Medicinal Chemistry Research
phospholipids, lipopolysaccharides, lipoteichoic acids and
lipoproteins, which pose an impermeable barrier to anti-
microbial agents (Alves et al. 2014). Therefore, the present
results are accord with these features already known.
Gyulkhandanyan A, Gyulkhandanyan L, Ghazaryan R, Fleury F,
Angelini M, Gyulkhandanyan G, Sakanyan V (2013) Assessment
of new cationic porphyrin binding to plasma proteins by planar
microarray and spectroscopic methods. J Biomol Struct Dyn 31
(4):363–375
Haeubl M, Reith LM, Gruber B, Karner U, Müller N, Knör G,
Schoefberger W (2009) DNA interactions and photocatalytic
strand cleavage by artificial nucleases based on water-soluble
gold(III) porphyrins. J Biol Inorg Chem 14(7):1037–1052
Kalyanasundaram K (1984) Photochemistry of water-soluble por-
phyrins: comparative study of isomeric tetrapyridyl- and
tetrakis(N-methylpyridiniumyl)porphyrins. Inorg Chem 23
(16):2453–2459
Kano K, Fukuda K, Wakami H, Nishiyabu R, Pasternack RF (2000)
Factors influencing self-aggregation tendencies of cationic por-
phyrins in aqueous solution. J Am Chem Soc 122(31):7494–7502
Kim YH, Jung SD, Lee MH, Im C, Kim YH, Jang YJ, Kim SK, Cho
DW (2013) Photoinduced reduction of manganese(III) meso-tet-
rakis(1-methylpyridinium-4-yl)porphyrin at AT and GC base
pairs. J Phys Chem B 117(33):9585–9590
Kubát P, Lang K, Anzenbacher Jr P, Jursíková K, Král V, Ehrenberg B
(2000) Interaction of novel cationic meso-tetraphenylporphyrins
in the ground and excited states with DNA and nucleotides. J
Chem Soc Perkin Trans 1(6):933–941
Lang K, Mosinger J, Wagnerová DM (2004) Photophysical properties
of porphyrinoid sensitizers non-covalently bound to host mole-
cules; models for photodynamic therapy. Coord Chem Rev 248
(3–4):321–350
Conclusion
Apy-bonded tricationic P-porphyrins (1) could photo-
inactivate E. coli. The [P] value for E. coli was optimized at
bis[5-(3-ethyl-1-pyridinio)-3-oxapentyloxo]tetra-
phenylporphyrinatophosphorus dibromide, chloride (1b).
Polycationic porphyrins have strong binding affinities to
DNA (Pasternack et al. 2001; Sirish et al. 2002; Marczak
et al. 2007; Haeubl et al. 2009; Tada-Oikawa et al. 2009;
Kim et al. 2013) and proteins (Gyulkhandanyan et al. 2013).
Alkyl chains might result in moderate hydrophobicity to
take advantage of passing through cell wall. Therefore, it is
important to provide the porphyrins with both polycationic
character and hydrophobicity for an efficient PDI of E. coli.
Acknowledgements This research was supported by a Grant-in-Aid
for Scientific Research (C) (16K05847) from the Japan Society for the
Promotion of Science (JSPS).
Marczak R, Sgobba V, Kutner W, Gadde S, D’Souza F, Guldi DM
(2007) Langmuir-Blodgett films of a cationic zinc porphyrin -
Imidazole- functionalized fullerene dyad: formation and photo-
electronchemical studies. Langmuir 23(4):1917–1923
Matsumoto J, Kai Y, Yokoi H, Okazaki S, Yasuda M (2016) Assis-
tance of human serum albumin to photo-sensitized inactivation of
Saccharomyces cerevisiae with axially pyridinio-bonded P-por-
phyrins. J Photochem Photobiol B 161:279–283
Compliance with ethical standards
Conflict of interest The authors declare that they have no conflict of
interest.
Matsumoto J, Kubo T, Shinbara T, Matsuda N, Shiragami T, Fujitsuka
M, Majima T, Yasuda M (2013) Spectroscopic analysis of the
interaction of human serum albumin with tricationic phosphorus
porphyrins bearing axial pyridinio groups. Bull Chem Soc Jpn 86
(11):1240–1247
Matsumoto J, Shiragami T, Hirakawa K, Yasuda M (2015) Water-
solubilization of P(V) and Sb(V) porphyrins and their photo-
Matsumoto J, Suemoto Y, Kanemaru H, Takemori K, Shigehara M,
Miyamoto A, Yokoi H, Yasuda M (2017a) Alkyl substituent
effect on photosensitized inactivation of Escherichia coli by
pyridinium- bonded P-porphyrins. J Photochem Photobiol B
168:124–131
Matsumoto J, Suzuki K, Uezono H, Watanabe K, Yasuda M (2017b)
Additive effect of heparin on the photoinactivation of Escherichia
coli using tricationic P-porphyrins. Bioorg Med Chem Lett
27:5258–5261
Nyman ES, Hynninen PH (2004) Research advances in the use of
tetrapyrrolic photosensitizers for photodynamic therapy. J Pho-
tochem Photobiol B 73(1–2):1–28
Pandey RK, Zheng G (2000) Porphyrins as photosensitizers in pho-
todynamic therapy. In: Kadish KM, Smith KM, Guilluy R (ed)
The porphyrin handbook. vol 6. Academic Press, San Diego, pp
157–230
Pasternack RF, Ewen S, Rao A, Meyer AS, Freedman MA, Collings
PJ, Frey SL, Ranen MC, De Paula JC (2001) Interactions of
copper(II) porphyrins with DNA. Inorg Chim Acta 317
(1–2):59–71
References
Alves E, Faustino MAF, Neves MGPMS, Cunha T, Nadais H,
Almeida A (2014) Potential applications of porphyrins in pho-
todynamic inactivation beyond the medical scope. J Photochem
Photobiol C 22:34–57
Banfi S, Caruso E, Buccafurni L, Battini V, Zazzaron S, Barbieri P,
Orlandi V (2006) Antibacterial activity of tetraaryl-porphyrin
photosensitizers: an in vitro study on Gram negative and Gram
positive bacteria. J Photochem Photobiol B 85(1):28–38
Batinic-Haberle I, Spasojevic I, Tse HM, Tovmasyan A, Rajic Z, Clair
DKS, Vujaskovic Z, Dewhirst MW, Piganelli JD (2012) Design
of Mn porphyrins for treating oxidative stress injuries and their
redox-based regulation of cellular transcriptional activities.
Amino Acids 42(1):95–113
Ben Amor T, Bortolotto L, Jori G (1998) Porphyrins and related
compounds as photoactivatable insecticides. 2. Phototoxic activ-
ity of meso-substituted porphyrins. Photochem Photobiol 68
(3):314–318
Clifton CE (1931) Photodynamic action of certain dyes on the inac-
tivation of Staphylococcus bacteriophage. Proc Soc Exp Biol
Med 28(7):745–746
Ethirajan M, Chen Y, Joshi P, Pandey RK (2011) The role of por-
phyrin chemistry in tumor imaging and photodynamic therapy.
Chem Soc Rev 40(1):340–362
Girek B, Sliwa W (2013) Porphyrins functionalized by quaternary
pyridinium units. J Porphyr Phthalocyanines 17(12):1139–1156