Probing the Intercalation of Noscapine from Sodium Dodecyl Sulfate Micelles to Calf Thymus Deoxyribose Nucleic Acid: A Mechanistic Approach

Noscapine (NOS) is efficient in inhibiting cellular proliferation and induces apoptosis in nonsmall cell, lung, breast, lymphatic, and prostate cancers. The micelle-assisted drug delivery is a well-known phenomenon; however, the proper mechanism is still unclear. Therefore, in the present study, we have shown a mechanistic approach for the delivery of NOS from sodium dodecyl sulfate (SDS) micelles to calf thymus deoxyribose nucleic acid (ctDNA) base-pairs using various spectroscopic techniques. The absorption and emission spectroscopy results revealed that NOS interacts with the SDS micelle and resides in its hydrophobic core. Further, the intercalation of NOS from SDS micelles to ctDNA was also shown by these techniques. The anisotropy and quenching results further confirmed the relocation of NOS from SDS micelles to ctDNA. The CD analysis suggested that SDS micelles do not perturb the structure of ctDNA, which supported that SDS micelles can be used as a safe delivery vehicle for NOS. This work may be helpful for the invention of advanced micelle-based vehicles for the delivery of an anticancer drug to their specific target site.

[1]  A. Alanazi,et al.  In Vitro Cytotoxicity and Interaction of Noscapine with Human Serum Albumin: Effect on Structure and Esterase Activity of HSA. , 2019, Molecular pharmaceutics.

[2]  Rajan Patel,et al.  Comparative effect of cationic gemini surfactant and its monomeric counterpart on the conformational stability of phospholipase A2 , 2019, Journal of Molecular Structure.

[3]  Rajan Patel,et al.  Esterase activity and conformational changes of bovine serum albumin toward interaction with mephedrone: Spectroscopic and computational studies , 2018, Journal of molecular recognition : JMR.

[4]  Abbul Bashar Khan,et al.  Effect of cationic gemini surfactant and its monomeric counterpart on the conformational stability and esterase activity of human serum albumin , 2018, Journal of Molecular Liquids.

[5]  Rajan Patel,et al.  Dynamics of Ionic Liquid-Assisted Refolding of Denatured Cytochrome c: A Study of Preferential Interactions toward Renaturation. , 2018, Molecular pharmaceutics.

[6]  M. Muti,et al.  Electrochemical monitoring of the interaction between anticancer drug and DNA in the presence of antioxidant. , 2018, Talanta.

[7]  Rajan Patel,et al.  Mechanism and Dynamics of Long-Term Stability of Cytochrome c Conferred by Long-Chain Imidazolium Ionic Liquids at Low Concentration , 2018 .

[8]  Abbul Bashar Khan,et al.  Hydrogen bonding-assisted interaction between amitriptyline hydrochloride and hemoglobin: spectroscopic and molecular dynamics studies , 2017, Journal of biomolecular structure & dynamics.

[9]  Abbul Bashar Khan,et al.  Comparative effect of cationic gemini surfactant and its monomeric counterpart on the conformational stability and activity of lysozyme , 2017 .

[10]  S. Chatterjee,et al.  Visualization of Stepwise Drug-Micelle Aggregate Formation and Correlation with Spectroscopic and Calorimetric Results. , 2016, The journal of physical chemistry. B.

[11]  Shailza Singh,et al.  Effect of 1,4-bis(3-dodecylimidazolium-1-yl) butane bromide on channel form of gramicidin vesicles , 2016 .

[12]  Saptarshi Ghosh,et al.  Endogenous Activation-Induced Delivery of a Bioactive Photosensitizer from a Micellar Carrier to Natural DNA. , 2016, The journal of physical chemistry. B.

[13]  Abbul Bashar Khan,et al.  An insight into the binding of an ester functionalized gemini surfactant to hemoglobin , 2016 .

[14]  H. Pal,et al.  Unraveling multiple binding modes of acridine orange to DNA using a multispectroscopic approach. , 2016, Physical chemistry chemical physics : PCCP.

[15]  Rajan Patel,et al.  A spectroscopic and molecular dynamic approach on the interaction between ionic liquid type gemini surfactant and human serum albumin , 2016, Journal of biomolecular structure & dynamics.

[16]  D. Nayak,et al.  First Evidence of the Liposome-Mediated Deintercalation of Anticancer Drug Doxorubicin from the Drug-DNA Complex: A Spectroscopic Approach. , 2016, Langmuir : the ACS journal of surfaces and colloids.

[17]  Antje Sommer,et al.  Principles Of Fluorescence Spectroscopy , 2016 .

[18]  Saptarshi Ghosh,et al.  DNA induced sequestration of a bioactive cationic fluorophore from the lipid environment: A spectroscopic investigation. , 2016, Journal of photochemistry and photobiology. B, Biology.

[19]  Rajan Patel,et al.  Molecular investigation of the interaction between ionic liquid type gemini surfactant and lysozyme: A spectroscopic and computational approach , 2015, Biopolymers.

[20]  Saptarshi Ghosh,et al.  Exploration of the binding interaction of a potential nervous system stimulant with calf-thymus DNA and dissociation of the drug-DNA complex by detergent sequestration. , 2015, Physical chemistry chemical physics : PCCP.

[21]  R. Chandra,et al.  Inhalable nanostructured lipid particles of 9-bromo-noscapine, a tubulin-binding cytotoxic agent: in vitro and in vivo studies. , 2015, Journal of colloid and interface science.

[22]  P. Scammells,et al.  Progress Toward the Development of Noscapine and Derivatives as Anticancer Agents. , 2015, Journal of medicinal chemistry.

[23]  J. Makowska,et al.  Thermodynamics of sodium dodecyl sulphate (SDS) micellization in the presence of some biologically relevant pH buffers , 2015, Journal of Thermal Analysis and Calorimetry.

[24]  Banibrata Maity,et al.  Interaction of the nonsteroidal anti-inflammatory drug indomethacin with micelles and its release. , 2015, The journal of physical chemistry. B.

[25]  N. Guchhait,et al.  Exploring the interaction of a micelle entrapped biologically important proton transfer probe with the model transport protein bovine serum albumin. , 2015, The journal of physical chemistry. B.

[26]  C. Emiliani,et al.  Spectroscopic investigation of interactions of new potential anticancer drugs with DNA and non-ionic micelles. , 2015, The journal of physical chemistry. B.

[27]  Bijan Kumar Paul,et al.  Prototropic transformation and rotational-relaxation dynamics of a biological photosensitizer norharmane inside nonionic micellar aggregates. , 2014, The journal of physical chemistry. B.

[28]  Xiaoming Xu,et al.  Synthesis, structure and molecular docking studies of dicopper(II) complexes bridged by N-phenolato-N′-[2-(dimethylamino)ethyl]oxamide: the influence of terminal ligands on cytotoxicity and reactivity towards DNA and protein BSA , 2014 .

[29]  Bijan Kumar Paul,et al.  Interaction of a potential chloride channel blocker with a model transport protein: a spectroscopic and molecular docking investigation. , 2014, Physical chemistry chemical physics : PCCP.

[30]  A. Riyasdeen,et al.  New ruthenium(II) arene complexes of anthracenyl-appended diazacycloalkanes: effect of ligand intercalation and hydrophobicity on DNA and protein binding and cleavage and cytotoxicity. , 2014, Dalton transactions.

[31]  R. K. Mitra,et al.  Entropy contribution toward micelle-driven deintercalation of drug-DNA complex. , 2014, The journal of physical chemistry. B.

[32]  Fengli Qu,et al.  Molecular spectroscopic studies on the interaction of ferulic acid with calf thymus DNA. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[33]  O. Katare,et al.  Sterically stabilized gelatin microassemblies of noscapine enhance cytotoxicity, apoptosis and drug delivery in lung cancer cells. , 2013, Colloids and surfaces. B, Biointerfaces.

[34]  Surajit Ghosh,et al.  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. , 2012, The journal of physical chemistry. B.

[35]  Richard A. Stanton,et al.  Drugs that target dynamic microtubules: A new molecular perspective , 2011, Medicinal research reviews.

[36]  Shan Ren,et al.  New perspectives on lipid and surfactant based drug delivery systems for oral delivery of poorly soluble drugs , 2010, The Journal of pharmacy and pharmacology.

[37]  S. Prakash,et al.  Human serum albumin nanoparticles as an efficient noscapine drug delivery system for potential use in breast cancer: preparation and in vitro analysis , 2010, International journal of nanomedicine.

[38]  Bijan Kumar Paul,et al.  Modulated photophysics of an ESIPT probe 1-hydroxy-2-naphthaldehyde within motionally restricted environments of liposome membranes having varying surface charges. , 2010, The journal of physical chemistry. B.

[39]  N. Chattopadhyay,et al.  Differential interaction of beta-cyclodextrin with lipids of varying surface charges: a spectral deciphering using a cationic phenazinium dye. , 2010, The journal of physical chemistry. B.

[40]  Ju Xie,et al.  Binding characteristics and molecular mechanism of interaction between ionic liquid and DNA. , 2010, The journal of physical chemistry. B.

[41]  Kamalakanta Behera,et al.  Modifying properties of aqueous cetyltrimethylammonium bromide with external additives: ionic liquid 1-hexyl-3-methylimidazolium bromide versus cosurfactant n-hexyltrimethylammonium bromide. , 2009, The journal of physical chemistry. B.

[42]  S. S. Sinha,et al.  Temperature-dependent simultaneous ligand binding in human serum albumin. , 2008, The journal of physical chemistry. B.

[43]  S. S. Sinha,et al.  Interactions of Nile Blue with Micelles, Reverse Micelles and a Genomic DNA , 2008, Journal of Fluorescence.

[44]  J. Chaires,et al.  Circular dichroism to determine binding mode and affinity of ligand–DNA interactions , 2007, Nature Protocols.

[45]  Arabinda Mallick,et al.  Photophysics of a cationic biological photosensitizer in anionic micellar environments: combined effect of polarity and rigidity. , 2007, Journal of Physical Chemistry B.

[46]  J. Chaires,et al.  A thermodynamic signature for drug-DNA binding mode. , 2006, Archives of biochemistry and biophysics.

[47]  S. Reis,et al.  Interaction of Grepafloxacin with Large Unilamellar Liposomes: Partition and Fluorescence Studies Reveal the Importance of Charge Interactions , 2002 .

[48]  I. Haq Thermodynamics of drug-DNA interactions. , 2002, Archives of biochemistry and biophysics.

[49]  J. Guharay,et al.  Fluorescence polarization anisotropy as a novel tool for the determination of critical micellar concentrations , 1996 .

[50]  L. Gaboury,et al.  Spectroscopic and photophysical properties of some new rhodamine derivatives in cationic, anionic and neutral micelles , 1996 .

[51]  W D Wilson,et al.  The search for structure-specific nucleic acid-interactive drugs: effects of compound structure on RNA versus DNA interaction strength. , 1993, Biochemistry.

[52]  R. Ludescher,et al.  Time-resolved fluorescence anisotropy for systems with lifetime and dynamic heterogeneity. , 1987, Biophysical chemistry.

[53]  J. K. Thomas,et al.  Dynamic and static aspects of solubilization of neutral arenes in ionic micellar solutions , 1979 .

[54]  J. Idänpään-Heikkilä,et al.  Evaluation of the antitussive effect of noscapine and codeine on citric acid cough in guinea-pigs. , 2009, Acta pharmacologica et toxicologica.

[55]  N. Weiner,et al.  Biphasic elimination of noscapine. , 1966, Journal of pharmaceutical sciences.

[56]  Joel H. Hildebrand,et al.  A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons , 1949 .