ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img
RETURN TO ISSUECommunicationNEXT

Inhibition of Pseudomonas aeruginosa Biofilm Formation with Bromoageliferin Analogues

View Author Information
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695, and Program in Molecular Genetics and Department of Microbiology and Immunology, Wake Forest University Health Sciences, Winston-Salem, North Carolina 27157
Cite this: J. Am. Chem. Soc. 2007, 129, 22, 6966–6967
Publication Date (Web):May 15, 2007
https://doi.org/10.1021/ja069017t
Copyright © 2007 American Chemical Society

    Article Views

    3222

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    Two analogues of the marine natural product bromoageliferin have been synthesized and subsequently assayed for the ability to inhibit the formation of Pseudomonas aeruginosa biofilms. Both compounds inhibited the ability of Pseudomonas aeruginosa strains PAO1 and PA14 to form biofilms; however, they displayed differential toxicity to planktonic bacteria. The cis analogue, CAGE, was found to possess greater toxicity than the trans analogue, TAGE. These compounds have no structural homology to any known inhibitors of Pseudomonas aeruginosa biofilms.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

     North Carolina State University.

     Program in Molecular Genetics, Wake Forest University Health Sciences.

    §

     Department of Microbiology and Immunology, Wake Forest University Health Sciences.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    Supporting Information Available

    ARTICLE SECTIONS
    Jump To

    Experimental procedures and characterization data for all new compounds; planktonic growth curves and colony counts for PAO1 and PA14 in the presence and absence of TAGE and CAGE. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 111 publications.

    1. Jin Jia, Dharmeshkumar Parmar, Joanna F. Ellis, Tianyuan Cao, Allison R. Cutri, Joshua D. Shrout, Jonathan V. Sweedler, Paul W. Bohn. Effect of Micro-Patterned Mucin on Quinolone and Rhamnolipid Profiles of Mucoid Pseudomonas aeruginosa under Antibiotic Stress. ACS Infectious Diseases 2023, 9 (1) , 150-161. https://doi.org/10.1021/acsinfecdis.2c00519
    2. Chunfang Zhu, Meng Zhang, Qiaoling Tang, Qian Yang, Jing Li, Xuan He, Yong Ye. Structure and Activity of the Camellia oleifera Sapogenin Derivatives on Growth and Biofilm Inhibition of Staphylococcus aureus and Escherichia coli. Journal of Agricultural and Food Chemistry 2019, 67 (51) , 14143-14151. https://doi.org/10.1021/acs.jafc.9b03577
    3. Sean E. Rossiter, Madison H. Fletcher, and William M. Wuest . Natural Products as Platforms To Overcome Antibiotic Resistance. Chemical Reviews 2017, 117 (19) , 12415-12474. https://doi.org/10.1021/acs.chemrev.7b00283
    4. Jiaul Hoque, Mohini M. Konai, Shanola S. Sequeira, Sandip Samaddar, and Jayanta Haldar . Antibacterial and Antibiofilm Activity of Cationic Small Molecules with Spatial Positioning of Hydrophobicity: An in Vitro and in Vivo Evaluation. Journal of Medicinal Chemistry 2016, 59 (23) , 10750-10762. https://doi.org/10.1021/acs.jmedchem.6b01435
    5. Stefanie Wagner, Roman Sommer, Stefan Hinsberger, Cenbin Lu, Rolf W. Hartmann, Martin Empting, and Alexander Titz . Novel Strategies for the Treatment of Pseudomonas aeruginosa Infections. Journal of Medicinal Chemistry 2016, 59 (13) , 5929-5969. https://doi.org/10.1021/acs.jmedchem.5b01698
    6. Vikas Chaudhary, Jubina B. Venghateri, Hemendra P. S. Dhaked, Anil S. Bhoyar, Sankar K. Guchhait, and Dulal Panda . Novel Combretastatin-2-aminoimidazole Analogues as Potent Tubulin Assembly Inhibitors: Exploration of Unique Pharmacophoric Impact of Bridging Skeleton and Aryl Moiety. Journal of Medicinal Chemistry 2016, 59 (7) , 3439-3451. https://doi.org/10.1021/acs.jmedchem.6b00101
    7. Roymon Joseph, Alissa Naugolny, Mark Feldman, Ido M. Herzog, Micha Fridman, and Yoram Cohen . Cationic Pillararenes Potently Inhibit Biofilm Formation without Affecting Bacterial Growth and Viability. Journal of the American Chemical Society 2016, 138 (3) , 754-757. https://doi.org/10.1021/jacs.5b11834
    8. Richele J. Thompson, Benjamin G. Bobay, Sean D. Stowe, Andrew L. Olson, Lingling Peng, Zhaoming Su, Luis A. Actis, Christian Melander, and John Cavanagh . Identification of BfmR, a Response Regulator Involved in Biofilm Development, as a Target for a 2-Aminoimidazole-Based Antibiofilm Agent. Biochemistry 2012, 51 (49) , 9776-9778. https://doi.org/10.1021/bi3015289
    9. Hans P. L. Steenackers, Denis S. Ermolat’ev, Bharat Savaliya, Ami De Weerdt, David De Coster, Anamik Shah, Erik V. Van der Eycken, Dirk E. De Vos, Jozef Vanderleyden, and Sigrid C. J. De Keersmaecker . Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa. Journal of Medicinal Chemistry 2011, 54 (2) , 472-484. https://doi.org/10.1021/jm1011148
    10. Hao Shen and Zuowei Xie. Atom-Economical Synthesis of N-Heterocycles via Cascade Inter-/Intramolecular C−N Bond-Forming Reactions Catalyzed by Ti Amides. Journal of the American Chemical Society 2010, 132 (33) , 11473-11480. https://doi.org/10.1021/ja101796k
    11. Yong-Gang Wang, Brandon I. Morinaka, Jeremy Chris P. Reyes, Jeremy J. Wolff, Daniel Romo and Tadeusz F. Molinski. Synthesis of 7-15N-Oroidin and Evaluation of Utility for Biosynthetic Studies of Pyrrole−Imidazole Alkaloids by Microscale 1H−15N HSQC and FTMS. Journal of Natural Products 2010, 73 (3) , 428-434. https://doi.org/10.1021/np900638e
    12. Steven A. Rogers, Robert W. Huigens III and Christian Melander. A 2-Aminobenzimidazole That Inhibits and Disperses Gram-Positive Biofilms through a Zinc-Dependent Mechanism. Journal of the American Chemical Society 2009, 131 (29) , 9868-9869. https://doi.org/10.1021/ja9024676
    13. Maren E. Buck, Anthony S. Breitbach, Sonja K. Belgrade, Helen E. Blackwell and David M. Lynn . Chemical Modification of Reactive Multilayered Films Fabricated from Poly(2-alkenyl azlactone)s: Design of Surfaces that Prevent or Promote Mammalian Cell Adhesion and Bacterial Biofilm Growth. Biomacromolecules 2009, 10 (6) , 1564-1574. https://doi.org/10.1021/bm9001552
    14. T. Eric Ballard, Justin J. Richards, Arianexys Aquino, Catherine S. Reed and Christian Melander. Antibiofilm Activity of a Diverse Oroidin Library Generated through Reductive Acylation. The Journal of Organic Chemistry 2009, 74 (4) , 1755-1758. https://doi.org/10.1021/jo802260t
    15. Justin J. Richards and Christian Melander. Synthesis of a 2-Aminoimidazole Library for Antibiofilm Screening Utilizing the Sonogashira Reaction. The Journal of Organic Chemistry 2008, 73 (13) , 5191-5193. https://doi.org/10.1021/jo800618q
    16. Srinivas Reddy Merugu, Sithabile Mokoena, Vincent A. Obakachi, Baji Baba Shaik, Babita Kushawaha, Narva Deshwar Kushwaha, Blessing Wisdom Ike, Mahesh B. Palkar, Chandrakant G. Bonde, Ab Majeed Ganai, Ruchika Chauhan, Afsana Kajee, Meenu Ghai, Saqib Kidwai, Ramandeep Singh, Rajshekhar Karpoormath. Novel 4,5-dibromo-N-phenyl-1H-pyrrole-2-carboxamide Hybrids as Promising DNA Gyrase Inhibitors: Design, synthesis and antimicrobial evaluation. Journal of Molecular Structure 2024, 1302 , 137359. https://doi.org/10.1016/j.molstruc.2023.137359
    17. Jun Liu, Qiu-Xian Chen, Wen-Fu Wu, Dong Wang, Si-Yu Zhao, Jia-Hao Li, Yi-Qun Chang, Shao-Gao Zeng, Jia-Yi Hu, Yu-Jie Li, Jia-Xin Du, Shu-Meng Jiao, Hai-Chuan Xiao, Qiang Zhang, Jun Xu, Jian-Fu Zhao, Hai-Bo Zhou, Yong-Heng Wang, Jian Zou, Ping-Hua Sun. Novel ligustilide derivatives target quorum sensing system LasR/LasB and relieve inflammatory response against Pseudomonas aeruginosa infection. European Journal of Medicinal Chemistry 2024, 263 , 115972. https://doi.org/10.1016/j.ejmech.2023.115972
    18. Sara Masihzadeh, Mansour Amin, Zahra Farshadzadeh. In vitro and in vivo antibiofilm activity of the synthetic antimicrobial peptide WLBU2 against multiple drug resistant Pseudomonas aeruginosa strains. BMC Microbiology 2023, 23 (1) https://doi.org/10.1186/s12866-023-02886-x
    19. Rasha Mohamed Hassan, Mohamed Samir Abd El-Maksoud, Iman Ahmed Youssef Ghannam, Aida Abdel- Sattar El-Azzouny, Mohamed Nabil Aboul-Enein. Synthetic non-toxic anti-biofilm agents as a strategy in combating bacterial resistance. European Journal of Medicinal Chemistry 2023, 262 , 115867. https://doi.org/10.1016/j.ejmech.2023.115867
    20. Maximiliano Martínez-Cifuentes, Emmanuel Soto-Tapia, Camila Linares-Pipón, Ben Bradshaw, Paulina Valenzuela-Hormazabal, David Ramírez, Patricio Muñoz-Torres, Claudio Parra. Design of β-Keto Esters with Antibacterial Activity: Synthesis, In Vitro Evaluation, and Theoretical Assessment of Their Reactivity and Quorum-Sensing Inhibition Capacity. Pharmaceuticals 2023, 16 (10) , 1339. https://doi.org/10.3390/ph16101339
    21. Neyaz A Khan, Nicolas Barthes, Grace McCormack, James P O'Gara, Olivier P Thomas, Aoife Boyd. Sponge-derived fatty acids inhibit biofilm formation of MRSA and MSSA by down-regulating biofilm-related genes specific to each pathogen. Journal of Applied Microbiology 2023, 134 (8) https://doi.org/10.1093/jambio/lxad152
    22. Suzia Aktar Suchi, Kyung Bin Nam, Young Kyun Kim, Hasan Tarek, Jin Cheol Yoo. A novel antimicrobial peptide YS12 isolated from Bacillus velezensis CBSYS12 exerts anti-biofilm properties against drug-resistant bacteria. Bioprocess and Biosystems Engineering 2023, 46 (6) , 813-828. https://doi.org/10.1007/s00449-023-02864-7
    23. Mei-Jun Chu, Meng Li, Yongda Zhao. Dimeric pyrrole-imidazole alkaloids: sources, structures, bioactivities and biosynthesis. Bioorganic Chemistry 2023, 133 , 106332. https://doi.org/10.1016/j.bioorg.2022.106332
    24. Yogesh Dutt, Ruby Dhiman, Tanya Singh, Arpana Vibhuti, Archana Gupta, Ramendra Pati Pandey, V. Samuel Raj, Chung-Ming Chang, Anjali Priyadarshini. The Association between Biofilm Formation and Antimicrobial Resistance with Possible Ingenious Bio-Remedial Approaches. Antibiotics 2022, 11 (7) , 930. https://doi.org/10.3390/antibiotics11070930
    25. Michael A. Trebino, Rahul D. Shingare, John B. MacMillan, Fitnat H. Yildiz. Strategies and Approaches for Discovery of Small Molecule Disruptors of Biofilm Physiology. Molecules 2021, 26 (15) , 4582. https://doi.org/10.3390/molecules26154582
    26. Roberta J. Melander, Akash K. Basak, Christian Melander. Natural products as inspiration for the development of bacterial antibiofilm agents. Natural Product Reports 2020, 37 (11) , 1454-1477. https://doi.org/10.1039/D0NP00022A
    27. Dawrin Pech-Puch, Mar Pérez-Povedano, Marta Martinez-Guitian, Cristina Lasarte-Monterrubio, Juan Carlos Vázquez-Ucha, Germán Bou, Jaime Rodríguez, Alejandro Beceiro, Carlos Jimenez. In Vitro and In Vivo Assessment of the Efficacy of Bromoageliferin, an Alkaloid Isolated from the Sponge Agelas dilatata, against Pseudomonas aeruginosa. Marine Drugs 2020, 18 (6) , 326. https://doi.org/10.3390/md18060326
    28. N.M. Jagadeesh, Mailar Karabasappa. Control of microbial biofilms: Application of natural and synthetic compounds. 2020, 101-115. https://doi.org/10.1016/B978-0-444-64279-0.00008-6
    29. Robert W. Huigens, Yasmeen Abouelhassan, Hongfen Yang. Phenazine Antibiotic‐Inspired Discovery of Bacterial Biofilm‐Eradicating Agents. ChemBioChem 2019, 20 (23) , 2885-2902. https://doi.org/10.1002/cbic.201900116
    30. Danica J. Walsh, Tom Livinghouse, Darla M. Goeres, Madelyn Mettler, Philip S. Stewart. Antimicrobial Activity of Naturally Occurring Phenols and Derivatives Against Biofilm and Planktonic Bacteria. Frontiers in Chemistry 2019, 7 https://doi.org/10.3389/fchem.2019.00653
    31. Keisham S. Singh, Mahesh S. Majik. Pyrrole-Derived Alkaloids of Marine Sponges and Their Biological Properties. 2019, 377-409. https://doi.org/10.1016/B978-0-444-64185-4.00010-1
    32. Tran Thi Thu Trang, Lise Dieltjens, Geert Hooyberghs, Kai Waldrant, Denis S. Ermolat'ev, Erik V. Van der Eycken, Hans P.L. Steenackers. Enhancing the anti-biofilm activity of 5-aryl-2-aminoimidazoles through nature inspired dimerisation. Bioorganic & Medicinal Chemistry 2018, 26 (8) , 1470-1480. https://doi.org/10.1016/j.bmc.2018.01.005
    33. Basit Yousuf, Keika Adachi, Jiro Nakayama. Developing Anti-virulence Chemotherapies by Exploiting the Diversity of Microbial Quorum Sensing Systems. 2018, 151-208. https://doi.org/10.1007/978-981-10-9026-4_9
    34. Rupinder Kaur Gill, Virender Kumar, Stijn C.A. Robijns, Hans P.L. Steenackers, Erik V. Van der Eycken, Jitender Bariwal. Polysubstituted 2-aminoimidazoles as anti-biofilm and antiproliferative agents: Discovery of potent lead. European Journal of Medicinal Chemistry 2017, 138 , 152-169. https://doi.org/10.1016/j.ejmech.2017.06.043
    35. Tiffany Le Norcy, Hendrik Niemann, Peter Proksch, Karen Tait, Isabelle Linossier, Karine Réhel, Claire Hellio, Fabienne Faÿ. Sponge-Inspired Dibromohemibastadin Prevents and Disrupts Bacterial Biofilms without Toxicity. Marine Drugs 2017, 15 (7) , 222. https://doi.org/10.3390/md15070222
    36. Guilong Tian, Pavel Fedoseev, Erik V. Van der Eycken. Hypervalent Iodine(III)‐Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C. Chemistry – A European Journal 2017, 23 (22) , 5224-5227. https://doi.org/10.1002/chem.201700934
    37. Hewen Zheng, Nischal Singh, Gauri S. Shetye, Yucheng Jin, Diana Li, Yan-Yeung Luk. Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa. Bioorganic & Medicinal Chemistry 2017, 25 (6) , 1830-1838. https://doi.org/10.1016/j.bmc.2017.01.042
    38. Yugen Zhu, Lakota Cleaver, Wei Wang, Jessica D. Podoll, Shane Walls, Austin Jolly, Xiang Wang. Tetracyclic indolines as a novel class of β-lactam-selective resistance-modifying agent for MRSA. European Journal of Medicinal Chemistry 2017, 125 , 130-142. https://doi.org/10.1016/j.ejmech.2016.09.034
    39. J. Gravel, A. R. Schmitzer. Imidazolium and benzimidazolium-containing compounds: from simple toxic salts to highly bioactive drugs. Organic & Biomolecular Chemistry 2017, 15 (5) , 1051-1071. https://doi.org/10.1039/C6OB02293F
    40. Roberta J. Melander, Hong-bing Liu, Matthew D. Stephens, Carole A. Bewley, Christian Melander. Marine sponge alkaloids as a source of anti-bacterial adjuvants. Bioorganic & Medicinal Chemistry Letters 2016, 26 (24) , 5863-5866. https://doi.org/10.1016/j.bmcl.2016.11.018
    41. Smita Pal, Asifa Qureshi, Hemant J. Purohit. Antibiofilm activity of biomolecules: gene expression study of bacterial isolates from brackish and fresh water biofouled membranes. Biologia 2016, 71 (3) , 239-246. https://doi.org/10.1515/biolog-2016-0045
    42. G.D. Mogoşanu, A.M. Grumezescu, L.E. Bejenaru, C. Bejenaru. Marine Natural Products in Fighting Microbial Infections. 2016, 351-375. https://doi.org/10.1016/B978-0-12-803642-6.00017-4
    43. Pavel Fedoseev, Nandini Sharma, Rupesh Khunt, Denis S. Ermolat'ev, Erik V. Van der Eycken. Iodine-mediated regioselective guanylation-amination of propargylamines towards the synthesis of diversely substituted 2-aminoimidazoles. RSC Advances 2016, 6 (79) , 75202-75206. https://doi.org/10.1039/C6RA13371A
    44. Nischal Singh, Gauri S. Shetye, Hewen Zheng, Jiayue Sun, Yan‐Yeung Luk. Chemical Signals of Synthetic Disaccharide Derivatives Dominate Rhamnolipids at Controlling Multiple Bacterial Activities. ChemBioChem 2016, 17 (1) , 102-111. https://doi.org/10.1002/cbic.201500396
    45. Yong Ye, Qian Yang, Fei Fang, Yue Li. The camelliagenin from defatted seeds of Camellia oleifera as antibiotic substitute to treat chicken against infection of Escherichia coli and Staphylococcus aureus. BMC Veterinary Research 2015, 11 (1) https://doi.org/10.1186/s12917-015-0529-z
    46. Yenny Martínez Díaz, Gina Vanegas Laverde, Luis Reina Gamba, Humberto Mayorga Wandurraga, Catalina Arévalo-Ferro, Freddy Ramos Rodríguez, Carmenza Duque Beltrán, Leonardo Castellanos Hernández. Biofilm inhibition activity of compounds isolated from two Eunicea species collected at the Caribbean Sea. Revista Brasileira de Farmacognosia 2015, 25 (6) , 605-611. https://doi.org/10.1016/j.bjp.2015.08.007
    47. W. Pan, M. Fan, H. Wu, C. Melander, C. Liu. A new small molecule inhibits Streptococcus mutans biofilms in vitro and in vivo. Journal of Applied Microbiology 2015, 119 (5) , 1403-1411. https://doi.org/10.1111/jam.12940
    48. Indira Deepa, Sasidharan N. Kumar, Ravikumar S. Sreerag, Vishnu S. Nath, Chellapan Mohandas. Purification and synergistic antibacterial activity of arginine derived cyclic dipeptides, from Achromobacter sp. associated with a rhabditid entomopathogenic nematode against major clinically relevant biofilm forming wound bacteria. Frontiers in Microbiology 2015, 6 https://doi.org/10.3389/fmicb.2015.00876
    49. K. Ratnakar Reddy, Y. Poornachandra, G. Jitender Dev, G. Mallareddy, Jagadeesh B. Nanubolu, C. Ganesh Kumar, B. Narsaiah. Synthesis of novel amide functionalized 2H-chromene derivatives by Ritter amidation of primary alcohol using HBF4·OEt2 as a mild and versatile reagent and evaluation of their antimicrobial and anti-biofilm activities. Bioorganic & Medicinal Chemistry Letters 2015, 25 (15) , 2943-2947. https://doi.org/10.1016/j.bmcl.2015.05.041
    50. Nira Rabin, Yue Zheng, Clement Opoku-Temeng, Yixuan Du, Eric Bonsu, Herman O Sintim. Agents that inhibit bacterial biofilm formation. Future Medicinal Chemistry 2015, 7 (5) , 647-671. https://doi.org/10.4155/fmc.15.7
    51. Sourav Sarkar, Marcos M. Pires, . d-Amino Acids Do Not Inhibit Biofilm Formation in Staphylococcus aureus. PLOS ONE 2015, 10 (2) , e0117613. https://doi.org/10.1371/journal.pone.0117613
    52. Yong Ye, Fei Fang, Yue Li. Synthesis and anti-biofilm activities of dihydro-pyrrol-2-one derivatives on Pseudomonas aeruginosa. Bioorganic & Medicinal Chemistry Letters 2015, 25 (3) , 597-601. https://doi.org/10.1016/j.bmcl.2014.12.010
    53. Tsiry Rasamiravaka, Quentin Labtani, Pierre Duez, Mondher El Jaziri. The Formation of Biofilms by Pseudomonas aeruginosa : A Review of the Natural and Synthetic Compounds Interfering with Control Mechanisms. BioMed Research International 2015, 2015 , 1-17. https://doi.org/10.1155/2015/759348
    54. Roberta J. Melander, Christian Melander. Innovative Strategies for Combating Biofilm-Based Infections. 2015, 69-91. https://doi.org/10.1007/978-3-319-09782-4_6
    55. Bruna de A. Lima, Simone P. de Lira, Miriam H. Kossuga, Reginaldo B. Gonçalves, Roberto G.S. Berlinck, Regianne U. Kamiya. Halistanol sulfate A and rodriguesines A and B are antimicrobial and antibiofilm agents against the cariogenic bacterium Streptococcus mutans. Revista Brasileira de Farmacognosia 2014, 24 (6) , 651-659. https://doi.org/10.1016/j.bjp.2014.11.002
    56. Jean‐Michel Kornprobst. Porifera (Sponges)–5. 2014, 951-1086. https://doi.org/10.1002/9783527335855.marprod195
    57. Jean‐Michel Kornprobst. Porifera (Sponges)–2. 2014, 703-792. https://doi.org/10.1002/9783527335855.marprod192
    58. Žiga Hodnik, Joanna M. Łoś, Aleš Žula, Nace Zidar, Žiga Jakopin, Marcin Łoś, Marija Sollner Dolenc, Janez Ilaš, Grzegorz Węgrzyn, Lucija Peterlin Mašič, Danijel Kikelj. Inhibition of biofilm formation by conformationally constrained indole-based analogues of the marine alkaloid oroidin. Bioorganic & Medicinal Chemistry Letters 2014, 24 (11) , 2530-2534. https://doi.org/10.1016/j.bmcl.2014.03.094
    59. Sijie Yang, Osama A. Abdel-Razek, Fei Cheng, Debjyoti Bandyopadhyay, Gauri S. Shetye, Guirong Wang, Yan-Yeung Luk. Bicyclic brominated furanones: A new class of quorum sensing modulators that inhibit bacterial biofilm formation. Bioorganic & Medicinal Chemistry 2014, 22 (4) , 1313-1317. https://doi.org/10.1016/j.bmc.2014.01.004
    60. Gabriel Navarro, Andrew T. Cheng, Kelly C. Peach, Walter M. Bray, Valerie S. Bernan, Fitnat H. Yildiz, Roger G. Linington. Image-Based 384-Well High-Throughput Screening Method for the Discovery of Skyllamycins A to C as Biofilm Inhibitors and Inducers of Biofilm Detachment in Pseudomonas aeruginosa. Antimicrobial Agents and Chemotherapy 2014, 58 (2) , 1092-1099. https://doi.org/10.1128/AAC.01781-13
    61. Narender Reddy Emmadi, Krishnaiah Atmakur, Chiranjeevi Bingi, Narender Reddy Godumagadda, Ganesh Kumar Chityal, Jagadeesh Babu Nanubolu. Regioselective synthesis of 3-benzyl substituted pyrimidino chromen-2-ones and evaluation of anti-microbial and anti-biofilm activities. Bioorganic & Medicinal Chemistry Letters 2014, 24 (2) , 485-489. https://doi.org/10.1016/j.bmcl.2013.12.038
    62. Hans Steenackers, Denis Ermolat'ev, Tran Thi Thu Trang, Bharat Savalia, Upendra K. Sharma, Ami De Weerdt, Anamik Shah, Jozef Vanderleyden, Erik V. Van der Eycken. Microwave-assisted one-pot synthesis and anti-biofilm activity of 2-amino-1H-imidazole/triazole conjugates. Org. Biomol. Chem. 2014, 12 (22) , 3671-3678. https://doi.org/10.1039/C3OB42282H
    63. Jie Zhou, Sarah Watt, Jingxin Wang, Shizuka Nakayama, David A. Sayre, Yiu-fai Lam, Vincent T. Lee, Herman O. Sintim. Potent suppression of c-di-GMP synthesis via I-site allosteric inhibition of diguanylate cyclases with 2′-F-c-di-GMP. Bioorganic & Medicinal Chemistry 2013, 21 (14) , 4396-4404. https://doi.org/10.1016/j.bmc.2013.04.050
    64. Robert E. Furlani, Andrew A. Yeagley, Christian Melander. A flexible approach to 1,4-di-substituted 2-aminoimidazoles that inhibit and disperse biofilms and potentiate the effects of β-lactams against multi-drug resistant bacteria. European Journal of Medicinal Chemistry 2013, 62 , 59-70. https://doi.org/10.1016/j.ejmech.2012.12.005
    65. Dimpy Kalia, Gökçe Merey, Shizuka Nakayama, Yue Zheng, Jie Zhou, Yiling Luo, Min Guo, Benjamin T. Roembke, Herman O. Sintim. Nucleotide, c-di-GMP, c-di-AMP, cGMP, cAMP, (p)ppGpp signaling in bacteria and implications in pathogenesis. Chem. Soc. Rev. 2013, 42 (1) , 305-341. https://doi.org/10.1039/C2CS35206K
    66. Andrew A. Yeagley, Zhaoming Su, Kára D. McCullough, Roberta J. Worthington, Christian Melander. N-Substituted 2-aminoimidazoleinhibitors of MRSA biofilm formation accessed through direct 1,3-bis(tert-butoxycarbonyl)guanidine cyclization. Org. Biomol. Chem. 2013, 11 (1) , 130-137. https://doi.org/10.1039/C2OB26469B
    67. Sivappa Rasapalli, Abasaheb Dhawane, Christiaan Rees, James A. Golen, Bal Ram Singh, Shuowei Cai, Jerry Jasinski, Steven M. Kwasny, Donald T. Moir, Timothy J. Opperman, Terry L. Bowlin. Design, synthesis and activities of 4/5-acyl-2-aminoimidazolyl analogues of oroidin for biofilm inhibition. MedChemComm 2013, 4 (11) , 1467. https://doi.org/10.1039/c3md00143a
    68. Zhaoming Su, Andrew A. Yeagley, Rui Su, Lingling Peng, Christian Melander. Structural Studies on 4,5-Disubstituted 2-Aminoimidazole-Based Biofilm Modulators that Suppress Bacterial Resistance to β-Lactams. ChemMedChem 2012, 7 (11) , 2030-2039. https://doi.org/10.1002/cmdc.201200350
    69. Sean D. Stowe, Ashley T. Tucker, Richele Thompson, Amanda Piper, Justin J. Richards, Steven A. Rogers, Laura D. Mathies, Christian Melander, John Cavanagh. Evaluation of the toxicity of 2-aminoimidazole antibiofilm agents using both cellular and model organism systems. Drug and Chemical Toxicology 2012, 35 (3) , 310-315. https://doi.org/10.3109/01480545.2011.614620
    70. Zhaoming Su, Lingling Peng, Christian Melander. A modular approach to the synthesis of 1,4,5-substituted-2-aminoimidazoles. Tetrahedron Letters 2012, 53 (10) , 1204-1206. https://doi.org/10.1016/j.tetlet.2011.12.090
    71. Erick A. Lindsey, Christopher M. Brackett, Trey Mullikin, Cristina Alcaraz, Christian Melander. The discovery of N-1 substituted 2-aminobenzimidazoles as zinc-dependent S. aureus biofilm inhibitors. MedChemComm 2012, 3 (11) , 1462. https://doi.org/10.1039/c2md20244a
    72. Erick A. Lindsey, Roberta J. Worthington, Cristina Alcaraz, Christian Melander. 2-Aminopyrimidine as a novel scaffold for biofilm modulation. Organic & Biomolecular Chemistry 2012, 10 (13) , 2552. https://doi.org/10.1039/c2ob06871k
    73. Roberta J. Worthington, Justin J. Richards, Christian Melander. Small molecule control of bacterial biofilms. Organic & Biomolecular Chemistry 2012, 10 (37) , 7457. https://doi.org/10.1039/c2ob25835h
    74. D. Linares, O. Bottzeck, O. Pereira, A. Praud-Tabariès, Y. Blache. Designing 2-aminoimidazole alkaloids analogs with anti-biofilm activities: Structure–activities relationships of polysubstituted triazoles. Bioorganic & Medicinal Chemistry Letters 2011, 21 (22) , 6751-6755. https://doi.org/10.1016/j.bmcl.2011.09.050
    75. Sean D. Stowe, Justin J. Richards, Ashley T. Tucker, Richele Thompson, Christian Melander, John Cavanagh. Anti-Biofilm Compounds Derived from Marine Sponges. Marine Drugs 2011, 9 (10) , 2010-2035. https://doi.org/10.3390/md9102010
    76. Tyler L. Harris, Roberta J. Worthington, Christian Melander. A facile synthesis of 1,5-disubstituted-2-aminoimidazoles: Antibiotic activity of a first generation library. Bioorganic & Medicinal Chemistry Letters 2011, 21 (15) , 4516-4519. https://doi.org/10.1016/j.bmcl.2011.05.123
    77. Hans P.L. Steenackers, Denis S. Ermolat’ev, Bharat Savaliya, Ami De Weerdt, David De Coster, Anamik Shah, Erik V. Van der Eycken, Dirk E. De Vos, Jozef Vanderleyden, Sigrid C.J. De Keersmaecker. Structure–activity relationship of 2-hydroxy-2-aryl-2,3-dihydro-imidazo[1,2-a]pyrimidinium salts and 2N-substituted 4(5)-aryl-2-amino-1H-imidazoles as inhibitors of biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. Bioorganic & Medicinal Chemistry 2011, 19 (11) , 3462-3473. https://doi.org/10.1016/j.bmc.2011.04.026
    78. Chang Liu, Roberta J. Worthington, Christian Melander, Hui Wu. A New Small Molecule Specifically Inhibits the Cariogenic Bacterium Streptococcus mutans in Multispecies Biofilms. Antimicrobial Agents and Chemotherapy 2011, 55 (6) , 2679-2687. https://doi.org/10.1128/AAC.01496-10
    79. Steven A. Rogers, Erick A. Lindsey, Daniel C. Whitehead, Trey Mullikin, Christian Melander. Synthesis and biological evaluation of 2-aminoimidazole/carbamate hybrid anti-biofilm and anti-microbial agents. Bioorganic & Medicinal Chemistry Letters 2011, 21 (4) , 1257-1260. https://doi.org/10.1016/j.bmcl.2010.12.057
    80. Lindsay Kalan, Gerard D. Wright. Antibiotic adjuvants: multicomponent anti-infective strategies. Expert Reviews in Molecular Medicine 2011, 13 https://doi.org/10.1017/S1462399410001766
    81. Kelly C. Peach, Walter M. Bray, Nicholas J. Shikuma, Nadine C. Gassner, R. Scott Lokey, Fitnat H. Yildiz, Roger G. Linington. An image-based 384-well high-throughput screening method for the discovery of biofilm inhibitors in Vibrio cholerae. Molecular BioSystems 2011, 7 (4) , 1176. https://doi.org/10.1039/c0mb00276c
    82. Ali Al-Mourabit, Manuel A. Zancanella, Supriya Tilvi, Daniel Romo. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids. Natural Product Reports 2011, 28 (7) , 1229. https://doi.org/10.1039/c0np00013b
    83. Samuel Reyes, Robert W. Huigens III, Zhaoming Su, Michel L. Simon, Christian Melander. Synthesis and biological activity of 2-aminoimidazole triazoles accessed by Suzuki–Miyaura cross-coupling. Organic & Biomolecular Chemistry 2011, 9 (8) , 3041. https://doi.org/10.1039/c0ob00925c
    84. Denis S. Ermolat'ev, Jitender B. Bariwal, Hans P. L. Steenackers, Sigrid C. J. De Keersmaecker, Erik V. Van der Eycken. Concise and Diversity‐Oriented Route toward Polysubstituted 2‐Aminoimidazole Alkaloids and Their Analogues. Angewandte Chemie International Edition 2010, 49 (49) , 9465-9468. https://doi.org/10.1002/anie.201004256
    85. Denis S. Ermolat'ev, Jitender B. Bariwal, Hans P. L. Steenackers, Sigrid C. J. De Keersmaecker, Erik V. Van der Eycken. Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues. Angewandte Chemie 2010, 122 (49) , 9655-9658. https://doi.org/10.1002/ange.201004256
    86. Cynthia A. Bunders, Justin J. Richards, Christian Melander. Identification of aryl 2-aminoimidazoles as biofilm inhibitors in Gram-negative bacteria. Bioorganic & Medicinal Chemistry Letters 2010, 20 (12) , 3797-3800. https://doi.org/10.1016/j.bmcl.2010.04.042
    87. S. A. Rogers, R. W. Huigens, J. Cavanagh, C. Melander. Synergistic Effects between Conventional Antibiotics and 2-Aminoimidazole-Derived Antibiofilm Agents. Antimicrobial Agents and Chemotherapy 2010, 54 (5) , 2112-2118. https://doi.org/10.1128/AAC.01418-09
    88. Dinty J. Musk. Zinc Fingered: New Compounds that Thwart Gram‐Positive Biofilm Formation by Sequestering Zinc. ChemBioChem 2010, 11 (6) , 758-760. https://doi.org/10.1002/cbic.200900691
    89. Katherine M. Schmalzer, Marc A. Benson, Dara W. Frank. Activation of ExoU Phospholipase Activity Requires Specific C-Terminal Regions. Journal of Bacteriology 2010, 192 (7) , 1801-1812. https://doi.org/10.1128/JB.00904-09
    90. Steven A. Rogers, Joseph D. Bero, Christian Melander. Chemical Synthesis and Biological Screening of 2‐Aminoimidazole‐Based Bacterial and Fungal Antibiofilm Agents. ChemBioChem 2010, 11 (3) , 396-410. https://doi.org/10.1002/cbic.200900617
    91. Robert W. Huigens, Samuel Reyes, Catherine S. Reed, Cynthia Bunders, Steven A. Rogers, Andrew T. Steinhauer, Christian Melander. The chemical synthesis and antibiotic activity of a diverse library of 2-aminobenzimidazole small molecules against MRSA and multidrug-resistant A. baumannii. Bioorganic & Medicinal Chemistry 2010, 18 (2) , 663-674. https://doi.org/10.1016/j.bmc.2009.12.003
    92. Zhaoming Su, Steven A. Rogers, W. Steve McCall, Alicia C. Smith, Sindhu Ravishankar, Trey Mullikin, Christian Melander. A nitroenolate approach to the synthesis of 4,5-disubstituted-2-aminoimidazoles. Pilot library assembly and screening for antibiotic and antibiofilm activity. Organic & Biomolecular Chemistry 2010, 8 (12) , 2814. https://doi.org/10.1039/c001479f
    93. Steven A. Rogers, Daniel C. Whitehead, Trey Mullikin, Christian Melander. Synthesis and bacterial biofilm inhibition studies of ethyl N-(2-phenethyl) carbamate derivatives. Organic & Biomolecular Chemistry 2010, 8 (17) , 3857. https://doi.org/10.1039/c0ob00063a
    94. Barbara Forte, Beatrice Malgesini, Claudia Piutti, Francesca Quartieri, Alessandra Scolaro, Gianluca Papeo. A Submarine Journey: The Pyrrole-Imidazole Alkaloids. Marine Drugs 2009, 7 (4) , 705-753. https://doi.org/10.3390/md7040705
    95. Justin J. Richards, Christian Melander. Controlling Bacterial Biofilms. ChemBioChem 2009, 10 (14) , 2287-2294. https://doi.org/10.1002/cbic.200900317
    96. Jeffrey L. Veesenmeyer, Alan R. Hauser, Thiago Lisboa, Jordi Rello. Pseudomonas aeruginosa virulence and therapy: Evolving translational strategies*. Critical Care Medicine 2009, 37 (5) , 1777-1786. https://doi.org/10.1097/CCM.0b013e31819ff137
    97. Robert L. Giles, John D. Sullivan, Andrew M. Steiner, Ryan E. Looper. Addition–Hydroamination Reactions of Propargyl Cyanamides: Rapid Access to Highly Substituted 2‐Aminoimidazoles. Angewandte Chemie International Edition 2009, 48 (17) , 3116-3120. https://doi.org/10.1002/anie.200900160
    98. Robert L. Giles, John D. Sullivan, Andrew M. Steiner, Ryan E. Looper. Addition–Hydroamination Reactions of Propargyl Cyanamides: Rapid Access to Highly Substituted 2‐Aminoimidazoles. Angewandte Chemie 2009, 121 (17) , 3162-3166. https://doi.org/10.1002/ange.200900160
    99. Steven A. Rogers, Michael Krayer, Jonathan S. Lindsey, Christian Melander. Tandem dispersion and killing of bacteria from a biofilm. Org. Biomol. Chem. 2009, 7 (3) , 603-606. https://doi.org/10.1039/B817923A
    100. Zhong Jin. Muscarine, imidazole, oxazole and thiazole alkaloids. Natural Product Reports 2009, 26 (3) , 382. https://doi.org/10.1039/b718045b
    Load all citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect