2-Methylenebutyrolactone

Catalog No.S5148 Synonyms: Tulipalin A, MBL, α-methylene-γ-butyrolactone

For research use only.

2-Methylenebutyrolactone (Tulipalin A, MBL, α-methylene-γ-butyrolactone), also known as α-methylene-γ-butyrolactone (MBL) (Tulipalin A), belongs to the class of sesquiterpene lactone family and is considered as cyclic analog of most common vinyl monomer methyl methacrylate (MMA).

2-Methylenebutyrolactone Chemical Structure

CAS No. 547-65-9

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Biological Activity

Description 2-Methylenebutyrolactone (Tulipalin A, MBL, α-methylene-γ-butyrolactone), also known as α-methylene-γ-butyrolactone (MBL) (Tulipalin A), belongs to the class of sesquiterpene lactone family and is considered as cyclic analog of most common vinyl monomer methyl methacrylate (MMA).
In vitro

After exposure of Jurkat T cells to 2-Methylenebutyrolactone (Tulipalin A , TUPA) for 72 h, a dose dependent toxicity is detected. Concentrations higher than 20 μM lead to a significant reduction of viable cells. Compared to vehicle-treated control cells, concentrations of 47.6 and 26.8 μM decrease the cell viability significantly by 50% (IC50) and 10% (IC10), respectively. In contrast, THP-1 cells are less sensitive toward TUPA. Concentrations >41 μM lead to a significant reduction of viable cells. IC10 is calculated with 50 μM, whereas a concentration of 83 μM is necessary to decrease the cell viability to 50% (IC50). In Jurkat T cells, four proteins responsible for the de novo purine synthesis, namely phosphoribosylformylglycinamidine synthase (PFAS), GMP synthase (GMPS), and ribosephosphate pyrophosphokinases 1 and 2 (PRPS1/2) are increased through TUPA treatment. Glutamine is also increased after TUPA treatment. In addition to the proteins belonging to the purine synthesis pathway, the abundances of proteins for DNA synthesis and repair (XRCC5, XRCC6, MCM3, MCM6, MCM7, TRA1) are also increased/induced during the treatment. While in THP-1 cells, no indication for higher purine synthesis induced by TUPA in subtoxic concentrations is discovered. TUPA induces the expression of proteins in Jurkat T cells responsible for cell stress, drug response, and protein folding: HYOU1, PDIA3, and DNAJB11. Additionally, the treatment with TUPA leads to the induction of three heat shock proteins (HSP90AA1, HSP90AB1, and HSP90B1) and three proteins belonging to the TRiC complex (CCT3,6,8) that are also responsible for proper protein folding. Treatment with TUPA leads to the induction of ROS that have adverse effects on Jurkat T cells and evokes slight cell stress responses in THP-1 cells. TUPA has influence on proteins in Jurkat T cells that contribute to different immune-specific, especially immunostimulating, reactions as allergic contact dermatitis. In THP-1 cells, no proteins regarding immune-specific reactions are up- or downregulated due to TUPA treatment[1].

Protocol (from reference)

Cell Research:

[1]

  • Cell lines: Human leukemic Jurkat T cells and human leukemic monocytes THP-1 cells
  • Concentrations: 10 to 82 μM (Jurkat cells); 20 to 163 μM (THP-1 cells)
  • Incubation Time: 72 h
  • Method:

    The influence of TUPA on the cell viability is measured using the MTT assay. Cells are seeded in flat bottom 96-well plates at a density of 4 × 105 cells/mL. Afterward, Jurkat cells are exposed to TUPA in concentrations ranging from 10 to 82 μM. THP-1 cells (4 × 105 cells/mL) are exposed to concentrations ranging from 20 to 163 μM. After incubation for 72 h under humidified conditions (5% CO2, 37℃), 10 μL of MTT (5 mg/mL) per well are added and cells are further incubated for 3 h. Subsequently, 200 μL DMSO are added for cell lysis and formazan solubilization following an incubation of the plates for 15 min while shaking. Afterward, absorbance is recorded at 550 and 620 nm using a microplate reader.

  • (Only for Reference)

Chemical Information

Molecular Weight 98.10
Formula

C5H6O2

Density 1.119 g/mL at 25 °C
CAS No. 547-65-9
Storage 2 years -20°C liquid
Smiles C=C1CCOC1=O

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Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05169541 Not yet recruiting -- Mannose-Binding Lectin Deficiency|Recurrent Pregnancy Loss|Recurrent Implantation Failure|Infertility|Habitual Abortion|Recurrent Miscarriage|Recurrent Spontaneous Abortion Aalborg University Hospital January 1 2022 --
NCT05081284 Not yet recruiting Device: Volume-stable collagen matrix Geistlich Fibro-Gide® Edentulous Alveolar Ridge University of Pisa November 2021 Not Applicable
NCT02435732 Not yet recruiting Drug: Placebo saline solution|Drug: Heparin|Drug: CINRYZE Kidney Failure University of Wisconsin Madison|Shire December 2020 Phase 1
NCT04552210 Recruiting Diagnostic Test: blood sample Infection Aljazeera Hospital|Cairo University September 16 2020 --
NCT04505982 Recruiting Other: Data extraction from medical files Rheumatoid Polyarthritis BADOT Valerie|Brugmann University Hospital July 14 2020 --
NCT04073654 Unknown status Procedure: Placement of dental implants (surgical procedure) Dental Implant Failed|Bone Resorption Osstem AIC September 26 2019 Not Applicable

(data from https://clinicaltrials.gov, updated on 2022-01-17)

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