Generation Biophys. J. 2000, 79, 898-903
19. Liu, Y.; Yan, E. C. Y.; Eisenthal, K. B. Effects of Bilayer Surface Charge Density on Molecular Adsorption and Transport across Liposome Bilayers Biophys. J. 2001, 80, 1004-1012
20. Shang, X. M.; Liu, Y.; Yan, E.; Eisenthal, K. B. Effects of Counterions on Molecular Transport Across Liposome Bilayer: Probed by Second Harmonic Generation J. Phys. Chem. B 2001, 105, 12816-12822
21. Liu, J.; Shang, X. M.; Pompano, R.; Eisenthal, K. B. Antibiotic assisted molecular ion transport across a membrane in real time Faraday Discuss. 2005, 129, 291-299
22. Liu, J.; Subir, M.; Nguyen, K.; Eisenthal, K. B. Second Harmonic Studies of Ions Crossing Liposome Membranes in Real Time J. Phys. Chem. B 2008, 112, 15263-15266
23. 6 Across Phosphatidyl Choline Liposome Bilayer Probed by Second Harmonic Generation J. Phys. Chem B 2012, 116, 4199-4205
24. Duan, X. M.; Konami, H.; Okada, S.; Oikawa, H.; Matsuda, H.; Nakanishi, H. Second-Order Hyperpolarizabilities of Stilbazolium Cations Studied by Semiempirical Calculation J. Phys. Chem. 1996, 100, 17780-17785
25. Ashwell, G. J.; Jackson, P. D.; Crossland, W. A. Non-centrosymmetry and second-harmonic generation in Z-type Langmuir-Blodgett films Nature 1994, 368, 438-440
26. Kim, O. K.; Choi, L. S.; Zhang, H. Y.; He, X. H.; Shih, Y. H. Second-Harmonic Generation by Spontaneous Self-Poling of Supramolecular Thin Films of an Amylose-Dye Inclusion Complex J. Am. Chem. Soc. 1996, 118, 12220-12221
27. Xu, J.; Lu, X.; Zhou, G.; Zhang, Z. Electric field induced molecular reorientation in stilbazolium salt Langmuir-Blodgett monolayers Thin Solid Films 1998, 312, 295-299
28. Peret-Almeida, L.; Cherubino, A. P. F.; Alves, R. J.; Dufosse, L.; Gloria, M. B. A. Separation and determination of the physico-chemical characteristics of curcumin, demethoxycurcumin and bisdemethoxycurcumin Food Res. Int. 2005, 38, 1039-1044
29. Moscho, A.; Orwar, O.; Chiu, D. T.; Modi, B. P.; Zare, R. W. Rapid preparation of giant unilamellar vesicles Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 11443-11447
30. Oezdirekcan, S.; Nyholm, T. K. M.; Raja, M.; Rijkers, D. T. S.; Liskamp, R. M. J.; Killian, J. A. Influence of Trifluoroethanol on Membrane Interfacial Anchoring Interactions of Transmembrane α-Helical Peptides Biophys. J. 2008, 94, 1315-1325
31. Adachi, S.; Nagao, T.; Ingolfsson, H. I.; Maxfield, F. R.; Andersen, O. S.; Kopelovich, L.; Weinstein, I. B. The Inhibitory Effect of (-)-Epigallocatechin Gallate on Activation of the Epidermal Growth Factor Receptor Is Associated with Altered Lipid Order in HT29 Colon Cancer Cells Cancer Res. 2007, 67, 6493-6501
32. Lundbaek, J. A.; Birn, P.; Tape, S. E.; Toombes, G. E. S.; Sogaard, R.; Koeppe, R. E.; Gruner, S. M.; Hansen, A. J.; Andersen, O. S. Capsaicin Regulates Voltage-Dependent Sodium Channels by Altering Lipid Bilayer Elasticity Mol. Pharmacol. 2005, 68, 680-689
33. Hwang, T. C.; Koeppe, R. E.; Andersen, O. S. Genistein Can Modulate Channel Function by a Phosphorylation-Independent Mechanism: Importance of Hydrophobic Mismatch and Bilayer Mechanics Biochemistry 2003, 42, 13646-13658
34. Lundbaek, J. A. Lipid Bilayer-mediated Regulation of Ion Channel Function by Amphiphilic Drugs J. Gen. Physiol. 2008, 131, 421-429
35. 2+ pumps by Curcumin Eur. J. Biochem. 2001, 268, 6318-6327
36. Ramamoorthy, A.; Lee, D.-K.; Narasimhaswamy, T.; Nanga, R. P. R. Cholesterol reduces pardaxin's dynamics-a barrel-stave mechanism of membrane disruption investigated by solid-state NMR Biochim. Biophys. Acta, Biomembr. 2010, 1798, 223-227
37. Brender, J. R.; McHenry, A. J.; Ramamoorthy, A. Does cholesterol play a role in the bacterial selectivity of antimicrobial peptides? Front. Immunol. 2012, 3, 1-3
38. McHenry, A. J.; Sciacca, M. F. M.; Brender, J. R.; Ramamoorthy, A. Does cholesterol suppress the antimicrobial peptide induced disruption of lipid raft containing membranes? Biochim. Biophys. Acta, Biomembr. 2012, 1818, 3019-3024
39. Parimita, S. P.; Ramshankar, Y. V.; Suresh, S.; Row, T. N. G. Redetermination of curcumin: (1 E,4 Z,6 E)-5-hydroxy-1,7-bis(4-hydroxy-3- methoxyphenyl)hepta-1,4,6-trien-3-one Acta Crystallogr., Sect. E: Struct. Rep. Online 2007, 63, O860-O862
40. Henzler Wildman, K. A.; Lee, D.-K.; Ramamoorthy, A. Mechanism of Lipid Bilayer Disruption by the Human Antimicrobial Peptide, LL-37 Biochemistry 2003, 42, 6545-6558
41. Ramamoorthy, A.; Thennarasu, S.; Lee, D.-K.; Tan, A.; Maloyy, L. Solid-State NMR Investigation of the Membrane-Disrupting Mechanism of Antimicrobial Peptides MSI-78 and MSI-594 Derived from Magainin 2 and Melittin Biophys. J. 2006, 91, 206-216
42. Brender, J. R.; Lee, E. L.; Cavitt, M. A.; Gafni, A.; Steel, D. G.; Ramamoorthy, G. Amyloid Fiber Formation and Membrane Disruption are Separate Processes Localized in Two Distinct Regions of IAPP, the Type-2-Diabetes-Related Peptide J. Am. Chem. Soc. 2008, 130, 6424-6429
43. 248-286, a Dramatic Enhancer of HIV Infectivity, Promotes Lipid Aggregation and Fusion Biophys. J. 2009, 97, 2474-2483