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Science | 1970

Cytokinin Activity of Ureidopurine Derivatives Related to a Modified Nucleoside Found in Transfer RNA

William H. Dyson; C. M. Chen; Syed N. Alam; Ross H. Hall; Chung Il Hong; Girish B. Chheda

By use of a radioactive labeling technique N-(nebularin-6-ylcarbamoyl)threonine has been detected in plant transfer RNA. Derivatives of this nucleoside promote cell division of a cytokinin-requiring soya bean tissue.


Biochemical Pharmacology | 1973

Metabolism of N-(purin-6-ylcarbamoyl)-l-threonine riboside in rat and man

Chung Il Hong; Girish B. Chheda; Gerald P. Murphy; Arnold Mittelman

Abstract N-(purin-6-ylcarbamoyl- L -threonine riboside-8-14C (Ado-CO-thr-8-14C) and N-(purin-6-ylcarbamoyl- l -[U-14C]threonine riboside (Ado-CO-thr-14C) were synthesized by using adenosine-8-14C and threonine [U-14C], respectively, as labeled starting materials. The Ado-CO-thr-8-14C and Ado-CO-thr-14C were given intravenously and orally to rat and to man. Of the 2·4 × 106 dis/min administered intravenously to rats, 73 per cent was excreted in urine. More than 79 per cent of this excreted activity was in unchanged Ado-CO-thr, 2·2 per cent in the free base, N-(purin-d-ylcarbamoyl)- l -threonine (Ade-CO-thr), and less than 2 per cent in adenosine. Radioactivity in adenine, inosine, hypoxanthine and uric acid was less than 0·1 per cent. When the labeled Ado-CO-thr was administered orally, less than 5 per cent of the radioactivity was excreted in urine. Similar results were obtained in man. These data revealed that Ado-CO-thr is quite a stable modified nucleoside in vivo. Intravenously administered, Ado-CO-thr was not incorporated into rat t-RNA. In vitro, it did not serve as a substrate for adenosine deaminase, xanthine oxidase and adenosine kinase. Incubation of Ado-CO-thr with urease, acylase, protease, peptidases and similar other enzymes did not lead to any structural change in the molecule. It is suggested that naturally occurring urinary Ado-CO-thr originates from t-RNA and is excreted quantitatively in urine.


Journal of Medicinal Chemistry | 1971

Synthesis of naturally occurring 6-ureidopurines and their nucleosides.

Girish B. Chheda; Chung Il Hong


Biochemical Journal | 1972

Biosynthesis of N-(purin-6-ylcarbamoyl)-l-threonine riboside. Incorporation of l-threonine in vivo into modified nucleoside of transfer ribonucleic acid

Girish B. Chheda; Chung Il Hong; Conrad F. Piskorz; G. A. Harmon


Journal of Medicinal Chemistry | 1973

Synthesis and biological activity of analogs of naturally occurring 6-ureidopurines and their nucleosides.

Chung Il Hong; Girish B. Chheda; Shib P. Dutta; Anne O'Grady-Curtis; George L. Tritsch


Journal of Medicinal Chemistry | 1975

Synthesis and antitumor activity of 5'-phosphates and cyclic 3',5'-phosphates derived from biologically active nucleosides

Chung Il Hong; George L. Tritsch; Arnold Mittelman; Peter Hebborn; Girish B. Chheda


Journal of Medicinal Chemistry | 1977

Synthesis and biological activities of some N6- and N9-carbamoyladenines and related ribonucleosides

Shib P. Dutta; Chung Il Hong; George L. Tritsch; Cox C; Parthasarthy R; Girish B. Chheda


Journal of Medicinal Chemistry | 1976

Synthesis and biological activities of some N4-substituted 4-aminopyrazolo(3,4-d)pyrimidines.

Chung Il Hong; De Nc; George L. Tritsch; Girish B. Chheda


Journal of Pharmaceutical Sciences | 1978

Synthesis and Biological Activity of N6- (n -Alkylureido) purine Ribonucleosides and Their 5′-Phosphates

Chung Il Hong; Arnold Mittelman; Girish B. Chheda


Journal of Medicinal Chemistry | 1973

Synthesis of 5'-phosphates of the naturally occurring 6-ureidopurine ribonucleosides and their analogs.

Chung Il Hong; Girish B. Chheda

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Arnold Mittelman

New York State Department of Health

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Shib P. Dutta

Roswell Park Cancer Institute

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