Y. Nitzan et al., STRUCTURE-ACTIVITY RELATIONSHIP OF PORPHINES FOR PHOTOINACTIVATION OFBACTERIA, Photochemistry and photobiology, 62(2), 1995, pp. 342-347
The antibacterial photodynamic effects of uncharged (o-tetrahydroxyphe
nyl porphine [THPP], m-THPP and p-THPP), cationic (5,10,15,20-tetra[4-
N-methylpyridyl]porphine [TMPyP]) and anionic (5,10,15,20-tetra[4-sulf
onatophenyl porphine] [TPPS4]) porphines on Staphylococcus aureus and
Escherichia ici coli bacteria inactivation were examined. The results
show that uncharged porphines provoked antibacterial photodynamic acti
vity on S. aureus, and also on E. coli in the presence of the membrane
-disorganizing peptide polymixin B nonapeptide (PMNP). The TMPyP compo
und was highly photoactive toward gram-positive bacteria but only marg
inally effective on gram-negative cells, whereas TPPS, showed no activ
ity on either gram-positive or gram-negative bacteria. The photoactivi
ty of TMPyP is due to the electrostatic attraction between the positiv
ely charged sensitizer molecule and the negatively charged membrane of
the gram-positive target cells. For TPPS4, the inactivity toward gram
-positive bacteria is due to electrostatic repulsion between the charg
ed sensitizer molecule and the cell membrane. For gram-negative bacter
ia, the inactivity is conceivably due to preferential (electrostatic)
binding to the positively charged PMNP, which is an adjuvant for membr
ane disorganization, but has a no effect on cell viability. For hydrop
hobic sensitizers, the photoactivity depends on the state of aggregati
on, The extent of deaggregation of the different THPP isomers was dete
rmined by fluorescence measurements of bound sensitizers and could be
positively correlated with their photoinactivation capacity. We conclu
de that the structure-activity relationships of these porphines are af
fected by their net charge and by aggregation.