Biodistribution of [35S]-cysteine and cysteine prodrugs: potential impact on chemoprotection strategies

Roberts, Jeanette C.; Phaneuf, Holly L.; Dominick, Pamela K.; Wilmore, Britta H.; Cassidy, Pamela B.

doi:10.1002/(sici)1099-1344(199905)42:5<485::aid-jlcr209>3.0.co;2-l

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“…1 H NMR (CDCl3, 500 MHz): δ 3.37 (t, 2H, J ) 8, 6.5 Hz), 3.59 (t, 2H, J ) 8, 6.5 Hz), 6.75 (br s, 1H) ppm. 13 C NMR (CDCl3, 125 MHz): δ 30.0, 43.4, 176.7 ppm. Anal.…”

Section: (Rs)-d-ribo-(1′2′3′4′-tetrahydroxybutyl)thiazolidine-4(r)-ca...mentioning

confidence: 99%

“…1 H NMR (DMSO-d6, 500 MHz): δ 2.49 (t, 2H, J ) 7.5 Hz), 3.39 (t, 2H, J ) 3 Hz), 3.95-4.00 (m, 4H), 4.31 (t, 2H, J ) 8, 6.5 Hz), 8.89 (br s, 3H) ppm. 13 C NMR (DMSO-d6, 125 MHz): δ 25.0, 25.3, 36.4, 41.5, 48.1, 171.1 ppm. Anal.…”

Section: (Rs)-d-ribo-(1′2′3′4′-tetrahydroxybutyl)thiazolidine-4(r)-ca...mentioning

confidence: 99%

“…Our prodrug strategy involves incorporating the parent thiolamine into a thiazolidine ring structure, which effectively masks the reactive thiol group, reduces potential side effects, and alters key physicochemical properties. , For the current studies, representatives of two classes of thiazolidine analogues were synthesized and evaluated. The 2-alkylthiazolidines (Scheme ) were designed to release the free thiolamine by nonenzymatic ring opening and hydrolysis. ,, Preliminary investigation of such radioprotectors has been promising. , In contrast, the 2-oxothiazolidines (Scheme ) were designed to be inherently more stable, releasing the parent thiolamine only upon enzymatic cleavage, if at all.…”

Section: Introductionmentioning

confidence: 99%

“…10,11 Our prodrug strategy involves incorporating the parent thiolamine into a thiazolidine ring structure, which effectively masks the reactive thiol group, reduces potential side effects, and alters key physicochemical properties. 12,13 For the current studies, representatives of two classes of thiazolidine analogues were synthesized and evaluated. The 2-alkylthiazolidines (Scheme 1) were designed to release the free thiolamine by nonenzymatic ring opening and hydrolysis.…”

Section: Introductionmentioning

confidence: 99%

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Thiazolidine Prodrugs as Protective Agents against γ-Radiation-Induced Toxicity and Mutagenesis in V79 Cells

et al. 2001

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Representatives of two classes of thiazolidine prodrug forms of the well-known radioprotective agents L-cysteine, cysteamine, and 2-[(aminopropyl)amino]ethanethiol (WR-1065) were synthesized by condensing the parent thiolamine with an appropriate carbonyl donor. Inherent toxicity of the prodrugs was assessed in V79 cells using a clonogenic survival assay. Protection against radiation-induced cell death was measured similarly after exposure to 0--8 Gy gamma ((137)Cs) radiation. Antimutagenic activity was determined at the hypoxanthine-guanine phosphoribosyltransferase (HGPRT) locus. All thiazolidine prodrugs exhibited less toxicity than their parent thiolamines, sometimes dramatically so. Protection against radiation-induced cell death was observed for the 2-alkylthiazolidine, 2(R,S)-D-ribo-(1',2',3',4'-tetrahydroxybutyl)thiazolidine (RibCyst), which produced a protection factor at 8 Gy of 1.8; the cysteine analogue, 2(R,S)-D-ribo-(1',2',3',4'-tetrahydroxybutyl)thiazolidine-4(R)-carboxylic acid (RibCys), was less active. RibCyst also exhibited excellent antimutational activity, rivaling that of WR-1065. The 2-oxothiazolidine analogues showed little activity in either determination under the conditions tested, perhaps due to their enhanced chemical and biochemical stability.

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“…1 H NMR (CDCl3, 500 MHz): δ 3.37 (t, 2H, J ) 8, 6.5 Hz), 3.59 (t, 2H, J ) 8, 6.5 Hz), 6.75 (br s, 1H) ppm. 13 C NMR (CDCl3, 125 MHz): δ 30.0, 43.4, 176.7 ppm. Anal.…”

Section: (Rs)-d-ribo-(1′2′3′4′-tetrahydroxybutyl)thiazolidine-4(r)-ca...mentioning

confidence: 99%

Section: (Rs)-d-ribo-(1′2′3′4′-tetrahydroxybutyl)thiazolidine-4(r)-ca...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Thiazolidine Prodrugs as Protective Agents against γ-Radiation-Induced Toxicity and Mutagenesis in V79 Cells

et al. 2001

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Biodistribution of [35S]-cysteine and cysteine prodrugs: potential impact on chemoprotection strategies

Cited by 1 publication

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Thiazolidine Prodrugs as Protective Agents against γ-Radiation-Induced Toxicity and Mutagenesis in V79 Cells

Thiazolidine Prodrugs as Protective Agents against γ-Radiation-Induced Toxicity and Mutagenesis in V79 Cells

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