Pyoverdine

Pyoverdine
Names
Other names
Pyoverdin
Identifiers
3D model (JSmol)
ChEBI
  • InChI=1S/C56H88N18O22/c1-27(79)43-53(91)61-15-4-3-8-31(46(84)65-34(11-7-19-73(96)26-78)49(87)70-44(28(2)80)54(92)71-43)64-47(85)33(10-6-18-72(95)25-77)67-50(88)36(23-75)68-48(86)32(9-5-16-62-56(58)59)66-51(89)37(24-76)69-52(90)38-14-17-60-45-35(63-42(83)13-12-30(57)55(93)94)20-29-21-40(81)41(82)22-39(29)74(38)45/h20-22,25-28,30-34,36-38,43-45,60,75-76,79-82,95-96H,3-19,23-24,57H2,1-2H3,(H,61,91)(H,63,83)(H,64,85)(H,65,84)(H,66,89)(H,67,88)(H,68,86)(H,69,90)(H,70,87)(H,71,92)(H,93,94)(H4,58,59,62)
  • Key: QIRRYPHVUMPBDX-UARRTFJPSA-N
  • CC(C1C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN(C=O)O)NC(=O)C(CCCN(C=O)O)NC(=O)C(CO)NC(=O)C(CCCN=C(N)N)NC(=O)C(CO)NC(=O)C2CCNC3N2C4=CC(=C(C=C4C=C3NC(=O)CCC(C(=O)O)N)O)O)C(C)O)O
Properties
C56H88N18O22
Molar mass 1365.424 g·mol−1
Appearance Solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyoverdines[1] (alternatively, and less commonly, spelled as pyoverdins) are fluorescent siderophores produced by certain pseudomonads.[2][3] Pyoverdines are important virulence factors, and are required for pathogenesis in many biological models of infection. Their contributions to bacterial pathogenesis include providing a crucial nutrient (i.e., iron), regulation of other virulence factors (including exotoxin A and the protease PrpL),[4] supporting the formation of biofilms,[5] and are increasingly recognized for having toxicity themselves.[6][7][8]

Pyoverdines have also been investigated as "Trojan Horse" molecules for the delivery of antimicrobials to otherwise resistant bacterial strains, as chelators that can be used for bioremediation of heavy metals, and as fluorescent reporters used to assay for the presence of iron and potentially other metals.[9]

Due to their bridging the gaps between pathogenicity, iron metabolism, and fluorescence, pyoverdines have piqued the curiosity of scientists around the world for over 100 years.[citation needed]

  1. ^ For the purposes of this page, pyoverdine will generally refer (unless otherwise noted) to the pyoverdine produced by Pseudomonas aeruginosa strain PAO1. It has been subjected to the most extensive study and can be considered the prototypical siderophore.
  2. ^ S. Wendenbaum; P. Demange; A. Dell; J. M. Meyer; M. A. Abdallah (1983). "The structure of pyoverdine Pa, the siderophore of Pseudomonas aeruginosa". Tetrahedron Letters. 24 (44): 4877–4880. doi:10.1016/S0040-4039(00)94031-0.
  3. ^ Menhart, N.; Thariath, A.; Viswanatha, T. (1991). "Characterization of the pyoverdines of Azotobacter vinelandii ATCC 12837 with regard to heterogeneity". Biology of Metals. 4 (4): 223–32. doi:10.1007/bf01141185. PMID 1838001. S2CID 8712926.
  4. ^ Lamont, Iain L.; Beare, Paul A.; Ochsner, Urs; Vasil, Adriana I.; Vasil, Michael L. (2002-05-14). "Siderophore-mediated signaling regulates virulence factor production in Pseudomonasaeruginosa". Proceedings of the National Academy of Sciences of the United States of America. 99 (10): 7072–7077. Bibcode:2002PNAS...99.7072L. doi:10.1073/pnas.092016999. ISSN 0027-8424. PMC 124530. PMID 11997446.
  5. ^ Banin, Ehud; Vasil, Michael L.; Greenberg, E. Peter (2005-08-02). "Iron and Pseudomonas aeruginosa biofilm formation". Proceedings of the National Academy of Sciences of the United States of America. 102 (31): 11076–11081. Bibcode:2005PNAS..10211076B. doi:10.1073/pnas.0504266102. ISSN 0027-8424. PMC 1182440. PMID 16043697.
  6. ^ Kirienko, Natalia V.; Kirienko, Daniel R.; Larkins-Ford, Jonah; Wählby, Carolina; Ruvkun, Gary; Ausubel, Frederick M. (2013-04-17). "Pseudomonas aeruginosa disrupts Caenorhabditis elegans iron homeostasis, causing a hypoxic response and death". Cell Host & Microbe. 13 (4): 406–416. doi:10.1016/j.chom.2013.03.003. ISSN 1934-6069. PMC 3641844. PMID 23601103.
  7. ^ Kirienko, Natalia V.; Ausubel, Frederick M.; Ruvkun, Gary (2015-02-10). "Mitophagy confers resistance to siderophore-mediated killing by Pseudomonas aeruginosa". Proceedings of the National Academy of Sciences of the United States of America. 112 (6): 1821–1826. Bibcode:2015PNAS..112.1821K. doi:10.1073/pnas.1424954112. ISSN 1091-6490. PMC 4330731. PMID 25624506.
  8. ^ Minandri, Fabrizia; Imperi, Francesco; Frangipani, Emanuela; Bonchi, Carlo; Visaggio, Daniela; Facchini, Marcella; Pasquali, Paolo; Bragonzi, Alessandra; Visca, Paolo (2016-08-01). "Role of Iron Uptake Systems in Pseudomonas aeruginosa Virulence and Airway Infection". Infection and Immunity. 84 (8): 2324–2335. doi:10.1128/IAI.00098-16. ISSN 1098-5522. PMC 4962624. PMID 27271740.
  9. ^ Yoder, Michael F.; Kisaalita, William S. (2011-01-01). "Iron specificity of a biosensor based on fluorescent pyoverdin immobilized in sol-gel glass". Journal of Biological Engineering. 5: 4. doi:10.1186/1754-1611-5-4. ISSN 1754-1611. PMC 3114707. PMID 21554740.