Nitric oxide-releasing quaternary ammonium-modified poly(amidoamine) dendrimers as dual action antibacterial agents

Bioconjugate Chemistry

Volumn 25, Issue 5, 2014, Pages 918-927

  Worley, Brittany V ^a   Slomberg, Danielle L ^a   Schoenfisch, Mark H ^a  

^a The University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CHAIN LENGTH; DENDRIMERS;

A-RINGS; ALKYL CHAIN LENGTHS; BACTERICIDAL ACTIVITY; DUAL ACTION; FUNCTIONALIZED; NITRIC OXIDE RELEASE; POLYAMIDOAMINE DENDRIMERS; QUATERNARY AMMONIUM; RING OPENING REACTION; SECONDARY AMINES;

NITRIC OXIDE;

ANTIINFECTIVE AGENT; BUTYL QUATERNARY AMMONIUM; BUTYL QUATERNARY AMMONIUM NITRIC OXIDE; DENDRIMER; DODECYL QUATERNARY AMMONIUM; DODECYL QUATERNARY AMMONIUM NITRIC OXIDE; METHYL QUATERNARY AMMONIUM; METHYL QUATERNARY AMMONIUM NITRIC OXIDE; NITRIC OXIDE; OCTYL QUATERNARY AMMONIUM; OCTYL QUATERNARY AMMONIUM NITRIC OXIDE; POLYAMIDOAMINE; QUATERNARY AMMONIUM DERIVATIVE; UNCLASSIFIED DRUG; POLYAMINE;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERICIDAL ACTIVITY; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG HALF LIFE; DRUG MECHANISM; DRUG SYNTHESIS; MINIMUM BACTERICIDAL CONCENTRATION; MOUSE; NONHUMAN; PSEUDOMONAS AERUGINOSA; RING OPENING; STAPHYLOCOCCUS AUREUS; TIME TO MAXIMUM PLASMA CONCENTRATION; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; DENDRIMERS; DOSE-RESPONSE RELATIONSHIP, DRUG; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NITRIC OXIDE; POLYAMINES; PSEUDOMONAS AERUGINOSA; QUATERNARY AMMONIUM COMPOUNDS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84901044971     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc5000719     Document Type: Article

References (39)

1. Boucher, H. W., Talbot, G. H., Bradley, J. S., Edwards, J. E., Gilbert, D., Rice, L. B., Scheld, M., Spellberg, B., and Bartlett, J. (2009) Bad bugs, no drugs: no ESKAPE! An update from the Infectious Diseases Society of America Clin. Infect. Dis. 48, 1-12
2. Cottarel, G. and Wierzbowski, J. (2007) Combination drugs, an emerging option for antibacterial therapy Trends Biotechnol. 25, 547-555
3. Eliopoulos, G. and Eliopoulos, C. (1988) Antibiotic combinations: should they be tested? Clin. Microbiol. Rev. 1, 139-156
4. Fischbach, M. A. (2011) Combination therapies for combating antimicrobial resistance Curr. Opin. Microbiol. 14, 519-523
5. Fang, F. C. (1997) Perspectives series: host/pathogen interactions. Mechanisms of nitric oxide-related antimicrobial activity J. Clin. Invest. 99, 2818
6. Fang, F. C. (2004) Antimicrobial reactive oxygen and nitrogen species: concepts and controversies Nat. Rev. Microbiol. 2, 820-832
7. Hetrick, E. M., Shin, J. H., Stasko, N. A., Johnson, C. B., Wespe, D. A., Holmuhamedov, E., and Schoenfisch, M. H. (2008) Bactericidal efficacy of nitric oxide-releasing silica nanoparticles ACS Nano 2, 235-246
8. Carpenter, A. W., Worley, B. V., Slomberg, D. L., and Schoenfisch, M. H. (2012) Dual action antimicrobials: nitric oxide release from quaternary ammonium-functionalized silica nanoparticles Biomacromolecules 13, 3334-3342
9. Privett, B. J., Deupree, S. M., Backlund, C. J., Rao, K. S., Johnson, C. B., Coneski, P. N., and Schoenfisch, M. H. (2010) Synergy of nitric oxide and silver sulfadiazine against gram-negative, gram-positive, and antibiotic-resistant pathogens Mol. Pharmaceutics 7, 2289-2296
10. Sun, B., Slomberg, D. L., Chudasama, S. L., Lu, Y., and Schoenfisch, M. H. (2012) Nitric oxide-releasing dendrimers as antibacterial agents Biomacromolecules 13, 3343-3354
11. Park, J., Kim, J., Singha, K., Han, D.-K., Park, H., and Kim, W. J. (2013) Nitric oxide integrated polyethylenimine-based tri-block copolymer for efficient antibacterial activity Biomaterials 34, 8766-8775
12. Simoncic, B. and Tomsic, B. (2010) Structures of novel antimicrobial agents for textiles-a review Text. Res. J. 80, 1721-1737
13. Chen, C. Z., Beck-Tan, N. C., Dhurjati, P., van Dyk, T. K., LaRossa, R. A., and Cooper, S. L. (2000) Quaternary ammonium functionalized poly (propylene imine) dendrimers as effective antimicrobials: structure-activity studies Biomacromolecules 1, 473-480
14. Thorsteinsson, T., Másson, M., Kristinsson, K. G., Hjálmarsdóttir, M. A., Hilmarsson, H., and Loftsson, T. (2003) Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds J. Med. Chem. 46, 4173-4181
15. Li, Z., Lee, D., Sheng, X., Cohen, R. E., and Rubner, M. F. (2006) Two-level antibacterial coating with both release-killing and contact-killing capabilities Langmuir 22, 9820-9823
16. Song, J., Kang, H., Lee, C., Hwang, S. H., and Jang, J. (2011) Aqueous synthesis of silver nanoparticle embedded cationic polymer nanofibers and their antibacterial activity ACS Appl. Mater. Interfaces 4, 460-465
17. Duncan, R. and Izzo, L. (2005) Dendrimer biocompatibility and toxicity Adv. Drug Delivery Rev. 57, 2215-2237
18. Tomalia, D. A. (2005) Birth of a new macromolecular architecture: dendrimers as quantized building blocks for nanoscale synthetic polymer chemistry Prog. Polym. Sci. 30, 294-324
19. Jevprasesphant, R., Penny, J., Attwood, D., McKeown, N. B., and DEmanuele, A. (2003) Engineering of dendrimer surfaces to enhance transepithelial transport and reduce cytotoxicity Pharm. Res. 20, 1543-1550
20. Wiwattanapatapee, R., Carreño-Gómez, B., Malik, N., and Duncan, R. (2000) Anionic PAMAM dendrimers rapidly cross adult rat intestine in vitro: a potential oral delivery system? Pharm. Res. 17, 991-998
21. Meyers, S. R., Juhn, F. S., Griset, A. P., Luman, N. R., and Grinstaff, M. W. (2008) Anionic amphiphilic dendrimers as antibacterial agents J. Am. Chem. Soc. 130, 14444-14445
22. Chen, C., Cooper, S., and Tan, N. B. (1999) Incorporation of dimethyldodecylammonium chloride functionalities onto poly (propylene imine) dendrimers significantly enhances their antibacterial properties Chem. Commun. 1585-1586
23. Charles, S., Vasanthan, N., Kwon, D., Sekosan, G., and Ghosh, S. (2012) Surface modification of poly (amidoamine)(PAMAM) dendrimer as antimicrobial agents Tetrahedron Lett. 53, 6670-6675
24. Lu, Y., Sun, B., Li, C., and Schoenfisch, M. H. (2011) Structurally diverse nitric oxide-releasing poly (propylene imine) dendrimers Chem. Mater. 23, 4227-4233
25. Beyth, N., Houri-Haddad, Y., Baraness-Hadar, L., Yudovin-Farber, I., Domb, A. J., and Weiss, E. I. (2008) Surface antimicrobial activity and biocompatibility of incorporated polyethylenimine nanoparticles Biomaterials 29, 4157-4163
26. Shi, Z., Neoh, K., Kang, E., and Wang, W. (2006) Antibacterial and mechanical properties of bone cement impregnated with chitosan nanoparticles Biomaterials 27, 2440-2449
27. Schenning, A. P., Elissen-Roman, C., Weener, J.-W., Baars, M. W., van der Gaast, S. J., and Meijer, E. (1998) Amphiphilic dendrimers as building blocks in supramolecular assemblies J. Am. Chem. Soc. 120, 8199-8208
28. Bjarnsholt, T., Kirketerp-Møller, K., Jensen, P. Ø., Madsen, K. G., Phipps, R., Krogfelt, K., Høiby, N., and Givskov, M. (2008) Why chronic wounds will not heal: a novel hypothesis Wound Repair Regen. 16, 2-10
29. Beveridge, T. J. (1999) Structures of gram-negative cell walls and their derived membrane vesicles J. Bacteriol. 181, 4725-4733
30. Yamanaka, M., Hara, K., and Kudo, J. (2005) Bactericidal actions of a silver ion solution on Escherichia coli, studied by energy-filtering transmission electron microscopy and proteomic analysis Appl. Environ. Microbiol. 71, 7589-7593
31. Maiti, P. K., Cagin, T., Wang, G., and Goddard, W. A. (2004) Structure of PAMAM dendrimers: Generations 1 through 11 Macromolecules 37, 6236-6254
32. Fréchet, J. M. (2002) Dendrimers and supramolecular chemistry Proc. Natl. Acad. Sci. U. S. A. 99, 4782-4787
33. Lv, H., Zhang, S., Wang, B., Cui, S., and Yan, J. (2006) Toxicity of cationic lipids and cationic polymers in gene delivery J. Controlled Release 114, 100-109
34. Dunne, W. M. (2002) Bacterial adhesion: seen any good biofilms lately? Clin. Microbiol. Rev. 15, 155-166
35. Lindsay, D. and Von Holy, A. (2006) Bacterial biofilms within the clinical setting: what healthcare professionals should know J. Hosp. Infect. 64, 313-325
36. Lu, Y., Slomberg, D. L., Shah, A., and Schoenfisch, M. H. (2013) Nitric oxide-releasing amphiphilic poly (amidoamine)(PAMAM) dendrimers as antibacterial agents Biomacromolecules 14, 3589-3598
37. Tomalia, D., Baker, H., Dewald, J., Hall, M., Kallos, G., Martin, S., Roeck, J., Ryder, J., and Smith, P. (1985) A new class of polymers: starburst-dendritic macromolecules Polym. J. 17, 117-132
38. Breed, R. S. and Dotterrer, W. (1916) The number of colonies allowable on satisfactory agar plates J. Bacteriol. 1, 321
39. Slomberg, D. L., Lu, Y., Broadnax, A. D., Hunter, R. A., Carpenter, A. W., and Schoenfisch, M. H. (2013) Role of size and shape on biofilm eradication for nitric oxide-releasing silica nanoparticles ACS Appl. Mater. Interfaces 5, 9322-9329