Pyochelin | CAS#69772-54-9 | siderophore

MedKoo Cat#: 585194 | Name: Pyochelin

Description:

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

Pyochelin is a phenolic iron-binding compound from Pseudomonas aeruginosa that promotes the growth of bacterium when added to iron-deficient media.

Chemical Structure

Pyochelin

CAS#69772-54-9

Theoretical Analysis

MedKoo Cat#: 585194

Name: Pyochelin

CAS#: 69772-54-9

Chemical Formula: C14H16N2O3S2

Exact Mass: 324.0602

Molecular Weight: 324.41

Elemental Analysis: C, 51.83; H, 4.97; N, 8.64; O, 14.80; S, 19.76

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Pyochelin; Pyochelin I; Pyocheline

IUPAC/Chemical Name

(4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid

InChi Key

NYBZAGXTZXPYND-GDVCOKDOSA-N

InChi Code

InChI=1S/C14H16N2O3S2/c1-16-10(14(18)19)7-21-13(16)9-6-20-12(15-9)8-4-2-3-5-11(8)17/h2-5,9-10,13,17H,6-7H2,1H3,(H,18,19)/t9-,10+,13?/m1/s1

SMILES Code

O=C([C@H]1N(C)C([C@@H]2N=C(C3=CC=CC=C3O)SC2)SC1)O

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).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 324.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Hoegy F, Mislin GL, Schalk IJ. Pyoverdine and pyochelin measurements. Methods Mol Biol. 2014;1149:293-301. doi: 10.1007/978-1-4939-0473-0_24. PubMed PMID: 24818914. 2: Youard ZA, Wenner N, Reimmann C. Iron acquisition with the natural siderophore enantiomers pyochelin and enantio-pyochelin in Pseudomonas species. Biometals. 2011 Jun;24(3):513-22. doi: 10.1007/s10534-010-9399-9. Epub 2010 Dec 25. Review. PubMed PMID: 21188474. 3: Noël S, Hoegy F, Rivault F, Rognan D, Schalk IJ, Mislin GL. Synthesis and biological properties of thiazole-analogues of pyochelin, a siderophore of Pseudomonas aeruginosa. Bioorg Med Chem Lett. 2014 Jan 1;24(1):132-5. doi: 10.1016/j.bmcl.2013.11.054. Epub 2013 Dec 4. PubMed PMID: 24332092. 4: Lin J, Zhang W, Cheng J, Yang X, Zhu K, Wang Y, Wei G, Qian PY, Luo ZQ, Shen X. A Pseudomonas T6SS effector recruits PQS-containing outer membrane vesicles for iron acquisition. Nat Commun. 2017 Mar 28;8:14888. doi: 10.1038/ncomms14888. PubMed PMID: 28348410; PubMed Central PMCID: PMC5379069. 5: Farmer KL, Thomas MS. Isolation and characterization of Burkholderia cenocepacia mutants deficient in pyochelin production: pyochelin biosynthesis is sensitive to sulfur availability. J Bacteriol. 2004 Jan;186(2):270-7. PubMed PMID: 14702294; PubMed Central PMCID: PMC305768. 6: Reimmann C, Serino L, Beyeler M, Haas D. Dihydroaeruginoic acid synthetase and pyochelin synthetase, products of the pchEF genes, are induced by extracellular pyochelin in Pseudomonas aeruginosa. Microbiology. 1998 Nov;144 ( Pt 11):3135-48. PubMed PMID: 9846750. 7: Michel L, González N, Jagdeep S, Nguyen-Ngoc T, Reimmann C. PchR-box recognition by the AraC-type regulator PchR of Pseudomonas aeruginosa requires the siderophore pyochelin as an effector. Mol Microbiol. 2005 Oct;58(2):495-509. PubMed PMID: 16194235. 8: Ben Haj Khalifa A, Moissenet D, Vu Thien H, Khedher M. [Virulence factors in Pseudomonas aeruginosa: mechanisms and modes of regulation]. Ann Biol Clin (Paris). 2011 Jul-Aug;69(4):393-403. doi: 10.1684/abc.2011.0589. Review. French. PubMed PMID: 21896403. 9: Cobessi D, Celia H, Pattus F. Crystal structure at high resolution of ferric-pyochelin and its membrane receptor FptA from Pseudomonas aeruginosa. J Mol Biol. 2005 Sep 30;352(4):893-904. PubMed PMID: 16139844. 10: Meisel JD, Panda O, Mahanti P, Schroeder FC, Kim DH. Chemosensation of bacterial secondary metabolites modulates neuroendocrine signaling and behavior of C. elegans. Cell. 2014 Oct 9;159(2):267-80. doi: 10.1016/j.cell.2014.09.011. PubMed PMID: 25303524; PubMed Central PMCID: PMC4194030. 11: Wendler S, Otto A, Ortseifen V, Bonn F, Neshat A, Schneiker-Bekel S, Walter F, Wolf T, Zemke T, Wehmeier UF, Hecker M, Kalinowski J, Becher D, Pühler A. Comprehensive proteome analysis of Actinoplanes sp. SE50/110 highlighting the location of proteins encoded by the acarbose and the pyochelin biosynthesis gene cluster. J Proteomics. 2015 Jul 1;125:1-16. doi: 10.1016/j.jprot.2015.04.013. Epub 2015 Apr 18. PubMed PMID: 25896738. 12: Tseng CF, Burger A, Mislin GL, Schalk IJ, Yu SS, Chan SI, Abdallah MA. Bacterial siderophores: the solution stoichiometry and coordination of the Fe(III) complexes of pyochelin and related compounds. J Biol Inorg Chem. 2006 Jun;11(4):419-32. Epub 2006 Mar 21. PubMed PMID: 16550426. 13: Youard ZA, Reimmann C. Stereospecific recognition of pyochelin and enantio-pyochelin by the PchR proteins in fluorescent pseudomonads. Microbiology. 2010 Jun;156(Pt 6):1772-82. doi: 10.1099/mic.0.037796-0. Epub 2010 Mar 4. PubMed PMID: 20203054. 14: Lin PC, Youard ZA, Reimmann C. In vitro-binding of the natural siderophore enantiomers pyochelin and enantiopyochelin to their AraC-type regulators PchR in Pseudomonas. Biometals. 2013 Dec;26(6):1067-73. doi: 10.1007/s10534-013-9676-5. Epub 2013 Sep 15. PubMed PMID: 24037597. 15: Orazi G, O'Toole GA. Pseudomonas aeruginosa Alters Staphylococcus aureus Sensitivity to Vancomycin in a Biofilm Model of Cystic Fibrosis Infection. MBio. 2017 Jul 18;8(4). pii: e00873-17. doi: 10.1128/mBio.00873-17. PubMed PMID: 28720732; PubMed Central PMCID: PMC5516255. 16: Yang B, Hoegy F, Mislin GL, Mesini PJ, Schalk IJ. Terbium, a fluorescent probe for investigation of siderophore pyochelin interactions with its outer membrane transporter FptA. J Inorg Biochem. 2011 Oct;105(10):1293-8. doi: 10.1016/j.jinorgbio.2011.03.016. Epub 2011 Apr 2. PubMed PMID: 21861955. 17: Maspoli A, Wenner N, Mislin GL, Reimmann C. Functional analysis of pyochelin-/enantiopyochelin-related genes from a pathogenicity island of Pseudomonas aeruginosa strain PA14. Biometals. 2014 Jun;27(3):559-73. doi: 10.1007/s10534-014-9729-4. Epub 2014 Mar 30. PubMed PMID: 24682869. 18: Ong KS, Cheow YL, Lee SM. The role of reactive oxygen species in the antimicrobial activity of pyochelin. J Adv Res. 2017 Jul;8(4):393-398. doi: 10.1016/j.jare.2017.05.007. Epub 2017 May 21. PubMed PMID: 28580180; PubMed Central PMCID: PMC5447373. 19: Reimmann C. Inner-membrane transporters for the siderophores pyochelin in Pseudomonas aeruginosa and enantio-pyochelin in Pseudomonas fluorescens display different enantioselectivities. Microbiology. 2012 May;158(Pt 5):1317-24. doi: 10.1099/mic.0.057430-0. Epub 2012 Feb 16. PubMed PMID: 22343350. 20: Cunrath O, Gasser V, Hoegy F, Reimmann C, Guillon L, Schalk IJ. A cell biological view of the siderophore pyochelin iron uptake pathway in Pseudomonas aeruginosa. Environ Microbiol. 2015 Jan;17(1):171-85. doi: 10.1111/1462-2920.12544. Epub 2014 Jul 15. PubMed PMID: 24947078.