Steric environment around acetylcholine head groups of bolaamphiphilic nanovesicles influences the release rate of encapsulated compounds

International Journal of Nanomedicine

Volumn 9, Issue 1, 2014, Pages 561-574

  Stern, Avital ^a   Guidotti, Matteo ^b   Shaubi, Eleonora ^a   Popov, Mary ^a   Linder, Charles ^a   Heldman, Eliahu ^a   Grinberg, Sarina ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b CNR   (Italy)

Author keywords

Acetylcholine; Acetylcholinesterase; Bolaamphiphiles; Controlled release; Drug delivery; Vesicles

Indexed keywords

9,10 EPOXYMETHYLSTEARATE; ACETYLCHOLINE; ACETYLCHOLINESTERASE; ALKYL GROUP; AMPHOPHILE; BOLAAMPHIPHILE; DECANE DIEPOXY DISTEARATE; DICHLOROACETIC ACID; DRUG CARRIER; METHYL GROUP; OLEIC ACID; UNCLASSIFIED DRUG; VERNOLIC ACID; 6-CARBOXYFLUORESCEIN; FLUORESCEIN DERIVATIVE; FLUORESCENT DYE; FURAN DERIVATIVE; NANOCAPSULE; PYRIDONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED DRUG RELEASE; DRUG DELIVERY SYSTEM; HYDROLYSIS; HYDROPHOBICITY; MICROENVIRONMENT; MOLECULAR STABILITY; NANOENCAPSULATION; SPECTROSCOPY; STERIC ENVIRONMENT; CHEMISTRY; HUMAN; NANOMEDICINE; ULTRASTRUCTURE;

ACETYLCHOLINE; ACETYLCHOLINESTERASE; DRUG DELIVERY SYSTEMS; FLUORESCEINS; FLUORESCENT DYES; FURANS; HUMANS; HYDROLYSIS; MOLECULAR STRUCTURE; NANOCAPSULES; NANOMEDICINE; PYRIDONES;

EID: 84892856652     PISSN: 11769114     EISSN: 11782013     Source Type: Journal    
DOI: 10.2147/IJN.S53563     Document Type: Article

References (44)

1. Pavlukhina S, Sukhishvili S. Polymer assemblies for controlled delivery of bioactive molecules from surfaces. Adv Drug Deliv Rev. 2011;63(9):822-836.
2. Sharma G, Anabousi S, Elrhardt C, Ravi Kumar MN. Liposomes as targeted drug delivery systems in the treatment of breast cancer. J Drug Target. 2006;14(5):301-310.
3. Immordino ML, Dosio F, Cattel L. Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential. Int J Nanomedicine. 2006;1(3):297-315.
4. Yuan F, Dellian M, Fukumura D, etal. Vascular permeability in a human tumor xenograft: molecular size dependence and cutoff size. Cancer Res. 1995;55(17):3752-3756.
5. Gabizon A, Papahadjopoulos D. Liposome formulations with prolonged circulation time in blood and enhanced uptake by tumors. Proc Natl Acad Sci U S A. 1988;85(18):6949-6953.
6. Gabizon AA. Pegylayed liposomal doxorubicin: metamorphosis of an old drug into a new form of chemotherapy. Cancer Invest. 2001;19:424-436.
7. Harrington KJ, Syrigos KN, Vile RG. Liposomally targeted cyto toxic drugs for the treatment of cancer. J Pharm Pharmacol. 2002;54(12):1573-1600.
8. Bikram M, West JL. Thermo-responsive systems for controlled drug delivery. Expert Opin Drug Deliv. 2008;5(10):1077-1091.
9. Kono K. Thermosensitive polymer-modified liposomes. Adv Drug Deliv Rev. 2001;53(3):307-319.
10. Grüll H, Langereis S. Hyperthermia-triggered drug delivery from temperature-sensitive liposomes using MRI-guided high intensity focused ultrasound. J Control Release. 2012;161(2):317-327.
11. Felber AE, Dufresne MH, Leroux JC. pH-sensitive vesicles, polymeric micelles, and nanospheres prepared with polycarboxylates. Adv Drug Deliv Rev. 2012;64(11):979-992.
12. Nappini S, Bonini M, Baldelli Bombelli F, etal. Controlled drug release under a low frequency magnetic field: effect of the citrate coating on magnetoliposomes stability. Soft Matter. 2011;7:1025-1037.
13. Yavlovich A, Smith B, Gupta K, Blumenthal R, Puri A. Light-sensitive lipid-based nanoparticles for drug delivery: design principles and future considerations for biological applications. Mol Membr Biol. 2010;27(7):364-381.
14. Menger FM, Johnston DE Jr. Specific enzyme-induced decapsulation. J Am Chem Soc. 1991;113(14):5467-5468.
15. Andresen TL, Thompson DH, Kaasgaard T. Enzyme-triggered nano medicine: drug release strategies in cancer therapy. Mol Membr Biol. 2010;27(7):353-363.
16. Grinberg S, Kolot V, Linder C, etal. Synthesis of novel cationic bolaam phiphiles from vernonia oil and their aggregated structures. Chem Phys Lipids. 2008;153(2):85-97.
17. Roussel M, Lognoné V, Plusquellec D, Benvegnu T. Mono layer lipid membrane-forming dissymmetrical bolaamphiphiles derived from alginate oligosaccharides. Chem Commun (Camb). 2006;(34):3622-3624.
18. Fuhrhop J-H, Wang T. Bolaamphiphiles. Chem Rev. 2004;104(6): 2901-2937.
19. Masuda M, Shimizu T. Lipid nanotubes and microtubes: experi mental evidence for unsymmetrical monolayer membrane formation from unsymmetrical bolaamphiphiles. Langmuir. 2004;20(14): 5969-5977.
20. Hutter T, Linder C, Heldman E, Grinberg S. Interfacial and self-assembly properties of bolaamphiphilic compounds derived from a multifunctional oil. J Colloid Interface Sci. 2012;365(1):53-62.
21. Chen ZX, Su XX, Deng SP. Molecular recognition of melamine by ves icles spontaneously formed from orotic acid derived bolaamphiphiles. J Phys Chem B. 2011;115(8):1798-1806.
22. Sun YL, Wang SS, Han X, Chen ZX. Realization of the revers ible vesicle-micelle transition of vitamin-derived bolaamphiphiles by heat change monitoring. J Phys Chem B. 2012;116(40): 12372-12380.
23. Philosof-Mazor L, Dakwar GR, Popov M, etal. Bolaamphiphilic vesicles encapsulating iron oxide nanoparticles: new vehicles for magnetically targeted drug delivery. Int J Pharm. 2013;450(1-2):241-249.
24. Popov M, Linder C, Deckelbaum RJ, etal. Cationic vesicles from novel bolaamphiphilic compounds. J Liposome Res. 2010;20(2):147-159.
25. Popov M, Grinberg S, Linder C, etal. Site-directed decapsulation of bolaamphiphilic vesicles with enzymatic cleavable surface groups. J Control Release. 2012;160(2):306-314.
26. Dakwar GR, Abu Hammad I, Popov M, etal. Delivery of proteins to the brain by bolaamphiphilic nano-sized vesicles. J Control Release. 2012;160(2):315-321.
27. Popov M, Abu Hammad I, Bachar T, etal. Delivery of analgesic peptides to the brain by nano-sized bolaamphiphilic vesicles made of monolayer membranes. Eur J Pharm Biopharm. 2013. pii: S0939-6411(13)00223-3.
28. Reiner E, Simeon V. Competition between substrates for acetylcho linesterase and cholinesterase. Biochim Biophys Acta. 1977;480(1): 137-142.
29. Komersová A, Komers K, Zdrazilová P. Kinetics of hydrolysis of acetylthiocholine and acetylcholine by cholinesterases. Chem Biol Interact. 2005;157-158:387-388.
30. Gunstone FD. Fatty acids. Part II. The nature of the oxygenated acid present in Vernonia anthelmintica (Willd.) seed oil. J Chem Soc. 1954:1611-1616.
31. Guidotti M, Ravasio N, Psaro R, Gianotti E, Marchese L, Coluccia S. Heterogeneous catalytic epoxidation of fatty acid methyl esters on titanium-grafted silicas. Green Chem. 2003;5:421-424.
32. Guidotti M, Psaro R, Ravasio N, Sgobba M, Gianotti E, Grinberg S. Titanium-silica catalysts for the production of fully epoxidized fatty acid methyl esters. Catal Lett. 2008;122:53-56.
33. Jay RR. Direct titration of epoxy compounds and aziridines. Anal Chem. 1964;36:667-668.
34. New RRC, editor. Liposomes: A Practical Approach, Oxford: Oxford University Press; 1990.
35. Torchilin V, Weissig V, editors. Liposomes. 2nd ed. Oxford: Oxford University Press; 2003.
36. Ellman GL, Courtney KD, Andres V Jr, Feather-Stone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961;7:88-95.
37. Carlson KD, Schneider WJ, Chang SP, Princen LH. Vernonia galamensis seed oil: a new source for epoxy coatings. In: Pryde EH, Princen LD, Mukherjee F, Mukherjee KD, editors. New Sources of Fats and Oils. Champaign, IL: American Oil Chemists' Society; 1981:297-318.
38. Halldorsson A, Magnusson CD, Haraldsson GG. Chemoenzymatic syn thesis of structured triacylglycerols by highly regioselective acylation. Tetrahedron. 2003;59(46):9101-9109.
39. Grinberg S, Kipnis N, Linder C, Kolot V, Heldman E. Asymmetric bolaamphiphiles from vernonia oil designed for drug delivery. Eur J Lipid Sci Technol. 2010;112(1):137-151.
40. Jung DI, Shin YJ, Lee ES, Moon TS, Yoon CN, Lee BH. Acetylcholinesterase(AChE)-catalyzed hydrolysis of long-chain hiocholine esters: shift to a new chemical mechanism. Bull Korean Chem Soc. 2003;24(1):65-69.
41. Vellom DC, Radić Z, Li Y, Pickering NA, Camp S, Taylor P. Amino acid residues controlling acetylcholinesterase and butyrylcholinesterase specificity. Biochemistry. 1993;32(1):12-17.
42. Radić Z, Pickering NA, Vellom DC, Camp S, Taylor P. Three distinct domains in the cholinesterase molecule confer selectivity for acetyl and butyrylcholinesterase inhibitors. Biochemistry. 1993;32(45): 12074-12084.
43. A, Barak D, Kronman C, etal. Dissection of the human acetylcholinesterase active center determinants of substrate specificity. Identification of residues constituting the anionic site, the hydrophobic site, and the acyl pocket. J Biol Chem. 1993;268(23): 17083-17095.
44. Armenta S, Blanco M. Ion mobility spectrometry: a valuable tool for kinetic studies in enzymology. Anal Chim Acta. 2011;685(1):1-8.