• Bulletin of the Korean Chemical Society
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• v.34 no.8
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• pp.2522-2524
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• 2013

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.174.1-174.1
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• 2003

We have previously reported the synthesis and cytotoxic activities of a series of azaanthraquinone derivatives using doxorubicin as a lead compound. Doxorubicin is known to intercalate into DNA and to inhibit topoisomerase II activity. But in the case of quinone compounds like Dox, its use is limited because of systemic toxicities, primarily cardiotoxicity and myelosuppression. In this study, we discuss the synthesis of isoindolobenzoquinoxaline derivatives. The quinone group of the azaanthraquinone derivatives were removed in the target compounds. (omitted)

• Korean Journal of Food Science and Technology
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• v.41 no.3
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• pp.326-333
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• 2009

Heterocyclic aromatic amines (HCAs) are mutagenic and carcinogenic substances that are formed during the heating of protein-rich foods. HCAs are generally found at low amounts in a complex matrix, which requires sophisticated analysis. In this study, HCAs were extracted from lyophilized fish and shellfish samples using solid-phase extraction (SPE) and determined by liquid chromatography-electrospray ionization/mass spectrometry (LC-ESI-MS). The HCA recoveries in the fish and shellfish ranged from 15.7 to 74.7% with standard deviations from 0.2 to 7.63%. And HCA concentrations ranged from 0.8 to 1,117.7 $ng/g^{-1}$ in cooked food samples. 1-methyl-9H-pyrido[3,4-b]indole (Harman), 9H-pyrido[3,4-b]indole (Norharman), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) were the most abundant HCAs formed in the muscle of fried mackerel, at levels of 1,117.7, 926.6, and 133.7 ng/g, respectively. 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2), 2-aminodipiryrido[1,2-a:3,2-d]imidazole(Glu-P-2), 2-amino-9H-pyrido[2,3-b]indole(A${\alpha}$C), 2-amino-3methyl-9H-pyrido [1,2-a:3,2-d]imidazole(MeA${\alpha}$C), 2-amino-3,4,7,8-tetramethylimidazo[4,5-f]quinoxaline (TriMeIQx), 2-amino-3,7,8-trimethylimidazo [4,5-f]quinoxaline(7,8-DiMeIQx), and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) were only detected by small quantities ranged from 1.5 to 98.6 ng/g. Overall, this study provides useful information on HCA levels in fish and shellfish products consumed in Korea.

• Food Science of Animal Resources
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• v.31 no.4
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• pp.563-569
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• 2011

Heterocyclic amines (HCAs) are food mutagens and carcinogens that are found in cooked fish, meat, and protein-rich foods. This study examined the inhibitory effect of marinades containing a Nelumbo nucifera leaf fraction on HCA formation in cooked beef steak. As a result of the Ames assay, cooked beef marinated with the N. nucifera leaf butanol fraction (2.0 g) cooked at $190^{\circ}C$ showed a 61.5% reduction in overall mutagenicity. However, these data revealed no significant difference in mutagenicity in the ethanol, ethyl acetate, or water fractions. Formation of MeIQx (2-amino-3,8 dimethylimidazo[4,5-f]-quinoxalin) and PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine) was inhibited 60.7-63.5%. Cooked beef marinated with the water fraction of the N. nucifera leaf significantly (p<0.05) reduced the formation of MeIQx, PhIP, and DiMeIQx (2-amino-3,4,8 trimethylimidazo[4,5-f]-quinoxaline) by 65.3, 67.6, and 73.9%, respectively. These results show that marinades containing the N. nucifera leaf fraction could be an alternative method for reducing HCA formation in cooked beef steak.

• Proceedings of the Korean Society of Toxicology Conference
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• 2000.11a
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• pp.45-67
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• 2000

2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) is a mutagenic and carcinogenic heterocyclic amino found in cooked meat. The in vivo mutagenicity and hepatocarcinogenicity of MeIQx were examined in mice harboring the lacZ mutation reporter gene ($Muta^{TM}$ Mice) and bitransgenic mice over-expressing the c-myc oncogene. C57B1/$\lambda$lacZ and bitransgenic c-myc (albumin promoter)/$\lambda$lacZ mice were bred and weaned onto an AIN-76 based diet containing $0.06\%$ (w/w) MeIQx or onto control diet. After 30 weeks on diet, only male bitransgenic mice on MeIQx developed hepatocellular carcinoma ($100\%$ incidence) indicating that there was synergism between c-myc over-expression and MeIQx. By 40 weeks, hepatic tumor incidence was $100\%$ ($17\%$) and $44\%$ ($0\%$) in male c-myc/$\lambda$lacZ and C57B1/$\lambda$lacZ mice given MeIQx (or control) diet, respectively, indicating that either MeIQx or c-myc over-expression alone eventually induced hepatic tumors. At either time point, mutant frequency in the lacZ gene was at least 40-fold higher in MeIQx-treated mice than in control mice of either strain. These findings suggest that MeIQx-induced hepatocarcinogenesis is associated with MeIQx-induced mutations. Elevated mutant frequency in MeIQx-treated mice also occurred concomitant with the formation of MeIQx-guanine adducts as detected by the $^{32}P$-postlabeling assay. Irrespective of strain or diet, sequence analysis of the lacZ mutants from male mouse liver showed that the principal sequence alteration was a single guanine-base substitution. Adenine mutations, however, were detected only in animals on control diet. MeIQx-fed mice harboring the c-myc oncogene showed a l.4-2.6-fold higher mutant frequency in the lacZ gene than mice not carrying the transgene. Although there was a trend toward higher adduct levels in c-myc mice, MeIQx-DNA adduct levels were not significantly different between c-myc/$\lambda$lacZ and C57B1/$\lambda$lacZ mice after 30 weeks on diet. Thus, it appeared that factors in addition to MeIQx-DNA adduct levels, such as the enhance rate of proliferation associated with c-myc over-expression, may have accounted for a higher mutant frequency in c-myc mice. In the control diet groups, the lacZ mutant frequency was significantly higher in c-myc/$\lambda$lacZ mice than in 057B1/$\lambda$1acZ mice. The findings are consistent with the notion that c-myc over-expression is associated with an increase in mutagenesis. The mechanism for the synergistic effects of c-myc over-expression on MeIQx hepatocarcinogenicity appears to involve an enhancement of MeIQx-induced mutations.

• Journal of the Korean Society of Safety
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• v.12 no.3
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• pp.173-178
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• 1997

The intrinsic flame retardant and heat resistant polymers such as PQXS [poly( quinoxaline )sulfide], PIQS [poly(isoquinoline)sulfide] and PQS [poly(quinoline)sulfide] were synthesized from 2, 3-dichloroquinoxaline, 1, 3-dichloroisoquinoline and 4, 7-dichloroquinoline. They were characterized by FT-IR, UV/Vis spectroscopy, DTA and elemental analysis. The melting point above $350^{\circ}C$ of the polymers show higher than that of the heat resistant PPS polymer(mp. $295^{\circ}C$), In the LOI test, the polymers exhibit an intrinsically high flame retardant property having the LOI values in the range of 41~42. The vertical burning test for the polymers also show an UL 94 V-0 performance.

• Food Science and Biotechnology
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• v.16 no.4
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• pp.576-579
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• 2007

The effects of temperature and Korean bramble (Rubus coreanum Miquel) tissue concentrate on heterocyclic aromatic amine (HAA) formation in fried ground beef patties were investigated. Various amounts of Korean bramble tissue (4.0, 7.0, and 11.0%, w/w) were added to ground beef patties were fried at 2 different temperatures (190 and $225^{\circ}C$) for 10 min/side. It was observed in the fried ground beef patties fried at $190^{\circ}C$ with the addition of 11.0%(w/w) Korean bramble that the mutagenicity decreased by 64%, and formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-I-methyl-6-phenylimidazo[4,5-b]-pyridine(PhIP) reduced by 55 and 86%, respectively. Although no difference in total mutagenicity was shown in patties fried at $225^{\circ}C$ with the addition of 4.0, 7.0, and 11.0%(w/w), different levels of reduction of PhIP formation in patties fried at $225^{\circ}C$ with the addition of 4.0, 7.0, and 11.0%(w/w) were shown 49, 63, and 75%, respectively.

• Elastomers and Composites
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• v.50 no.2
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• pp.138-145
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• 2015

A series of wholly aromatic poly(hydroxyamide)s(PHAs), containing varying amounts of 2,6-dimethylphenoxy group and quinoxaline ring in the main chain, were synthesized by a direct polycondensation method. The inherent viscosities of the PHAs in either DMAc or DMAc/LiCl solution at $35^{\circ}C$ were found to be in the range of 1.02~1.90 dL/g. In the solubility study, we observed that PHA 1, PHA 2, and PHA 3 were dissolved in aprotic solvents such as DMAc, NMP, DMF, and DMSO with LiCl on heating; however, PHA 4, PHA 5, and PHA 6 could be dissolved in aprotic solvents on heating without LiCl. For poly(benzoxazole)s(PBOs), the 10% and maximum weight loss temperatures were in the range of $582{\sim}622^{\circ}C$ and $630{\sim}659^{\circ}C$, respectively. Residues of PBOs at $900^{\circ}C$ were found to be relatively high, which were in the range of 65.3~70.8%.

• Elastomers and Composites
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• v.53 no.3
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• pp.141-149
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• 2018

A series of aromatic poly(o-hydroxyamide)s (PHAs) were synthesized by the direct polycondensation reaction of 4,4′-(2,3-quinoxalinedioxy) dibenzoic acid and/or 4,4′-(2,3-pyridinedioxy) dibenzoic acid with bis(o-aminophenol) including 2,2-bis-(amino-4-hydroxyphenyl)hexafluoropropane. The PHAs exhibited inherent viscosities in the range of 0.17-0.35 dL/g at $35^{\circ}C$ in a DMAc solution. These polymers showed low inherent viscosities and yielded brittle films. All the PHAs showed excellent solubility in aprotic solvents such as DMAc, DMSO, NMP, and DMF at room temperature and in less polar solvents such as pyridine and THF. However, all the PBOs were only partially soluble in $H_2SO_4$. The PBOs exhibited 10% weight loss at temperatures in the range of $537-551^{\circ}C$. The maximum weight loss temperature increased with an increase in the content of the quinoxaline-containing monomer. The residue of the PBOs showed a weight loss of 45.8-56.7% at $900^{\circ}C$ in a nitrogen atmosphere.

• Journal of the Korean Society of Food Science and Nutrition
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• v.24 no.1
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• pp.160-168
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• 1995

Desmutagenicities against 2-amino-1-methyl-6-phenylimidazo[4, 5-b] pyridine(PhIP) and 2-amino-3, 8-dimethylimidazo[4, 5-f]quinoxaline(MelQx) of tea extracts (steamed green tea, roasted green tea, oolong tea and black tea) were investigated. All the fractions obtained from tea extracts showed strong desmutagenic activity against PhIP and MeIQx toward S. typhimurium TA 98 in the presence of the S-9 mix. The crude catechin fraction exhibited the strongest desmutagenic activity. Among these tea extracts, black tea especially exhibited the strongest desmutagenic activity and the activity was 70.9~91.0% against PhIP and 92.2~98.8% against MelQx at a concentration(0.5~1.0mg/plate) for drinking. The activity of authentic catechins of (-)-EGC, (-)-EGCg, (-)-ECg and (-)-EC were 79.5%, 60.2%, 46.1% and 43.5% against PhIP, and were 52.3%, 11.6%, 8.2% and 22.1% against MelQx by addition of 1.0mg/plate, respectively. The desmutagenic activity was supposedly due to the (-)-EGCg, (-)-EGC and (-)-EC in tea polyphenols, and the browning materials. The desmutagenicity was stronger when mutagens were preincubated with S-9 mix after reaciton with black tea extracts than when preincubated with them after reaction with S-9 mix. The desmutagenicity of tea extracts was rather expressed by reacting directly with mutagens than by deactivating the activated forms of mutagens.