• Archives of Pharmacal Research
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• 제17권3호
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• pp.170-174
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• 1994

We have synthesized various 6-substituted 2-oxo-purine nucleosides from key intemediate, 6-[(4-methylphenylthio)-2-oxo-9(2, 3, 5tri-o-acetyl-$\beta$-D-ribofuanoslyl)]-2, 3- dihydropurine in relatively high yields by one step nucleophilic substitution. Various isoguanosine, xanthosine analogs and other 2-oxo-purine nucleosides containing nitrogen, sulfur and oxygen at C-6 of purine base were easily obtained by this method. The structures of the products were established on the basis of their spectral data studies. And cytotoxicity of resulting synthetic 6-substituted-2-oxo-purine nucleosides against some tumor cell-lines was examined. $Ed_{50}$ values of these synthetic compounds were above $100\;{\mu}g/ml$ except isoguanosine, $N^6$-methyl isoguanosine and thioxanthosine analogs.

• 대한방사성의약품학회지
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• 제5권1호
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• pp.61-68
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• 2019

Purine type compounds has been recently reported to cause the death for lung cancer cell, related to microtubules-targeting agents (MTAs). Therefore it can be used to develop as theranostic radiopharmceuticals in nuclear medicine or gadolinium-based MRI imaging agents by chelate chemistry. In the study, we tried to chemically bind a DOTA chelate on the end of purine compound and obtained a specific conjugate of DOTA-purine for metal coordination. In particular, radiometal like Cu-64, for the development of MRI imaging agents, can be utilized to choice good candidates before the synthesis of gadolinium complexes. By the screening of radioisotope technique, Gd-DOTA-purine type complex was successfully prepared and showed MRI imaging for lung cancer cell into the mouse model.

• Journal of Microbiology
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• 제35권1호
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• pp.15-20
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• 1997

Kinetic studies were done to elucidate the reaction mechanism of purine nucleoside phosphorylase (PNP) in Micrococcus Luteus. PNP catalyzes the reversible phosphorolysis of ribonucleosides to their respective base. The effect of alternative competing substrates suggested that a single enzyme was involved in binding to the active site for all purine nucleosides, inosine, deoxyiosine, guanosine, deoxyguanosine, adenosine and deoxyadenosine. Affinity studies showed that pentose moiety reduced the binding capacity and methylation of ring N-1 of inosine and guanosine had little effect on binding to bacterial enzyme, whereas these compounds did not bind to the mammalian enzymes. The initial velocity and product inhibition studies demonstrated that the predominant mechanism of reaction was an ordered bi, bi reaction. The nucleoside bound to the enzyme first, followed by phosphate. Ribose 1-phosphate was the first product to leave, followed by base.

• 공업화학
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• 제17권3호
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• pp.317-320
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• 2006

본 연구에서는 HCI프로그램을 이용하여 여섯 가지 퓨린 유도체(caffeine, guanine, hypoxanthine, purine, theobromine, and theophylline)의 최적 분석 조건을 결정하였다. 이동상으로 물과 메탄올을 사용하는 역상 HPLC를 사용하였다. 체류모델로는 Snyder, Langmuir, Binary polynomial 중에서 체류인자를 가장 잘 예측한 Binary polynomial을 사용하였고 용출곡선을 계산하기 위해서는 단 이론(plate theory)을 사용하였으며 모든 계산은 HCI 프로그램을 이용하여 계산하였다. 이동상의 조건은 일정용매조성법(isocratic mode)과 계단함수 구배용매조성법(step-gradient mode)을 이용하였다. 일정용매조성법에서 물과 메탄올의 조성비가 93/7 (v/v)일 때 최적 분석조건을 얻을 수 있었다. 분석시간의 단축을 위하여 계단함수 구배용매조성법을 사용하여 이동상의 조성을 물/메탄올 93/7 (v/v)에서 5 min 후에 75/25 (v/v)로 변경하는 최적조건을 계산했다. 위의 두 조건에서 실험을 수행하여 계산 용출 곡선과 실험값을 비교하였으며, 매우 잘 일치함을 보였다.

• Archives of Pharmacal Research
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• 제17권2호
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• pp.60-65
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• 1994

Reaction of c-chloro-9-benzyl-8-(methylthio)purine 3 with primary amines afforoded, the comesponding 6-(substitutedamino)purines 4a-g. The latter products when methylated with methyl iodide yielded smoothly $N^3$-methyl purinium iodide salts 5a-f rather than the probable $N^1\;and\;N^7$-derivatives. 9-Benzyl-3-methyl-6-(methylmino)-8-(methylthio)purine 8 was obtained upon treating the purinium iodide 5a with alkali. Most of the synthesized compounds were screened for their antitumor activity.

• Asian-Australasian Journal of Animal Sciences
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• 제20권8호
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• pp.1201-1207
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• 2007

This study compared the recovery rate of intrajugular-administered allantoin in the urine and saliva between swamp buffaloes and zebu cattle to examine whether it could explain the lower excretion rate of urinary purine derivatives (PD) in the buffaloes. Three male swamp buffalo yearlings, with an average body weight of $349{\pm}40.35$ kg, and three Thai native cattle ($154{\pm}3.26$ kg) of similar age and sex were used in the study. Animals were kept in individual pens and fed at a maintenance energy level with a diet containing 65% monk bean husk (Vigna radiata) as roughage and 35% concentrates. Allantoin solution was infused into the jugular vein in four incremental rates equivalent to 0, 5, 10 and 15 mmol/d and urine was collected daily in acidified form. Daily PD excretion was linearly correlated with intrajugular allantoin infusion in both species. The relationship between daily urinary PD excretion (Y, mmol/d) and intrajugular allantoin infused (X, mmol/d) was $Y=0.75{\pm}0.318X+22.45{\pm}2.98$ ($r^2$ = 0.36, n = 12, MSE = 38.02, CV = 21.9, p<0.01) for swamp buffaloes and $Y=0.96{\pm}0.10X+15.93{\pm}0.92$ ($r^2$ = 0.91, n = 12, MSE = 3.60, CV = 8.27, p<0.01) for zebu cattle. The salivary PD concentration was not correlated with intrajugular allantoin infusion in both species, with values for buffaloes numerically lower than those for cattle. The present study reconfirmed previous studies that buffaloes have a lower plasma PD excretion rate via the renal route and a significant proportion (22%) of the plasma PD loss is via the saliva. However, results of our present and previous studies suggest that differences in purine base (PB) metabolism between buffaloes and zebu cattle occur before the purine compounds reach the plasma pool.

• 한국식품영양과학회지
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• 제21권3호
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• pp.286-290
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• 1992

부추 잎으로부터 purine nucleoside인 adenosine을 분리하고 그 구조를 기기적인 분석방법에 의하여 동정하였으며 또한 유리 아미노산 관련 화합물들의 조성과 상대함량을 표준품과 동일 조건하에서 아미노산 자동 분석 기기로 비교 검토하였다. 가장 함량이 많은 유리 아미노산들은 ala-nine, glutamic acid, aspartic acid 그리고 valine이었다.

• 약학회지
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• 제37권3호
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• pp.228-234
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• 1993

A new series of 7-deazapurine derivatives[7,8] as purine antagonists was prepared. Diethyl 4-cyano-N-(diphenyimethylene)-3-arylglutamate[3] were synthesized by LDA-catalyzed Michael addition of N-(diphenylrnethylene)glycine ethyl ester with (E)-2-cyano-3-arylacrylate. Deprotection yields diethyl 4-cyano-3-arylglutamate, which were easily cyclized to 4-cyano-2-ethoxycarbonyl-5-oxo-3-arylpyrrolidine[4]. The compounds[4] were treated with NaBH$_{4}$ and then with (C$_{2}$H$_{5}$)$_{3}$OBF$_{4}$ to give 4-cyano-5-ethoxy-2H-2-ethoxymethyl-3-aryl-3,4-dihydropyrrole[6], which were converted to 7-aryl-6-amino-8-ethoxymethyl-7,8-dihydro-7(3H, 9H)-deazapurine-2-thione[7] and 7-aryl-2,6-diamino-8-ethoxymethyl-7,8-dihydro-7(9H)-deazapurine[8] with possible activity against neoplastic disease.

• 농약과학회지
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• 제5권1호
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• pp.36-45
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• 2001

본 연구는 새로운 제초제 후보물질을 탐색하기 위하여 식물특이적 효소 저해제로 알려진 107개 기존 화합물에 대하여 생물활성을 조사하였다. Germination test, seedling assay, wheat leaf disc assay, cyanobacteria assay, whole plant assay를 통하여 15종의 저해제를 선발하였고 이들은 34종 효소를 저해하는 것으로 확인되었다. 이들 화합물 중에서 phenylhydrazine, purine, o-phenanthroline, oleylamine, 7,8-benzoquinoline, aminooxyacetic acid, dicyclohexylcarbodiimide 등은 성체를 이용한 온실 실험에서 높은 제초활성을 나타내었다. 7,8-benzoquinone, 8-hydroxyquinoline, 2,2'-dipyridyl 및 o-phenanthroline 등은 피, 벼, 토마토의 발아를 $1.25{\sim}5{\mu}M$의 농도에서도 억제하였다. 7,8-benzoquinoline, cyanuric fluoride, 4-methylpyrazole, tranylcypromine, oleylamine과 trifluoperazine 등은 $30{\sim}100{\mu}M$ 농도에서 cyanobacteria의 생육을 저해하였다. Dicyclohexyl carbodiimide와 chlorpromazine은 $100{\mu}M$ 농도에서 wheat leaf disc의 백화현상을 유기시켰다. 이상과 같이 생물학적 활성을 갖는 식물 특이적 효소저해제들은 신규제초제 후보물질을 선발하기 위한 새로운 대상효소로 이용될 수 있을 것으로 생각된다.

• Asian-Australasian Journal of Animal Sciences
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• 제32권8호
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• pp.1172-1185
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• 2019

Objective: Meat quality attributes in postmortem muscle tissues depend on skeletal muscle metabolites. The objective of this study was to determine the key metabolic compounds and pathways that are associated with postmortem aging and beef quality in Japanese Black cattle (JB; a Japanese Wagyu breed with highly marbled beef). Methods: Lean portions of Longissimus thoracis (LT: loin) muscle in 3 JB steers were collected at 0, 1, and 14 days after slaughter. The metabolomic profiles of the samples were analyzed by capillary electrophoresis time-of-flight mass spectrometry, followed by statistical and multivariate analyses with bioinformatics resources. Results: Among the total 171 annotated compounds, the contents of gluconic acid, gluconolactone, spermidine, and the nutritionally vital substances (choline, thiamine, and nicotinamide) were elevated through the course of postmortem aging. The contents of glycolytic compounds increased along with the generation of lactic acid as the beef aging progressed. Moreover, the contents of several dipeptides and 16 amino acids, including glutamate and aromatic and branched-chain amino acids, were elevated over time, suggesting postmortem protein degradation in the muscle. Adenosine triphosphate degradation also progressed, resulting in the generation of inosine, xanthine, and hypoxanthine via the temporal increase in inosine 5'-monophosphate. Cysteine-glutathione disulfide, thiamine, and choline increased over time during the postmortem muscle aging. In the Kyoto encyclopedia of genes and genomes database, a bioinformatics resource, the postmortem metabolomic changes in LT muscle were characterized as pathways mainly related to protein digestion, glycolysis, citric acid cycle, pyruvate metabolism, pentose phosphate metabolism, nicotinamide metabolism, glycerophospholipid metabolism, purine metabolism, and glutathione metabolism. Conclusion: The compounds accumulating in aged beef were shown to be nutritionally vital substances and flavor components, as well as potential useful biomarkers of aging. The present metabolomic data during postmortem aging contribute to further understanding of the beef quality of JB and other breeds.