• Bulletin of the Korean Chemical Society
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• 제34권8호
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• pp.2522-2524
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• 2013

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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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)

• 한국식품과학회지
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• 제41권3호
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• pp.326-333
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• 2009

국내에서 주로 섭취되는 어패류(고등어, 삼치, 조기, 대합, 바지락, 꼬막, 백합)를 가열조리 하였을 때 형성되는 HCAs를 분리, 동정하여 그 함량을 모니터링 하였다. 추출 및 정제는 고체상 추출 방법을 사용하였고 정성, 정량을 위한 분석장비는 LC/MS를 사용하였다. 모니터링 결과 생선류에서는 고등어(2.2-1,1117.7 ng/g), 삼치(9.1-443.6 ng/g), 조기(17.5-179.5 ng/g)순으로 HCAs가 많이 검출되었으며 특히 고등어 muscle에서 많은 양(1,1117.7 ng/g, Harman)이 검출되었다. 조개류 중에서는 대합(12.2-196.4 ng/g), 꼬막(2.2-76.2 ng/g), 바지락(1.7-25.8 ng/g), 백합(1.5-2.7 ng/g)순으로 많이 검출되었으며 대합의 Norharman(196.4 ng/g)이 가장 많이 검출되었다. 15종의 HCAs 중 ${beta}$-carbolines에 속하는 Norharman과 Harman이주로 검출되었으며 그 밖에 PhIP, Trp-P-1. Trp-P-2 등의 발암가능성이 있는 물질들이 검출되었다. 조리방법 측면에서 보면 간장을 이용한 조림방법보다는 직접적인 가열을 통한 구이방법이 많은 양의 HCAs를 형성시켰으며 구이 중에서도 muscle만 있는 부위에서의 검출함량보다는 muscle과 skin이 함께 있는 부위에서 검출함량이 더 많았다. 가열 조리한 어패류 분석방법에 대한 유효성을 확인해 본 결과 정량한계는 0.8-23.9 ng/mL, 검출한계는 0.2-7.2 ng/mL이었으며 회수율은 15.7-74.7%이었다.

• 한국축산식품학회지
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• 제31권4호
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• pp.563-569
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• 2011

일상 생활에서 섭취하는 가열한 생선, 육류 등의 고단백질 식품에서는 돌연변이원, 발암가능성 물질인 heterocyclic amine류가 생성된다. 안전성 측면을 고려하고자 백련 잎을 이용한 마리네이드 소스를 첨가하여 쇠고기의 HCAs의 형성억제효과와 돌연변이원성 억제효과를 알아보았다. Ames assay 결과 백련 잎 butanol fraction을 2.0 g 첨가하여 가열한 쇠고기 스테이크에서 61.5%로 높은 돌연변이원성 억제효과를 나타내었지만 용매 별 fraction 첨가군 사이에서는 유의적인 차이를 나타내지 않았다. 가열 전 쇠고기 마리네이드 소스에 식용이 가능한 백련잎 water fraction(2.0, 4.0, 8.0 g)을 첨가한 후 $190^{\circ}C$에서 가열한 결과 MeIQx(2-amino-3,8 dimethylimidazo[4,5-f]-quinoxalin)는 30.9-63.5%, PhIP(2-amino-1-methyl-6-pheny-limidazo[4,5-b]-pyridine)는 31.6-60.7% 억제되었다. $225^{\circ}C$에서의 가열된 쇠고기에서는 MeIQx가 38.1-65.3%, DiMeIQx (2-amino-3,4,8 trimethylimidazo[4,5-f]-quinoxaline)는 36.8-73.9%, PhIP는 33.9- 67.6%의 억제효과를 보였다. 따라서 백련 잎 추출물은 heterocyclic amine류 형성과 돌연변이 원성을 억제하는 효과가 있는 것으로 나타나 고단백질 식품 섭취시 안전성 측면에서 긍정적인 영향을 미칠 것으로 판단된다.

• 한국독성학회:학술대회논문집
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• 한국독성학회 2000년도 국제심포지움 및 추계학술대회
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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.

• 한국안전학회지
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• 제12권3호
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• pp.173-178
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• 1997

본질적인 난연 및 내열성의 PQXS, PIQS, PQS 3종류의 폴리머를 2,3-dichloroquinoxaline, 1,3-dichloroisoquinoline, 4,7-dichloroquinoline을 각각 출발 물질로 하여 합성하였다. 이들을 FT-IR, UV/Vis 분광분석, DTA, 원소분석 등에 따라 특성분석을 행하였다. 이들 폴리머소재는 내열 및 난연특성 시험에서 녹는점 기준 $350^{\circ}C$ 이상의 높은 내열성과 LOI값 기준으로 41~42의 높은 수치의 난연특성을 나타내었으며 또한 수직연소시험에서 UL 94 V-0 등급의 높은 난연특성을 나타내었다.

• Food Science and Biotechnology
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• 제16권4호
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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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• 제50권2호
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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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• 제53권3호
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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.

• 한국식품영양과학회지
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• 제24권1호
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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.