Simple physics in and easy manipulating of the interfacial behavior of charged molecules on drug delivery vesicles

Théry, 2009, Membrane vesicles as conveyors of immune responses, Nat. Rev. Immunol., 9, 581, 10.1038/nri2567 Doktorova, 2018, Preparation of asymmetric phospholipid vesicles for use as cell membrane models, Nat. Protoc., 13, 2086, 10.1038/s41596-018-0033-6 Walsby, 1994, Gas vesicles, Microbiol. Rev., 58, 94, 10.1128/MR.58.1.94-144.1994 Discher, 2002, Polymer vesicles, Science, 297, 967, 10.1126/science.1074972 Garrett, 2005 Yu, 2015, Ellipsoidal relaxation of deformed vesicles, Phys. Rev. Lett., 115, 128303, 10.1103/PhysRevLett.115.128303 Hindley, 2018, Light-triggered enzymatic reactions in nested vesicle reactors, Nat. Commun., 9, 1093, 10.1038/s41467-018-03491-7 Pierce, 1982, Invertebrate cell volume control mechanisms: a coordinated use of intracellular amino acids and inorganic ions as osmotic solute, Biol. Bull., 163, 405, 10.2307/1541452 van Meer, 2008, Membrane lipids: where they are and how they behave, Nat. Rev. Mol. Cell Biol., 9, 112, 10.1038/nrm2330 Holthuis, 2014, Lipid landscapes and pipelines in membrane homeostasis, Nature, 510, 48, 10.1038/nature13474 Melcrová, 2016, The complex nature of calcium cation interactions with phospholipid bilayers, Sci. Rep., 6, 38035, 10.1038/srep38035 Bilkova, 2017, Calcium directly regulates phosphatidylinositol 4,5-bisphosphate headgroup conformation and recognition, J. Am. Chem. Soc., 139, 4019, 10.1021/jacs.6b11760 Zucker, 2009, Liposome drugs' loading efficiency: a working model based on loading conditions and drug's physicochemical properties, J. Control. Release, 139, 73, 10.1016/j.jconrel.2009.05.036 Bourgaux, 2014, Interactions of anticancer drugs with biomembranes: what can we learn from model membranes?, J. Control. Release, 190, 127, 10.1016/j.jconrel.2014.05.012 Crissman, 1982, Rapid, one step staining procedures for analysis of cellular DNA and protein by single and dual laser flow cytometry, Cytometry, 3, 84, 10.1002/cyto.990030204 Wang, 2018, Rational design of a water-soluble NIR AIEgen, and its application in ultrafast wash-free cellular imaging and photodynamic cancer cell ablation, Chem. Sci., 9, 3685, 10.1039/C7SC04963C Shen, 1989, Surface-properties probed by 2nd-harmonic and sum-frequency generation, Nature, 337, 519, 10.1038/337519a0 Eisenthal, 1996, Liquid interfaces probed by second-harmonic and sum-frequency spectroscopy, Chem. Rev., 96, 1343, 10.1021/cr9502211 Wang, 2016, Sum frequency generation vibrational spectroscopy (SFG-VS) for complex molecular surfaces and interfaces: spectral lineshape measurement and analysis plus some controversial issues, Prog. Surf. Sci., 91, 155, 10.1016/j.progsurf.2016.10.001 Wen, 2016, Unveiling microscopic structures of charged water interfaces by surface-specific vibrational spectroscopy, Phys. Rev. Lett., 116, 10.1103/PhysRevLett.116.016101 Ohno, 2016, Phase-referenced nonlinear spectroscopy of the α-quartz/water interface, Nat. Commun., 7, 13587, 10.1038/ncomms13587 Liang, 2018, Lyophobicity may not be the main driving force for long chain surfactants from the bulk phase to the interface, Phys. Chem. Chem. Phys., 20, 10165, 10.1039/C7CP07322D Wang, 2000, In situ, nonlinear optical probe of surfactant adsorption on the surface of microparticles in colloids, Langmuir, 16, 2475, 10.1021/la9909087 Eckenrode, 2005, Adsorption of a cationic dye molecule on polystyrene microspheres in colloids: effect of surface charge and composition probed by second harmonic generation, J. Phys. Chem. B, 109, 4646, 10.1021/jp045610q Jen, 2006, Probing molecules adsorbed at the surface of nanometer colloidal particles by optical second-harmonic generation, J. Phys. Chem. B, 110, 23000, 10.1021/jp0644762 Gan, 2011, Activation of thiols at a silver nanoparticle surface, Angew. Chem. Int. Ed., 50, 6622, 10.1002/anie.201101430 You, 2012, Real-time kinetics of surfactant molecule transfer between emulsion particles probed by in situ second harmonic generation spectroscopy, J. Am. Chem. Soc., 134, 4264, 10.1021/ja2104608 Sang, 2015, Molecular interactions at the hexadecane/water interface in the presence of surfactants studied with second harmonic generation, J. Chem. Phys., 142, 224704, 10.1063/1.4922304 Gonella, 2016, Second harmonic and sum-frequency generation from aqueous interfaces is modulated by interference, J. Chem. Phys. C, 120, 9165, 10.1021/acs.jpcc.5b12453 Yang, 2017, The ionic strength dependent zeta potential at the surface of hexadecane droplets in water and the corresponding interfacial adsorption of surfactants, Soft Matter, 13, 638, 10.1039/C6SM02174C Kim, 2017, Two-step adsorption kinetics of malachite green on anionic polystyrene microspheres in aqueous solution probed by second harmonic generation, Phys. Chem. Chem. Phys., 19, 21887, 10.1039/C7CP03088F Srivastava, 1998, Kinetics of molecular transport across a liposome bilayer, Chem. Phys. Lett., 292, 345, 10.1016/S0009-2614(98)00662-9 Yamaguchi, 2006, Longitudinal diffusion behavior of hemicyanine dyes across phospholipid vesicle membranes as studied by second-harmonic generation and fluorescence spectroscopies, Anal. Bioanal. Chem., 386, 627, 10.1007/s00216-006-0470-x Kim, 2007, Temperature effect on the transport dynamics of a small molecule through a liposome bilayer, Eur. Phys. J. E, 23, 313, 10.1140/epje/i2006-10212-0 Kumal, 2017, Impacts of salt, buffer, and lipid nature on molecular adsorption and transport in liposomes as observed by second harmonic generation, J. Chem. Phys. C, 121, 15851, 10.1021/acs.jpcc.7b05058 Varshney, 2017, Effect of curcumin addition on the adsorption and transport of a cationic dye across DPPG-POPG liposomes probed by second harmonic spectroscopy, Langmuir, 33, 8302, 10.1021/acs.langmuir.7b01783 Zeng, 2013, Time-resolved molecular transport across living cell membranes, Biophys. J., 104, 139, 10.1016/j.bpj.2012.11.3814 Gh, 2018, Azithromycin-induced changes to bacterial membrane properties monitored in vitro by second-harmonic light scattering, ACS Med. Chem. Lett., 9, 569, 10.1021/acsmedchemlett.7b00499 Chen, 2018, Order-disorder transition of carboxyl terminated chains in polydiacetylenes vesicles probed by second harmonic generation and two-photon fluorescence, Chin. J. Chem. Phys., 31, 269, 10.1063/1674-0068/31/cjcp1712238 Kim, 2008, In-situ observation of the inside-to-outside molecular transport of a liposome, J. Phys. Chem. B, 112, 15673, 10.1021/jp8075657 Shang, 2001, Effects of counterions on molecular transport across liposome bilayer: probed by second harmonic generation, J. Phys. Chem. B, 105, 12816, 10.1021/jp0120918 Liu, 2001, Effects of bilayer surface charge density on molecular adsorption and transport across liposome bilayers, Biophys. J., 80, 1004, 10.1016/S0006-3495(01)76079-1 Varshney, 2013, Effect of curcumin on the diffusion kinetics of a hemicyanine dye, LDS-698, across a lipid bilayer probed by second harmonic spectroscopy, Langmuir, 29, 2912, 10.1021/la304778d Liu, 2008, Second harmonic studies of ions crossing liposome membranes in real time, J. Phys. Chem. B, 112, 15263, 10.1021/jp806690z Avdeef, 2012 Gennis, 2013 Mann, 2002, Natural products in cancer chemotherapy: past, present and future, Nat. Rev. Canc., 2, 143, 10.1038/nrc723 Zhang, 2012, Identification of the molecular basis of doxorubicin-induced cardiotoxicity, Nat. Med., 18, 1639, 10.1038/nm.2919 Potisatityuenyong, 2008, Electronic absorption spectroscopy probed side-chain movement in chromic transitions of polydiacetylene vesicles, Langmuir, 24, 4461, 10.1021/la800354q Brunori, 1985, Mechanism of control of cytochrome oxidase activity by the electrochemical-potential gradient, EMBO J., 4, 2365, 10.1002/j.1460-2075.1985.tb03940.x Liu, 2005, Antibiotic assisted molecular ion transport across a membrane in real time, Faraday Discuss, 129, 291, 10.1039/b405410e Smolentsev, 2016, Intermolecular headgroup interaction and hydration as driving forces for lipid transmembrane asymmetry, J. Am. Chem. Soc., 138, 4053, 10.1021/jacs.5b11776 Nghiem, 2006, Role of electrostatic interactions in the retention of pharmaceutically active contaminants by a loose nanofiltration membrane, J. Membr. Sci., 286, 52, 10.1016/j.memsci.2006.09.011 Wilhelm, 2015, Gram's stain does not cross the bacterial cytoplasmic membrane, ACS Chem. Biol., 10, 1711, 10.1021/acschembio.5b00042 Tarun, 2018, Label-free and charge-sensitive dynamic imaging of lipid membrane hydration on millisecond time scales, Proc. Natl. Acad. Sci. Unit. States Am., 115, 4081, 10.1073/pnas.1719347115 Nuriya, 2006, Imaging membrane potential in dendritic spines, Proc. Nat. Acad. Sci. USA, 103, 786, 10.1073/pnas.0510092103 Barenholz, 2012, Doxil® — the first FDA-approved nano-drug: lessons learned, J. Control. Release, 160, 117, 10.1016/j.jconrel.2012.03.020 Ahmed, 2018, Liposome: composition, characterisation, preparation, and recent innovation in clinical applications, J. Drug Target., 1