Compounds > 2-Methylindole-3-acetic-acid

2-Methylindole-3-acetic-acid and indoleacetic-acid

2-Methylindole-3-acetic-acid has been researched along with indoleacetic-acid* in 2 studies

Other Studies

2 other study(ies) available for 2-Methylindole-3-acetic-acid and indoleacetic-acid

Article	Year
Binding of ring-substituted indole-3-acetic acids to human serum albumin. Bioorganic & medicinal chemistry, 2007, Jul-01, Volume: 15, Issue:13 The plant hormone, indole-3-acetic acid (IAA), and its ring-substituted derivatives have recently attracted attention as promising pro-drugs in cancer therapy. Here we present relative binding constants to human serum albumin for IAA and 34 of its derivatives, as obtained using the immobilized protein bound to a support suitable for high-performance liquid chromatography. We also report their octanol-water partition coefficients (logK(ow)) computed from retention data on a C(18) coated silica gel column. A four-parameter QSPR (quantitative structure-property relationships) model, based on physico-chemical properties, is put forward, which accounts for more than 96% of the variations in the binding affinities of these compounds. The model confirms the importance of lipophilicity as a global parameter governing interaction with serum albumin, but also assigns significant roles to parameters specifically related to the molecular topology of ring-substituted IAAs. Bulky substituents at ring-position 6 increase affinity, those at position 2 obstruct binding, while no steric effects were noted at other ring-positions. Electron-withdrawing substituents at position 5 enhance binding, but have no obvious effect at other ring positions. Topics: Algorithms; Chemical Phenomena; Chemistry, Physical; Chromatography, High Pressure Liquid; Data Interpretation, Statistical; Humans; Indoleacetic Acids; Protein Binding; Quantitative Structure-Activity Relationship; Serum Albumin	2007
Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy. Bioorganic & medicinal chemistry letters, 2002, Sep-16, Volume: 12, Issue:18 Substituted indole-3-acetic acid (IAA) derivatives, plant auxins with potential for use as prodrugs in enzyme-prodrug directed cancer therapies, were oxidised with horseradish peroxidase (HRP) and toxicity against V79 Chinese hamster lung fibroblasts was determined. Rate constants for oxidation by HRP compound I were also measured. Halogenated IAAs were found to be the most cytotoxic, with typical surviving fractions of <10(-3) after incubation for 2h with 100 microM prodrug and HRP. Topics: Animals; Antineoplastic Agents; Cell Line; Cricetinae; Halogens; Horseradish Peroxidase; Indoleacetic Acids; Kinetics; Oxidation-Reduction; Prodrugs	2002

Article

Year

Binding of ring-substituted indole-3-acetic acids to human serum albumin.

Bioorganic & medicinal chemistry, 2007, Jul-01, Volume: 15, Issue:13

The plant hormone, indole-3-acetic acid (IAA), and its ring-substituted derivatives have recently attracted attention as promising pro-drugs in cancer therapy. Here we present relative binding constants to human serum albumin for IAA and 34 of its derivatives, as obtained using the immobilized protein bound to a support suitable for high-performance liquid chromatography. We also report their octanol-water partition coefficients (logK(ow)) computed from retention data on a C(18) coated silica gel column. A four-parameter QSPR (quantitative structure-property relationships) model, based on physico-chemical properties, is put forward, which accounts for more than 96% of the variations in the binding affinities of these compounds. The model confirms the importance of lipophilicity as a global parameter governing interaction with serum albumin, but also assigns significant roles to parameters specifically related to the molecular topology of ring-substituted IAAs. Bulky substituents at ring-position 6 increase affinity, those at position 2 obstruct binding, while no steric effects were noted at other ring-positions. Electron-withdrawing substituents at position 5 enhance binding, but have no obvious effect at other ring positions.

Topics: Algorithms; Chemical Phenomena; Chemistry, Physical; Chromatography, High Pressure Liquid; Data Interpretation, Statistical; Humans; Indoleacetic Acids; Protein Binding; Quantitative Structure-Activity Relationship; Serum Albumin

2007

Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy.

Bioorganic & medicinal chemistry letters, 2002, Sep-16, Volume: 12, Issue:18

Substituted indole-3-acetic acid (IAA) derivatives, plant auxins with potential for use as prodrugs in enzyme-prodrug directed cancer therapies, were oxidised with horseradish peroxidase (HRP) and toxicity against V79 Chinese hamster lung fibroblasts was determined. Rate constants for oxidation by HRP compound I were also measured. Halogenated IAAs were found to be the most cytotoxic, with typical surviving fractions of <10(-3) after incubation for 2h with 100 microM prodrug and HRP.

Topics: Animals; Antineoplastic Agents; Cell Line; Cricetinae; Halogens; Horseradish Peroxidase; Indoleacetic Acids; Kinetics; Oxidation-Reduction; Prodrugs

2002