PN-III-P2-2.1-PED-2019-3037

Funded by a grant of the Romanian Ministry of
Education and Research, CCCDI - UEFISCDI, project number PN-III-P2-
2.1-PED-2019-3037, within PNCDI III, contract number 385PED


PROJECT CODE: PN-III-P2-2.1-PED-2019-3037, contract number 385PED ⁄ 2020
PROJECT TITLE:
Intelligent and active systems in food packaging based on biopolymers and novel flavylium dyes
Sisteme inteligente si active pentru impachetarea alimentelor, bazate pe biopolimeri si coloranti noi de tip ioni de flaviliu
ACRONYM: SMARTBIOPACK
PROJECT COORDINATOR: Politehnica University of Timişoara
PROJECT DIRECTOR: Conf. Dr. Ing. Mihai Medeleanu

BUDGET: 595.000 RON (Public budget)
START TIME: 01/11/2020
END TIME: 31/10/2022


PROJECT LAYOUT
The food industry faces two major problems: the accumulation of synthetic plastic and food waste, so the research interest for intelligent and active systems, as well as biodegradable materials has constantly increased in recent years. Cost efficient biodegradable and edible packaging may be the friendly solution to the environment, while active and intelligent packaging providing valuable information on the quality and safety of the food products appear to be the solution to reduce food waste and increase the protection of the consumers.
The main scope of the project is to develop a demonstration model for production of new materials used in food packaging systems based on biopolymers and synthetic dyes from flavylium derivatives as indicators and monitor of packed food quality. To obtain these materials, the synthesis and evaluation of photochromic properties of some novel dye derivatives of the flavylium ion based on an initial procedure of the properties evaluation by computational methods will be carried on. The synthetic dyes after full physicochemical characterization and photochromic properties evaluation with pH and thermal variation, will be mixed with biopolymers (based on chitosan or a blend of chitosan with polyvinyl alcohol or polylactic acid) to obtain the needed packaging material which will be tested again to determine the behavior in contact with food.


PROJECT TEAM:
Project leader: Conf. Dr. Ing. Mihai Medeleanu
Reasearchers:
Ș.l. dr. ing. Iulia Maria Păușescu
Ș.l. dr. ing. Anamaria Todea
Ș.l. dr. ing. Valentin Badea
PhD Students:
Drd. Eng. Ionut-Mihai Tănase
Drd. Eng. Ioan Bîtcan

OBJECTIVE: The main objective of the project is to develop a demonstration model for production of new materials used in food packaging systems based on biopolymers and synthetic dyes from flavylium derivatives as indicators and monitor of packed food quality.

STAGES
Stage 1 (2020, 2 months) – Design of flavylium dyes

Stage 2 (2021, 12 months) – Synthesis and characterization of proposed flavylium dyes and preparation and characterization of films based on biopolymers and the synthesized dyes

Stage 3 (2022, 10 months) – Evaluation of the properties of the films based on biopolymers and the synthesized dyes for food packaging applications.

DELIVERABLES:
Stage 1
A list of proposed compounds with all the computed properties, ordered by the two type of activities: antioxidant and photochromic;
Stage 1 report.
Stage 2
Synthesis protocol for the novel flavylium based dyes;
Protocol for the pH-dependent photochromic properties;
Protocol for the antioxidant properties of the synthesized dyes;
A set of flavylium based dyes with full physicochemical characterization and antioxidant, photochromic and toxicological properties evaluated – grams quantities;
Scientific article submitted to an ISI quoted journal;
Abstract for one presentation at scientific conference in the field.
Stage 2 report.
Stage 3
Gram quantities of obtained films together with their characterization by depicted methods;
Abstracts for two presentations at scientific conferences in the field;
Scientific article submitted to an ISI quoted journal
Stage 3 report
Final report.

RESULTS

Stage 1 (2020, 2 months) Design of flavylium dyes

Abstract:

The objectives:

A list of proposed compounds with all the computed properties, ordered by the two type of activities: antioxidant and photochromic; Stage 1 report.

In this stage two series of flavylium type compounds were selected: S1 based on the structure of malvidine and S2 based on peonidine. For these compounds some computational studies were made in order to evaluate their specific properties like stability, reactivity, antioxidant activity, photochromic properties and also evaluation of their possible toxicity. The computations were done by Gaussian09 package on 6-31+G(d,p) basis set and the DFT-B3LYP method and the results were a list of molecular descriptors for chemical reactivity: HOMO-LUMO gap, electronegativity, absolute hardness and electrophilicity. For the S1 series compounds the photochromic properties were evaluated by prediction of UV-VIS spectrum for the main chemical species that arise during the spectral radiation. The predictions were made also by Gaussian09 with 6-31+G(d,p) in the frame of TD-DFT (Time dependent DFT) and water as solvent. The antioxidant properties were evaluated by computing some energetic molecular descriptors like BDE- bond dissociation enthalpy of O-H bond, IP-ionization potential, PDE-Proton dissociation enthalpy in O-H system, PA-proton affinity, ETE-electron transfer enthalpy, all associated with three reactions mechanisms that characterize the antioxidant reactivity of phenolic structures: HAT- hydrogen atom transfer, SET-PT single-electron transfer – proton transfer, SPLET - sequential proton loss electron transfer. The possible toxicity of S1 compounds were estimated by OSIRIS Property Explorer, a system which evaluate the toxicity risks like mutagenic, tumorigenic, irritant and reproductive effective together with some drug-relevant properties (octanol/water partition coefficient, solubility, molecular weight, topological polar surface area, drug-likeness and drug-score (bioactivity score)). The results of these computations were analyzed and four compounds from S1 series were proposed for synthesis.

All the objectives of this stage were fulfilled.

Stage 2 (2021, 12 months)Synthesis and characterization of proposed flavylium dyes and preparation and characterization of films based on biopolymers and the synthesized dyes

Abstract:

The objectives: Synthesis protocol for the novel flavylium based dyes; Protocol for the pH-dependent photochromic properties; Protocol for the antioxidant properties of the synthesized dyes; A set of flavylium based dyes with full physicochemical characterization and antioxidant, photochromic and toxicological properties evaluated – grams quantities; Scientific article submitted to an ISI quoted journal; Abstract for one presentation at scientific conference in the field. Stage 2 report.

In this stage the computational studies were finalized for the prediction of antioxidant activity, photochromic properties and also evaluation of the possible toxicity of the S2 series of flavylium dyes type. The procedure was similar to the studies in the stage 1.

The computations were done by Gaussian09 package on 6-31+G(d,p) basis set and the DFT-B3LYP method and the results were a list of molecular descriptors for chemical reactivity: HOMO-LUMO gap, electronegativity, absolute hardness and electrophilicity. For the S2 series compounds the photochromic properties were evaluated by prediction of UV-VIS spectrum for the main chemical species that arise during the spectral radiation. The predictions were made also by Gaussian09 with 6-31+G(d,p) in the frame of TD-DFT (Time dependent DFT) and water as solvent. The antioxidant properties were evaluated by computing some energetic molecular descriptors like BDE- bond dissociation enthalpy of O-H bond, IP-ionization potential, PDE-Proton dissociation enthalpy in O-H system, PA-proton affinity, ETE-electron transfer enthalpy, all associated with three reactions mechanisms that characterize the antioxidant reactivity of phenolic structures: HAT- hydrogen atom transfer, SET-PT single-electron transfer – proton transfer, SPLET - sequential proton loss electron transfer. The possible toxicity of S1 compounds were estimated by OSIRIS Property Explorer, a system which evaluate the toxicity risks like mutagenic, tumorigenic, irritant and reproductive effective together with some drug-relevant properties (octanol/water partition coefficient, solubility, molecular weight, topological polar surface area, drug-likeness and drug-score (bioactivity score)). The results of these computations were analyzed and four compounds from S2 series were proposed for synthesis.

Based on the previous computations studies 8 selected compounds were synthesized (4 form S1 series and 4 from S2 series). They were analyzed and characterized by spectroscopic methods: FT-IR, UV-VIS, 1H-NMR, 13C-NMR, 2D-NMR and by thermogravimetric methods. By UV-VIS spectroscopy the dependence of photochromic properties under pH variation in time were evaluated. For the observed transformations a set of reversible reactions were proposed and the halochromic effect of these compounds was emphasized. For antioxidant properties the colorimetric method with DPPH was used. For two of the 8 compounds (S1_4 and S2_4) the results were even better than those obtained for some conventional standard antioxidants (vitamin C and curcumin). For 6 of the compounds cytotoxic properties were investigated on cell lines containing tumor cells type HT29, specific for colon cancer. Two compounds (S1_3 and S2_3) provided a higher toxicity against the tumor cell. However the others had no significant activity.

Insertion of dyes in polymer film implies two kind of films: monocomponent (based on chitosan with 4 of the synthesized dyes: S1_4, S2_2, S2_3, S2_4) and polycomponent (based by mixtures chitosan-polyvinyl alcohol, chitosan-cellulose and chitosan starch using S1_4, S1_10, S2_2 and S2_3 dyes). The films were characterized by FT-IR and UV-VIS spectroscopy and by thermogravimetric methods for thermal properties. For obtained polymeric films three material properties were measured: water content, solubility in water and swollen degree.

The results were presented in 3 international conferences (two abroad and one in Romania) and one paper sent to an ISI journal (under evaluation).

All the objectives of this stage were fulfilled.

 

Conferences:

  1. Corneanu C., Păușescu I., Todea A., Peter F., Medeleanu M., Ledeți I., Chitosan/PVA pH indicator films with potential food packaging applications, Advances in Food Chemistry Conference, AdFoodChem, 15-17 Aprilie 2021, online.
  2. Corneanu C., Păușescu I., Peter F., Medeleanu M., Synthesis, characterization and halochromism of a new xanthylium derivative, International Conference on Photochemistry – Ediția a 30-a, IPC30, 19-23 Iulie 2021, online.
  3. Bîtcan I., Argetoianu R., Dăescu D., Dreavă D.-M., Medeleanu M., Păușescu I., Bio-based pH indicator films for intelligent food packaging applications, EuroFoodChem – Ediția a 21-a, 22-24 Noiembrie 2021, online.

Publications:

  1. Dăescu D. , Dreavă D.-M. , Bîtcan I., Medeleanu M., I. Păușescu, Studies on the halochromic and antioxidant properties of a new flavylium dye, Studia UBB Chemia – under evaluation procedure.

 

Stage 3 (2022, 10 months) – Evaluation of the properties of the films based on biopolymers and the synthesized dyes for food packaging applications

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