Dataset Information

Interactions between ?-Lactoglobulin and 3,3'-Diindolylmethane in Model System.

ABSTRACT: The compound 3,3'-diindolylmethane (DIM) has a broad spectrum of anticancer activities. However, low stability and bioavailability limit its application. Elucidating interactions between DIM and ?-lactoglobulin (?-LG) may be useful for fabricating whey protein-based protecting systems. Interaction with DIM increased the diameter and absolute zeta potential value of ?-LG. UV-absorption spectra suggested that there was a complex of DIM and ?-LG. ?-LG showed enhanced fluorescence intensity by complexing with DIM with a binding constant of 6.7 × 105 M-1. Upon interaction with DIM, ?-LG was decreased in secondary structure content of helix and turn while increased in ?-sheet and unordered. FT-IR spectra and molecular docking results indicated the roles of hydrophobic interaction and hydrogen bond for the formation of DIM and ?-LG nanocomplexes. Data suggested that ?-LG may be a good vehicle for making a protein-based DIM protection and delivery system due to the tight binding of DIM to ?-LG.

SUBMITTER: Wang C

PROVIDER: S-EPMC6600512 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Publications

Interactions between β-Lactoglobulin and 3,3'-Diindolylmethane in Model System.

Wang Cuina C Zhou Xinhui X Wang Hao H Sun Xiaomeng X Guo Mingruo M

Molecules (Basel, Switzerland) 20190607 11

The compound 3,3'-diindolylmethane (DIM) has a broad spectrum of anticancer activities. However, low stability and bioavailability limit its application. Elucidating interactions between DIM and β-lactoglobulin (β-LG) may be useful for fabricating whey protein-based protecting systems. Interaction with DIM increased the diameter and absolute zeta potential value of β-LG. UV-absorption spectra suggested that there was a complex of DIM and β-LG. β-LG showed enhanced fluorescence intensity by compl ...[more]

PMID: 31181617

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Project description:3,3'-Diindolylmethane (DIM), a major phytochemical derived from ingestion of cruciferous vegetables, is also a dietary supplement. In preclinical models, DIM is an effective cancer chemopreventive agent and has been studied in a number of clinical trials. Previous pharmacokinetic studies in preclinical and clinical models have not reported DIM metabolites in plasma or urine after oral dosing, and the pharmacological actions of DIM on target tissues is assumed to be solely via the parent compound. Seven subjects (6 males and 1 female) ranging from 26-65 years of age, on a cruciferous vegetable-restricted diet prior to and during the study, took 2 BioResponse DIM 150-mg capsules (45.3 mg DIM/capsule) every evening for one week with a final dose the morning of the first blood draw. A complete time course was performed with plasma and urine collected over 48 hours and analyzed by UPLC-MS/MS. In addition to parent DIM, two monohydroxylated metabolites and 1 dihydroxylated metabolite, along with their sulfate and glucuronide conjugates, were present in both plasma and urine. Results reported here are indicative of significant phase 1 and phase 2 metabolism and differ from previous pharmacokinetic studies in rodents and humans, which reported only parent DIM present after oral administration. 3-((1H-indole-3-yl)methyl)indolin-2-one, identified as one of the monohydroxylated products, exhibited greater potency and efficacy as an aryl hydrocarbon receptor agonist when tested in a xenobiotic response element-luciferase reporter assay using Hepa1 cells. In addition to competitive phytochemical-drug adverse reactions, additional metabolites may exhibit pharmacological activity highlighting the importance of further characterization of DIM metabolism in humans. SIGNIFICANCE STATEMENT: 3,3'-Diindolylmethane (DIM), derived from indole-3-carbinol in cruciferous vegetables, is an effective cancer chemopreventive agent in preclinical models and a popular dietary supplement currently in clinical trials. Pharmacokinetic studies to date have found little or no metabolites of DIM in plasma or urine. In marked contrast, we demonstrate rapid appearance of mono- and dihydroxylated metabolites in human plasma and urine as well as their sulfate and glucuronide conjugates. The 3-((1H-indole-3-yl)methyl)indolin-2-one metabolite exhibited significant aryl hydrocarbon receptor agonist activity, emphasizing the need for further characterization of the pharmacological properties of DIM metabolites.

Dataset Information

Interactions between ?-Lactoglobulin and 3,3'-Diindolylmethane in Model System.

Publications

Interactions between β-Lactoglobulin and 3,3'-Diindolylmethane in Model System.

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