Iminothiol/thiourea tautomeric equilibrium in thiourea lipids impacts DNA compaction by inducing a cationic nucleation for complex assembly

Biophysical Chemistry

Volumn 145, Issue 1, 2009, Pages 7-16

  Breton, Marie ^a   Bessodes, Michel ^a   Bouaziz, Serge ^a   Herscovici, Jean ^b   Scherman, Daniel ^a   Mignet, Nathalie ^a  

^a INSERM   (France)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

13C NMR; Cationic lipids; DNA compaction; Supramolecular assemblies; Tautomerism; Thiourea protonation

Indexed keywords

CARBON 13; CATION; DNA; HYDROGEN; IMINOTHIOL; LIPID; LIPOSOME; SOLVENT; THIOUREA DERIVATIVE;

ACIDITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; CONTROLLED STUDY; ELECTRICITY; EQUILIBRIUM CONSTANT; HYDROGEN BOND; HYDROXYLATION; LIPOGENESIS; MOLECULAR STABILITY; MOLECULAR WEIGHT; PH MEASUREMENT; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN DNA INTERACTION; SUPRAMOLECULAR CHEMISTRY; ULTRAVIOLET SPECTROSCOPY;

CATIONS; DNA; FURANS; GENE TRANSFER TECHNIQUES; LIPID METABOLISM; LIPIDS; THIOUREA; X-RAY DIFFRACTION;

EID: 70349253873     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2009.08.003     Document Type: Article

References (32)

1. Simberg D., Weisman S., Talmon Y., and Barenholz Y. DOTAP (and other cationic lipids): Chemistry, biophysics, and transfection. Crit. Rev. Ther. Drug Carr. Syst. 21 (2004) 257-317
2. Ewert K., Slack N.L., Ahmad A., Evans H.M., Lin A.J., Samuel C.E., and Safinya C.R. Cationic lipid-DNA complexes for gene therapy: understanding the relationship between complex structure and gene delivery pathways at the molecular level. Curr. Med. Chem. 11 (2004) 133-149
3. Tandia B.M., Vandenbranden M., Wattiez R., Lakhdar Z., Ruysschaert J.M., and Elouahabi A. Identification of human plasma proteins that bind to cationic lipid/DNA complex and analysis of their effects on transfection efficiency: implications for intravenous gene transfer. Mol. Ther. 8 (2003) 264-273
4. Eliyahu H., Servel N., Domb A.J., and Barenholz Y. Lipoplex-induced hemagglutination: potential involvement in intravenous gene delivery. Gene Ther. 9 (2002) 850-858
5. Dass C.R. Lipoplex-mediated delivery of nucleic acids: factors affecting in vivo transfection. J. Mol. Med. 82 (2004) 579-591
6. Nicolazzi C., Mignet N., de la Figuera N., Cadet M., Ibad R.T., Seguin J., Scherman D., and Bessodes M. Anionic polyethyleneglycol lipids added to cationic lipoplexes increase their plasmatic circulation time. J. Control. Release 88 (2003) 429-443
7. Thompson B., Mignet N., Hofland H., Lamons D., Seguin J., Nicolazzi C., de la Figuera N., Kuen R.L., Meng X.Y., Scherman D., and Bessodes M. Neutral postgrafted colloidal particles for gene delivery. Bioconjug. Chem. 16 (2005) 608-614
8. Aoyama Y., Kanamori T., Nakai T., Sasaki T., Horiuchi S., Sando S., and Niidome T. Artificial viruses and their application to gene delivery. Size-controlled gene coating with glycocluster nanoparticles. J. Am. Chem. Soc. 125 (2003) 3455-3457
9. Arigon J., Prata C.A.H., Grinstaff M.W., and Barthelemy P. Nucleic acid complexing glycosyl nucleoside-based amphiphile. Bioconjug. Chem. 16 (2005) 864-872
10. Nakai T., Kanamori T., Sando S., and Aoyama Y.J. Remarkably size-regulated cell invasion by artificial viruses. Saccharide-dependent self-aggregation of glycoviruses and its consequences in glycoviral gene delivery. Am. Chem. Soc. 125 (2003) 8465-8475
11. Chabaud P., Camplo M., Payet D., Serin G., Moreau L., Barthelemy P., and Grinstaff M.W. Cationic nucleoside lipids for gene delivery. Bioconjug. Chem. 17 (2006) 466-472
12. Bailey A.L., and Sullivan S.M. Efficient encapsulation of DNA plasmids in small neutral liposomes induced by ethanol and calcium. Biochim. Biophys. Acta, Biomembr. 1468 (2000) 239-252
13. Roux D., Cheneviera P., Pott T., Navailles L., Regev O., and Monval O.M. Conception and realization of a non-cationic non-viral DNA vector. Curr. Med. Chem. 11 (2004) 169-177
14. Takemoto Y. Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors. Org. Biomol. Chem. 3 (2005) 4299-4306
15. - by neutral bis-thiourea hosts. Tetrahedron 53 (1997) 1647-1654
16. Tranchant I., Mignet N., Crozat E., Leblond J., Girard C., Scherman D., and Herscovici J. DNA complexing lipopolythiourea. Bioconjug. Chem. 15 (2004) 1342-1348
17. Leblond J., Mignet N., Leseurre L., Largeau C., Bessodes M., Scherman D., and Herscovici J. Design, synthesis, and evaluation of enhanced DNA binding new lipopolythioureas. Bioconjug. Chem. 17 (2006) 1200-1208
18. Leblond J., Mignet N., Largeau C., Spanedda M.V., Seguin J., Scherman D., and Herscovici J. Lipopolythioureas: a new non-cationic system for gene transfer. Bioconjug. Chem. 18 (2007) 484-493
19. Leblond J., Mignet N., Largeau C., Seguin J., Scherman D., and Herscovici J. Lipopolythiourea transfecting agents: LYSINE thiourea derivatives. Bioconjug. Chem. 19 (2008) 306-314
20. Allegretti P.E., Castro E.A., and Furlong J.J.P. Tautomeric equilibrium of amides and related compounds: theoretical and spectral evidences. J. Mol. Struct.-Theochem 499 (2000) 121-126
21. Congdon W.I., and Edward J.T. Monoprotonation and diprotonation of n-acylthioureas in aqueous sulfuric-acid. J. Am. Chem. Soc. 94 (1972) 6096-6099
22. Walter J.L., Ryan J.A., and Lane T.J. A study of thiourea and substituted thiourea analogs by the bjerrum titration method. J. Am. Chem. Soc. 78 (1956) 5560-5562
23. Vasilev V.P., Raskova O.G., Degtyareva N.K., and Katrovtseva A.V. Thermochemistry of thiourea protonation. Zh. Obshch. Khim. 52 (1982) 1470-1473
24. Olah G.A., Burrichter A., Rasul G., Hachoumy M., and Prakash G.K.S. H-1, C-13, N-15 NMR and ab initio IGLO GIAO-MP2 study of mono-, di-, tri-, and tetraprotonated guanidine. J. Am. Chem. Soc. 119 (1997) 12929-12933
25. Schiessl W.C., Summa N.K., Weber C.F., Gubo S., Ducker-Benfer C., Puchta R., Hommes N., and van Eldik R.Z. Experimental and theoretical approaches to the protonation of thiourea: a convenient nucleophile in coordination chemistry revisited. Anorg. Allg. Chem. 631 (2005) 2812-2819
26. Cobas J.C., and Sardina F.J. Nuclear magnetic resonance data processing. MestRe-C: a software package for desktop computers. Concepts Magn. Reson. Part A 19A (2003) 80-96
27. Hind A.R. To improvements in spectrophotometry. Am. Lab. 34 (2002) 32-35
28. Escriou V., Carriere M., Bussone F., Wils P., and Scherman D. Critical assessment of the nuclear import of plasmid during cationic lipid-mediated gene transfer. J. Gene Med. 3 (2001) 179-187
29. Nelson J.W., and Kallenbach N.R. Stabilization of the rnase s-peptide alpha-helix by trifluoroethanol. Prot. Struct. Func. Gen. 1 (1986) 211-217
30. Sierra P.S., Tejuca C.C., Garcia-Blanco F., Oliva C.D., Sierra J.C., and Gorostidi G.E. Properties of 2,2,2-trifluoroethano/water mixtures: acidity, basicity, and dipolarity. Helv. Chim. Acta 88 (2005) 312-324
31. Allen F.H., Bird C.M., Rowland R.S., and Raithby P.R. Hydrogen-bond acceptor and donor properties of divalent sulfur (Y-S-Z and R-S-H). Acta Crystallogr., B Struct. Sci. 53 (1997) 696-701
32. Allen F.H., Bird C.M., Rowland R.S., and Raithby P.R. Resonance-induced hydrogen bonding at sulfur acceptors in R1R2C{double bond, short}C and R1CS2-systems. Acta Crystallogr., B Struct. Sci. 53 (1997) 680-695