PA Autoinducer

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 563421

CAS#: 152833-54-0

Description: PA Autoinducer is a Pseudomonas aeruginosa autoinducer.


Price and Availability

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PA Autoinducer is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 563421
Name: PA Autoinducer
CAS#: 152833-54-0
Chemical Formula: C16H27NO4
Exact Mass: 297.194
Molecular Weight: 297.39
Elemental Analysis: C, 64.62; H, 9.15; N, 4.71; O, 21.52


Synonym: PA Autoinducer; PA-Autoinducer; 3O-C12 autoinducer;

IUPAC/Chemical Name: N-(3-Oxododecanoyl)homoserine lactone

InChi Key: PHSRRHGYXQCRPU-AWEZNQCLSA-N

InChi Code: InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1

SMILES Code: O=C1[C@H](CCO1)NC(CC(CCCCCCCCC)=O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.03.00


References

1: Everett J, Gabrilska R, Rumbaugh KP, Vikström E. Assessing Pseudomonas aeruginosa Autoinducer Effects on Mammalian Epithelial Cells. Methods Mol Biol. 2018;1673:213-225. doi: 10.1007/978-1-4939-7309-5_17. PubMed PMID: 29130176.

2: Amoh T, Murakami K, Kariyama R, Hori K, Irie Y, Viducic D, Hirota K, Igarashi J, Suga H, Kumon H, Miyake Y. A Pseudomonas aeruginosa Quorum-Sensing autoinducer analog enhances the activity of antibiotics against resistant strains. J Med Invest. 2017;64(1.2):101-109. doi: 10.2152/jmi.64.101. PubMed PMID: 28373605.

3: Woźniak-Karczewska M, Myszka K, Sznajdrowska A, Szulc A, Zgoła-Grześkowiak A, Ławniczak Ł, Corvini PF, Chrzanowski Ł. Isolation of rhamnolipids-producing cultures from faeces: Influence of interspecies communication on the yield of rhamnolipid congeners. N Biotechnol. 2017 May 25;36:17-25. doi: 10.1016/j.nbt.2016.12.008. Epub 2016 Dec 30. PubMed PMID: 28043869.

4: Horke S, Xiao J, Schütz EM, Kramer GL, Wilgenbus P, Witte I, Selbach M, Teiber JF. Novel Paraoxonase 2-Dependent Mechanism Mediating the Biological Effects of the Pseudomonas aeruginosa Quorum-Sensing Molecule N-(3-Oxo-Dodecanoyl)-L-Homoserine Lactone. Infect Immun. 2015 Sep;83(9):3369-80. doi: 10.1128/IAI.00141-15. Epub 2015 Jun 8. PubMed PMID: 26056385; PubMed Central PMCID: PMC4534671.

5: Oh MH, Choi CH. Role of LuxIR Homologue AnoIR in Acinetobacter nosocomialis and the Effect of Virstatin on the Expression of anoR Gene. J Microbiol Biotechnol. 2015 Aug;25(8):1390-400. doi: 10.4014/jmb.1504.04069. PubMed PMID: 25975610.

6: Losa D, Köhler T, Bacchetta M, Saab JB, Frieden M, van Delden C, Chanson M. Airway Epithelial Cell Integrity Protects from Cytotoxicity of Pseudomonas aeruginosa Quorum-Sensing Signals. Am J Respir Cell Mol Biol. 2015 Aug;53(2):265-75. doi: 10.1165/rcmb.2014-0405OC. PubMed PMID: 25562674.

7: Grosso-Becerra MV, Croda-García G, Merino E, Servín-González L, Mojica-Espinosa R, Soberón-Chávez G. Regulation of Pseudomonas aeruginosa virulence factors by two novel RNA thermometers. Proc Natl Acad Sci U S A. 2014 Oct 28;111(43):15562-7. doi: 10.1073/pnas.1402536111. Epub 2014 Oct 13. PubMed PMID: 25313031; PubMed Central PMCID: PMC4217398.

8: Eum SY, Jaraki D, Bertrand L, András IE, Toborek M. Disruption of epithelial barrier by quorum-sensing N-3-(oxododecanoyl)-homoserine lactone is mediated by matrix metalloproteinases. Am J Physiol Gastrointest Liver Physiol. 2014 Jun 1;306(11):G992-G1001. doi: 10.1152/ajpgi.00016.2014. Epub 2014 Apr 17. PubMed PMID: 24742991; PubMed Central PMCID: PMC4042118.

9: Yang YX, Xu ZH, Zhang YQ, Tian J, Weng LX, Wang LH. A new quorum-sensing inhibitor attenuates virulence and decreases antibiotic resistance in Pseudomonas aeruginosa. J Microbiol. 2012 Dec;50(6):987-93. doi: 10.1007/s12275-012-2149-7. Epub 2012 Dec 30. PubMed PMID: 23274985.

10: Minagawa S, Inami H, Kato T, Sawada S, Yasuki T, Miyairi S, Horikawa M, Okuda J, Gotoh N. RND type efflux pump system MexAB-OprM of Pseudomonas aeruginosa selects bacterial languages, 3-oxo-acyl-homoserine lactones, for cell-to-cell communication. BMC Microbiol. 2012 May 10;12:70. PubMed PMID: 22574700; PubMed Central PMCID: PMC3460771.

11: Pasotti L, Quattrocelli M, Galli D, De Angelis MG, Magni P. Multiplexing and demultiplexing logic functions for computing signal processing tasks in synthetic biology. Biotechnol J. 2011 Jul;6(7):784-95. doi: 10.1002/biot.201100080. Epub 2011 Jun 17. PubMed PMID: 21681964.

12: Khajanchi BK, Kirtley ML, Brackman SM, Chopra AK. Immunomodulatory and protective roles of quorum-sensing signaling molecules N-acyl homoserine lactones during infection of mice with Aeromonas hydrophila. Infect Immun. 2011 Jul;79(7):2646-57. doi: 10.1128/IAI.00096-11. Epub 2011 May 2. PubMed PMID: 21536794; PubMed Central PMCID: PMC3191994.

13: Hosono Honda N, Kimura S, Tateda K, Horikawa M, Ueda C, Ishii Y, Ishiguro M, Miyairi S, Yamaguchi K. Roles of Pseudomonas aeruginosa autoinducers and their degradation products, tetramic acids, in bacterial survival and behavior in ecological niches. Microbes Environ. 2011;26(2):160-4. Epub 2011 Mar 29. PubMed PMID: 21502732.

14: Seet Q, Zhang LH. Anti-activator QslA defines the quorum sensing threshold and response in Pseudomonas aeruginosa. Mol Microbiol. 2011 May;80(4):951-65. doi: 10.1111/j.1365-2958.2011.07622.x. Epub 2011 Mar 22. PubMed PMID: 21392132.

15: Mayer ML, Sheridan JA, Blohmke CJ, Turvey SE, Hancock RE. The Pseudomonas aeruginosa autoinducer 3O-C12 homoserine lactone provokes hyperinflammatory responses from cystic fibrosis airway epithelial cells. PLoS One. 2011 Jan 31;6(1):e16246. doi: 10.1371/journal.pone.0016246. PubMed PMID: 21305014; PubMed Central PMCID: PMC3031552.

16: Garner AL, Yu J, Struss AK, Lowery CA, Zhu J, Kim SK, Park J, Mayorov AV, Kaufmann GF, Kravchenko VV, Janda KD. Synthesis of 'clickable' acylhomoserine lactone quorum sensing probes: unanticipated effects on mammalian cell activation. Bioorg Med Chem Lett. 2011 May 1;21(9):2702-5. doi: 10.1016/j.bmcl.2010.11.122. Epub 2010 Dec 4. PubMed PMID: 21190852; PubMed Central PMCID: PMC3081916.

17: Chai H, Hazawa M, Shirai N, Igarashi J, Takahashi K, Hosokawa Y, Suga H, Kashiwakura I. Functional properties of synthetic N-acyl-L-homoserine lactone analogs of quorum-sensing gram-negative bacteria on the growth of human oral squamous carcinoma cells. Invest New Drugs. 2012 Feb;30(1):157-63. doi: 10.1007/s10637-010-9544-x. Epub 2010 Sep 28. PubMed PMID: 20878204.

18: Ueda C, Tateda K, Horikawa M, Kimura S, Ishii Y, Nomura K, Yamada K, Suematsu T, Inoue Y, Ishiguro M, Miyairi S, Yamaguchi K. Anti-Clostridium difficile potential of tetramic acid derivatives from Pseudomonas aeruginosa quorum-sensing autoinducers. Antimicrob Agents Chemother. 2010 Feb;54(2):683-8. doi: 10.1128/AAC.00702-09. Epub 2009 Nov 16. PubMed PMID: 19917748; PubMed Central PMCID: PMC2812153.

19: Kristiansen S, Bjarnsholt T, Adeltoft D, Ifversen P, Givskov M. The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells. APMIS. 2008 May;116(5):361-71. doi: 10.1111/j.1600-0463.2008.00966.x. PubMed PMID: 18452426.

20: Jahoor A, Patel R, Bryan A, Do C, Krier J, Watters C, Wahli W, Li G, Williams SC, Rumbaugh KP. Peroxisome proliferator-activated receptors mediate host cell proinflammatory responses to Pseudomonas aeruginosa autoinducer. J Bacteriol. 2008 Jul;190(13):4408-15. doi: 10.1128/JB.01444-07. Epub 2008 Jan 4. PubMed PMID: 18178738; PubMed Central PMCID: PMC2446782.