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Chemical Structure| 24280-93-1 Chemical Structure| 24280-93-1

Structure of Mycophenolic acid
CAS No.: 24280-93-1

Chemical Structure| 24280-93-1

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CAS No.: 24280-93-1

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Mycophenolic acid is an effective non-competitive inosine monophosphate dehydrogenase (IMPDH) inhibitor with an EC50 of 0.24 μM. Mycophenolic acid has antiviral activity against various RNA viruses, including influenza. It is also an immunosuppressant with antiangiogenic and antitumor effects.

Synonyms: Mycophenolate; MPA; Mycophenolic acid, Mycophenolate mofetil, Cellcept, Myfortic, RS-61443

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Agata M. Kieliszek ; Daniel Mobilio ; Blessing I. Bassey-Archibong ; Jarrod W. Johnson ; Mathew L. Piotrowski ; Elvin D. de Araujo , et al.

Abstract: Patients with brain metastases (BM) face a 90% mortality rate within one year of diagnosis and the current standard of care is palliative. Targeting BM-initiating cells (BMICs) is a feasible strategy to treat BM, but druggable targets are limited. Here, we apply Connectivity Map analysis to lung-, breast-, and melanoma-pre-metastatic BMIC gene expression signatures and identify inosine monophosphate dehydrogenase (IMPDH), the rate-limiting enzyme in the de novo GTP synthesis pathway, as a target for BM. We show that pharmacological and genetic perturbation of IMPDH attenuates BMIC proliferation in vitro and the formation of BM in vivo. Metabolomic analyses and CRISPR knockout studies confirm that de novo GTP synthesis is a potent metabolic vulnerability in BM. Overall, our work employs a phenotype-guided therapeutic strategy to uncover IMPDH as a relevant target for attenuating BM outgrowth, which may provide an alternative treatment strategy for patients who are otherwise limited to palliation.

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Walczak, Juliusz Maksymilian ; Iwaszkiewicz-Grzes, Dorota ; Ziomkowska, Michalina ; Sliwka-Kaszynska, Magdalena ; Dasko, Mateusz ; Trzonkowski, Piotr , et al.

Abstract: The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5′-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (A2) revealed the most promising activity. Subsequently, an observed structure-activity relationship was discussed.

Keywords: Mycophenolic acid ; amide derivatives ; heterocycles ; benzoxazole ; IMPDH inhibition

Alternative Products

Product Details of Mycophenolic acid

CAS No. :24280-93-1
Formula : C17H20O6
M.W : 320.34
SMILES Code : O=C(O)CC/C(C)=C/CC1=C(OC)C(C)=C2COC(C2=C1O)=O
Synonyms :
Mycophenolate; MPA; Mycophenolic acid, Mycophenolate mofetil, Cellcept, Myfortic, RS-61443
MDL No. :MFCD00036814
InChI Key :HPNSFSBZBAHARI-RUDMXATFSA-N
Pubchem ID :446541

Safety of Mycophenolic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

Target

  • Dehydrogenase

In Vitro:

Cell Line
Concentration Treated Time Description References
Murine podocytes 10 mg/L ,4 mg/L 24 h MPA significantly affected the expression of 351 genes in podocytes, particularly those related to actin and inflammation-related cell death. MPA increased the thickness and number of actin filaments in BSA-treated podocytes and significantly reduced TNF-α and cycloheximide-induced cell death. PMC10017704
Vero cells 55 μg/ml 5 days Evaluate the inhibitory effect of MPA on CBV3 replication, EC50 value was 55 μg/ml PMC317291
Human myocardial fibroblasts (HMF) 80 μg/ml 5 days Evaluate the inhibitory effect of MPA on CBV3 replication, EC50 value was 80 μg/ml PMC317291

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT00262132 Pulmonary Sarcoidosis PHASE3 TERMINATED 2025-08-06 Medical University of South Ca... More >>rolina, Charleston, South Carolina, 29425, United States Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.12mL

0.62mL

0.31mL

15.61mL

3.12mL

1.56mL

31.22mL

6.24mL

3.12mL

References

 

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