Interaction between a cationic bolaamphiphile and DNA: The route towards nanovectors for oligonucleotide antimicrobials

Colloids and Surfaces B: Biointerfaces

Volumn 143, Issue , 2016, Pages 139-147

  Mamusa, Marianna ^a   Resta, Claudio ^a   Barbero, Francesco ^b   Carta, Davide ^c,d   Codoni, Doroty ^c,e   Hatzixanthis, Kostas ^c,f   McArthur, Michael ^c,g   Berti, Debora ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b NANOVECTOR S R L   (Italy)

^c Procarta Biosystems Ltd   (United Kingdom)

^d JOHN INNES CENTRE   (United Kingdom)

^e Kuecept Ltd 16/17 Station Close ^*  (United Kingdom)

^f UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^g UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Bacterial resistance; Bolaamphiphile; Circular dichroism; DNA delivery; Light scattering; Transcription factor decoy

Indexed keywords

BACTERIA; CATIONIC SURFACTANTS; CELL MEMBRANES; CIRCULAR DICHROISM SPECTROSCOPY; CYTOLOGY; DICHROISM; DNA; DRUG THERAPY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; LIGHT SCATTERING; OLIGONUCLEOTIDES; SOLUTIONS; SURFACE ACTIVE AGENTS; TRANSCRIPTION; TRANSCRIPTION FACTORS;

ABSORPTION AND FLUORESCENCE SPECTROSCOPY; BACTERIAL RESISTANCE; BOLAAMPHIPHILES; DNA DELIVERY; ELONGATED STRUCTURES; PHYSICAL CHEMICAL PROPERTY; SURFACTANT ASSEMBLIES; TRANSFECTION ACTIVITY;

DYES;

ANTIINFECTIVE AGENT; DNA; DNA FRAGMENT; OLIGONUCLEOTIDE; TAUROCHOLIC ACID; TRANSCRIPTION FACTOR; BACTERIAL PROTEIN; BOLAAMPHIPHILE; FURAN DERIVATIVE; PROTEIN BINDING; PYRIDONE DERIVATIVE; SURFACTANT; TACRINE;

ANTIBIOTIC RESISTANCE; AQUEOUS SOLUTION; ARTICLE; BACTERIAL CELL WALL; BODY FLUID; CIRCULAR DICHROISM; CONTROLLED STUDY; CYTOPLASM; DEGRADATION; FLUORESCENCE SPECTROSCOPY; LIGHT SCATTERING; MASS SPECTROMETRY; MICROORGANISM; MORPHOLOGY; NONHUMAN; PRIORITY JOURNAL; SYNCHROTRON; X RAY CRYSTALLOGRAPHY; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; CONFORMATION; GENETIC TRANSFECTION;

ANTI-INFECTIVE AGENTS; BACTERIAL PROTEINS; BINDING SITES; DNA; FURANS; NUCLEIC ACID CONFORMATION; OLIGONUCLEOTIDES; PROTEIN BINDING; PYRIDONES; SURFACE-ACTIVE AGENTS; TACRINE; TAUROCHOLIC ACID; TRANSCRIPTION FACTORS; TRANSFECTION;

EID: 84961205438     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2016.03.031     Document Type: Article

References (42)

1. Silver L.L. Challenges of antibacterial discovery. Clin. Microbiol. Rev. 2011, 24:71-109. 10.1128/CMR.00030-10.
2. Payne D.J., Gwynn M.N., Holmes D.J., Pompliano D.L. Drugs for bad bugs: confronting the challenges of antibacterial discovery. Nat. Rev. Drug Discov. 2007, 6:29-40. 10.1038/nrd2201.
3. Leung E., Weil D.E., Raviglione M., Nakatani H. The WHO policy package to combat antimicrobial resistance. Bull. World Health Organ. 2011, 89:390-392. 10.2471/BLT.11.088435.
4. Kutateladze M., Adamia R. Bacteriophages as potential new therapeutics to replace or supplement antibiotics. Trends Biotechnol. 2010, 28:591-595. 10.1016/j.tibtech.2010.08.001.
5. Extance A. Biologics target bad bugs. Nat. Rev. Drug Discov. 2010, 9:177-178. 10.1038/nrd3129.
6. Lind T.K., Zielińska P., Wacklin H.P., Urbańczyk-Lipkowska Z., Cárdenas M. Continuous flow atomic force microscopy imaging reveals fluidity and time-dependent interactions of antimicrobial dendrimer with model lipid membranes. ACS Nano 2014, 8:396-408. 10.1021/nn404530z.
7. Geller B.L. Antibacterial antisense. Curr. Opin. Mol. Ther. 2005, 7:109-113. (PMID:15844617).
8. Mann M.J., Dzau V.J. Therapeutic applications of transcription factor decoy oligonucleotides. J. Clin. Invest. 2000, 106:1071-1075. 10.1172/JCI11459.
9. McArthur M., Bibb M.J. Manipulating and understanding antibiotic production in Streptomyces coelicolor A3(2) with decoy oligonucleotides. Proc. Natl. Acad. Sci. 2008, 105:1020-1025. 10.1073/pnas.0710724105.
10. Komagata K., Suzuki K.-I. Lipid and cell-wall analysis in bacterial systematics. Methods in Microbiology 1987, vol. 19. Academic Press Ltd.
11. Simberg D., Danino D., Talmon Y., Minsky A., Ferrari M.E., Wheeler C.J., et al. Phase behavior, DNA ordering, and size instability of cationic lipoplexes: relevance to optimal transfection activity. J. Biol. Chem. 2001, 276:47453-47459. 10.1074/jbc.M105588200.
12. Weissig V., Lasch J., Erdos G., Meyer H.W., Rowe T.C., Hughes J. DQAsomes: a novel potential drug and gene delivery system made from Dequalinium™. Pharm. Res. 1998, 15:334-337. 10.1023/A:1011991307631.
13. Lasch J., Meye A., Taubert H., Koelsch R., Mansa-ard J., Weissig V. Dequalinium TM vesicles form stable complexes with plasmid DNA which are protected from DNase attack. Biol. Chem. 1999, 380. 10.1515/BC.1999.080.
14. Weissig V., Lizano C., Torchilin V.P. Selective DNA release from DQAsome/DNA complexes at mitochondria-like membranes. Drug Deliv. 2000, 7:1-5. 10.1080/107175400266722.
15. M. McArthur, Transcription factor decoys for the treatment and prevention of infections caused by bacteria including clostridium difficile. US Patent App. 13/802, 103, 2013.
16. van de Hulst H.C. Light Scattering by Small Particles 1991, Dover Publications, New York.
17. Pusey P.N. Dynamic light scattering. Neutrons X-Rays Light Scattering Methods Applied Soft Condensed Matter 2002, North Holland. P. Lindner, T. Zemb (Eds.).
18. Provencher S.W. A constrained regularization method for inverting data represented by linear algebraic or integral equations. Comput. Phys. Commun. 1982, 27:213-227. 10.1016/0010-4655(82) 90173-4.
19. Ulmius J., Lindman B., Lindblom G., Drakenberg T. 1H, 13C, 35Cl, and 81Br NMR of aqueous hexadecyltrimethylammonium salt solutions: solubilization, viscoelasticity, and counterion specificity. J. Colloid Interface Sci. 1978, 65:88-97. 10.1016/0021-9797(78) 90261-8.
20. Nuraje N., Bai H., Su K. Bolaamphiphilic molecules: assembly and applications. Prog. Polym. Sci. 2013, 38:302-343. 10.1016/j.progpolymsci.2012.09.003.
21. Ziserman L., Lee H.-Y., Raghavan S.R., Mor A., Danino D. Unraveling the mechanism of nanotube formation by chiral self-Assembly of amphiphiles. J. Am. Chem. Soc. 2011, 133:2511-2517. 10.1021/ja107069f.
22. Nagarajan R. Self-assembly of bola amphiphiles. Chem. Eng. Commun. 1987, 55:251-273. 10.1080/00986448708911931.
23. Kalyanasundaram K., Thomas J.K. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J. Am. Chem. Soc. 1977, 99:2039-2044. 10.1021/ja00449a004.
24. Lakowicz J.R. Principles of Fluorescence Spectroscopy 2006, Springer. Third edition.
25. Memoli A., Palermiti L.G., Travagli V., Alhaique F. Effects of surfactants on the spectral behaviour of calcein(II): a method of evaluation. J. Pharm. Biomed. Anal. 1999, 19:627-632. 10.1016/S0731-7085(98)00229-5.
26. Menger F., Wrenn S. Interfacial and micellar properties of bolaform electrolytes. J. Phys. Chem. 1974, 78:1387-1390. 10.1021/j100607a600.
27. Yiv S., Kale K.M., Lang J., Zana R. Chemical relaxation and equilibrium studies of association in aqueous solutions of bolaform detergents. 1. Dodecane-1,12-bis(trimethylammonium bromide). J. Phys. Chem. 1976, 80:2651-2655. 10.1021/j100565a006.
28. ®. J. Liposome Res. 2002, 12:51-56. 10.1081/LPR-120004776.
29. Van de Sande W., Persoons A. The size and shape of macromolecular structures: determination of the radius, the length and the persistance length of rod-like micelles of dodecyldimethylammonium chloride and bromide. J. Phys. Chem. 1985, 89:404-406. 10.1021/j100249a007.
30. Israelachvili J.N. Intermolecular and Surface Forces 2011, Elsevier Acad. Press. 3rd ed.
31. Guida V. Thermodynamics and kinetics of vesicles formation processes. Adv. Colloid Interface Sci. 2010, 161:77-88. 10.1016/j.cis.2009.11.004.
32. Saha R., Verma P.K., Mitra R.K., Pal S.K. Structural and dynamical characterization of unilamellar AOT vesicles in aqueous solutions and their efficacy as potential drug delivery vehicle. Colloids Surf. B Biointerfaces 2011, 88:345-353. 10.1016/j.colsurfb.2011.07.012.
33. Kypr J., Kejnovska I., Renciuk D., Vorlickova M. Circular dichroism and conformational polymorphism of DNA. Nucleic Acids Res. 2009, 37:1713-1725. 10.1093/nar/gkp026.
34. Jadhav V.M., Valaske R., Maiti S. Interaction between 14mer DNA oligonucleotide and cationic surfactants of various chain lengths. J. Phys. Chem. B. 2008, 112:8824-8831. 10.1021/jp8017452.
35. Zhou T., Xu G., Ao M., Yang Y., Wang C. DNA compaction to multi-molecular DNA condensation induced by cationic imidazolium gemini surfactants. Colloids Surf. Physicochem. Eng. Asp. 2012, 414:33-40. 10.1016/j.colsurfa.2012.08.060.
36. Pietralik Z., Krzysztoń R., Kida W., Andrzejewska W., Kozak M. Structure and conformational dynamics of DMPC/Dicationic surfactant and DMPC/Dicationic Surfactant/DNA systems. Int. J. Mol. Sci. 2013, 14:7642-7659. 10.3390/ijms14047642.
37. Luo D., Saltzman M.W. Synthetic DNA delivery systems. Nat. Biotechnol. 2000, 18:33-37. 10.1038/71889.
38. Sohrabi B., Khani V., Moosavi-Movahedi A.A., Moradi P. Investigation of DNA-cationic bolaform surfactants interaction with different spacer length. Colloids Surf. B Biointerfaces 2013, 110:29-35. 10.1016/j.colsurfb.2013.04.032.
39. Khan M., Ang C.Y., Wiradharma N., Yong L.-K., Liu S., Liu L., et al. Diaminododecane-based cationic bolaamphiphile as a non-viral gene delivery carrier. Biomaterials 2012, 33:4673-4680. 10.1016/j.biomaterials.2012.02.067.
40. Kunath K. Low-molecular-weight polyethylenimine as a non-viral vector for DNA delivery: comparison of physicochemical properties, transfection efficiency and in vivo distribution with high-molecular-weight polyethylenimine. J. Controlled Release 2003, 89:113-125. 10.1016/S0168-3659(03)00076-2.
41. Long E.C., Barton J.K. On demonstrating DNA intercalation. Acc. Chem. Res. 1990, 23:271-273. 10.1021/ar00177a001.
42. Boulanger C., Di Giorgio C., Gaucheron J., Vierling P. Transfection with fluorinated lipoplexes based on new fluorinated cationic lipids and in the presence of a bile salt surfactant. Bioconjug. Chem. 2004, 15:901-908. 10.1021/bc049942+.