The role of carboxymethyl substituents in the interaction of tetracationic porphyrins with DNA

Kovaleva, Oxana; Цветков, В. Б.; Shchyolkina, Anna K.; Borisova, O. F.; Ol’shevskaya, V. A.; Makarenkov, Anton V.; Semeikin, А. S.; Shtil, Alexander A.; Kaluzhny, Dmitry N.

doi:10.1007/s00249-012-0848-y

Cited by 12 publications

(2 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One should take note of the increasing number of reports concerning porphyrins functionalized by pyridinium units for their useful applications in biological studies [116][117][118][119], as well as for showing other valuable properties [120][121][122].…”

Section: Resultsmentioning

confidence: 99%

Porphyrins functionalized by quaternary pyridinium units

Girek

Śliwa

2013

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

In this review, free-base and metalloporphyrins, functionalized on meso-positions by quaternary pyridinium units, also referred to as cationic porphyrins, are presented. The article consists of five parts. In the first part free-base porphyrins are described, especially taking account on generation of singlet oxygen; next parts concern metalloporphyrins. The second and third parts deal with zinc and manganese porphyrins, respectively; in the fourth part copper, palladium, and platinum porphyrins are presented. In the fifth part, describing porphyrins with various metal ions an attention is paid to porphyrin metal-organic frameworks (MOFs) and metal-organic materials (MOMs) in which metalloporphyrins are immobilized; syntheses and characterization of obtained products are shown.

show abstract

Section: Resultsmentioning

confidence: 99%

Porphyrins functionalized by quaternary pyridinium units

Girek

Śliwa

2013

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

show abstract

“…The P4 was TMPyP4 (Sigma Aldrich, Saint Louis, MO, USA). The compounds ZnP4, P1, and ZnP1 were obtained as described previously [ 8 , 21 , 22 ]. Stock solutions with a porphyrin concentration of 10 mM in DMSO (PanEko, Moscow, Russia) were used.…”

Section: Methodsmentioning

confidence: 99%

Mechanisms of Phototoxic Effects of Cationic Porphyrins on Human Cells In Vitro

et al. 2023

Self Cite

View full text Add to dashboard Cite

The toxic effects of four cationic porphyrins on various human cells were studied in vitro. It was found that, under dark conditions, porphyrins are almost nontoxic, while, under the action of light, the toxic effect was observed starting from nanomolar concentrations. At a concentration of 100 nM, porphyrins caused inhibition of metabolism in the MTT test in normal and cancer cells. Furthermore, low concentrations of porphyrins inhibited colony formation. The toxic effect was nonlinear; with increasing concentrations of various porphyrins, up to about 1 μM, the effect reached a plateau. In addition to the MTT test, this was repeated in experiments examining cell permeability to trypan blue, as well as survival after 24 h. The first visible manifestation of the toxic action of porphyrins is blebbing and swelling of cells. Against the background of this process, permeability to porphyrins and trypan blue appears. Subsequently, most cells (even mitotic cells) freeze in this swollen state for a long time (24 and even 48 h), remaining attached. Cellular morphology is mostly preserved. Thus, it is clear that the cells undergo mainly necrotic death. The hypothesis proposed is that the concentration dependence of membrane damage indicates a limited number of porphyrin targets on the membrane. These targets may be any ion channels, which should be considered in photodynamic therapy.

show abstract

Preferential DNA photocleavage potency of Zn(II) over Ni(II) derivatives of carboxymethyl tetracationic porphyrin: the role of the mode of binding to DNA

et al. 2014

View full text Add to dashboard Cite

The porphyrin-based photosensitizers capable of binding to DNA are perspective drug candidates. Here we report the interactions with calf thymus DNA of 5,10,15,20-tetrakis(N-carboxymethyl-4-pyridinium)porphyrin (P1) and its derivatives containing Zn(II) or Ni(II) in the coordination sphere. These interactions were studied with absorption and circular dichroism spectroscopy. NiP1 and ZnP1 formed different types of complexes with DNA. NiP1 intercalated into the double helix, whereas ZnP1 bound the DNA groove. Compound P1 displayed both binding modes. The ZnP1-DNA binding constant was approximately three times smaller than the respective values for P1-DNA and NiP1-DNA complexes. Light induced degradation of the reactive oxygen species (ROS) trap 1,3-diphenylisobenzofuran in the presence of P1 and its metal derivatives revealed that NiP1 was a weaker photooxidative agent, whereas P1 and ZnP1 generated ROS to similar extents. Nevertheless, the DNA photodamaging effect of ZnP1 was the most pronounced. Illumination of the supercoiled plasmid caused single-strand DNA photocleavage in the presence of P1 and ZnP1; double strand breaks were detectable with micromolar concentrations of ZnP1. The concentration of ZnP1 required for plasmid photonicking was two times smaller than that of P1 and ~20 times lower than that for NiP1. Thus, the modes of P1, NiP1 and ZnP1 binding to DNA determine the differential photodamaging potency of these porphyrins. A greater accessibility to the solvent of the groove binder ZnP1, compared to the shielded intercalator NiP1 and the intercalated P1 molecules, allows for an efficient local generation of ROS followed by DNA photocleavage.

show abstract

The role of carboxymethyl substituents in the interaction of tetracationic porphyrins with DNA

Cited by 12 publications

References 31 publications

Porphyrins functionalized by quaternary pyridinium units

Porphyrins functionalized by quaternary pyridinium units

Mechanisms of Phototoxic Effects of Cationic Porphyrins on Human Cells In Vitro

Preferential DNA photocleavage potency of Zn(II) over Ni(II) derivatives of carboxymethyl tetracationic porphyrin: the role of the mode of binding to DNA

Contact Info

Product

Resources

About