HHQ

• CAT Number: I011924
• CAS Number: 40522-46-1
• Molecular Formula: C16H21NO
• Molecular Weight: 243.35
• Purity: ≥95%
• Synonyms: HHQ;2-Heptylquinolin-4(1H)-one
• Target: Alkaloids
• Solubility: Soluble in DMSO
• Storage: 2-8°C
• IUPAC Name: 2-heptyl-1H-quinolin-4-one
• InChI: InChI=1S/C16H21NO/c1-2-3-4-5-6-9-13-12-16(18)14-10-7-8-11-15(14)17-13/h7-8,10-12H,2-6,9H2,1H3,(H,17,18)
• InChIKey: UYRHHBXYXSYGHA-UHFFFAOYSA-N
• SMILES: CCCCCCCC1=CC(=O)C2=CC=CC=C2N1

HHQ (Cat No.:I011924) acts as an antagonist of PqsR (Pseudomonas quinolone signal receptor), a protein involved in quorum-sensing pathways in certain bacteria. As an antagonist, HHQ interferes with the binding of PqsR to its target molecules, thereby inhibiting its signaling functions. This disruption of PqsR activity can have significant effects on bacterial behaviors regulated by quorum sensings, such as virulence and biofilm formation.

Reference

1: Kamal AAM, Petrera L, Eberhard J, Hartmann RW. Structure-functionality relationship and pharmacological profiles of Pseudomonas aeruginosa alkylquinolone quorum sensing modulators. Org Biomol Chem. 2017 May 31;15(21):4620-4630. doi: 10.1039/c7ob00263g. PubMed PMID: 28513746.2: Maura D, Drees SL, Bandyopadhaya A, Kitao T, Negri M, Starkey M, Lesic B, Milot S, Déziel E, Zahler R, Pucci M, Felici A, Fetzner S, Lépine F, Rahme LG. Polypharmacology Approaches against the Pseudomonas aeruginosa MvfR Regulon and Their Application in Blocking Virulence and Antibiotic Tolerance. ACS Chem Biol. 2017 May 19;12(5):1435-1443. doi: 10.1021/acschembio.6b01139. Epub 2017 Apr 12. PubMed PMID: 28379691.3: He HQ, Ye RD. The Formyl Peptide Receptors: Diversity of Ligands and Mechanism for Recognition. Molecules. 2017 Mar 13;22(3). pii: E455. doi: 10.3390/molecules22030455. Review. PubMed PMID: 28335409.4: Soga S, Ota N, Shimotoyodome A. Reduction in hydroxyhydroquinone from coffee increases postprandial fat utilization in healthy humans: a randomized double-blind, cross-over trial. Biosci Biotechnol Biochem. 2017 Mar 21:1-3. doi: 10.1080/09168451.2017.1301802. [Epub ahead of print] PubMed PMID: 28322128.5: Birmes FS, Wolf T, Kohl TA, Rüger K, Bange F, Kalinowski J, Fetzner S. Mycobacterium abscessus subsp. abscessus Is Capable of Degrading Pseudomonas aeruginosa Quinolone Signals. Front Microbiol. 2017 Mar 2;8:339. doi: 10.3389/fmicb.2017.00339. eCollection 2017. PubMed PMID: 28303132; PubMed Central PMCID: PMC5332414.6: Turnpenny P, Padfield A, Barton P, Teague J, Rahme LG, Pucci MJ, Zahler R, Rubio A. Bioanalysis of Pseudomonas aeruginosa alkyl quinolone signalling molecules in infected mouse tissue using LC-MS/MS; and its application to a pharmacodynamic evaluation of MvfR inhibition. J Pharm Biomed Anal. 2017 May 30;139:44-53. doi: 10.1016/j.jpba.2017.02.034. Epub 2017 Feb 28. PubMed PMID: 28273650.7: Zhou Z, Ma S. Recent Advances in the Discovery of PqsD Inhibitors as Antimicrobial Agents. ChemMedChem. 2017 Mar 17;12(6):420-425. doi: 10.1002/cmdc.201700015. Epub 2017 Mar 6. Review. PubMed PMID: 28195681.8: Kamae R, Nojima S, Akiyoshi K, Setsu S, Honda S, Masuda T, Oyama Y. Hydroxyhydroquinone, a by-product of coffee bean roasting, increases intracellular Ca(2+) concentration in rat thymic lymphocytes. Food Chem Toxicol. 2017 Apr;102:39-45. doi: 10.1016/j.fct.2017.01.025. Epub 2017 Jan 30. PubMed PMID: 28153638.9: Prothiwa M, Szamosvári D, Glasmacher S, Böttcher T. Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa. Beilstein J Org Chem. 2016 Dec 20;12:2784-2792. doi: 10.3762/bjoc.12.277. eCollection 2016. PubMed PMID: 28144351; PubMed Central PMCID: PMC5238532.10: Laube JGR, Shapiro MF. Comparison of Patient Health History Questionnaires Used in General Internal and Family Medicine, Integrative Medicine, and Complementary and Alternative Medicine Clinics. J Altern Complement Med. 2017 May;23(5):385-393. doi: 10.1089/acm.2016.0281. Epub 2017 Jan 9. PubMed PMID: 28068145.11: Reen FJ, Phelan JP, Woods DF, Shanahan R, Cano R, Clarke S, McGlacken GP, O/’Gara F. Harnessing Bacterial Signals for Suppression of Biofilm Formation in the Nosocomial Fungal Pathogen Aspergillus fumigatus. Front Microbiol. 2016 Dec 22;7:2074. doi: 10.3389/fmicb.2016.02074. eCollection 2016. PubMed PMID: 28066389; PubMed Central PMCID: PMC5177741.12: Lucas AL, Tarlecki A, Van Beck K, Lipton C, RoyChoudhury A, Levinson E, Kumar S, Chung WK, Frucht H, Genkinger JM. Self-Reported Questionnaire Detects Family History of Cancer in a Pancreatic Cancer Screening Program. J Genet Couns. 2016 Dec 30. doi: 10.1007/s10897-016-0057-4. [Epub ahead of print] PubMed PMID: 28039657.13: Shanahan R, Reen FJ, Cano R, O/’Gara F, McGlacken GP. The requirements at the C-3 position of alkylquinolones for signalling in Pseudomonas aeruginosa. Org Biomol Chem. 2017 Jan 4;15(2):306-310. doi: 10.1039/c6ob01930g. PubMed PMID: 27901165.14: Meis M, Huber R, Fischer RL, Schulte M, Spilski J, Meister H. Development and psychometric properties of the sound preference and hearing habits questionnaire (SP-HHQ). Int J Audiol. 2016 Nov 22:1-12. [Epub ahead of print] PubMed PMID: 27875658.15: Rampioni G, Falcone M, Heeb S, Frangipani E, Fletcher MP, Dubern JF, Visca P, Leoni L, Cámara M, Williams P. Unravelling the Genome-Wide Contributions of Specific 2-Alkyl-4-Quinolones and PqsE to Quorum Sensing in Pseudomonas aeruginosa. PLoS Pathog. 2016 Nov 16;12(11):e1006029. doi: 10.1371/journal.ppat.1006029. eCollection 2016 Nov. PubMed PMID: 27851827; PubMed Central PMCID: PMC5112799.16: Thammaiah S, Manchaiah V, Easwar V, Krishna R, McPherson B. Psychometric properties of the hearing handicap questionnaire: a Kannada (South-Indian) translation. Int J Audiol. 2017 Mar;56(3):194-201. doi: 10.1080/14992027.2016.1247500. Epub 2016 Nov 4. PubMed PMID: 27809619.17: Barr HL, Halliday N, Barrett DA, Williams P, Forrester DL, Peckham D, Williams K, Smyth AR, Honeybourne D, L Whitehouse J, Nash EF, Dewar J, Clayton A, Knox AJ, Cámara M, Fogarty AW. Diagnostic and prognostic significance of systemic alkyl quinolones for P. aeruginosa in cystic fibrosis: A longitudinal study. J Cyst Fibros. 2017 Mar;16(2):230-238. doi: 10.1016/j.jcf.2016.10.005. Epub 2016 Oct 20. PubMed PMID: 27773591; PubMed Central PMCID: PMC5345566.18: Ji C, Sharma I, Pratihar D, Hudson LL, Maura D, Guney T, Rahme LG, Pesci EC, Coleman JP, Tan DS. Designed Small-Molecule Inhibitors of the Anthranilyl-CoA Synthetase PqsA Block Quinolone Biosynthesis in Pseudomonas aeruginosa. ACS Chem Biol. 2016 Nov 18;11(11):3061-3067. Epub 2016 Sep 22. PubMed PMID: 27658001; PubMed Central PMCID: PMC5117135.19: Nguyen AT, Jones JW, Cámara M, Williams P, Kane MA, Oglesby-Sherrouse AG. Cystic Fibrosis Isolates of Pseudomonas aeruginosa Retain Iron-Regulated Antimicrobial Activity against Staphylococcus aureus through the Action of Multiple Alkylquinolones. Front Microbiol. 2016 Jul 27;7:1171. doi: 10.3389/fmicb.2016.01171. eCollection 2016. PubMed PMID: 27512392; PubMed Central PMCID: PMC4961689.20: Reen FJ, Phelan JP, Gallagher L, Woods DF, Shanahan RM, Cano R, Ó Muimhneacháin E, McGlacken GP, O/’Gara F. Exploiting Interkingdom Interactions for Development of Small-Molecule Inhibitors of Candida albicans Biofilm Formation. Antimicrob Agents Chemother. 2016 Sep 23;60(10):5894-905. doi: 10.1128/AAC.00190-16. Print 2016 Oct. PubMed PMID: 27458231; PubMed Central PMCID: PMC5038327.