Rate assay for estimation of thiol affinity of sulfhydryl-reactive agents: Estimation of SH-reactivity

Louis-Ferdinand, Robert T.; Fuller, George C.

doi:10.1002/jps.2600580931

Cited by 8 publications

(2 citation statements)

References 4 publications

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“…7,[9][10][11] The unsaturated nitroolefinic bond in b-nitrostyrenes has been recognized as an essential fragment in its bioactivity, as it can interact with cellular protein cysteine sulfhydryls via the Michael addition mechanism. 14,15 The reactivity of b-nitrostyrenes following the Michael addition is dependent on the position of the withdrawing group in the A ring. In contrast, methyl substitution in the b position resulted in a reduced reaction rate.…”

Section: Cytotoxic Activitymentioning

confidence: 99%

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The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes

Hsieh

Chang

Chuang

et al. 2010

Bioorganic & Medicinal Chemistry

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Section: Cytotoxic Activitymentioning

confidence: 99%

“…The platelet suspension was then prepared according to the washing procedure previously described. 15 Platelets were finally suspended in Tyrode 0 s solution containing Ca 2+ (2 mM), glucose (11.1 mM) and bovine serum albumin (3.5 mg/ml) at a concentration of 3 Â 10 8 platelets/ml.…”

Section: Preparation Of Washed Human Plateletsmentioning

confidence: 99%

The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes

Hsieh

Chang

Chuang

et al. 2010

Bioorganic & Medicinal Chemistry

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Röntgen‐Strukturanalyse, absolute Konfiguration und Circulardichroismus von β‐Nitrostyrol‐Addukten des Cysteins

et al. 1979

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Synthesis, Circular Dichroism, and X-Ray Structure Analysis of P-Nitrostyrene Adducts of CysteineAll four isomeric N-acetyl-S-(2-nitro-l-phenylethyl)cysteines were synthesized by addition of N-acetyl-L-and -D-cysteine to P-nitrostyrene. Fractional crystallization gave the two diastereomers of both the L-and D-CySteine derivatives, which do not differ significantly in their 'H and I3C NMR spectra or IR and UV absorption. However, they exhibit characteristic Cotton effects with opposite signs at 285 nm. In this range of wave lengths the chiroptical properties of the adducts depend entirely on the configuration of the new center of asymmetry. Its immediate environment is formed by the nitro group, the sulfide group, and the phenyl residue. X-Ray analysis of that b-nitrostyrene adduct of N-acetyl-L-cysteine, which has a negative long wave length Cotton effect revealed its ( R , R ) configuration. It is shown that the configuration of configurational isomers and of various substituted analogues of the S-(2-nitro-l-phenylethyl) group may be also determined by CD measurements.Die Thiolgruppe des Cysteins addiert an B-Nitrostyrole unter Bildung von S-(2-Nitro-1-phenylethy1)-Derivaten'). Wir haben die Anwendbarkeit der P-Nitrostyrole als SH-Schutzgruppe zu Peptidsynthesen untersucht, da Addukte wie N-tert-Butoxycarbon yl-S-( 2-nit ro-1 -p henylethy1)-L-cystein leich t zuganglich sind ' 3 *).Bei der Addition eines chiralen Thiols wie N-Acetyl-L-cystein an P-Nitrostyrol bildet sich ein weiteres Asymmetriezentrum (s. Formelschema); es entstehen somit zwei Diastereomere in gleicher Menge, sofern nicht eine Konfiguration bevorzugt ist. Bei syste-

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Quantitative untersuchungen zum acidolyseund jodolyseverlauf bei S-arylalkyl-schutzgruppen

Losse

Stölzel

1972

Tetrahedron

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Rate assay for estimation of thiol affinity of sulfhydryl-reactive agents: Estimation of SH-reactivity

Cited by 8 publications

References 4 publications

The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes

The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes

Röntgen‐Strukturanalyse, absolute Konfiguration und Circulardichroismus von β‐Nitrostyrol‐Addukten des Cysteins

Quantitative untersuchungen zum acidolyseund jodolyseverlauf bei S-arylalkyl-schutzgruppen

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