• Title/Summary/Keyword: Heterocyclic compounds

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分子軌道論의 生物化學에의 應用 (第 2 報). 發癌物質과 DNA 鹽基와의 相互作用 (Application of Molecular Orbital Theory to Biological chemistry (II). Interactions of Chemical Carcinogens with DNA Bases)

  • 김호순;박윤열;박병각
    • 대한화학회지
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    • 제24권4호
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    • pp.280-287
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    • 1980
  • 發癌物質과 DNA 鹽基雙間의 分子錯物形成에서 可能性있는 配置(orientation)를 決定하였다. 아데닌-티민 염기쌍에서는 티민쪽에서, 구아닌-시토신 염기쌍에서는 구아닌쪽에서 分子錯物을 形成한다.

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Thioacetamide 와 피리딘계 헤테로고리 화합물 사이의 수소 결합에 대한 연구 (Hydrogen Bonding between Thioacetamide and a Series of Heterocyclic Compounds of Pyridine)

  • 박재헌;이미경;오인철;윤창주;최영상
    • 대한화학회지
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    • 제38권5호
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    • pp.345-350
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    • 1994
  • 클로로포름과 사염화탄소 속에서 티오아세트아미드(TA)와 pyridine(Py), quinoline(Qu), and acridine(Ac)간의 수소 결합에 대한 열역학적 상수들을 조사하기 위해 5$^{\circ}C$ 에서 55$^{\circ}C$까지 TA의 $v_{a^+}$ Amide II조합띠를 사용하였다. 이 조합띠는 두 개의 Lorentzian-Gauss 곱함수의 띠로 분해되며, 각각은 TA단위체 및 수소결합을 이룬 TA의 복합체임이 확인되었다. 온도 및 농도에 따른 이 조합띠의 변화로부터 TA의 수소 결합에 대한 여러가지 열역학적 상수들을 구하였다. 클로로포름에서 TA 와 pyridine, quinoline, acridine의 수소결합 엔탈피는 각각 -7.6 kJ/mol, -6.5 kJ/mol, -5.4 kJ/mol이었고, 사염화탄소에서 TA 와 pyridine, quinoline의 결합 엔탈피는 각각 -13.3kJ/mol, -12.0kJ/mol이었다.

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Decomposition of Nitogen Heterocyclic Compounds(NHCs) in Aqueous Solution by Sonication

  • Yoo, Young-Eok;Maeda, Yasuaki
    • 한국환경과학회:학술대회논문집
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    • 한국환경과학회 2003년도 International Symposium on Clean Environment
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    • pp.171-176
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    • 2003
  • The sonolytic decomposition of NHCs, such as atrazine[6-chloro-N-ethyl-N' -(1-methylethyl)-1,3,5-triazine-2,4-diamine], simazine( 6-chloro-N,N' -diethyl-l ,3,5-triazine-2,4-diamine), trietazine(6-chloro-N,N,N'-triethyl-l,3,5-triazine-2,4-diamine), in water was investigated at a ultrasound frequency of 200kHz with an acoustic intensity of 200W under argon and air atmospheres. The concentration of NHCs decreased with irradiation, indicating pseudo-first-order kinetics. The rates were in the range 1.06∼2.07 (x10/sup -3/ min/sup -1/) under air and 1.30∼2.59(x10/sup -3/ min/sup -1/)under argon at a concentration of 200μM of NHCs. The rate of hydroxyl radicals(·OH) formation from water is 19.8μM min/sup -1/ under argon and 14.7 μM min/sup -1/ under air in the same sonolysis conditions. The sonolysis of NHCs is effectively inhibited, but not completely, by the addition of t-BuOH(2-methyl-2-propanol), which is known to be an efficient ·OH radical scavenger in aqueous sonolysis. This suggests that the main decomposition of NHCs proceeds via reaction with ·OH radical; a thermal reaction also occurs, although its contribution is small. The addition of appropriate amounts of Fenton's reagent [Fe/sup 2+/] accelerates the decomposition. This is probably due to the regeneration of ·OH radicals from hydrogen peroxide, which would be formed from recombination of ·OH radicals and which may contribute a little to the decomposition.

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황색종 NC82와 KFl14의 건조단계별 정유성분의 변화 (Change of Essential Oil Constituents during Flue-curing Process in Flue-cured Tobacco, NC82 & KF114)

  • 홍열;임흥빈;석영선;신주식;김종열;나도영;이학수
    • 한국연초학회지
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    • 제23권2호
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    • pp.168-178
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    • 2001
  • Essential oil in tobacco leaves influences the taste and aroma of cigarette smoke and is important to tobacco quality. This study was conducted to investigate the change in the level of essential oil components during flue-curing process of two flue-cured tobaccos, NC82 and KEl14. Flue-curing process was divided by six steps; harvest stage, the end of yellowing stage, the middle of color fixing stage, the end of color fixing stage, the middle of midrib drying stage, full-cured stage. NC82 in each stage contained 0.28%, 0.30%, 0.35%, 0.36%, 0.40% and 0.42% essential oil, respectively, and KF114 were 0.29%, 0.31%, 0.34%, 0.36%, 0.39% and 0.41%, respectively. Almost all hydrocarbons on the basis of relative peak area were gradually increased in two varieties with curing, neophytadiene content in them was highest at the full-cured stage. Most of alcohols and esters with curing showed a declining trend, but benzyl alcohol was increased in two tobaccos. Ketones were largely increased at the midrib drying stage during the curing process, especially, the most largely increasing constituent was $\beta$-damascenone among them. The content of 2-butylterahydrofuran, heterocyclic compounds, was largely increased at tile color fixing stage. There was no considerable difference between NC82 and KFl14 at the GC profile of essential oil and the pattern of each components during flue-curing process.

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Inhibition of Carcinogen-Activating Cytochrome P450 Enzymes by Xenobiotic Chemicals in Relation to Antimutagenicity and Anticarcinogenicity

  • Shimada, Tsutomu
    • Toxicological Research
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    • 제33권2호
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    • pp.79-96
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    • 2017
  • A variety of xenobiotic chemicals, such as polycyclic aromatic hydrocarbons (PAHs), aryl- and heterocyclic amines and tobacco related nitrosamines, are ubiquitous environmental carcinogens and are required to be activated to chemically reactive metabolites by xenobiotic-metabolizing enzymes, including cytochrome P450 (P450 or CYP), in order to initiate cell transformation. Of various human P450 enzymes determined to date, CYP1A1, 1A2, 1B1, 2A13, 2A6, 2E1, and 3A4 are reported to play critical roles in the bioactivation of these carcinogenic chemicals. In vivo studies have shown that disruption of Cyp1b1 and Cyp2a5 genes in mice resulted in suppression of tumor formation caused by 7,12-dimethylbenz[a]anthracene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, respectively. In addition, specific inhibitors for CYP1 and 2A enzymes are able to suppress tumor formation caused by several carcinogens in experimental animals in vivo, when these inhibitors are applied before or just after the administration of carcinogens. In this review, we describe recent progress, including our own studies done during past decade, on the nature of inhibitors of human CYP1 and CYP2A enzymes that have been shown to activate carcinogenic PAHs and tobacco-related nitrosamines, respectively, in humans. The inhibitors considered here include a variety of carcinogenic and/or non-carcinogenic PAHs and acethylenic PAHs, many flavonoid derivatives, derivatives of naphthalene, phenanthrene, biphenyl, and pyrene and chemopreventive organoselenium compounds, such as benzyl selenocyanate and benzyl selenocyanate; o-XSC, 1,2-, 1,3-, and 1,4-phenylenebis(methylene)selenocyanate.

Aflatoxin과 그 생성(生成)에 관련되는 주요인(主要因) (Aflatoxin: Factors Affecting Aflatoxin Production)

  • 박건영
    • 한국식품영양과학회지
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    • 제13권1호
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    • pp.117-126
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    • 1984
  • Aflatoxins are toxic and carcinogenic secondary metabolites which are produced by trains of A. flavus and A. parasiticus during their growth on foods and feedstuffs. Aflatoxins are a group of closely related heterocyclic compounds of which $B_1$, $B_2$, and $G_2$ are the major members. Aflatoxins are synthesized via a polyketide pathway in which the general steps are acetate, an-thraquinones, xanthone and aflatoxins. Aflatoxin formation is favored by high moisture or high $a_w$(0.95${\sim}$0.99). The limiting $a_w$ for aflatoxin production on agricultural commodities is 0.83. Optimum temperature for aflatoxin production by the molds is $25{\sim}30^{\circ}C$ and the incubation time for the maximum production of the toxin is 7${\sim}$15 days. The limiting temperatures for aflatoxin production are ${\leq}7.5^{\circ}C\;and\;\geq40^{\circ}C$. Cycling temperatures may or may not stimulate aflatoxin production depending on the amplitude of cycling, substrate and strains of molds. Aflatoxin pro-ducing molds are aerobic organisms and thus have a requirement for oxygen. A decreasing $O_2$ concentration and/or increasing concentrations of $CO_2$ or $N_2$ depress the mold growth and aflatoxin formation. A. flavus grows competitively or associatively in the presence of other microorganisms and occasionally loses the competition with other microorganisms. Some lactic acid bacteria have been shown to reduce growth and aflatoxin production by A. parasiticus. Carbon source is the most important nutritional factors affecting aflatoxin formation by the molds. Sucrose, fructose and glucose are the most favorable carbon sources. Food substrates of plant derived products which have high carbohydrate content such as agricultural commodities and their products are most vulnerable to contamination by aflatoxins.

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Interaction of 2-Hydroxyquinoxaline (2-HQ) on Soil Enzymes and Its Degradation: A Review

  • Gangireddygari, Venkata Subba Reddy;Bontha, Rajasekhar Reddy;Yoon, Ju-Yeon
    • 인간식물환경학회지
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    • 제23권4호
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    • pp.399-410
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    • 2020
  • The United Nations project the world population to reach 10 billion by the year 2057. To increase the food of the ever-increasing world population, agrochemicals are indispensable tools to the boon in agriculture production. These agrochemicals are a serious threat to the health of humans, plants, and animals. Agrochemicals are ultimately reached to the main reservoir/sink such as soil and contaminating the groundwater, disturb the soil health and in turn a serious threat to biogeochemical cycling and the entire biosphere. Among agrochemicals, quinalphosis one of the most repeatedly and widely used insecticides in the control of a wide range of pests that attack various crops. Quinalphos is shown to be primarily toxic in organisms by acetylcholinesterase enzyme action. Hydrolysis of quinalphos produces amajor metabolite 2-hydroxyquinoxaline (2-HQ), which has shown secondary toxicity in organisms. 2-HQ is reported to be mutagenic, carcinogenic, growth inhibition and induce oxidative stress in organisms. Quinoline is a heterocyclic compound and structural resemblance of 2-HQ with minor changes, but its degradation studies are enormous compared to the 2-HQ compound. Biotic factors in fate and behavior of 2-HQ in the environment are least studied. 2-HQ interactions with soil enzymes are vary from soil to soil. Based on the toxicity of 2-HQ in our stockpile we need to isolate a handful of microorganisms to treat this persistent metabolite and also other metabolites/compounds.This brief review will be significant from the point of biological and environmental safety.

Sources, Components, Structure, Catalytic Mechanism and Applications: a Critical Review on Nicotinate Dehydrogenase

  • Zhi Chen;Xiangjing Xu;Xin Ju;Lishi Yan;Liangzhi Li;Lin Yang
    • Journal of Microbiology and Biotechnology
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    • 제33권6호
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    • pp.707-714
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    • 2023
  • Plant-derived insecticide-neonicotinoid insecticides (NIs) played a crucial role in the development of agriculture and food industry in recent years. Nevertheless, synthesis of these nitrogen-containing heterocyclic compounds with an effective and greener routing remains challenging especially to the notion raise of "green chemistry" and "atom economy". While bio-catalyzed methods mediated by nicotinate dehydrogenase (NDHase) then provide an alternative. The current review mainly focuses on the introduction of sources, components, structure, catalytic mechanism and applications of NDHase. Specifically, NDHase is known as nicotinic acid hydroxylase and the sources principally derived from phylum Proteobacteria. In addition, NDHase requires the participation of the electron respiratory chain system on the cell membrane. And the most important components of the electron respiratory chain are hydrogen carrier, which is mainly composed of iron-sulfur proteins (Fe-S), flavin dehydrogenase (FAD), molybdenum binding protein and cytochromes. Heterologous expression studies were hampered by the plasmid and host with high efficiency and currently only Pseudomonas entomophila L48 as well as Comamonas testosterone was successfully utilized for the expression of NDHase. Furthermore, it is speculated that the conjugate and inductive effects of the substituent group at position 3 of the substrate pyridine ring exerts a critical role in the hydroxylation reactions at position 6 concerning about the substrate molecular recognition mechanism. Finally, applications of NDHase are addressed in terms of pesticide industry and wastewater treatment. On conclusion, this critical review would not only deepen our understanding of the theory about NDHase, but also provides the guideline for future investigation of NDHase.

7H-Dibenzo [c,g] carbazole과 Dibenz[a,j] acridine에 의한 DNA adduct의 32P-postlabeling 분석 (32P-postlabeling Analysis of 7H-Dibenzo [c,g] carbazole and Dibenz [a,j] acridine DNA Adduct in Mice)

  • 노재훈;문영한;데이비드 봐르쇼브스키;글렌 탈라스카
    • 한국산업보건학회지
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    • 제3권1호
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    • pp.14-21
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    • 1993
  • 7H-dibenzo[c,g]carbazole(DBC)과 dibenz[a, j]acridine(DBA) 및 이의 대사물 trans-DBA-1,2-dihydrodiol(DBA-1,2-DHD), trans-DBA-3,4-dihydrodiol(DBA-3,4-DHD), trans-DBA-5,6-dihydrodiol(DBA-5,6-DHD)]에 의한 DNA adduct형성을 알기 위해 Hsd:ISR 생쥐 피부에 이를 투여하고 용매 추출법으로 DNA를 분리하고 $^{32}P$-postlabeling법으로 DNA adduct를 분석하였다. DBC를 피부에 투여하여 DNA adduct가 국소작용 부위인 피부와 내장기관인 간, 폐 및 신장에 형성되어 DBC는 국소 및 전신 발암작용이 있음을 알 수 있었다. 또한 DNA adduct활성도가 간에서는 높고 피부, 폐, 신장에서는 상대적으로 낮아 DBC에 의한 발암의 주 표적 장기는 간임을 추측할 수 있었다. DBA, DBA-3,4-DHD 및 DBA-5,6-DHD 투여에 의해 두개의 adduct가 피부에서 관찰되었다. 대사 물질인 DBA-5,6-DHD에 의해 2개의 adduct가 형성되었으나 그 양상이 DBA 및 DBA-3,4-DHD와는 달랐으며 DBA-1,2-DHD에 의해서는 DNA adduct 형성이 관찰되지 않았다. 이상의 결과로 DBA는 국소발암작용이 있으며 활성 대사물인 DBA-3,4-DHD가 최종 발암원(ultimate carcinogen)이고 DBA-1,2-DHD는 무독화 대사물질로 추측된다.

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Synthesis and Antitumor Evaluation of cis-(1,2-Diaminoethane) dichloroplatinum (II) Complexes Linked to 5- and 6-Methyleneuracil and -uridine Analogues

  • Kim, Jack-C.;Lee, Min-Hwa;Choi, Soon-Kyu
    • Archives of Pharmacal Research
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    • 제21권4호
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    • pp.465-469
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    • 1998
  • The search for platinum (II)-based compounds with improved therapeutic properties was prompted to design and synthesize a new family of water-soluble, third generation cis-diaminedichloroplatinum (II) complexes linked to uracil and uridine. Six heretofore unreported uracil and uridine-platinum (II) complexes are; [N-(uracil-5-yl-methyl)ethane-1,2-di-amine]dichloroplatinum (II) (3a), [N-(uracil-6-yl-methyl)ethane-1,2-diaminel dichloroplatinum (II) (3b), t[N-($2^1$, $3^1$,$5^1$-tri-O-acetyl)uridine-5-yl-methyl] ethane-1,2-diamineldichloroplatinum (II) (6a), {[N-($2^1$,$3^1$, $5^1$-tri-O-acetyl) uridine-6-yl-methyl]ethane-1,2-diamine)dichloroplatinum (II) (6b),[N-(uridine- 5-yl-methyl)ethane-1,2-diamine]dichloroplatinum (II) (7a), [N-(uridine-6-yl- methyl)ethane-1,2-diamine]dichloroplatinum (II) (7b). These analogues were prepared from the key starting materials, 5-chloromethyluracil (1a) and 6-chloromethyluracil (1b) which were reacted with ethylenediamine to afford the respective 5-[(2-aminoethyl)aminol methyluracil (2a) and 6-[(2-aminoethyl)amino]methyluracil (2b). The cis-platin complexes 3a and 3b were obtained through the reaction of the respective 2a and 2b with potassium tetrachloroplatinate (II). The heterocyclic nucleic acid bases 1a and 1b were efficiently introduced on the .betha.-D-ribose ring via a Vorbruggen-type nucleoside coupling procedure with hexamethyldisilazane, trimethylchlorosilane and stannic chloride under anhydrous acetonitrile to yield the stereospecific .betha.-anomeric 5-chloromethyl- $2^1$,$3^1$,$5^1$-tri-O-acetyluridine (4a) and 6-chloromethyl-$2^1$,$3^1$,$5^1$-tri-O-acetyluridine (4b), respectively. The nucleosides 4a and 4b were coupled with ethylenediamine to provide the respective 5-[(amino-ethyl)aminolmethyl-$2^1$,$3^1$,$5^1$-tri-O-acetyluridine (5a) and 6-[(aminoethyl)amino] methyl-$2^1$,$3^1$,$5^1$-tri-O-acetyluridine (5b). The diamino-uridines 5a and 5b were reacted with potassium tetrachloroplatinate (II) to give the novel nucleoside complexes, 6a and 6b, respectively which were deacetylated into the free nucleosides, 7a and 7b by the treatment with CH$_{3}$ONa. The cytotoxic activities were evaluated against three cell lines (FM-3A, P-388 and J-82) and none of the synthesized compounds showed any significant activity.

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