Exploring the drug-lipid interaction of weak-hydrophobic drug loaded solid lipid nanoparticles by isothermal titration calorimetry
Source abstract
Abstract
Drug-lipid interaction was a vital issue for weak-hydrophobic drug-loaded solid lipid nanoparticles (WHD-SLNs). With a weak drug-lipid interaction, the drug loading capacity and physical stability could be low, and thus the drug-lipid interaction should be investigated. This paper was aimed to explore the drug-lipid interactions of WHD-SLNs by isothermal titration calorimetry (ITC). Benzoic acid (BEA) and salicylic acid (SAA) were chosen as the model weak-hydrophobic drugs, and stearic acid (SA) was selected as the model lipid material. For reference, the melting point depression (the proof of molecular interaction) of BEA-SA system and SAA-SA system was explored by differential scanning calorimetry (DSC) and hot stage polarized-light microscopy (HSPM). The ITC results demonstrated that BEA-SA interaction had negative ΔH and negative ΔS, while SAA-SA interaction possessed slightly negative ΔH and positive ΔS. It was indicated that the major interactions in BEA-SA interaction and SAA-SA interaction were hydrogen bonds and hydrophobic forces, respectively. Shown by DSC and HSPM results, the melting point depression in BEA-SA system was more significant than SAA-SA system. Therefore, melting point depression was mainly associated with hydrogen bond interactions, rather than hydrophobic forces. This study could provide new insight for the interpretation of drug-lipid interaction of WHD-SLNs.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: thermodynamics and calorimetric analyses · Lipid Membrane Structure and Behavior · Analytical Chemistry and Chromatography
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (56)
Show source-provided references
1. Aditya NP, Ko S (2015) Solid lipid nanoparticles (SLNs): delivery vehicles for food bioactives. RSC Adv 5:30902–3091110.1039/C4RA17127F ↗
2. Baghel S, Cathcart H, O’Reilly NJ (2016) Theoretical and experimental investigation of drug-polymer interaction and miscibility and its impact on drug supersaturation in aqueous medium. Eur J Pharm Biopharm 107:16–3110.1016/j.ejpb.2016.06.024 ↗
3. Bouchemal K, Mazzaferro S (2012) How to conduct and interpret ITC experiments accurately for cyclodextrin-guest interactions. Drug Discov Today 17:623–62910.1016/j.drudis.2012.01.023 ↗
4. Brautigam CA, Zhao HY, Vargas C, Keller S, Schuck P (2016) Integration and global analysis of isothermal titration calorimetry data for studying macromolecular interactions. Nat Protoc 11:882–89410.1038/nprot.2016.044 ↗
5. Chanphai P, Kreplak L, Tajrnir-Riahi HA (2017) Al cation induces aggregation of serum proteins. J Pharm Biomed Anal 141:234–24010.1016/j.jpba.2017.04.027 ↗
6. Chantaburanan T, Teeranachaideekul V, Chantasart D, Jintapattanakit A, Junyaprasert VB (2017) Effect of binary solid lipid matrix of wax and triglyceride on lipid crystallinity, drug-lipid interaction and drug release of ibuprofen-loaded solid lipid nanoparticles (SLN) for dermal delivery. J Colloid Interface Sci 504:247–25610.1016/j.jcis.2017.05.038 ↗
7. Chavan SS, Ingle SG, Vavia PR (2013) Preparation and characterization of solid lipid nanoparticle-based nasal spray of budesonide. Drug Deliv Transl Res 3:402–40810.1007/s13346-012-0105-z ↗
8. Chaves OA, da Silva VA, Sant’Anna CMR, Ferreira ABB, Ribeiro TAN, de Carvalho MG, Cesarin-Sobrinho D, Netto-Ferreira JC (2017) Binding studies of lophirone B with bovine serum albumin (BSA): combination of spectroscopic and molecular docking techniques. J Mol Struct 1128:606–61110.1016/j.molstruc.2016.09.036 ↗
9. Dengale SJ, Grohganz H, Rades T, Lobmann K (2016) Recent advances in co-amorphous drug formulations. Adv Drug Deliv Rev 100:116–12510.1016/j.addr.2015.12.009 ↗
10. Din FU, Mustapha O, Kim DW, Rashid R, Park JH, Choi JY, Ku SK, Yong CS, Kim JO, Choi HG (2015) Novel dual-reverse thermosensitive solid lipid nanoparticle-loaded hydrogel for rectal administration of flurbiprofen with improved bioavailability and reduced initial burst effect. Eur J Pharm Biopharm 94:64–7210.1016/j.ejpb.2015.04.019 ↗
11. Duff, M.R., Grubbs, J., Howell, E.E., 2011. Isothermal titration calorimetry for measuring macromolecule-ligand affinity. Jove-J Vis Exp.10.3791/2796 ↗
12. Dyer AM, Smith A (2017) Riluzole 5 mg/mL oral suspension: for optimized drug delivery in amyotrophic lateral sclerosis. Drug Des Dev Ther 11:59–6410.2147/DDDT.S123776 ↗
13. Fatouh AM, Elshafeey AH, Abdelbary A (2017) Intranasal agomelatine solid lipid nanoparticles to enhance brain delivery: formulation, optimization and in vivo pharmacokinetics. Drug Des Dev Ther 11:1815–182510.2147/DDDT.S102500 ↗
14. Frank HS, Evans MW (1945) Free volume and entropy in condensed systems III. entropy in inary liquid mixtures; partial molar entropy in dilute solutions; structure and thermodynamics in aqueous electrolytes. J Chem Phys 13:507–53210.1063/1.1723985 ↗
15. Frederix PWJM, Scott GG, Abul-Haija YM, Kalafatovic D, Pappas CG, Javid N, Hunt NT, Ulijn RV, Tuttle T (2015) Exploring the sequence space for (tri-) peptide self-assembly to design and discover. Nat Chem 7:30–3710.1038/nchem.2122 ↗
16. Gray DG, Mu XY (2015) Chiral nematic structure of cellulose nanocrystal suspensions and films; polarized light and atomic force microscopy. Materials 8:7873–788810.3390/ma8115427 ↗
17. Henderson KL, Francis DH, Lewis EA, Emerson JP (2016) Thermodynamics of substrate binding to the metal site in homoprotocatechuate 2,3-dioxygenase: Using ITC under anaerobic conditions to study enzyme-substrate interactions. Bba-Gen Subjects 1860:910–91610.1016/j.bbagen.2015.07.013 ↗
18. Huang Y, Dai W-G (2014) Fundamental aspects of solid dispersion technology for poorly soluble drugs. Acta Pharm Sin B 4:18–2510.1016/j.apsb.2013.11.001 ↗
19. Jain A, Kesharwani P, Garg NK, Jain A, Jain SA, Jain AK, Nirbhavane P, Ghanghoria R, Tyagi RK, Katare OP (2015) Galactose engineered solid lipid nanoparticles for targeted delivery of doxorubicin. Colloid Surface B 134:47–5810.1016/j.colsurfb.2015.06.027 ↗
20. Jecklin MC, Schauer S, Dumelin CE, Zenobi R (2009) Label-free determination of protein-ligand binding constants using mass spectrometry and validation using surface plasmon resonance and isothermal titration calorimetry. J Mol Recognit 22:319–32910.1002/jmr.951 ↗
21. Jiao JM, Shen JL, Wang L, Xie ZC, Xia CX, Xin X (2018) Tunable solid-state fluorescent materials self-assembled by a cationic dye acridine orange and an anionic biosurfactant sodium deoxycholate. Colloid Surface A 545:8–1510.1016/j.colsurfa.2018.02.013 ↗
22. Kong XQ, Brinkmann A, Terskikh V, Wasylishen RE, Bernard GM, Duan Z, Wu QC, Wu G (2016) Proton Probability distribution in the O center dot center dot center dot H center dot center dot center dot O low-barrier hydrogen bond: a combined solid-state NMR and quantum chemical computational study of dibenzoylmethane and curcumin. J Phys Chem B 120:11692–1170410.1021/acs.jpcb.6b08091 ↗
23. Kumar S, Randhawa JK (2013) High melting lipid based approach for drug delivery: solid lipid nanoparticles. Mat Sci Eng C-Mater 33:1842–185210.1016/j.msec.2013.01.037 ↗
24. Leavitt S, Freire E (2001) Direct measurement of protein binding energetics by isothermal titration calorimetry. Curr Opin Struct Biol 11:560–56610.1016/S0959-440X(00)00248-7 ↗
25. Lee MH, Shin GH, Park HJ (2018) Solid lipid nanoparticles loaded thermoresponsive pluronic-xanthan gum hydrogel as a transdermal delivery system. J Appl Polym Sci:13510.1002/app.46004 ↗
26. Li G, Lin RS, Zong HX (2000) Thermodynamics of carboxyl group’s protonation of alpha-amino acids in water-ethanol mixtures at 298. 15 K. Acta Phys -Chim Sin 16:188–19210.3866/PKU.WHXB20000218 ↗
27. Liu Y, Li XY, Zhang HY, Li CJ, Ding F (2007) Cyclodextrin-driven movement of cucurbit[7]uril. J Organomet Chem 72:3640–364510.1021/jo0624288 ↗
28. Ma C, Wang W, Huang Z, Chen X, Ye W, Pan K, Ma R, Xue K, Cai S, Huang Y, Pan X, Wu C (2019) Effect of the cargo lipophilicity on powder micromeritics properties of drug-loaded solid lipid microparticles. J Drug Deliv Sci Tech 51:614–62010.1016/j.jddst.2019.03.025 ↗
29. Ma GX, Liu S, Xie SL, Jing Y, Zhang QY, Sun JH, Jia YZ (2017) Binary eutectic mixtures of stearic acid-n-butyramide/n-octanamide as phase change materials for low temperature solar heat storage. Appl Therm Eng 111:1052–105910.1016/j.applthermaleng.2016.10.004 ↗
30. Makwana V, Jain R, Patel K, Nivsarkar M, Joshi A (2015) Solid lipid nanoparticles (SLN) of Efavirenz as lymph targeting drug delivery system: elucidation of mechanism of uptake using chylomicron flow blocking approach. Int J Pharm 495:439–44610.1016/j.ijpharm.2015.09.014 ↗
31. Manin AN, Voronin AP, Drozd KV, Manin NG, Bauer-Brandl A, Perlovich GL (2014) Cocrystal screening of hydroxybenzamides with benzoic acid derivatives: a comparative study of thermal and solution-based methods. Eur J Pharm Sci 65:56–6410.1016/j.ejps.2014.09.003 ↗
32. McCalley DV (2018) A study of the analysis of acidic solutes by hydrophilic interaction chromatography. J Chromatogr A 1534:64–7410.1016/j.chroma.2017.12.045 ↗
33. Medic-Saric M, Mornar A, Jasprica I (2007) Lipophilicity of flavonoids and phenolic acids determined by shake-flask and high performance liquid chromatography methods. Drugs Future 32:133–133
34. Mohanty B, Majumdar DK, Mishra SK, Panda AK, Patnaik S (2015) Development and characterization of itraconazole-loaded solid lipid nanoparticles for ocular delivery. Pharm Dev Technol 20:458–46410.3109/10837450.2014.882935 ↗
35. Moschetta EG, Gans KM, Rioux RM (2013) Characterization of sites of different thermodynamic affinities on the same metal center via isothermal titration calorimetry. J Catal 302:1–910.1016/j.jcat.2013.02.020 ↗
36. Muller RH, Mader K, Gohla S (2000) Solid lipid nanoparticles (SLN) for controlled drug delivery - a review of the state of the art. Eur J Pharm Biopharm 50:161–17710.1016/S0939-6411(00)00087-4 ↗
37. Muller RH, Runge SA, Ravelli V, Thunemann AF, Mehnert W, Souto EB (2008) Cyclosporine-loaded solid lipid nanoparticles (SLN (R)): drug-lipid physicochemical interactions and characterization of drug incorporation. Eur J Pharm Biopharm 68:535–54410.1016/j.ejpb.2007.07.006 ↗
38. Nafee N, Husari A, Maurer CK, Lu CB, de Rossi C, Steinbach A, Hartmann RW, Lehr CM, Schneider M (2014) Antibiotic-free nanotherapeutics: ultra-small, mucus-penetrating solid lipid nanoparticles enhance the pulmonary delivery and anti-virulence efficacy of novel quorum sensing inhibitors. J Control Release 192:131–14010.1016/j.jconrel.2014.06.055 ↗
39. Ninkovic DB, Vojislavljevic-Vasilev DZ, Medakovic VB, Hall MB, Brothers EN, Zaric SD (2016) Aliphatic-aromatic stacking interactions in cyclohexane-benzene are stronger than aromatic-aromatic interaction in the benzene dimer. Phys Chem Chem Phys 18:25791–2579510.1039/C6CP03734H ↗
40. Nunes S, Madureira AR, Campos D, Sarmento B, Gomes AM, Pintado M, Reis F (2017) Solid lipid nanoparticles as oral delivery systems of phenolic compounds: overcoming pharmacokinetic limitations for nutraceutical applications. Crit Rev Food Sci 57:1863–1873
41. Orgovan Z, Ferenczy GG, Steinbrecher T, Szilagyi B, Bajusz D, Keseru GM (2018) Validation of tautomeric and protomeric binding modes by free energy calculations. A case study for the structure based optimization of D-amino acid oxidase inhibitors. J Comput Aid Mol Des 32:331–34510.1007/s10822-018-0097-y ↗
42. Pierce MM, Raman CS, Nall BT (1999) Isothermal titration calorimetry of protein-protein interactions. Methods 19:213–22110.1006/meth.1999.0852 ↗
43. Poureshghi F, Ghandforoushan P, Safarnejad A, Soltani S (2017) Interaction of an antiepileptic drug, lamotrigine with human serum albumin (HSA): application of spectroscopic techniques and molecular modeling methods. J Photochem Photobiol B 166:187–19210.1016/j.jphotobiol.2016.09.046 ↗
44. Qin PF, Pan XR, Liu RT, Qiu JC, Fang XY (2017) Experimental and computational characterization on the binding of two fluoroquinolones to bovine hemoglobin. J Mol Recognit 3010.1002/jmr.2647 ↗
45. Schmid R (2001) Recent advances in the description of the structure of water, the hydrophobic effect, and the like-dissolves-like rule. Monatsh Chem 132:1295–132610.1007/s007060170019 ↗
46. Siddiqui AA, Feroz A, Khaki PSS, Bano B (2017) Binding of lambda-carrageenan (a food additive) to almond cystatin: an insight involving spectroscopic and thermodynamic approach. Int J Biol Macromol 98:684–69010.1016/j.ijbiomac.2017.01.143 ↗
47. Tesmar A, Wyrzykowski D, Munoz E, Pilarski B, Pranczk J, Jacewicz D, Chmurzynski L (2017) Simultaneous determination of thermodynamic and kinetic parameters of aminopolycarbonate complexes of cobalt(II) and nickel(II) based on isothermal titration calorimetry data. J Mol Recognit 30:e258910.1002/jmr.2589 ↗
48. Torge A, Wagner S, Chaves PS, Oliveira EG, Guterres SS, Pohlmann AR, Titz A, Schneider M, Beck RCR (2017) Ciprofloxacin-loaded lipid-core nanocapsules as mucus penetrating drug delivery system intended for the treatment of bacterial infections in cystic fibrosis. Int J Pharm 527:92–10210.1016/j.ijpharm.2017.05.013 ↗
49. Turnbull WB, Daranas AH (2003) On the value of c: can low affinity systems be studied by isothermal titration calorimetry? J Am Chem Soc 125:14859–1486610.1021/ja036166s ↗
50. Vasconcelos T, Sarmento B, Costa P (2007) Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs. Drug Discov Today 12:1068–107510.1016/j.drudis.2007.09.005 ↗
51. Velazquez-Campoy A, Leavitt SA, Freire E (2015) Characterization of protein-protein interactions by isothermal titration calorimetry. In: Meyerkord CL, Fu H (eds) protein-protein interactions: methods and applications. Springer New York, New York, pp 183–20410.1007/978-1-4939-2425-7_11 ↗
52. Vijayakumar A, Baskaran R, Jang YS, Oh SH, Yoo BK (2017) Quercetin-loaded solid lipid nanoparticle dispersion with improved physicochemical properties and cellular uptake. AAPS PharmSciTech 18:875–88310.1208/s12249-016-0573-4 ↗
53. Wang QP, Lu DZ, Shen L, Yang JZ (2001) Thermodynamic properties of dissociation of amino acid in mixed solvents of ethanol and water. Acta Phys -Chim Sin 17:952–95510.3866/PKU.WHXB20011018 ↗
54. Yan YD, Kim JA, Kwak MK, Yoo BK, Yong CS, Choi HG (2011) Enhanced oral bioavailability of curcumin via a solid lipid-based self-emulsifying drug delivery system using a spray-drying technique. Biol Pharm Bull 34:1179–118610.1248/bpb.34.1179 ↗
55. Young LM, Saunders JC, Mahood RA, Revill CH, Foster RJ, Tu LH, Raleigh DP, Radford SE, Ashcroft AE (2015) Screening and classifying small-molecule inhibitors of amyloid formation using ion mobility spectrometry-mass spectrometry. Nat Chem 7:73–8110.1038/nchem.2129 ↗
56. Zhou W, Liu W, Zou LQ, Liu WL, Liu CM, Liang RH, Chen J (2014) Storage stability and skin permeation of vitamin C liposomes improved by pectin coating. Colloid Surface B 117:330–33710.1016/j.colsurfb.2014.02.036 ↗