Fliposomes: Stimuli-triggered conformational flip of novel amphiphiles causes an instant cargo release from liposomes

Biomolecular Concepts

Volumn 5, Issue 2, 2014, Pages 131-141

  Samoshin, Vyacheslav V ^a  

^a UNIVERSITY OF THE PACIFIC   (United States)

Author keywords

acid triggered leakage; conformational switch; controlled drug release; peacock effect; pH sensitive liposomes

Indexed keywords

LIPID BILAYER; LIPOSOME; SURFACTANT;

CHEMISTRY; CONFORMATION; DRUG DELIVERY SYSTEM; HUMAN; LIPID BILAYER; METABOLISM;

DRUG DELIVERY SYSTEMS; HUMANS; LIPID BILAYERS; LIPOSOMES; MOLECULAR CONFORMATION; SURFACE-ACTIVE AGENTS;

EID: 84900457436     PISSN: 18685021     EISSN: 1868503X     Source Type: Journal    
DOI: 10.1515/bmc-2014-0002     Document Type: Review

References (60)

1. Puri A. Phototriggerable liposomes: current research and future perspectives. Pharmaceutics 2014; 6: 1-25.
2. Perche F, Torchilin VP. Recent trends in multifunctional liposomal nanocarriers for enhanced tumor targeting. J Drug Deliv 2013; 2013: 705265, 32 pp.
3. Ganta S, Devalapally H, Shahiwala A, Amiji M. A review of stimuli-responsive nanocarriers for drug and gene delivery. J Control Release 2008; 126: 187-204.
4. Bibi S, Lattmann E, Mohammed AR, Perrie Y. Trigger release liposome systems: local and remote controlled delivery? J Microencapsulation 2012; 29: 262-76.
5. Morilla MJ, Romero EL. Liposomal pH-sensitive nanomedicines in preclinical development. In: Reisner DE, editor. Bionanotechnology II. Boca Raton: CRC Press, 2012: 383-413.
6. Lehner R, Wang X, Marsch S, Hunziker P. Intelligent nanomaterials for medicine: carrier platforms and targeting strategies in the context of clinical application. Nanomedicine 2013; 9: 742-57.
7. Lehner R, Wang X, Wolf M, Hunziker P. Designing switchable nanosystems for medical application. J Control Release 2012; 161: 307-16.
8. Oude Blenke E, Mastrobattista E, Schiffelers RM. Strategies for triggered drug release from tumor targeted liposomes. Expert Opin Drug Deliv 2013; 10: 1399-410.
9. Huang Z, Szoka FC Jr. Bioresponsive liposomes and their use for macromolecular delivery. In: Gregoriadis G, editor. Liposome technology, 3rd ed., vol. 1. New York: Informa Healthcare, 2007: 165-96.
10. Hatakeyama H, Akita H, Harashima H. The polyethyleneglycol dilemma: advantage and disadvantage of PEGylation of liposomes for systemic genes and nucleic acids delivery to tumors. Biol Pharm Bull 2013; 36: 892-9.
11. Yue X, Dai Z. Recent advances in liposomal nanohybrid cerasomes as promising drug nanocarriers. Adv Colloid Interface Sci 2014. Epub ahead of print; doi: 10.1016/j.cis.2013.11.014.
12. Ta T, Porter TM. Thermosensitive liposomes for localized delivery and triggered release of chemotherapy. J Control Release 2013; 169: 112-25.
13. Kristl J. Implication of nanotechnology on development of medicines. Farmacevtski Vestnik 2012; 63: 67-73.
14. Patel S, Bhirde AA, Rusling JF, Chen X, Gutkind JS, Patel V. Nano delivers big: designing molecular missiles for cancer therapeutics. Pharmaceutics 2011; 3: 34-52.
15. Alaouie AM, Sofou S. Liposomes with triggered content release for cancer therapy. J Biomed Nanotechnol 2008; 4: 234-44.
16. Guo X, Szoka FC Jr. Chemical approaches to triggerable lipid vesicles for drug and gene delivery. Acc Chem Res 2003; 36: 335-41.
17. Hamano N, Negishi Y, Omata D, Takahashi Y, Manandhar M, Suzuki R, Maruyama K, Nomizu M, Aramaki Y. Bubble liposomes and ultrasound enhance the antitumor effects of AG73 liposomes encapsulating antitumor agents. Mol Pharmaceutics 2013; 10: 774-9.
18. Yi J, Barrow AJ, Yu N, O'Neill BE. Efficient electroporation of liposomes doped with pore stabilizing nisin. J Liposome Res 2013; 23: 197-202.
19. Kaiden T, Yuba E, Harada A, Sakanishi Y, Kono K. Dual signalresponsive liposomes for temperature-controlled cytoplasmic delivery. Bioconjugate Chem 2011; 22: 1909-15.
20. Yuba E, Kono Y, Harada A, Yokoyama S, Arai M, Kubo K, Kono K. The application of pH-sensitive polymer-lipids to antigen delivery for cancer immunotherapy. Biomaterials 2013; 34: 5711-21.
21. Li W, Nicol F, Szoka FC. GALA: a designed synthetic pH-responsive amphipathic peptide with applications in drug and gene delivery. Adv Drug Delivery Rev 2004; 56: 967-85.
22. Lee HM, Chmielewski J. Liposomal cargo unloading induced by pH-sensitive peptides. J Pept Res 2005; 65: 355-63.
23. Zhou W, An X, Wang J, Shen W, Chen Z, Wang X. Characteristics, phase behavior and control release for copolymer-liposome with both pH and temperature sensitivities. Colloids Surf A 2012; 395: 225-32.
24. Cho EC, Lim HJ, Kim HJ, Son ED, Choi HJ, Park JH, Kim J-W, Kim J. Role of pH-sensitive polymer-liposome complex in enhancing cellular uptake of biologically active drugs. Mater Sci Eng C 2009; 29: 774-8.
25. Schneider H-J, editor. Applications of supramolecular chemistry. Boca Raton: CRC Press, 2012.
26. Shahinpoor M, Schneider H-J, editors. Intelligent materials. Cambridge, UK: RSC Publishing, 2008.
27. Kay ER, Leigh DA, Zerbetto F. Synthetic molecular motors and mechanical machines. Angew Chem Int Ed 2007; 46: 72-191.
28. Feringa BL, editor. Molecular switches. Weinheim, Germany: Wiley-VCH, 2001.
29. Samoshin VV. Cyclohexane-based conformationally controlled crowns and podands. Mini-Rev Org Chem 2005; 2: 225-35.
30. Samoshin VV. Conformational control of cyclohexane derivatives by external stimuli. Rev J Chem 2011; 1: 250-74.
31. Costero AM, Parra M, Gil S, Andreu MR. Multichannel sensors based on biphenyl and cyclohexane conformational changes. Springer Ser Chem Sens Biosens 2013; 12: 1-32.
32. Mamasheva E, O'Donnell C, Bandekar A, Sofou S. Heterogeneous liposome membranes with pH-triggered permeability enhance the in vitro antitumor activity of folate-receptor targeted liposomal doxorubicin. Mol Pharmaceutics 2011; 8: 2224-32.
33. Bandekar A, Zhu C, Gomez A, Menzenski MZ, Sempkowski M, Sofou S. Masking and triggered unmasking of targeting ligands on liposomal chemotherapy selectively suppress tumor growth in vivo. Mol Pharmaceutics 2013; 10: 152-60.
34. Kim H-K, Van dBJ, Hyun S-H, Thompson DH. Acid-triggered release via dePEGylation of fusogenic liposomes mediated by heterobifunctional phenyl-substituted vinyl ethers with tunable pH-sensitivity. Bioconjugate Chem 2012; 23: 2071-7.
35. Wehunt MP, Winschel CA, Khan AK, Guo TL, Abdrakhmanova GR, Sidorov V. Controlled drug-release system based on pH-sensitive chloride-triggerable liposomes. J Liposome Res 2013; 23: 37-46.
36. Brazdova B, Zhang N, Samoshin VV, Guo X. trans-2-Aminocyclohexanol as a pH-sensitive conformational switch in lipid amphiphiles. Chem Commun 2008; 4774-6.
37. Samoshina NM, Liu X, Brazdova B, Franz AH, Samoshin VV, Guo X. Fliposomes: pH-sensitive liposomes containing a trans-2-morpholinocyclohexanol- based lipid that performs a conformational flip and triggers an instant cargo release in acidic medium. Pharmaceutics 2011; 3: 379-405.
38. Zheng Y, Liu X, Samoshina NM, Chertkov VA, Franz AH, Guo X, Samoshin VV. Fliposomes: pH-controlled release from liposomes containing new trans-2-morpholinocyclohexanol-based amphiphiles that perform a conformational flip and trigger an instant cargo release upon acidification. Nat Prod Commun 2012; 7: 353-8.
39. Liu X, Zheng Y, Samoshina NM, Franz AH, Guo X, Samoshin VV. Fliposomes: pH-triggered conformational flip of new trans- 2-aminocyclohexanol-based amphiphiles causes instant cargo release in liposomes. J Liposome Res 2012; 22: 319-28.
40. Liu X. Fliposomes: pH-sensitive liposomes comprising novel trans-2-aminocyclohexanol-based amphiphiles as conformational switches for the liposome membrane. PhD Dissertation, University of the Pacific, Stockton, CA, 2013.
41. Zheng Y. Synthesis and conformational study of trans-2-aminocyclohexanol- based pH-triggered molecular switches and their application in gene delivery. PhD Dissertation, University of the Pacific, Stockton, CA, 2013.
42. Samoshin AV, Veselov IS, Chertkov VA, Yaroslavov AA, Grishina GV, Samoshina NM, Samoshin VV. Fliposomes: new amphiphiles based on trans-3,4-bis(acyloxy)-piperidine able to perform a pH-triggered conformational flip and cause an instant cargo release from liposomes. Tetrahedron Lett 2013; 54: 5600-4.
43. Contreras FX, Sanchez-Magraner L, Alonso A, Goni FM. Transbilayer (flip-flop) lipid motion and lipid scrambling in membranes. FEBS Lett 2010; 584: 1779-86.
44. Demina T, Grozdova I, Krylova O, Zhirnov A, Istratov V, Frey H, Kautz H, Melik-Nubarov N. Relationship between the structure of amphiphilic copolymers and their ability to disturb lipid bilayers. Biochemistry 2005; 44: 4042-54.
45. Schreier S, Malheiros SVP, de Paula E. Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochim Biophys Acta Biomembr 2000; 1508: 210-34.
46. Yaroslavov AA, Melik-Nubarov NS, Menger FM. Polymer-induced flip-flop in biomembranes. Acc Chem Res 2006; 39: 702-10.
47. Samoshin VV, Chertkov VA, Gremyachinskiy DE, Dobretsova EK, Shestakova AK, Vatlina LP. trans-2-Aminocyclohexanols as pH-triggers for conformationally controlled crowns and podands. Tetrahedron Lett 2004; 45: 7823-6.
48. Samoshin VV, Brazdova B, Chertkov VA, Gremyachinskiy DE, Shestakova AK, Dobretsova EK, Vatlina LP, Yuan J, Schneider H-J. trans-2-Aminocyclohexanols as pH-triggered molecular switches. ARKIVOC 2005; 129-41.
49. Chourasia MK, Jain SK. Pharmaceutical approaches to colon targeted drug delivery systems. J Pharm Pharm Sci 2003; 6: 33-66.
50. Samoshin AV, Huynh L, Tran C, Samoshin VV. trans-3,4-Diacetoxypiperidine as a prototype of novel pH-triggered molecular switches. J Undergrad Chem Res 2011; 10: 50-5.
51. Samoshin AV, Veselov IS, Huynh L, Shestakova AK, Chertkov VA, Grishina GV, Samoshin VV. trans-3,4-Diacetoxypiperidine as a model for novel pH-triggered conformational switches. Tetrahedron Lett 2011; 52: 5375-8.
52. Jones CH, Chen C-K, Ravikrishnan A, Rane S, Pfeifer BA. Overcoming nonviral gene delivery barriers: perspective and future. Mol Pharmaceutics 2013; 10: 4082-98.
53. Liu X, Zheng Y, Samoshina NM, Franz AH, Samoshin VV, Guo X. Luciferase gene transfection mediated by cationic liposomes comprising novel trans-2-aminocyclohexanol-based amphiphiles. 243rd ACS National Meeting & Exposition. San Diego, CA: American Chemical Society, 2012, MEDI-414.
54. Veremeeva PN, Lapteva VL, Palyulin VA, Davydov DA, Yaroslavov AA, Zefirov NS. Novel amphiphilic compounds for the design of stimulus-sensitive liposomal containers. Dokl Chem 2012; 447: 275-7.
55. Veremeeva PN, Lapteva VL, Palyulin VA, Sybachin AV, Yaroslavov AA, Zefirov NS. Bispidinone-based molecular switches for construction of stimulus-sensitive liposomal containers. Tetrahedron 2014; 70: 1408-11.
56. Merino E, Ribagorda M. Control over molecular motion using the cis-trans photoisomerization of the azo group. Beilstein J Org Chem 2012; 8: 1071-90.
57. Liu X-M, Yang B, Wang Y-L, Wang J-Y. Photoisomerizable cholesterol derivatives as photo-trigger of liposomes: effect of lipid polarity, temperature, incorporation ratio, and cholesterol. Biochim Biophys Acta Biomembr 2005; 1720: 28-34.
58. Kauscher U, Samanta A, Ravoo BJ. Photoresponsive vesicle permeability based on intramolecular host-guest inclusion. Org Biomol Chem 2014; 12: 600-6.
59. Ruggiero E, Habtemariam A, Yate L, Mareque-Rivas JC, Salassa L. Near infrared photolysis of a Ru polypyridyl complex by upconverting nanoparticles. Chem Commun 2014; 50: 1715-8.
60. Askes SHC, Bahreman A, Bonnet S. Activation of a photodissociative ruthenium complex by triplet-triplet annihilation upconversion in liposomes. Angew Chem Int Ed 2014; 53: 1029-33.