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Review

Antimicrobial properties of porphyrins

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Pages 309-320 | Published online: 24 Feb 2005

Bibliography

  • ASANAKA M, KURIMURA T, TOYA H et al.: Anti-HIV activity of protoporphyrin. AIDS (1989) 3:403–404.
  • BALLA J, BALLA G, JENEY V et al.: Ferriporphyrins and endothelium: a 2-edged sword-promotion of oxidation and induction of cytoprotectants. He1770. Thromb. Vascular Biol. (2000) 95:3442–3450.
  • BEALE SI: Biosynthesis of hemes. In: Escherichia coil and Salmonella 07phimurium (Second Edition). Neidhardt FC et al. (Eds.), ASM Press Washington D.C., USA (1996):731–748.
  • BERT R, CHANDRA R: Chemistry and biology of heme. Drug Met. Rev. (1993) 25:49–85.
  • BERNSTEIN LR: Mechanisms of therapeutic activity of gallium. Pharmacol. Rev. (1998) 50:665–681.
  • BERTOLINI G, SACCHETTO R, JORI G et al.: Protopor-phyrin photosensitization of Enterococcus hirae and Candida albicans cells. Laser. Life Sci. (1993) 5:267–275.
  • BERTOLONI G, ROSSI F, VALDUGA G et al.: Photosensi-tizing activity of water- and lipid-soluble phthalocya-nines on prokaryotic and eukaryotic microbial cells. Microbial. (1992) 71:33–46.
  • BERTOLONI G, SALVATO B, ACQUA MD et al.:Hematoporphyrin-sensitized photoinactivation of Streptococcus faecalis. Photochem. Photobial (1984) 39:811–816.
  • BERTOLONI G, REDDI E, GATTA M, BURLINI C, JORI G:Factors influencing the haematoporphyrin-sensitized photoinactivation of Candida albicans cells. J. Gen. Microbial (1989) 135:957–966.
  • BHATTI M, MACROBERT A, MEGHJI S et al.: Effects of dosimetric and physiological factors on the lethal photosensitization of Porphyromanas gingivalis in vitro. Photochem. Photobiol. (1997) 65:1026–1031.
  • BONNETT R: Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chem. Soc. Rev. (1995) 24:19–33.
  • BONNETT R, BUCKLEY DG, BURROW T et al.: Photobac-tericidal materials based on porphyrins and phthalo-cyanines. J. Mater. Chem. (1993) 3:323–324.
  • BRACKEN CS, BAER MT, ABDUR-RASHID A, HELMS W,STOJILJKOVIC I: Use of heme-protein complexes by the Yersinia enterocolitica HemR receptor: histidine residues are essential for receptor function. J. Bacterial. (1999) 181:6063–6072.
  • CALVIN M: Chemical Evolution. Oxford University Press, New York, USA (1969):9–26.
  • CANNON JB: Pharmaceutics and drug delivery aspects of heme and porphyrin therapy. J. Pharm. Sci. (1993) 82:435–448.
  • CANNON JB, KUO F-S, PASTERNACK RF et al.: Kinetics ofthe interaction of hemin liposomes with heme binding proteins. Biochemistry (1984) 23:3715–3721.
  • COX GS, BOBILLIER C, WHITTEN DG: Photooxidation and singlet oxygen sensitization by protoporphyrin IX and its photooxidation products. Photochem. Photobiol. (1982) 36:401–407.
  • COUTSOLELOS A, GUILARD R: Synthese et caracteris-tiques physicochimiques de gallioporphyrines a liason a metal-carbone. J. Organometal. Chem. (1983) 253:273–282.
  • DEBNATH AK, JIANG S, STRICK N: Three-dimensionalstructure-activity analysis of a series of porphyrin derivatives with anti-111V-1 activity targeted to the V3 loop of the gp120 envelope glycoprotein of the human immunodeficiency virus typel. J. Med. Chem. (1994) 37:1099–1108.
  • DECAMP DL, BABE LM, SALTO M et al.: Specific inhibi-tion of HIV-1 protease by boronated porphyrins. Med. Chem. (1992) 35:3426–3428.
  • DIXON DW, KIM MS, KUMAR V et al.: Amino- andhydroxytetraphenylporphyrins with activity against the human immunodeficiency virus. Antiviral Chem. Chemother. (1992) 3:279–282.
  • DOBSON J, WILSON M: Sensitization of oral bacteria inbilfilms to killing by light from a low-power laser. Archs. Oral Biol. (1992) 37:883–887.
  • DOUGHERTY TJ, GOMER CJ, HENDERSON N et al.: Photodynamic therapy. J. Natl. Cancer Inst. (1998) 90:889–905.
  • DRAZEK ES, HAMMACK CA, SCHMITT MP: Carynebacte-rium diphtheriae genes required for acquisition of iron from haemin and haemoglobin are homologous to ABC haemin transporters. Mol. Microbial. (2000) 36:68–84.
  • EVERSE J, HSIA N: The toxicites of native and modified hemoglobins. Fr. Rad. Biol. Med. (1997) 22:1075–1099.
  • FALK JE: Porphyrins and Metalloporphyrins. Elsevier Publishing Company, Netherlands (1964).
  • FROLOVA El, IVANOVA EM, ZARYTOVA VF et al.: Synthesis and sequence-specific modification of ssDNA. FEBS (1990) 269:101–104.
  • GHOSH A, GHOSH M, NIU C et al.: Iron transport-mediated drug delivery using mixed-ligand siderophore-beta-lactam conjugates. Chem. Biol. (1996) 3:1011–1019.
  • GRANDADAM M, INGRAND D, HURAUX J-M et al.: Photodynamic inactivation of cell-free HIV strains by a red-absorbing chlorin-type photosensitizer. J. Photochem. Photobiol. B (1995) 31:171–177.
  • HUBBARD JAM, LEWANDOWSKA KB, HUGHES K et al.:Effects of iron-limitation of Escherichia coli on growth, the respiratory chains and gallium uptake. Arch. Microbial. (1986) 146:80–86.
  • HUGHES TE, HANSEN LA: Gallium nitrate. Ann.Pharmacol. (1992) 26:354–371.
  • JENKINS RD, STEVENS S, CRAYTHORN JM et al.: Falsesusceptibility of enterococci to aminoglycosides with blood-enriched mueller-hinton agar for disk suscepti-bility testing. J. Clin. Microbial (1985) 22:369–374.
  • JORI G, SPIKES JD: Photobiochemistry of porphyrins. In: Topics in Photomedicine. Smith KC (Ed.) (1984):183–318.
  • KAPLAN ML, DYE W: Growth requirements of some small-colony-forming variants of Staphylococcus aureus. J. Clin. Microbial. (1976) 4:343–348.
  • LABBE RF: History and background of protoporphyrin testing. Clin. Chem. (1977) 23:256–262.
  • LADAN H, NITZAN Y, MALIK Z: The antibacterial activity of haemin compared with cobalt, zinc and magnesium protoporphyrin and its effect on potassium loss and ultrastructure of Staphylococcus aureus. FEMS Microbial. Lett. (1993) 112:173–177.
  • LAMOLA AA, YAMME T: Zinc protoporphyrin in the erythrocytes of patients with lead intoxication and iron deficiency anemia. Science (1974) 186:936.
  • LEVERE RD, GONG YF, KAPPAS A et al.: Herne inhibits human immunodeficiency virus 1 replication in cell cultures and enhances the antiviral effect of zidovu-dine. Proc. Natl. Acad. Sci. USA (1991) 88:1756–1759.
  • LIGHT WR, OLSON JS: Transmembrane movement of heme. J. Biol. Chem. (1990) 265:15623–15631.
  • LIN H, EVERSE J: The cytotoxic activity of hematoheme: Evidence for two different mechanisms. Anal. Biochem. (1987) 161:323–331.
  • LU X-M, FISCHMAN AJ, STEVENS E et al.: Sn-chlorin e6 antibacterial immunoconjugates An in vitro and in vivoanalysis.j Immunological Methods (1992) 156:85–99.
  • MAINES MD: Herne oxygenase: clinical applications and functions. CRC Press, Inc. Boca Raton, USA (1992).
  • MALIK Z, HANANIA J, NITZAN Y: Bactericidal effects ofphotoactivated porphyrins - an alternative approach to antimicrobial drugs. J. Photochem. Photobiol. B (1990) 5:281–293.
  • MALIK Z, LADAN H, NITZAN Y: The bactericidal activityof a deuteroporphyrin-hemin mixture on Gram-positive bacteria. A microbiological and spectroscopic study. J. Photochem. Photobiol. B (1990) 6:419–430.
  • MINNOCK A, VERNON DI, SCHOFIELD J et al.:Mechanism of uptake of a cationic water-soluble pyridinium zinc phthalocyanine across the outer membrane of Escherichia coli. Antimicrob. Agents Chemother. (2000) 44:522–527.
  • MINNOCK A, VERNON, DI, SCHOFIELD J, GRIFFITHS J,PARISH JH, BROWN SB: Photoinactivation of bacteria. Use of a cationic water-soluble zinc phthalocyanine to photo inactivate both Gram-positive and Gram-negative bacteria. J. Photochem. Photobiol. B Biol. (1996) 32:159–164.
  • MERCHAT M, BERTOLINI G, GIACOMINI P et al.: Meso-substituted cationic porphyrins as efficient photosensitizers of Gram-positive and Gram-negative bacteria. J. Photochem. Photobiol. B (1996) 32:153–157.
  • MILGROM LR: The Colours of Life. Oxford University Press, New York, USA (1997).
  • MOAN J, BERG K: The photodegradation of porphyrins in cells can be used to estimate the lifetime of singlet oxygen. Photochem. Photobiol. (1991) 53:549–553.
  • MOORE DG, YANCEY RJ, LANKFORD CE, EARHART CF:Bacteriostatic enterochelin-specific immunoglobulin from normal human serum. Infect. Immun. (1980) 27:418–423.
  • NEU HC: The crisis in antibiotic resistance. Science (1992) 257:1064–1073.
  • NELLY AN, MALEY MP: Survival of enterococci and staphylococci on hospital fabrics and plastic. J Clin. Microbial (2000) 38:724–726.
  • NIKAIDO H: Prevention of drug access to bacterial targets: permeability barriers and active efflux. Science (1994) 264:382–385.
  • NIR U, LADAN H, MALIK Z et al.: In vivo effects ofporphyrins on bacterial DNA./ Photochem. Photobiol. B (1991) 11:295–306.
  • NITZAN Y, DROR R, LADAN H et al.: Structure-activityrelationship of porphines for photoinactivation of bacteria. Photochem. Photobiol. (1995) 62:342–347.
  • NITZAN Y, GUTTERMAN M, MALIK Z et al.: Inactivation ofGram-negative bacteria by photosensitized porphyrins. Photochem. Photobiol. (1992) 55:89–96.
  • NITZAN Y, LADAN H, GOZANSKY S et al: Characteriza-tion of hemin antibacterial action on Staphylococcus aureus. FEMS Microbial. Lett. (1987) 48:401–406.
  • NITZAN Y, LADAN H, MALIK Z: Growth-inhibitory effect of hemin on Staphylococci. CWT. Microbial. (1987) 14:279–284.
  • NORTH J, NEYNDORFF H, LEVY JG: Photosensitizers asvirucidal agents. J. Photochem. Photobiol. B (1993) 17:99–108.
  • OLAKANMI 0, BRITIGAN BE, SCHLESINGER LS: Galliumdisrupts iron metabolism of mycobacteria residing within human macrophages. Infect. 1177177L117. (2000) 68:5619-5627.
  • OENBRINK G, JURGENLIMKE P, GABEL D: Accumulationof porphyrins in cells: Influence of hydrophobicity aggregation and protein binding. Photochem. Photobiol. (1988) 48:451–456.
  • PHELPS CE: Bug/drug resistance: sometimes less ismore. Medical Care (1989) 27:194–203.
  • PRIOLA SA, RAINES A, CAUGHEY WS: Porphyrin and phtalocyanine antiscrapie compounds. Science (2000) 287:1503–1506.
  • PROCTOR RA, BALWIT JM, VESGA 0: Variant subpopula-tions of Staphylococcus aureus as cause of persistent and recurrent infections. Infect. Agents Dis. (1994) 3:302–312.
  • PROFET M: Menstruation as a defense againstpathogens transported by sperm. Quart. Rev. Biol. (1993) 68:335–385.
  • SANTUS R, GRELLIER P, SCHREVEL J et al.: Photodecon-tamination of blood components: advantages and drawbacks. Clin. Hemorh. Microcirc. (1998) 18:299–308.
  • SCHRYVERS AB, STOJILJKOVIC I: Iron acquisition in the pathogenic Neisseria. Mol. Microbiol. (1 9 9 9) 3 2:1117-1123.
  • SCHNEIDER R, HANTKE K: Iron-hydroxamate uptake systems in Bacillus subtilis: identification of a lipopr o-tein as part of a binding protein-dependent transport system. Mol. Microbial. (1993) 8:111–121.
  • SHAWAR R, COOPER BH: Comparative kinetics of hematoporphyrin derivative uptake and susceptibility of Bacillus subtilis and Streptococcus faecalis to photodynamic action. Photochem. Photobiol. (1990) 52:825–830.
  • STAUDINGER R, ABRAHAM NG, LEVERE RD et al.: Inhibi-tion of human immunodeficiency virus-1 reverse transcriptase by heme and synthetic analogs. Proc. Assoc. Am. Physicians (1996) 108:47–54.
  • STOJILJKOVIC I, HANTKE K: Transport of haemin across the cytoplasmic membrane through a haemin-specific periplasmic binding protein-dependent transport system in Yersinia enterocolitica. Mal Microbiol. (1994) 13:719–732.
  • STOJILJKOVIC I, HANTKE K: Hemin-uptake system in Yersinia enterocolitica: similarities with other TonB-dependent systems in Gram negative bacteria. EMBO J (1992) 11:4359–4367.
  • STOJILJKOVIC I, KUMAR V, SRINIVASAN N: Non-iron metalloporphyrins: potent antibacterial compounds that exploit heme/Hb uptake systems of pathogenic bacteria. Mol. Microbiol. (1999) 31:429–442.
  • SOL V, BRANLAND P, GRANET R et al.: Mtroglycosylated meso-arylporphyrins as photoinhibitors of Gram positive bacteria. Bioorg. Med. Chem. Lett. (1998) 8:3007–3010.
  • SOUKOS NS, XIMENEZ-FYVIE LA, HAMBLIN MR et al.:Targeted antimicrobial photochemotherapy. Antimi-crab. Agents Chemother. (1998) 42:2595–2601.
  • SZOCS K, GABOR F, CSIK G et al.: 8-Aminolaevulinicacid-induced porphyrin synthesis and photodynamic inactivation of Escherichia coli B. J. Photochem. Photobiol. B (1990) 50:8–17.
  • TILBURY RN, QUICKENDEN TI: Spectral and timedependence studies of the ultraweak bioluminiscence emitted by the bacterium Escherichia coil. Photochem. Photobiol. (1988) 47:145–150.
  • TIPPING E, KETTERER B, CHRISTODOULIDES L: Interac-tions of small molecules with phospholipid bilayers. Biochem. J (1979) 180:327–337.
  • TSOLIS R, BAUMLER AJ, HEFFRON F et al.: Contributionof different Salmonella typhimurium iron-uptake systems in virulence for mice. Infect. 1177177L117. (1996) 64:4549-4556.
  • TSUTSUI K, MUELLER GC: Hemin inhibits virion-associated reverse transcriptase of murine leukemia virus. Biochem. Biophys. Res. Commun. (1987) 149:628–634.
  • VAN DER MEULEN FW, IBRAHIM K, STERENBORG HJCM etal.: Photodynamic destruction of Haemophilus parainfluenzae by endogenously produced porphyrins. J. Photochem. Photobiol. B (1997) 40:204–208.
  • VENZIO FR, DIVINCENZO RS, REICHMAN M et al.: Bacteri-cidal effects of photoradiation therapy with hemato-porphyrin derivative. J. Infect. Dis. (1985) 151:166–169.
  • VILLANUEVA A: The cationic mesosubstitutedporphyrins -an interesting group of photosensitizers. J. Photochem. Photobiol. B (1993) 23:295–296.
  • WAINWRIGHT M: Photodynamic antimicrobial chemotherapy (PACT). J. Antimicrob. Chem. (1998) 42:13–28.
  • WAINWRIGHT M: Non-porphyrin photosensitizers in biomedicine. Chem. Soc. Rev. (1996) 351–359.
  • WANDERSMAN C, STOJILJKOVIC I: Bacterial heme sources. Curr. Opin. Microbial. (2000) 3:215–220.
  • WARREN MJ, SCOTT Al. Tertrapyrrole assembly and modification into the ligands of biologically functional cofactors. Trends Biol. Sci. (1990) 15:486–491.
  • WILSON M, DOBSON J: Lethal photosensitization of oral anaerobic bacteria. CID (1993) 16:414–417.
  • ZHU W, HUNT JT, RICHARDSON AR, STOJILJKOVIC I: Use of heme compounds as iron sources by pathogenic Neisseriae requires the product of the hem° gene J. Bacterial. (2000) 182:439–447.
  • ZHU W, WILKS A, STOJILJKOVIC I: Degradation of heme in Gram-negative bacteria: the product of the hem() gene of neisseriae is a heme oxygenase. j Bacterial. (2000) 182:6783–6790.

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