Photodynamic effects of a novel pterin derivative on a pancreatic cancer cell line

Yamada, Hiroko; Arai, Toshiyuki; Endo, Nobuyuki; Yamashita, Kouhei; Nonogawa, Mitsuru; Makino, Keisuke; Fukuda, Kazuhiko; Sasada, Masataka; Uchiyama, Takashi

doi:10.1016/j.bbrc.2005.05.185

Cited by 18 publications

(21 citation statements)

References 15 publications

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“…In our current study, we explored the mechanism by which antibodies produce ozone from singlet oxygen and water. We previously established a cell-free system, in which 6-formylpterin (6FP), a potent xanthine oxidase inhibitor, produces singlet oxygen without superoxide formation under UVA radiation in aqueous solutions (9). Using this system, we found that the portion of F(abЈ) 2 of antibodies, albumin, and chemotactic peptide, formyl-methionyl-leucyl-phenylalanine (FMLP), had the potential to generate an oxidant with the chemical signature of ozone, as intact antibodies (IgG) did, as denoted by the oxidation reaction of indigo carmine to isatin sulfonic acids, detected by a spectrophotometric assay (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…6FP was obtained from Sankyo Kasei Kogyo. 6FP-tBu-DMF was synthesized in our laboratories at the Institute of Advanced Energy, Kyoto University (9). CLA was purchased from Tokyo Kasei Kogyo; MVP, DHR, and the Amplex Red H2O2 kit were from Molecular Probes.…”

Section: Methodsmentioning

confidence: 99%

“…Bactericidal studies were performed on catalase-positive bacteria, Escherichia coli, NIHJ-JC2. In this experiment, to increase solubility in water, we used a variant of 6FP, 2-(N,N-dimethylaminomethyleneamino)-6-formyl-3-pivaloylpteridine-4-one (6FP-tBu-DMF), which generates singlet oxygen to a similar extent to 6FP (9). Viable E. coli were nearly undetectable with the addition of 6FP-tBu-DMF and amino acids (Trp or Met) after a 2-h irradiation, whereas 6FP-tBu-DMF alone had little effect on the viability of E. coli even with a 2-h irradiation (Fig.…”

Section: Ozone Produced By Amino Acids Exhibits Bactericidal Activitymentioning

confidence: 99%

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Ozone production by amino acids contributes to killing of bacteria

Yamashita¹,

Miyoshi²,

Arai

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

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Reactive oxygen species produced by phagocytosing neutrophils are essential for innate host defense against invading microbes. Previous observations revealed that antibody-catalyzed ozone formation by human neutrophils contributed to the killing of bacteria. In this study, we discovered that 4 amino acids themselves were able to catalyze the production of an oxidant with the chemical signature of ozone from singlet oxygen in the wateroxidation pathway, at comparable level to antibodies. The resultant oxidant with the chemical signature of ozone exhibited significant bactericidal activity in our distinct cell-free system and in human neutrophils. The results also suggest that an oxidant with the chemical signature of ozone produced by neutrophils might potentiate a host defense system, when the host is challenged by high doses of infectious agents. Our findings provide biological insights into the killing of bacteria by neutrophils.host defense ͉ singlet oxygen ͉ neutrophil ͉ chronic granulomatous disease

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Ozone Produced By Amino Acids Exhibits Bactericidal Activitymentioning

confidence: 99%

See 1 more Smart Citation

Ozone production by amino acids contributes to killing of bacteria

Yamashita¹,

Miyoshi²,

Arai

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

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“…Second, DFP generates ROS through NADH oxidation at much higher rate than 6FP (10), which may induce undesirable cell death without UV-A irradiation. Third, the photodynamic effects of DFP on Panc-1 cells were not so potent, and high concentrations as much as 500 μM were required to induce cell death (9).…”

mentioning

confidence: 98%

“…1B), which is more soluble in water and lipid than 6FP (8). Furthermore, DFP was taken up by Panc-1 cells and photodynamically induced cell death, indicating that DFP may have applicability in anticancer PDT (9). However, DFP has drawbacks as a photosensitizer.…”

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confidence: 99%

Anticancer Photodynamic and Non-photodynamic Effects of Pterin Derivatives on a Pancreatic Cancer Cell Line

Miyoshi¹,

Arai²,

Nonogawa³

et al. 2008

J Pharmacol Sci

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Abstract. To evaluate the feasibility of two kinds of pterin derivatives, 2-(N,N-dimethylaminomethyleneamino)-6-formyl-3-pivaloylpteridin-4-one (DFP) and 2-(N,N-dimethylaminomethyleneamino)-3-pivaloylpteridin-4-one (DP), as anticancer drugs, their photodynamic and non-photodynamic effects on pancreatic cancer cell line Panc-1 cells were examined. For photodynamic effects, cell death 48 h after UV-A irradiation was more prominent in cells preloaded with DP than DFP. When cells were simply incubated for 96 h without irradiation, DFP induced cell death, while DP suppressed cell proliferation. Furthermore, DP was much more soluble in water than DFP. These findings collectively indicated that DP is more feasible as an anticancer drug than DFP.

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Natural neo acids and neo alkanes: Their analogs and derivatives

Dembitsky

2006

Lipids

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This review presents more than 260 naturally occurring (as well as 47 synthesized) neo fatty (carboxylic) acids, neo alkanes, and their analogs and derivatives, isolated and identified from plants, algae, fungi, marine invertebrates, and microorganisms, that demonstrate different biological activities. These natural metabolites are good prospects for future chemical preparations as antioxidants, and also as anticancer, antimicrobial, and antibacterial agents. Described also are some synthetic bioactive compounds containing a tertiary butyl group(s) that have shown high anticancer, antifungal, and other activities. Applications of some neo fatty (carboxylic) acid derivatives in cosmetic, agronomic, and pharmaceutical industries also are considered. This is the first review to consider naturally occurring neo fatty (carboxylic) acids, neo alkanes, and other metabolites containing a tertiary butyl group(s) [or tert-butyl unit(s)].

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Photodynamic effects of a novel pterin derivative on a pancreatic cancer cell line

Cited by 18 publications

References 15 publications

Ozone production by amino acids contributes to killing of bacteria

Ozone production by amino acids contributes to killing of bacteria

Anticancer Photodynamic and Non-photodynamic Effects of Pterin Derivatives on a Pancreatic Cancer Cell Line

Natural neo acids and neo alkanes: Their analogs and derivatives

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