• Journal of Pharmaceutical Investigation
• /
• v.23 no.3
• /
• pp.155-163
• /
• 1993

Inclusion complexation of 1,7,21,27-tetraaza[7.1.7.1]paracyclophane (CPM 55) with 2,7-dihydroxynaphthalene (2,7-DHN) or 1,3-dihydroxynaphthalene (1,3-DHN) in pD 1.17 $DCl-D_2O$ solution was investigated by $^1H$ nuclear magnetic resonance spectroscopy (NMR) using 4,4'-dimethylaminodiphenylmethane (ACM 11) as an acyclic analog of CPM 55. In CPM 55-naphthalene derivative complex, alkyl protons located in the cavity of CPM 55 were shown to be subjected to anisotropic shielding and protons of naphthalene moiety shifted remarkably to upfield. However, in ACM 11-naphthalene derivative systems, chemical shifts for protons of both DHN compounds were not significant. The remarkable chemical shift changes suggested that the naphthalene moiety of 2,7-DHN or 1,3-DHN was included in the hydrophobic cavity of CPM 55 in aqueous solution. From the continuous variation plots of induced chemical shifts of 2,7-DHN, it was found that 2,7-DHN was included in the cavity of CPM 55 at 1:1 molar stoichiometry. Both computer simulation of a inclusion complex and strong upfield chemical shift changes of 2,7-DHN protons supported the conformation of pseudoaxial inclusion as the presumed geometry of the host-guest complex.

• Natural Product Sciences
• /
• v.26 no.4
• /
• pp.279-282
• /
• 2020

Chemical investigation of the methanol extract of Koordersiodendron pinnatum Merr. leaves resulted a new naphthalene derivative, (Z)-4-(tetradec-3-enyl)naphthalene-1,2,7-triol (1), together with three known compounds, ��-sitosterol (2), 20-epibryonolic acid (3), and scopoletin (4). The structure of the new compound was elucidated based on spectroscopic evidence. The isolated compounds (1-4) were tested their cytotoxic activities against the P-388 murine leukemia cell line and compound 1 has highest activity with IC50 1.94 μM.

• Journal of Microbiology
• /
• v.44 no.5
• /
• pp.473-479
• /
• 2006

A well characterized naphthalene-degrading strain, Pseudomonas putida PpG7 was observed to utilize limonin, a highly-oxygenated triterpenoid compound as a sole source of carbon and energy. Limonin concentrations evidenced a 64% reduction over 48 h of growth in batch cultures. Attempts were made to acquire a plasmid-less derivative via various methods (viz. Ethidium Bromide, SDS, elevated temperature & mitomycin C), among which the method involving mitomycin C ($20{\mu}g/ml$) proved successful. Concomitant with the loss of plasmid in P. putida PpG7 strain, the cured derivative was identified as a $lim^-$ phenotype. The $lim^+$ phenotype could be conjugally transferred to the cured derivative. Based on the results of curing with mitomycin C, conjugation studies and presence of ndo gene encoding naphthalene 1,2 dioxygenase, it was demonstrated that genes for the limonin utilization were encoded on an 83 kb indigenous transmissible Inc. P9 NAH plasmid in Pseudomonas putida PpG7 strain.

• Bulletin of the Korean Chemical Society
• /
• v.28 no.5
• /
• pp.851-854
• /
• 2007

• Bulletin of the Korean Chemical Society
• /
• v.32 no.spc8
• /
• pp.3171-3174
• /
• 2011

• Biomolecules & Therapeutics
• /
• v.31 no.1
• /
• pp.68-72
• /
• 2023

Pancreatic cancer is one of the most fatal cancers with a poor prognosis. Standard chemotherapies have proven largely ineffective because of their toxicity and the development of resistance. Therefore, there is an urgent need to develop novel therapies. In this study, we investigated the antitumor activity of MS-5, a naphthalene derivative, on BxPC-3, a human pancreatic cancer cell line. We observed that MS-5 was cytotoxic to BxPC-3 cells, as well as inhibited the growth of cells in a concentration- and time- dependent manner. Flow cytometry analysis revealed that the percentage of annexin V-positive cells increased after MS-5 treatment. We also observed cleavage of caspases and poly (ADP-ribose) polymerase, and downregulation of Bcl-xL protein. Flow cytometry analysis of intracellular levels of reactive oxygen species (ROS) and mitochondrial superoxide suggested that MS-5 induced the generation of mitochondrial superoxide while lowering the overall intracellular ROS levels. Thus, MS-5 may be potential candidate for pancreatic cancer treatment.

• Bulletin of the Korean Chemical Society
• /
• v.7 no.2
• /
• pp.120-124
• /
• 1986

In order to investigate effective solar energy conversion system, the light-induced electron transfer reactions have been examined across single-lamellar liposomes incorporated organic photosensitizers such as anthracene and naphthalene derivatives. We have observed photosensitized reduction of methyl viologen (1,1'-dimethyl-4,4'-$bipyridinium^{2+}$) dissolved in the exterior aqueous phase of the pigmented phospholipid liposomes when EDTA, as electron donor, is dissolved in the enclosed aqueous phase of the liposomes. The anthroyl stearic acid incorporated in the hydrophobic bilayer of liposomes leads to much less quantum yield for the photosensitized reduction of $MV^{2+}$ than the anthracene carboxylate incorporated in the outer hydrophilic layer. However, ${\beta}$-carotene with anthroyl stearic acid incorporated into the bilayer enhances the quantum yield significantly (${\Phi}{\simeq}0.2-0.3$), preventing the reverse reaction of electron transfer ($MV^+_\ {\rightarrow}MV^{2+}$) so that it might be useful for solar energy conversion into chemical energy. A naphthalene derivative, octadecyl naphthylamine sulfonic acid incorporated into the outer layer of liposomes results in less efficiency of $MV^{2+}$ reduction than anthroyl stearic acid. These results have been also tested with respect to lipid components of liposomes.

• Korean Journal of Pharmacognosy
• /
• v.27 no.2
• /
• pp.111-116
• /
• 1996

The components were isolated from the root of Astragalus membranaceus and their structures were characterized as 3,4-methylenedioxypyrrolealdehyde, $7-O-{\beta}-D-glucopyranosyl$ 7, 3'-dihydroxy-4'-methoxy isoflavone and a naphthalene derivative on the basis of spectral and physical methods. $7-O-{\beta}-D-glucopyranosyl$ 7, 3'-dihydroxy-4'-methoxy isoflavone and the naphthalene compound showed protective effect on $CC_{l4}-induced$ cytotoxicity in primary cultured rat hepatocytes.

• Journal of Electrochemical Science and Technology
• /
• v.10 no.2
• /
• pp.99-103
• /
• 2019

A derivative of 1,4-Naphthoquinone coded HBU671 was synthesized and used in addition to activated carbon as composite electrode for supercapacitor application. From the electrochemical properties analysis, a specific capacitance of about $300F\;g^{-1}$ exhibited almost two times of that of activated carbon at a scan rate of $100mV\;s^{-1}$ and a potential window of - 0.2 - 1V. This improvement is due to the inherent redox reaction in HBU671. Cycle test also proved that this composite is still stable even after 1000 cycle within the applied potential window and it is highly recommended for practical application.

• Biomolecules & Therapeutics
• /
• v.27 no.1
• /
• pp.48-53
• /
• 2019

Reactive oxygen species (ROS) are widely generated in biological processes such as normal metabolism and response to xenobiotic exposure. While ROS can be beneficial or harmful to cells and tissues, generation of ROS by diverse anti-cancer drugs or phytochemicals plays an important role in the induction of apoptosis. We recently identified a derivative of naphthalene, MS-5, that induces apoptosis of an ovarian cell, CAOV-3. Interestingly, MS-5 induced apoptosis by down-regulating the ROS. Cell viability was evaluated by water-soluble tetrazolium salt (WST-1) assay. Apoptosis was evaluated by flow cytometry analysis. Intracellular ROS ($H_2O_2$), mitochondrial superoxide, mitochondrial membrane potential (MMP) and effect on cycle were determined by flow cytometry. Protein expression was assessed by western blotting. The level of ATP was measured using ATP Colorimetric/Fluorometric Assay kit. MS-5 inhibited growth of ovarian cancer cell lines, CAOV-3, in a concentration- and time-dependent manner. MS-5 also induced G1 cell cycle arrest in CAOV-3 cells, while MS-5 decreased intracellular ROS generation. In addition, cells treated with MS-5 showed the decrease in MMP and ATP production. In this study, we found that treatment with MS-5 in CAOV-3 cells induced apoptosis but decreased ROS level. We suspect that MS-5 might interfere with the minimum requirements of ROS for survival. These perturbations appear to be concentration-dependent, suggesting that MS-5 may induce apoptosis by interfering with ROS generation. We propose that MS-5 may be a potent therapeutic agent for inducing apoptosis in ovarian cancer cell through regulation of ROS.