4-Methylumbelliferone - CAS 90-33-5
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
4-Methylumbelliferone
Catalog Number:
90-33-5
Synonyms:
4-MU
CAS Number:
90-33-5
Description:
4-Methylumbelliferone is a hyaluronic acid (HA) synthesis inhibitor with an IC50 of 0.4 mM, used as choleretic and antispasmodic drugs and as a standard for the fluorometric determination of enzyme activity.
Molecular Weight:
176.17
Molecular Formula:
C10H8O3
COA:
Inquire
MSDS:
Inquire
Chemical Structure
CAS 90-33-5 4-Methylumbelliferone

Reference Reading


1.Inhibition of Hyaluronic Acid Synthesis Suppresses Angiogenesis in Developing Endometriotic Lesions.
Olivares CN1, Alaniz LD2, Menger MD3, Barañao RI1, Laschke MW3, Meresman GF1. PLoS One. 2016 Mar 28;11(3):e0152302. doi: 10.1371/journal.pone.0152302. eCollection 2016.
BACKGROUND: The development and long-term survival of endometriotic lesions is crucially dependent on an adequate vascularization. Hyaluronic acid (HA) through its receptor CD44 has been described to be involved in the process of angiogenesis.
2.Targeting hyaluronan for the treatment of pancreatic ductal adenocarcinoma.
Sato N1, Cheng XB1, Kohi S1, Koga A1, Hirata K1. Acta Pharm Sin B. 2016 Mar;6(2):101-5. doi: 10.1016/j.apsb.2016.01.002. Epub 2016 Jan 21.
Progression of cancer is often associated with interactions between cancer cells and extracellular matrix (ECM) surrounding them. Increasing evidence has suggested that accumulation of hyaluronan (HA), a major component of ECM, provides a favorable microenvironment for cancer progression. Pancreatic ductal adenocarcinoma (PDAC) is characterized typically by a dense desmoplastic stroma with a large amount of HA, making this molecule as an attractive target for therapy. Several studies have shown efficacy of inhibitors of HA synthesis or signaling for the treatment of PDAC. Recent studies have also demonstrated substantial improvements in the effects of chemotherapy by a targeted depletion of stromal HA in PDAC using an enzymatic agent. Thus, targeting HA has been recognized as a promising therapeutic strategy to treat this highly aggressive neoplasm. In this review article, we summarize our current understanding of the role of HA in the progression of PDAC and discuss possible therapeutic approaches targeting HA.
3.The fucosidase-pool of Emticicia oligotrophica: Biochemical characterization and transfucosylation potential.
Liu S1, Kulinich A1, Cai ZP1, Ma HY2, Du YM1, Lv YM1, Liu L3, Voglmeir J3. Glycobiology. 2016 Mar 3. pii: cww030. [Epub ahead of print]
Three novel bacterial α-l-fucosidases, which cleave terminal fucosyl residues from glycoconjugates are reported in this work. Originating from the recently discovered bacteriumEmticicia oligotrophica, recombinant fucosidase isoforms designated as Eo0918, Eo3066 and Eo3812 were shown to have the highest activity between pH 6.0 and 7.0 and temperature optima between 30 and 45°C. All enzymes catalyzed the hydrolysis of the model substratepNP-α-l-fucose and revealed significantly different regiospecificities towards fucose-containing oligosaccharides: Eo0918 liberated exclusively α1,6-linked fucose and Eo3812 released only α1,3-fucosyl residues, whereas Eo3066 showed broader substrate promiscuity. The enzymatic activity of Eo0918 and Eo3812 increased upon the addition of Ca2+, Mn2+and Zn2+ions, whereas the activity of Eo3066 was significantly decreased in the presence of these metal ions. In addition, Eo0918 also catalyzed the transfer of fucose frompNP-α-l-fucose to the 7-hydroxyl group of 4-methylumbelliferone with up to 15% transglycosylation yield.
4.Design and synthesis of antimicrobial, anticoagulant, and anticholinesterase hybrid molecules from 4-methylumbelliferone.
Zayane M1, Rahmouni A1, Daami-Remadi M2, Ben Mansour M3, Romdhane A1, Ben Jannet H1. J Enzyme Inhib Med Chem. 2016 Apr 1:1-10. [Epub ahead of print]
We designed and synthesized new series of diverse triazoles, isoxazoles, isoxazolines, and aziridines linked 4-methylumbelliferone 1 using intermolecular 1,3-dipolar cycloaddition reactions. Structures of these compounds were established on the basis of 1H NMR, 13C NMR, and ESI-HRMS. All prepared compounds were evaluated for their antimicrobial, anticoagulant, and anticholinesterase activities. Interestingly, among the tested molecules, some of the analogs displayed better activities than the parent 4-methylumbelliferone 1 such as 6a and 6d for their antifungal properties. Moreover, compounds 4, 5, 6, and 7 showed the importance of the added fragments to 4-methylumbelliferone 1 via the linker methylene to have good activity.