• Biomolecules & Therapeutics
• /
• v.31 no.2
• /
• pp.219-226
• /
• 2023

Furanocoumarin 8-methoxypsoralen (8-MOP) is the parent compound that naturally occurs in traditional medicinal plants used historically. 8-MOP has been employed as a photochemotherapeutic component of Psoralen + Ultraviolet A (PUVA) therapy for the treatment of vitiligo and psoriasis. Although the role of 8-MOP in PUVA therapy has been studied, little is known about the effects of 8-MOP alone on human gastric cancer cells. In this study, we observed anti-proliferative effect of 8-MOP in several human cancer cell lines. Among these, the human gastric cancer cell line SNU1 is the most sensitive to 8-MOP. 8-MOP treated SNU1 cells showed G1-arrest by upregulating p53 and apoptosis by activating caspase-3 in a dose-dependent manner, which was confirmed by loss-of-function analysis through the knockdown of p53-siRNA and inhibition of apoptosis by Z-VAD-FMK. Moreover, 8-MOP-induced apoptosis is not associated with autophagy or necrosis. The signaling pathway responsible for the effect of 8-MOP on SNU1 cells was confirmed to be related to phosphorylated PI3K, ERK2, and STAT3. In contrast, 8-MOP treatment decreased the expression of the typical metastasis-related proteins MMP-2, MMP-9, and Snail in a p53-independent manner. In accordance with the serendipitous findings, treatment with 8-MOP decreased the wound healing, migration, and invasion ability of cells in a dose-dependent manner. In addition, combination treatment with 8-MOP and gemcitabine was effective at the lowest concentrations. Overall, our findings indicate that oral 8-MOP has the potential to treat early human gastric cancer, with fewer side effects.

• Bulletin of the Korean Chemical Society
• /
• v.12 no.5
• /
• pp.554-559
• /
• 1991

The photophysical and photochemical properties of khellin were compared with those of 8-methoxypsoralen (8-MOP). Quantum yields of fluorescence and triplet formation decreases as solvent polarity increases, which is opposite to 8-MOP, and photocycloadditivity of khellin to olefins is much lower than that of 8-MOP. Electron ejection from khellin by laser flash was not observed, but observed from 8-MOP. As models of 4',5'-monoadducts of khellin or 8-MOP with thymine base, khellin<>dimethylfumarate 4',5'-monoadduct (KDF) was also compared with 8-MOP<>thymidine 4',5'-monoadduct (F-2) in those properties to give some insight on the second-step biadduct formation resulting in cross-links of DNA duplex. KDF and F-2 were very similar to khellin and 8-MOP in photophysical properties, respectively. However, KDF did not form adducts with various olefins, and thus it is thought that 2,3-double bond of chromone moiety in khellin is hardly reactive in contrast with 3,4-double bond of coumarin moiety in 8-MOP. These results indicate that khellin is fairly photostable compound, a poor type Ⅰ photodynamic sensitizer and producer of ${O_2}^{-}$ which is some cause of phototoxic erythemal reactions and undesirable side effects. Therefore khellin is safer to use than 8-MOP in photochemotherapy of some skin diseases. Although khellin is much less reactive than 8-MOP, khellin must be also a monofunctional drug. Since khellin is, however, as effective as 8-MOP in photochemotherapy of some skin diseases, it is suggested that khellin may be different from 8-MOP in the action mechanism.

• The korean journal of orthodontics
• /
• v.51 no.3
• /
• pp.157-165
• /
• 2021

Objective: This study aimed to identify the clinical effectiveness of two different penetration depths of micro-osteoperforations (MOPs) on the rate of orthodontic tooth movement. Methods: Twenty-four patients requiring the removal of the upper first premolar teeth were selected and randomly divided into two groups. The control group participants did not undergo MOPs. Participants in the experimental group underwent three MOPs each at 4-mm (MOP-4) and 7-mm (MOP-7) depths, which were randomly and equally performed to either the left or right side distal to the canine. The retraction amount was measured on three-dimensional digital models on the 28th day of retraction. MOP-related pain was measured using a visual analog scale (VAS). Between-group statistical differences in the VAS scores were determined using an independent t-test and those in canine retraction were determined using analysis of variance and post-hoc Tukey test. Results: No significant difference was found between the MOP-4 (1.22 ± 0.29 mm/month) and MOP-7 (1.29 ± 0.31 mm/month) groups in terms of the canine retraction rate. Moreover, both the groups demonstrated a significantly higher canine movement than the control group (0.88 ± 0.19 mm/month). MOPs did not significantly affect the mesialization of the posterior teeth (p > 0.05). Moreover, the pain scores in the MOP-4 and MOP-7 groups were similar and showed no statistically significant difference. Conclusions: Three MOPs with a depth of 4 mm can be performed as an effective method to increase the rate of tooth movement. However, three MOPs with depths of 4-7 mm does not additionally enhance tooth movement.

• Bulletin of the Korean Chemical Society
• /
• v.4 no.2
• /
• pp.95-99
• /
• 1983

Photoreaction of 8-methoxypsoralen (8-MOP) with thymine (${\ge}$ 300 nm) was carried out in the dioxane-water frozen state. One major and two minor monoaddition products between 8-MOP and thymine were isolated by various chromatographic methods. Major monoadduct was characterized to be a C4 cycloaddition product formed between 5,6-double bond of thymine and 3,4-double bond of 8-MOP with cis-anti stereochemistry. Two minor adducts were proved to be stereoisomers of this major adduct.

• Journal of Photoscience
• /
• v.3 no.1
• /
• pp.29-31
• /
• 1996

Psoralens are metabolized in the liver and thus can produce liver damage in laboratory animals when given in excessive doses. However, in humans, reports of the effects of psoralens on liver functions during photochemotherapy have been contradictory. We studied 311 patients t o observe the effects of various phototoxic drugs: 8-methoxypsoralen (8-MOP), 5-methoxypsoralen (5-MOP), 4,5,8-trimethylpsoralen (TMP)-on liver function during photochemotherapy. Of the 311 patients, only seven had transient elevations of transaminases. Incidence of hepatotoxicity of 8-MOP, TMP and 5-MOP showed 0.6%, 6% and 3%, respectively. Although the effects of psoralens on liver functions during photochemotherapy have been contradictory in humans and there have been few cases showing transient elevated values of liver transaminases during photochemotherapy, it is advisable to obtain serial liver function tests before and during photochemotherapy.

• Bulletin of the Korean Chemical Society
• /
• v.28 no.10
• /
• pp.1715-1719
• /
• 2007

New bispsoralen derivatives 5-10, 8-MOP-NHCO(CH2)nCONH-8-MOP (BPSBA-Cn, n = 0, 1, 2, 3, 4 and 5) in which 5 position of an 8-methoxypsoralen (8-MOP) is linked by various lengths of bisamide polymethylene chain to 5 position of the other 8-MOP, have been synthesized by the amidation of 5-amino-8-methoxypsoralen (12) with α,ω-alkanoyl dichloride. Photophysical properties of their derivatives including π?π stacking interaction between the two aromatic moieties were investigated by UV absorption and fluorescence emission spectra. Efficient ring-ring stacking interactions have been observed in BPSBA-C4 (9) from the percent hypochromism (%H) of the models.

• Journal of Photoscience
• /
• v.5 no.4
• /
• pp.163-167
• /
• 1998

Candida albcans growth inhibition experiments were carried out to determine the photoxicity of new monofunctional psoralen derivatives, PzPs and HMPzPs, as well as well known 8-MOP an d5-MOP. Although 8-MOP and 5-MOP showed distince photoxicity, PzPs and HMPzPs did not inhibit the growth of Candida albicans strain indicating that PzPs derivatives were not good candidate for the treatment of psoriasis. However, vitili해 could be treated by PzPs derivatives without severe phototosicity because psoralens are known to treat vitiligo by stimulating melanogenesis on skin.

• Bulletin of the Korean Chemical Society
• /
• v.2 no.3
• /
• pp.112-114
• /
• 1981

The photocycloaddition reaction of 8-methoxypsoralen with purine and/or pyrimidine bases is studied as a model for the charge transfer interactions of psoralens with DNA bases by the FMO method. The results indicate that, in the case of the molecular complex formation between psoralens and purine and/or pyrimidine bases, the most probable photocycloaddition should occur in the following order: Thy (5,6)<>(3,4) 8-MOP, Cyt(5,6)<>(3,4)8-MOP, Ade (7,8)<>(3,4)8-MOP, Gua(7,8)<>(3,4)8-MOP. The theoretical results for the photocycloaddition reaction are also correlated with the experimental results. The photoadducts between 8-methoxypsoralen and adenine are likely to be C4-cycloadducts through the cycloaddition of 3,4-pyrone double bond of 8-methoxypsoralen to 7,8-double bond of adenine.

• Korean Architects
• /
• s.501
• /
• pp.72-75
• /
• 2011

• Journal of the Korean Chemical Society
• /
• v.53 no.3
• /
• pp.244-256
• /
• 2009

The psoralen-pyrimidine base complexes resulting from interstrand cross-linking through $C_4$-cycloaddition is studied by ab initio and DFT methods. The results indicate that in the case of the molecular complex formation between psoralens and pyrimidine base, the most probable photocycloadditions are 8-MOP< >Thy, Ps< >Cyt and Ps< >Thy. The geometries of photoadducts were optimized at the HF levels and ${\Delta}{G^{\circ}}$ were calculated. The photocycloadduct was inferred to be a C4-cycloaddition product with the stereochemistry of trans-syn 8-MOP< >Thy, trans-anti Ps(3, 4)< >Cyt, trans-anti Ps(12, 13)< >Cyt, trans-syn Ps(3, 4)< >Thy, trans-syn Ps(12, 13)< >Thy, trans-anti Ps(12, 13)< >Ps(12, 13), cis syn, cis anti Thy< >(3, 4)Ps(12, 13)< >Thy.