• Archives of Pharmacal Research
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• 제21권6호
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• pp.738-743
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• 1998

Thirty six 5,8-dimethoxy-1,4-naphthoquinone derivatives, which bear unsaturated alkyl side chain with ester bond, were synthesized and tested cytotoxic activity on L1210 cells a nd antitumor activity against ICR mice bearing S-180 cells. It could be recognized that the cytotoxicities of naphthoquinones with R1, being methyl and propyl (IV1~24) were not enhanced by replacing the alkanoyls with alkenoyls. In contrast, the introduction of the alkenoyl moieties on the compounds with $R_1$=hexyl (IV25~36) resulted in the enhancement of their cytotoxicities. Replacement of alkanoyl group with an alkenoyl group generally increased the T/C value of the mice bearing S-180 cells.

• 한국독성학회:학술대회논문집
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• 한국독성학회 2001년도 International Symposium on Signal transduction in Toxicology
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• pp.160-160
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• 2001

We recently reported that, 2-chloro-3-(4-hexylphenyI)-amino-l, 4-naphthoquinone(NQ304), a naphthoquinone derivative, had potent inhibitory effects on the platelet aggregation in vitro and thrombosis in vivo. Furthermore, we reported the antiplatelet mechanism of NQ304 by the reduction of the thromboxane A2 formation, inhibition of adenosine triphosphate release and intracellular calcium mobilization.(omitted)

• Journal of Photoscience
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• 제3권2호
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• pp.61-64
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• 1996

Photoaddition reactions of p-quinones to 1, 4-diphenylbubl-en-3-yne (BEY) have been investigated. Irradiation (300 nm) of BEY and 1, 4-benzoquinones in dichloromethane afforded quinone methides. I rradiation of 1, 4-naphthoquinone and BEY leaded to the formation of unstable spiro oxetene intermediate, followed by the rearrangement to give quinone methide, and finally the oxidative photocyclization. In contrast, irradiation 2, 3-dichloro-1, 4-naphthoquinone (or anthraquinone) and BEY yielded another type of quinone methides in one pot.

• Bulletin of the Korean Chemical Society
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• 제28권4호
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• pp.691-694
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• 2007

• Applied Biological Chemistry
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• 제43권3호
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• pp.228-230
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• 2000

• 한국독성학회:학술대회논문집
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• 한국독성학회 2002년도 Current Trends in Toxicological Sciences
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• pp.119-119
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• 2002

Several 1,4-naphthoquinone derivatives have been reported to possess many pharmacological effects such as anti-viral, anti-fungal, anti-cancer and anti-platelet activities. However, little has been known about functional role in vascular smooth muscle cells (VSMCs).(omitted)

• 대한화학회지
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• 제19권4호
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• pp.280-285
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• 1975

Polyglyceryl phthalate, bisphenol A-epichlorohydrin 縮重合物 및 polyvinyl alcohol의 naphthoquinone-1,2-diazide-5-sulfonyl esters(PGND, BEND 및 PVAND)에 대해 未增感 및 增感한 경우의 IR 스펙트럼을 측정하여 그들의 光分解機構를 硏究하였다. o-quinonediazide에 기인하는 C=N= 및 C=0의 흡수가 露光에 의해 減少내지는 消失하고있었고 또한 indene carboxylic acid의 C=0 흡수강도가 증가되고 있는 것으로 보아 o-quinonediazide group 이 光에 依하여 分解하여 알카리 수용액에 가용성인 indene carboxylic acid로 분해되는 것으로 추정된다. 한편, 露光時間에 대한 增感 및 未增感試料의 吸收强度의 變化를 측정하므로서 增感劑의 增感效果도 아울러 검토하였다.

• Archives of Pharmacal Research
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• 제26권5호
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• pp.405-410
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• 2003

Vitamin K-related analogs induce growth inhibition in various cancer cell lines. A naphthoquinone analog, termed 2,3-dichloro-5, 8-dihydroxy-1,4-naphthoquinone (DDN), induces apoptosis in human promyeloid leukemic HL-60 cells, and shows antitumor activity in vivo. Following treatment with DDN, evidence of apoptosis, including DNA fragmentation and cleavage of poly ADP ribose polymerase (PARP), was observed. DDN induced an upregulation of proapoptotic Bax protein, and Bid cleavage. Antiapoptotic Bcl-2 protein levels were not changed by DDN, but the expression of Bcl-xL was decreased. In addition, DDN reduced the mass of solid tumor in the Sarcoma 180 tumor-bearing mouse model. These results indicate that DDN exerts antitumor activity, which appears to be related to the induction of apoptosis by regulating Bcl-2 family proteins.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1997년도 춘계학술대회
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• pp.109-109
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• 1997

Inhibitory effect on DNA topoisomerase-I, rate of glutathione conjugation and cytotoxicity of naphthoquinone derivatives were correlated. During 5 min exposure of the derivatives to glutathione (GSH), it was found that 14% of 5,8-dimethoxy-1,4-naphthoquinone(DMNQ) was converted into a GSH-conjugate, whereas 5,8-dihydroxy-1,4-naphthoquinone(DHNQ) did not interact with GSH, implying that DMNQ exerted higher electrophilicity than DHNQ. However, DHNQ (IC$\_$50/, 0.15 ${\mu}$M) showed stronger cytotoxicity in L1210 cells than DMNQ(IC$\_$50/, 0.45 ${\mu}$M). The stronger cytotoxicity of DHNQ, compared to DMNQ, could be ascribed to more rapid redox cycling. Both naphthoquinones (IC$\_$50/, 60-65 ${\mu}$M) exhibiting about the same inhibitory effect on DNA topoisomerase-I were more potent than 1,4-naphthoquinone(1,4-NQ, IC$\_$50/, 134 ${\mu}$M). Thus, 5,8-oxy groups in the structure seem to be important for the inhibition of the enzyme. DMNQ showed a broader dose range while maintaining a good antitumor activity against S-180 fluid tumor. For these reasons, DMNQ was taken as useful pharmacophore for structural modification. Introduction of 1-hydroxyalkyl groups at C-2 of DMNQ lowered all of the activities mentioned above, while acetylation of 1-hydroxyalkyl moiety enhanced the activities by 4-5 times. Introduction of the same side chains at C-6 exhibited stronger activities than 2-substituted ones. Based on these results it was suggested that the quinonoid moiety in 6-substituted DMNQ was more exposed to cellular nucleophiles such as DNA, thiols of enzymes and so on. The synthesis of DHNQ or DMNQ derivatives are going on, and the corelationship between structure-activity will be discussed.

• Ecology and Resilient Infrastructure
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• 제2권3호
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• pp.224-236
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• 2015

겨울철 한강과 낙동강에서 규조 Stephanodiscus hantzschii에 의한 조류발생이 빈번하게 일어나며, 이로 인한 수자원의 질적변화와 정수과정에 많은 경제적 손실을 주고 있다. 본 연구진은 조류대발생의 원인종인 S. hantzschii을 제어할 수 있는 naphthoquinone (Nq) 화합물을 개발하였다. 본 연구는 개발된 Nq 화합물 중 가장 친환경적인 화합물을 선정하기 위한 실험으로 물질의 살조범위 실험과 낙동강 현장수를 이용한 10 L 규모의 미소생태 실험을 수행하였다. 그 결과 Nq 4-6 화합물의 살조범위는 원반형 규조류에 특이적으로 나타났으며, 남조류 및 녹조류에 대해 살조 활성이 나타나지 않았다. 미소생태 실험 결과, 대조구에서 S. hantzschii가 지속적으로 세포밀도가 증가한 반면, Nq 4-6 화합물을 접종한 처리구에서는 처리 7일째 대조구 대비 S. hantzschii가 94.4% 감소하였으며, S. hantzschii를 제외한 나머지 규조류 및 녹조류에서는 Nq 4-6 화합물 처리 후 살조활성이 관찰되지 않았다. 식물플랑크톤 군집 분석 결과 대조구에 비해 처리구에서 우점도는 낮게 나타났으며, 다양도, 풍부도, 균등도 등은 처리구에서 높게 나타났다. 물리화학적요인 (용존산소, pH, 영양염) 및 미소생물 (heterotrophic nanoflagellates, 섬모충, 박테리아) 등에서도 Nq 4-6 화합물 처리 후 특이적인 변화는 나타나지 않았다. 따라서 본 연구에서 개발된 Nq 4-6 화합물은 생태독성이 낮고, 겨울철 국내 하천에서 매년 대발생을 일으키는 규조 S. hantzschii만을 특이적으로 제어함을 확인하였으며, 적용 시 식물플랑크톤 종 다양성을 증진시키는 친환경적인 조류제어제로 판단된다.