Faculty Profiles - KIM Hye-Sook

Papers - KIM Hye-Sook

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Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals

Y Nonami, T Tokuyasu, A Masuyama, M Nojima, KJ McCullough, HS Kim, Y Wataya

TETRAHEDRON LETTERS 41 ( 23 ) 4681 - 4684 2000.6

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

Treatment of unsaturated hydroperoxy peracetals with bis(sym-collidine)iodine(I) hexafluorophosphate affords a series of iodine-containing spiro-1,2,4,5-tetraoxacycloalkane derivatives in high yield. In addition, ozonolysis of unsaturated hydroperoxy peracetals in AcOH-CH2Cl2 also results in the formation of spirol,2,4,5-tetraoxacycloalkanes. Two of the new compounds, 3-methyl-3-methyldioxy-1,2,6,7-tetraoxaspiro[7.11]nonadecane and dimethyl-4-iodo-1,2,6,7-tetraoxaspiro[7.11]nonadecane, exhibit significant in vitro antimalarial activity against P. falciparum with EC50 values of ca. 10(-7) M. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(00)00688-2

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Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals

T Tokuyasu, A Masuyama, M Nojima, HS Kim, Y Wataya

TETRAHEDRON LETTERS 41 ( 17 ) 3145 - 3148 2000.4

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

Ozonolysis of a vinyl ether 2, prepared from dihydrocarvone 1 (a 1:4 mixture of cis- and trans-isomer), in methanol gave two isomeric unsaturated hydroperoxy acetals cis- and trans-3. Iodonium ion- or ozone-mediated cyclizations of the hydroperoxide cis-3 gave the corresponding yingzhaosu A analogues 4 and 6 in moderate yields. The peroxide 8, obtained by the Ag2O-mediated methylation of 6, showed notable anti-malarial activity in vitro (IC50=1.0x10(-7) M). (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(00)00372-5

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Potent in vivo antimalarial activity of 3,15-di-O-acetylbruceolide against Plasmodium berghei infection in mice

Hye-Sook Kim, Yasuharu Shibata, Naoko Ko, Naomi Ikemoto, Yuki Ishizuka, Nobutoshi Murakami, Masanori Sugimoto, Motomasa Kobayashi, Yusuke Wataya

Parasitology International 48 ( 3 ) 271 - 274 2000.1

Language：English

The antimalarial activity of the O-acylated bruceolide derivative, 3,15-di-O-acetylbruceolide, was evaluated against Plasmodium berghei in vivo. The concentration of 3,15-di-O-acetylbruceolide required for 50% suppression (ED50) of P. berghei in mice was 0.46±0.06 mg/kg/day, whereas bruceolide was only half as effective as 3,15-di-O-acetylbruceolide. Two antimalarial drugs used clinically, chloroquine and artemisinin, demonstrated only low activity corresponding to 1/4 and 1/12 of the ED50 value of 3,15-di-O-acetylbruceolide, respectively. These results may be helpful in the design of better chemotherapeutic bruceolides against falciparum malaria. Copyright (C) 2000 Elsevier Science Ireland Ltd.

DOI： 10.1016/S1383-5769(99)00023-9

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Synthesis, crystal structure and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane

Kevin J. McCullough, Yuji Nonami, Araki Masuyama, Masatomo Nojima, Hye-Sook Kim, Yusuke Wataya

Tetrahedron Letters 40 ( 51 ) 9151 - 9155 1999.12

Language：English Publishing type：Research paper (scientific journal) Publisher：Elsevier Ltd

Photooxygenation of 2-phenylnorbornene 1 in the presence of 30% aqueous hydrogen peroxide in acetonitrile afforded the labile 1,2-bis-hydroperoxide 3 which could be cycloalkylated to provide the tricyclic peroxides 5, albeit in low yield, on treatment with silver oxide and a 1,ω-diiodoalkane. Trimethylsilylation of 3, followed by TMSOTf-catalyzed cyclocondensation with carbonyl compounds led to the formation of the tricyclic peroxides 8 containing a 1,2,4,5-tetroxepane structure. The structures of two novel tricyclic peroxides 5a and 8a were unambiguously determined by the X-ray crystallographic analysis.

DOI： 10.1016/S0040-4039(99)01944-9

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Structure-activity relationships of quaternary protoberberine alkaloids having an antimalarial activity

Kinuko Iwasa, Yumi Nishiyama, Momoyo Ichimaru, Masataka Moriyasu, Hye-Sook Kim, Yusuke Wataya, Takao Yamori, Turuo Takashi, Dong-Ung Lee

European Journal of Medicinal Chemistry 34 ( 12 ) 1077 - 1083 1999.12

Catalytic Asymmetric Synthesis of Antimalarial Alkaloids Febrifugine and Isofebrifugine and Their Biological Activity. Reviewed

Shu Kobayashi, Masaharu Ueno, Ritsu Suzuki, Haruro Ishitani, Hye-Sook Kim, Yusuke Wataya

The Journal of Organic Chemistry Vol.64 ( No.18 ) 6833 - 6841 1999.9

New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite

Y Takaya, H Tasaka, T Chiba, K Uwai, M Tanitsu, HS Kim, Y Wataya, M Miura, M Takeshita, Y Oshima

JOURNAL OF MEDICINAL CHEMISTRY 42 ( 16 ) 3163 - 3166 1999.8

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Febrifugine (1) and isofebrifugine (2), isolated from the roots of Dichroa febrifuga Lour. (Chinese name: Chang Shan), are active principles against malaria. Adducts of 1 and 2 with acetone, Df-l (3) and Df-2 (4), respectively, were obtained using silica gel and acetone. They showed high activity against P. falciparum malaria in vitro. Compound 3 was found to be equally effective against P. berghei in vivo as the clinically used drug chloroquine, whereas 4 showed only 1/24 of the activity of 3. Metabolism studies of these compounds revealed that compound 4 is readily metabolized in mouse liver. Accordingly, the dose of 4 must be higher than that of 3 to attain blood levels sufficient for a favorable therapeutic effect.

DOI： 10.1021/jm990131e

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Synthesis and antimalarial activity of cyclic peroxides, 1,2,4,5,7-pentoxocanes and 1,2,4,5-tetroxanes

HS Kim, Y Shibata, Y Wataya, K Tsuchiya, A Masuyama, M Nojima

JOURNAL OF MEDICINAL CHEMISTRY 42 ( 14 ) 2604 - 2609 1999.7

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

A variety of 1,2,4,5,7-pentoxocane and 1,2,4,5-tetroxane derivatives were prepared as potential peroxide antimalarial agents. In both series of cyclic peroxides, the steric and electronic effects of the substituents attached to the peroxide ring exert a remarkable influence on the antimalarial activity. For some cyclic peroxides, which were found to be highly effective in vitro, the study in vivo has been also conducted.

DOI： 10.1021/jm990014j

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A colorimetric DNA diagnostic method for falciparum malaria and vivax malaria: A field trial in the Solomon Islands

M Arai, K Kunisada, HS Kim, H Miyake, C Mizukoshi, T Kakutani, A Yamane, S Nakagami, S Kawai, H Nakano, F Kawamoto, Y Wataya

NUCLEOSIDES & NUCLEOTIDES 15 ( 1-3 ) 719 - 731 1996

Language：English Publishing type：Research paper (scientific journal) Publisher：MARCEL DEKKER INC

We have developed a colorimetric assay, ''microtiter plate-hybridization'', for the detection of malaria parasites Plasmodium falciparum and P. vivax in human blood, in which the target DNA sequences (18S small subunit ribosomal RNA gene) amplified by polymerase chain reaction (PCR) are hybridized with the species-specific probes immobilized on a microtiter well, This assay system was tested in Guadalcanal, Solomon Islands, where malaria is highly endemic. We obtained blood samples by finger puncture from 130 asymptomatic donors. Among the 130 samples, 30 (23 %) were P. falciparum positive, 28 (22 %) were P. vivax positive, and 8 (6 %) were mixed infections, The results of our DNA diagnostic method showed good correlation with those of acridine orange microscopy.

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Species-specific PCR detection of malaria parasites by microtiter plate hybridization: Clinical study with malaria patients

M. Kimura, H. Miyake, H. S. Kim, M. Tanabe, M. Arai, S. Kawai, A. Yamane, Y. Wataya

Journal of Clinical Microbiology 33 ( 9 ) 2342 - 2346 1995

Language：English Publishing type：Research paper (scientific journal)

A simple and convenient PCR method that amplifies the 18S rRNA genes has been developed for the purpose of detecting and differentiating four species causing malaria in humans. The advantage of the assay is that the biotinylated PCR product is visualized following hybridization with specific probes which are immobilized on plate wells (microtiter plate hybridization). This method has been previously evaluated in a field study and was found to be sensitive and specific for the detection of Plasmodium falciparum and Plasmodium vivax. In the current study, the microtiter plate hybridization PCR method was evaluated by using blood specimens from malaria patients. All of 36 cases of falciparum malaria, 26 of 27 cases of vivax malaria, all of 11 cases of ovale malaria, and 2 cases of malariae malaria were diagnosed species specifically by the PCR method. There were four smear-negative, PCR- positive cases that seemed to correspond to the convalescent stage of malaria. In contrast, 30 cases for which the diagnosis of malaria has been excluded on the basis of microscopy and clinical courses showed negative PCR results. By comparing parasite densities and PCR results following antimalarial treatment of some patients, it was revealed that the PCR results largely paralleled the parasite densities and that PCR could detect as few as 10 parasites per μl of blood. We conclude that this PCR method is highly sensitive and specific for the detection of all four parasite species and can serve as a useful supplement to microscopy for the clinical management of malaria.

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