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外観
白色～わずかにうすい黄色, 粉末
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溶解性
エタノール, クロロホルムに可溶、水にほとんど不溶。冷水にほとんど不溶、アルコールに易溶、エタノール,クロロホルムに可溶、ベンゼンにやや可溶。
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用途
阻害剤、培地添加用。
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用途
抗腫瘍性抗生物質です。グア
ノシン一りん酸（GMP）合成経路中の酵素で
あるイノシン一りん酸脱水素酵素を阻害しま
す。
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効能
免疫抑制薬, イノシン一リン酸脱水素酵素阻害薬
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説明
Mycophenolic acid is an immunosuppresive microbial metabolite that has been found in P. brevicompactum. It is also an active metabolite of mycophenolate mofetil that is formed via carboxylesterase 1 (CES1) and CES2. Mycophenolic acid is an inhibitor of IMP dehydrogenase (IMPDH) type I and type II (IC50s = 32 and 11 nM, respectively, in cell-free assays) and inhibits DNA synthesis in L strain mouse fibroblasts when used at concentrations ranging from 0.1 to 10 μg/ml. It is active against several strains of C. albicans, C. parakrusei, C. tropicalis, and C. neoformans (MICs = 3.9-31.25 μg/ml), as well as various strains of S. aureus (MICs = 31.25-125 μg/ml). Mycophenolic acid (150 mg/kg) reduces splenomegaly in a mouse model of Friend virus-induced leukemia. It decreases the number of hemolytic plaque forming cells isolated from the spleen of mice immunized with sheep red blood cells (RBCs) when administered at doses ranging from 60 to 240 mg/kg. Formulations containing mycophenolic acid have been used as immunosuppressive agents in the prevention of organ transplant rejection.
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化学的特性
White to Off-White Powder
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使用
Mycophenolic acid is a common Penicillium metabolite first reported in the 1930s as a possible mycotoxin. Re-investigation showed mycophenolic acid to display broad antitumour, antiviral, antifungal and antiprotozoan activities. Its potent immunosuppressant activity led to its commercial development to prevent kidney transplant rejection. Mycophenolic acid acts by inhibiting inosine monophosphate dehydrogenase, controlling the rate of de novo purine synthesis in proliferating B and T lymphocytes.
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定義
ChEBI: A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an
antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mo
etil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.
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一般的な説明
Assayed in therapeutic drug monitoring to ensure patients remain within the drug′s therapeutic range, mycophenolic acid is an immunosuppressant drug and the active metabolite of the prodrug mycophenolate mofetil. This analytical standard is suitable for LC-MS/MS applications including therapeutic drug monitoring and other clinical or diagnostic applications.
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生物活性
Immunosuppressive agent with antiviral and antitumor effects in vitro and in vivo . Potently inhibits inosine monophosphate dehydrogenase, thus inhibiting de novo GTP synthesis leading to decreased RNA and DNA synthesis. Reversibly inhibits proliferation of T and B lymphocytes and antibody formation.
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作用機序
Mycophenolic acid (MPA) is a potent inhibitor of inosine monophosphate dehydrogenase (IMPDH) that prevents the ab initio biosynthesis of purine nucleotides. It predominantly affects lymphocytes, leading to inhibition of DNA synthesis in T cells and B cells, thereby suppressing cell-mediated immune responses and antibody formation.MPA also inhibits glycosylation and expression of adhesion molecules, as well as the recruitment of lymphocytes and monocytes to sites of inflammation.MPA depletes tetrahydrobiopterin and reduces nitric oxide production via inducible NO synthase without affecting the activity of constitutive NO synthase[1].
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純化方法
Purify the acid by dissolving it in the minimum volume of EtOAc, applying onto a silica gel column (0.05-0.2 mesh) and eluting with a mixture of EtOAc/CHCl3/AcOH (45:55:1) followed by recrystallisation from heptane/EtOAc, from aqueous EtOH or from hot H2O and drying in vacuo. It is a weak dibasic acid, moderately soluble in Et2O, CHCl3 and hot H2O but weakly soluble in *C6H6 and toluene. [Birch & Wright Aust J Chem 22 2635 1969, Canonica et al. J Chem Soc, Perkin Trans 1 2639 1972, Birkinshaw et al. Biochem J 50 630 1952, Beilstein 18 II 393, 18 III/IV 6513.]
