Calcein release from DPPC liposomes by phospholipase A2 activity: Effect of cholesterol and amphipathic copolymers

References

• Ahmed K, Hussein S, Ali A, et al. Liposome: composition, characterization, preparation, and recent innovation in clinical applications. J Drug Target. 2019a;27(7):742–761.
   PubMed Web of Science ®Google Scholar
• Allen TM, Cullis PR. Liposomal drug delivery systems: from concept to clinical applications. Adv. Drug Delivery Rev. 2013;65(1):36–48. doi: 10.1016/j.addr.2012.09.037.
   PubMed Web of Science ®Google Scholar
• Kumar-Sriraman S, Torchilin VP. 2014. Recent advances with liposomes as drug carriers. In: Tiwari A, Nordin A, editors. Advanced biomaterials and biodevices. John Wiley & Sons, Inc. Scrivener Publishing; 2014. p. 79–119. doi: 10.1002/9781118774052.ch3.
   Google Scholar
• Nsairat H, Khater D, Sayed U, et al. Liposomes: structure, composition, types, and clinical applications. Heliyon. 2022;8(5):e09394. 13, doi: 10.1016/j.heliyon.2022.e09394.
   PubMed Web of Science ®Google Scholar
• Nunes SS, Fernandes RS, Cavalcante CH, et al. Influence of PEG coating on the biodistribution and tumor accumulation of pH-sensitive liposomes. Drug Deliv Transl Res. 2019;9(1):123–130. doi: 10.1007/s13346-018-0583-8.
   PubMed Web of Science ®Google Scholar
• Ye H, Zhou L, Jin H, et al. Sorafenib-Loaded Long-Circulating nanoliposomes for liver cancer therapy. Biomed Res Int. 2020;6:1351046.
   Google Scholar
• Mohamed M, Abu Lila AS, Shimizu T, et al. PEGylated liposomes: immunological responses. Sci Technol Adv Mater. 2019;20(1):710–724. doi: 10.1080/14686996.2019.1627174.
   PubMed Web of Science ®Google Scholar
• Petralito S, Spera R, Pacelli S, et al. Design and development of PEG-DMA gel-in-liposomes as a new tool for drug delivery. React Funct Polym. 2014;77:30–38. doi: 10.1016/j.reactfunctpolym.2014.02.002.
   Web of Science ®Google Scholar
• Susanti TM, Haris D, Rushdan MS, et al. PEGylated liposomes enhance the effect of cytotoxic drug: a review. Heliyon. 2023;9(3):e13823. 17, doi: 10.1016/j.heliyon.2023.e13823.
   PubMed Web of Science ®Google Scholar
• Guimarães D, Cavaco-Paulo A, Nogueira E. Design of liposomes as drug delivery system for therapeutic applications. Int J Pharm. 2021;601:120571. doi: 10.1016/j.ijpharm.2021.120571.
   PubMed Web of Science ®Google Scholar
• De Leo V, Milano F, Agostiano A, et al. Recent advancements in polymer/liposome assembly for drug delivery: from surface modifications to hybrid vesicles. Polymers (Basel). 2021;13(7):1027. 26, doi: 10.3390/polym13071027.
   PubMed Web of Science ®Google Scholar
• Chatterjee S, Ooya T. Copolymers composed of 2‑(methacryloyloxy)ethyl phosphorylcholine and methacrylated polyhedral oligomeric silsesquioxane as a simple modifier for liposomes. ACS Appl Polym Mater. 2020;2(5):1909–1916. doi: 10.1021/acsapm.0c00129.
   Web of Science ®Google Scholar
• Chountoulesi M, Selianitis D, Pispas S, et al. Recent advances on PEO-PCL block and graft copolymers as nanocarriers for drug delivery applications. Materials (Basel). 2023;16(6):1–22. 162298, doi: 10.3390/ma16062298.
   Web of Science ®Google Scholar
• Dash TK, Konkimalla VBJ. Poly-є-caprolactone based formulations for drug delivery and tissue engineering: a review. J. Control. Release. 2012;158:15–33.
   PubMed Web of Science ®Google Scholar
• Figarol A, Gibot L, Golzio M, et al. A journey from the endothelium to the tumor tissue: Distinct behavior between PEO-PCL micelles and polymersomes nanocarriers. Drug Deliv. 2018;25:1766–1778.
   PubMed Web of Science ®Google Scholar
• Ibrahim M, Abuwatfa WH, Awad NS, et al. Encapsulation, release, and cytotoxicity of doxorubicin loaded in liposomes, micelles, and Metal-Organic frameworks: a review. Pharmaceutics. 2022;14(2):254. doi: 10.3390/pharmaceutics14020254.
   PubMed Web of Science ®Google Scholar
• Kulkarni B, Qutub S, Ladelta V, et al. AIE-Based fluorescent triblock copolymer micelles for simultaneous drug delivery and intracellular imaging. Biomacromolecules. 2021;22(12):5243–5255. doi: 10.1021/acs.biomac.1c01165.
   PubMed Web of Science ®Google Scholar
• Luo D, Carter KA, Razi A, et al. Doxorubicin encapsulated in stealth liposomes conferred with light-triggered drug release. Biomaterials. 2016;75:193–202. doi: 10.1016/j.biomaterials.2015.10.027.
   PubMed Web of Science ®Google Scholar
• Pippa N, Pispas S, Demetzos D. Polymer self-assembled nanostructures as innovative drug nanocarrier platforms. Curr Pharm Des. 2016;22:2788–2795.
   PubMed Web of Science ®Google Scholar
• Kieler-Ferguson HM, Chan D, Sockolosky J, et al. Encapsulation, controlled release, and antitumor efficacy of cisplatin delivered in liposomes composed of sterol-modified phospholipids. Eur J Pharm Sci. 2017;103:85–93. doi: 10.1016/j.ejps.2017.03.003.
   PubMed Web of Science ®Google Scholar
• Kuznetsova D, Gabdrakhmanov D, Gaynanova G, et al. Novel biocompatible liposomal formulations for encapsulation of hydrophilic drugs – chloramphenicol and cisplatin. Colloids Surf, A. 2021;610:125673. doi: 10.1016/j.colsurfa.2020.125673.
   Google Scholar
• Somekawa S, Masutani K, Hsu YI, et al. Size-Controlled nanomicelles of poly(lactic acid)–poly(ethylene glycol) copolymers with a multiblock configuration. Polymers. 2015;7(6):1177–1191. doi: 10.3390/polym7061177.
   Web of Science ®Google Scholar
• Quaglia F, Ostacolo L, Nese G, et al. Micelles based on amphiphilic PCL-PEO triblock and star-shaped diblock copolymers: Potential in drug delivery applications. J Biomed Mater Res. 2008;87A(3):563–574. doi: 10.1002/jbm.a.31804.
   Web of Science ®Google Scholar
• Lombardo D, Kiselev MA. Methods of liposomes preparation: Formation and control factors of versatile nanocarriers for biomedical and nanomedicine application. Pharmaceutics. 2022;14(3):543. doi: 10.3390/pharmaceutics14030543.
   PubMed Web of Science ®Google Scholar
• Wu G, Khant HA, Chiu W, et al. Effects of bilayer phases on phospholipid-poloxamer interactions. Soft Matter. 2009;5(7):1496–1503. doi: 10.1039/b813354a.
   Web of Science ®Google Scholar
• Dutta S, Watson BG, Mattoo S, et al. Calcein release assay to measure membrane permeabilization by recombinant Alpha-Synuclein. Bio Protoc. 2020;10(14):e3690. doi: 10.21769/bioprotoc.3690.
   PubMed Web of Science ®Google Scholar
• Hausig-Punke F, Richter F, Hoernke M, et al. Tracking the endosomal escape: a closer look at calcein and related reporters. Macromol. Biosci. 2022;22(10):1–26. doi: 10.1002/mabi.202270027.
   Web of Science ®Google Scholar
• Maherani B, Arab-Tehrany E, Kheirolomoom A, et al. Calcein release behaviour from liposomal bilayer; influence of physicochemical mechanical structural properties of lipids. Biochimie. 2013;95(11):2018–2033. doi: 10.1016/j.biochi.2013.07.006.
   PubMed Web of Science ®Google Scholar
• Hansen A, Mouritsen O, Arouri A. Enzymatic action of phospholipase A2 on liposomal drug delivery systems. Int J Pharm. 2015;491(1-2):49–57. doi: 10.1016/j.ijpharm.2015.06.005.
   PubMedGoogle Scholar
• Langton M, Scriven L, Williams N, et al. Triggered release from lipid bilayer vesicles by an artificial transmembrane signal transduction system. J Am Chem Soc. 2017;139(44):15768–15773. doi: 10.1021/jacs.7b07747.
   PubMed Web of Science ®Google Scholar
• Palominos M, Vilches D, Bossel E, et al. Interaction between amphipathic triblock copolymers and L-α-dipalmitoyl phosphatidylcholine large unilamellar vesicles. Colloids Surf. B: Biointerfaces. 2016;148:30–40.
   PubMed Web of Science ®Google Scholar
• Flandez K, Bonardd S, Soto-Arriaza MA. Physicochemical properties of L-alpha dipalmitoyl phosphatidylcholine large unilamellar vesicles: Effect of hydrophobic block (PLA/PCL) of amphipathic diblock copolymers. Chem Phys Lipids. 2020;230:104927. doi: 10.1016/j.chemphyslip.2020.104927.
   PubMed Web of Science ®Google Scholar
• Kaddah S, Khreich N, Kaddah F, et al. Cholesterol modulates the liposome membrane fluidity and permeability for a hydrophilic molecule. Food Chem Toxicol. 2018;113:40–48. doi: 10.1016/j.fct.2018.01.017.
   PubMed Web of Science ®Google Scholar
• Liu W, Wei F, Ye A, et al. Kinetic stability and membrane structure of liposomes during in vitro infant intestinal digestion: Effect of cholesterol and lactoferrin. Food Chem. 2017;230:6–13. doi: 10.1016/j.foodchem.2017.03.021.
   PubMed Web of Science ®Google Scholar
• Briuglia ML, Rotella C, McFarlane A, et al. Influence of cholesterol on liposome stability and on in vitro drug release. Drug Deliv. Transl. Res. 2015;5(3):231–242.
   PubMed Web of Science ®Google Scholar
• Khan SA, Ilies MA. The phospholipase A2 superfamily: Structure, isozymes, catalysis, physiologic and pathologic roles. Int J Mol Sci. 2023;10(2):1–35.
   Google Scholar
• Avoranta T, Sundström J, Korkeila E, et al. The expression and distribution of group IIA phospholipase A2 in human colorectal tumours. Virchows Arch. 2010;457(6):659–667. doi: 10.1007/s00428-010-0992-7.
   PubMed Web of Science ®Google Scholar
• Brglez V, Lambeau G, Petan T. Secreted phospholipases A2 in cancer: diverse mechanisms of action. Biochimie. 2014a;107 Pt A:114–123. doi: 10.1016/j.biochi.2014.09.023.
   PubMed Web of Science ®Google Scholar
• Brglez V, Pucer A, Pungerčar J, et al. Secreted phospholipases A2 are differentially expressed and epigenetically silenced in human breast cancer cells. Biochem Biophys Res Commun. 2014b;445(1):230–235., doi: 10.1016/j.bbrc.2014.01.182.
   PubMed Web of Science ®Google Scholar
• Qu J, Zhao X, Wan G J, et al. Plasma phospholipase A2 activity may serve as a novel diagnostic biomarker for the diagnosis of breast cancer. Oncol Lett. 2018;15(4):5236–5242. doi: 10.3892/ol.2018.7915.
   PubMed Web of Science ®Google Scholar
• Yu JA, Li H, Meng X, et al. Group IIa secretory phospholipase expression correlates with group IIa secretory phospholipase inhibition–mediated cell death in K-Ras mutant lung cancer cells. J. Thorac Cardiovasc Surg. 2012;144(6):1479–1485.
   PubMed Web of Science ®Google Scholar
• Quach N, Arnold R, Cummings B. Secretory phospholipase A2 enzymes as pharmacological targets for treatment of disease. Biochem Pharmacol. 2014;90(4):338–348. doi: 10.1016/j.bcp.2014.05.022.
   PubMed Web of Science ®Google Scholar
• Alekseeva AS, Volynsky PE, Boldyrev IA. Estimation of the phospholipase A2 selectivity on POPC/POPG membranes using the interaction map. Biochem Moscow Suppl Ser A. 2021;15(4):329–333. doi: 10.1134/S1990747821050032.
   Web of Science ®Google Scholar
• Andresen TL, Jørgensen K. Synthesis and membrane behavior of a new class of unnatural phospholipid analogs useful as phospholipase A2 degradable liposomal drug carriers. Biochim Biophys Acta. 2005;1669(1):1–7.
   PubMed Web of Science ®Google Scholar
• Bohr SS, Thorlaksen C, Kühnel RM, et al. Label-Free fluorescence quantification of hydrolytic enzyme activity on native substrates reveals how lipase function depends on membrane curvature. Langmuir. 2020;36(23):6473–6481. doi: 10.1021/acs.langmuir.0c00787.
   PubMed Web of Science ®Google Scholar
• Fouladi F, Steffen KJ, Mallik S. Enzyme-responsive liposomes for the delivery of anticancer drugs. Bioconjug Chem. 2017;28(4):857–868. doi: 10.1021/acs.bioconjchem.6b00736.
   PubMed Web of Science ®Google Scholar
• Hong CY, Han CT, Chao L. Nonspecific binding domains in lipid membranes induced by phospholipase A2. Langmuir. 2016;32(27):6991–6999. doi: 10.1021/acs.langmuir.5b03915.
   PubMed Web of Science ®Google Scholar
• Kambayashi Y, Yamamoto Y, Nakano M. Preferential hydrolysis of oxidized phosphatidylcholine in cholesterol-Containing phosphatidylcholine liposome by phospholipase A2. Biochem Biophys Res Commun. 1998;245(3):705–708. doi: 10.1006/bbrc.1998.8421.
   PubMed Web of Science ®Google Scholar
• Mouchlis VD, Chen Y, McCammon AJ, et al. Membrane allostery and unique hydrophobic sites promote enzyme substrate specificity. J Am Chem Soc. 2018;140(9):3285–3291. doi: 10.1021/jacs.7b12045.
   PubMed Web of Science ®Google Scholar
• Nag OK, Awasthi V. Surface engineering of liposomes for stealth behavior. Pharmaceutics. 2013;5(4):542–569. 25, doi: 10.3390/pharmaceutics5040542.
   PubMedGoogle Scholar
• Temprana CF, Prieto MJ, Igartúa DE, et al. Diacetylenic lipids in the design of stable lipopolymers able to complex and protect plasmid DNA. Plos One. 2017;12(10):e0186194. doi: 10.1371/journal.pone.0186194.
   PubMed Web of Science ®Google Scholar
• Zhu G, Mock JN, Aljuffali I, et al. Secretory phospholipase A2 responsive liposomes. J Pharm Sci. 2011;100(8):3146–3159. doi: 10.1002/jps.22530.
   PubMed Web of Science ®Google Scholar
• Mumtaz Virk M, Reimhult E. Phospholipase A2-Induced degradation and release from lipid-Containing polymersomes. Langmuir. 2018;34(1):395–405. doi: 10.1021/acs.langmuir.7b03893.
   PubMed Web of Science ®Google Scholar
• Large DE, Abdelmessih RG, Fink EA, et al. Liposome composition in drug delivery design, synthesis, characterization, and clinical application. Adv Drug Deliv Rev. 2021;176:1–14.
   Web of Science ®Google Scholar
• Zhang H. 2017. Thin-Film hydration followed by extrusion method for liposome preparation. In: D’Souza G, editor. Liposomes. Methods in molecular biology. Vol. 1522. New York (NY): Humana Press. p. 17–22.
   Google Scholar
• Costa AP, Xu X, Burgess DJ. Freeze-anneal-thaw cycling of unilamellar liposomes: effect on encapsulation efficiency. Pharm Res. 2014;31(1):97–103. doi: 10.1007/s11095-013-1135-z.
   PubMed Web of Science ®Google Scholar
• Stewart J. Colorimetric determination of phospholipids with ammoniumferrothiocyanate. Anal Biochem. 1980;104(1):10–14. doi: 10.1016/0003-2697(80)90269-9.
   PubMed Web of Science ®Google Scholar
• Hein R, Uzundal C, Hennig A. Simple and rapid quantification of phospholipidsfor supramolecular membrane transport assays. Organ Biomol Chem. 2016;14:2182–2185.
   PubMed Web of Science ®Google Scholar
• Tagami T, Ando Y, Ozeki T. Fabrication of liposomal doxorubicin exhibiting ultrasensitivity against phospholipase A2 for efficient pulmonary drug delivery to lung cancers. Int J Pharm. 2017;517(1-2):35–41. doi: 10.1016/j.ijpharm.2016.11.039.
   PubMedGoogle Scholar
• Aydinoglu F, Ogulener N. The role of arachidonic acid/cyclooxygenase Cascade, phosphodiesterase IV, and rho-kinase in H2S-induced relaxation in the mouse corpus cavernosum. Pharmacol Rep. 2017;69(4):610–615.
   PubMed Web of Science ®Google Scholar
• Sampat GH, Hiremath K, Dodakallanavar J, et al. Unravelling snake venom phospholipase A2: an overview of its structure, pharmacology, and inhibitors. Pharmacol Rep. 2023;75(6):1454–1473. doi: 10.1007/s43440-023-00543-8.
   PubMed Web of Science ®Google Scholar
• Matile S, Sakai N. 2012. Analytical methods in supramolecular chemistry. Schalley CA, editor. Wiley: Weinheim, p. 711–742.
   Google Scholar
• Riss TL, Moravec RA, AL, et al. 2004. Cell viability assays. In: Markossian S, Grossman A, Brimacombe K, editors. Assay Guidance Manual. Bethesda (MD): Eli Lilly & Company and the National Center for Advancing Translational Sciences.
   Google Scholar
• Bodratti AM, Alexandridis P. Formulation of poloxamers for drug delivery. J Funct Biomater. 2018;18(11):1–24. 9(1),
   Google Scholar
• Feng H, Lu X, Wang W, et al. Block copolymers: Synthesis, self-assembly, and applications. Polymers (Basel). 2017;9(10):494. doi: 10.3390/polym9100494.
   PubMed Web of Science ®Google Scholar
• Kuperkar K, Patel D, Atanase LI, et al. Amphiphilic block copolymers: Their structures, and self-Assembly to polymeric micelles and polymersomes as drug delivery vehicles. Polymers. 2022;14(21):4702. doi: 10.3390/polym14214702.
   PubMed Web of Science ®Google Scholar
• Zhou Q, Zhang Z, Chen T, et al. Preparation and characterization of thermosensitive pluronic F127-b-poly(ε-caprolactone) mixed micelles. Colloids and Surface B: Biointerfaces. 2011;86(1):45–57.
   PubMed Web of Science ®Google Scholar
• Ahmed S, Corvis Y, Gahoual R, et al. Conception of nanosized hybrid liposome/poloxamer particles to thicken the interior core of liposomes and delay hydrophilic drug delivery. Int J Pharm. 2019b;567:118488. doi: 10.1016/j.ijpharm.2019.118488.
   PubMed Web of Science ®Google Scholar
• Cheng C, Wang J, Kausik R, et al. Nature of interactions between PEO-PPO-PEO triblock copolymers and lipid membranes: (II) role of hydration dynamics revealed by dynamic nuclear polarization. Biomacromolecules. 2012;13(9):2624–2633. doi: 10.1021/bm300848c.
   PubMed Web of Science ®Google Scholar
• Kim M, Heinrich F, Haugstad G, et al. Spatial distribution of PEO − PPO − PEO block copolymer and PEO homopolymer in lipid bilayers. Langmuir. 2020;36(13):3393–3403. doi: 10.1021/acs.langmuir.9b03208.
   PubMed Web of Science ®Google Scholar
• Wang JY, Chin J, Marks JD, et al. Effects of PEO-PPO-PEO triblock copolymers on phospholipid membrane integrity under osmotic stress. Langmuir. 2010;26(15):12953–12961. doi: 10.1021/la101841a.
   PubMed Web of Science ®Google Scholar
• Wang J, Marks J, Lee K. Nature of interactions between PEO-PPO-PEO triblock copolymers and lipid membranes: (I) Effect of polymer hydrophobicity on its ability to protect liposomes from peroxidation. Biomacromolecules. 2012;13(9):2616–2623. doi: 10.1021/bm300847x.
   PubMed Web of Science ®Google Scholar
• Lu T, Wang Z, Ma Y, et al. Influence of polymer size, liposomal composition, surface charge, and temperature on the permeability of pH-sensitive liposomes containing lipid-anchored poly(2-ethylacrylic acid). Int J Nanomedicine. 2012;7:4917–4926.
   PubMed Web of Science ®Google Scholar
• Lopes de Azambuja CR, Gomes dos Santos L, Rodrigues M, et al. Physic-chemical characterization of asolectin–genistein liposomal system: an approach to analyze it’s in vitro antioxidant potential and effect in glioma cells viability. Chem Phys Lipids. 2015;193:24–35. doi: 10.1016/j.chemphyslip.2015.10.001.
   PubMed Web of Science ®Google Scholar
• Németh Z, Csóka I, Semnani Jazani R, et al. Quality by Design-Driven zeta potential optimisation study of liposomes with charge imparting membrane additives. Pharmaceutics. 2022;14(9):1–25. 141798, doi: 10.3390/pharmaceutics14091798.
   Web of Science ®Google Scholar
• Aleandri S, Bombelli C, Bonicelli M, et al. Fusion of gemini based cationic liposomes with cell membrane models: implications for their biological activity. Biochim Biophys Acta. 2013;1828(2):382–390. doi: 10.1016/j.bbamem.2012.10.001.
   PubMed Web of Science ®Google Scholar
• Georgieva R, Mircheva K, Vitkova V, et al. Phospholipase A2‑induced remodeling processes on LiquidOrdered/liquid-Disordered membranes containing docosahexaenoic or oleic acid: a comparison study. Langmuir. 2016;32(7):1756–1770. doi: 10.1021/acs.langmuir.5b03317.
   PubMed Web of Science ®Google Scholar
• Gudmand M, Rocha S, Hatzakis N, et al. Influence of lipid heterogeneity and phase behavior on phospholipase A2 action at the single molecule level. Biophys J. 2010;98(9):1873–1882. doi: 10.1016/j.bpj.2010.01.035.
   PubMed Web of Science ®Google Scholar
• Mohtar LG, Ledesma AE, Disalvo EA, et al. Influence of carbonyl groups on the interaction of PLA2 with lipid interphases. Colloid Interface Sci Commun. 2020;39:100309, 1–8. doi: 10.1016/j.colcom.2020.100309.
   Web of Science ®Google Scholar
• Sanchez SA, Bagatolli LA, Gratton E, et al. A Two-Photon view of an enzyme at work: Crotalus atrox venom PLA2 interaction with Single-Lipid and mixed-lipid giant unilamellar vesicles. Biophys J. 2002;82(4):2232–2243., doi: 10.1016/S0006-3495(02)75569-0.
   PubMed Web of Science ®Google Scholar
• Zhang P, Villanueva V, Kalkowski J, et al. Polyunsaturated phospholipid modified membrane degradation catalyzed by a secreted phospholipase A2. Langmuir. 2019;35(36):11643–11650. doi: 10.1021/acs.langmuir.9b01476.
   PubMed Web of Science ®Google Scholar
• Heiner AL, Gibbons E, Fairbourn JL, et al. Effects of cholesterol on physical properties of human erythrocyte membranes: impact on susceptibility to hydrolysis by secretory phospholipase A2. Biophys J. 2008;15(8):3084–3093.
   Google Scholar
• McConnell H, Radhakrishna A. Condensed complexes of cholesterol and phospholipids. Biochim. Biophys Acta Biomembrane. 2003;1610(2):159–173.
   Web of Science ®Google Scholar
• Mills T, Toombes G, Tristram-Nagle S, et al. Order parameters and areas in fluid-phase oriented lipid membranes using wide angle x-ray scattering. Biophys J. 2008;95(2):669–681. doi: 10.1529/biophysj.107.127845.
   PubMed Web of Science ®Google Scholar
• Saito H, Shinoda W. Cholesterol effect on water permeability through DPPC and PSM lipid bilayers: a molecular dynamics study. J Phys Chem B. 2011;115(51):15241–15250. doi: 10.1021/jp201611p.
   PubMed Web of Science ®Google Scholar
• Cournia Z, Ullmann G, Smith J. Differential effects of cholesterol, ergosterol and lanosterol on a dipalmitoyl phosphatidylcholine membrane? A molecular dynamics simulation study. J Phys Chem B. 2007;111(7):1786–1801. doi: 10.1021/jp065172i.
   PubMed Web of Science ®Google Scholar
• Decker C, Fahr A, Kuntsche J, et al. Selective partitioning of cholesterol and a model drug into liposomes of varying size. Chem Phys Lipids. 2012;165(5):520–529. doi: 10.1016/j.chemphyslip.2012.04.001.
   PubMed Web of Science ®Google Scholar
• Hung WC, Lee MT, Chen FY, et al. The condensing effect of cholesterol in lipid bilayers. Biophys J. 2007;1(92 (11):3960–3967.
   Google Scholar
• Arriaga LR, López-Montero I, Monroy F, et al. Stiffening effect of cholesterol on disordered lipid phases: a combined neutron spin echo + dynamic light scattering analysis of the bending elasticity of large unilamellar vesicles. Biophys J. 2009;96(9):3629–3637. doi: 10.1016/j.bpj.2009.01.045.
   PubMed Web of Science ®Google Scholar
• Favarin B, Andrade M, Bolean M, et al. Effect of the presence of cholesterol in the interfacial microenvironment on the modulation of the alkaline phosphatase activity during in vitro mineralization. Colloids Surf, B. 2017;155:466–476. doi: 10.1016/j.colsurfb.2017.04.051.
   PubMed Web of Science ®Google Scholar
• Burke J, Dennis E. Phospholipase A2 structure/function, mechanism, and signalling. J. Lipid Res. 2009;50(Suppl):S237–S242.
   PubMed Web of Science ®Google Scholar
• Murakami M, Sato H, Taketomi Y. Updating phospholipase A2 biology. Biomolecules. 2020;10(10):1457. doi: 10.3390/biom10101457.
   PubMed Web of Science ®Google Scholar
• Salas D, Flores E, Meléndez J, et al. Increased delivery and cytotoxicity of doxorubicin in HeLa cells using the synthetic cationic peptide pEM-2 functionalized liposomes. Colloids Surf B Biointerfaces. 2023;228:113420, 1–9. doi: 10.1016/j.colsurfb.2023.113420.
   Web of Science ®Google Scholar