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渥曼青霉素

PI3-激酶抑制剂
规格或纯度: 98%
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mechanistic target of rapamycin kinase Inhibitor phosphatidylinositol 4-kinase alpha Inhibitor phosphatidylinositol 4-kinase beta Inhibitor phosphatidylinositol-4，5-bisphosphate 3-kinase catalytic subunit alpha Inhibitor phosphatidylinositol-4，5-bisphosphate 3-kinase catalytic subunit beta Inhibitor phosphatidylinositol-4，5-bisphosphate 3-kinase catalytic subunit delta Inhibitor phosphatidylinositol-4，5-bisphosphate 3-kinase catalytic subunit gamma Inhibitor protein kinase，DNA-activated，catalytic subunit Inhibitor
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基本描述

规格或纯度 98%
英文名称 Wortmannin
别名 渥曼青霉素;抗生素SL-2052
英文别名 KY 12420;Antibiotic SL-2052
生化机理 Wortmannin, a fungal metabolite, is a potent and selective inhibitor of PI 3-kinase. Wortmannin inhibits repair of DNA double-strand breaks in irradiated normal human cells. Wortmannin displays a similar potency in vitro for the class I, II, and III PI 3-kinase members, althoμgh it can also inhibit other PI 3-kinase-related enzymes such as FRAP (mTOR), DNA-PKCS, some phosphatidylinositol 4-kinases, myosin light chain kinase (MLCK) and mitogen-activated protein kinase (MAPK) at high concentrations. Wortmannin has also been reported to inhibit members of the polo-like kinase family with IC50 in the same range as for PI 3-kinase. The half-life of Wortmannin in tissue culture is about 10 minutes due to the presence of the highly reactive C20 carbon that is also responsible for its ability to covalently inactivate PI 3-kinase. Wortmannin is an inhibitor of Fnk and Plk.Potent, selective and cell-permeable inhibitor of phosphatidylinositol-3-kinase (PI3-kinase) (IC 50 ~ 3 nM)
应用 A fungal metabolite which inhibits Pl3-kinase
来源 from Penicillium) wortmannii
储存温度 -20°C储存
运输条件 超低温冰袋运输
备注 如果有可能，您尽量在使用的当天配置溶液，并在当天使用完它。但是，如果您需要预先配制储备溶液，我们建议您将溶液等份保存在-20°C的密封小瓶中。通常，它们最多可以使用一个月。在使用前和打开样品瓶之前，我们建议您让您的产品在室温下平衡至少1小时。有毒，请参阅SDS以获取更多信息。需要更多关于溶解度，用法和处理的建议吗？请访问我们的常见问题（FAQ）页面以获取更多详细信息。
产品介绍

Wortmannin是一种PI3K抑制剂，IC50为3 nM，抑制自噬体的形成，也有效抑制DNA-PK/ATM，IC50分别为16 nM和150 nM。A fungal metabolite which inhibits Pl3-kinase

Wortmannin is the first described PI3K inhibitor with IC50 of 3 nM, with little selectivity within the PI3K family. Also blocks autophagosome formation and potently inhibits DNA-PK/ATM with IC50 of 16 nM and 150 nM.
A fungal metabolite which inhibits Pl3-kinase

名称和标识符

IUPAC Name [(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate
INCHI InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1
InChi Key QDLHCMPXEPAAMD-QAIWCSMKSA-N
Canonical SMILES CC(=O)OC1CC2(C(CCC2=O)C3=C1C4(C(OC(=O)C5=COC(=C54)C3=O)COC)C)C
分子式

C23H24O8
UN Number 3462
PubChem CID 312145
Beilstein号 67676
分子量 428.43

化学和物理性质

溶解性 Soluble in DMSO (50 mg/ml), ethanol (25 mg/ml), methanol, 1:8 DMSO:PBS(pH 7.2) (~0.1 mg/ml), and DMF (~14 mg/ml).
密度 1.39
敏感性 对热、湿度和光线敏感
熔点 237 °C

安全信息

象形图
ghs06

Toxic
信号词 Danger
危险声明 H300: Fatal if swallowed
H310: Fatal in contact with skin
H330: Fatal if inhaled
预防措施声明 P280,P302+P352,P321,P405,P501,P264,P260,P284,P271,P270,P304+P340,P403+P233,P330,P262,P320,P361+P364,P301+P316,P316
WGK Germany 3
RTECS CB9641000
Merck Index 10053
个人防护装备 Eyeshields,Faceshields,full-face particle respirator type N100 (US),Gloves,respirator cartridge type N100 (US),type P1 (EN143) respirator filter,type P3 (EN 143) respirator cartridges

靶标

Target ID 2109
名称 mechanistic target of rapamycin kinase
缩写名 mTOR
家族 FRAP subfamily
基因和蛋白信息
Species Transmembrane Domains Amino Acids Chromosomal Location Gene Symbol Gene Name
Human 2 2549 1p36.22 MTOR mechanistic target of rapamycin kinase
Mouse 2 2549 4 78.76 cM Mtor mechanistic target of rapamycin kinase
Rat 2 2549 5q36 Mtor mechanistic target of rapamycin kinase
Ensembl Gene ENSG00000198793 (Hs) , ENSMUSG00000028991 (Mm) , ENSRNOG00000009615 (Rn)
Entrez Gene 2475 (Hs) , 56717 (Mm) , 56718 (Rn)
OMIM 601231 (Hs)
UniProtKB P42345 (Hs) , P42346 (Rn) , Q9JLN9 (Mm)
RefSeq Nucleotide NM_004958 (Hs) , NM_019906 (Rn) , NM_020009 (Mm)
RefSeq Protein NP_004949 (Hs) , NP_063971 (Rn) , NP_064393 (Mm)
Protein GI 4826730 (Hs) , 227330586 (Mm) , 9845251 (Rn)
DrugBank Target P42345 (Hs)
CATH/Gene3D 1.10.1070.11 (N/A) , 1.20.120.150 (N/A) , 1.25.10.10 (N/A)
ChEMBL Target CHEMBL1075134 (Rn) , CHEMBL1255165 (Mm) , CHEMBL2842 (Hs)
Target ID 2148
名称 phosphatidylinositol 4-kinase alpha
缩写名 PI4KIIIα/PIK4CA
家族 1-phosphatidylinositol 4-kinase family
别名 Fz2
基因和蛋白信息
Species Transmembrane Domains Amino Acids Chromosomal Location Gene Symbol Gene Name
Human 2 2102 22q11.21 PI4KA phosphatidylinositol 4-kinase alpha
Mouse 2 2044 16 A3 Pi4ka phosphatidylinositol 4-kinase alpha
Rat 2 2041 11 q23 Pi4ka phosphatidylinositol 4-kinase alpha
Ensembl Gene ENSG00000241973 (Hs) , ENSMUSG00000041720 (Mm) , ENSRNOG00000060045 (Rn)
Entrez Gene 5297 (Hs) , 64161 (Rn) , 224020 (Mm)
OMIM 600286 (Hs)
UniProtKB P42356 (Hs)
RefSeq Nucleotide NM_001001983 (Mm) , NM_022301 (Rn) , NM_058004 (Hs)
RefSeq Protein NP_001001983 (Mm) , NP_071637 (Rn) , NP_477352 (Hs)
Protein GI 348041302 (Hs) , 241982771 (Mm) , 25742825 (Rn)
CATH/Gene3D 1.10.1070.11 (N/A) , 1.25.10.10 (N/A)
ChEMBL Target CHEMBL3667 (Hs)
Target ID 2149
名称 phosphatidylinositol 4-kinase beta
缩写名 PI4KIIIβ/PIK4CB
家族 1-phosphatidylinositol 4-kinase family
别名 Fz2
基因和蛋白信息
Species Transmembrane Domains Amino Acids Chromosomal Location Gene Symbol Gene Name
Human 2 816 1q21.3 PI4KB phosphatidylinositol 4-kinase beta
Mouse 2 816 3 F2.1 Pi4kb phosphatidylinositol 4-kinase beta
Rat 2 816 2q34 Pi4kb phosphatidylinositol 4-kinase beta
Ensembl Gene ENSG00000143393 (Hs) , ENSMUSG00000038861 (Mm) , ENSRNOG00000021024 (Rn)
Entrez Gene 5298 (Hs) , 81747 (Rn) , 107650 (Mm)
OMIM 602758 (Hs)
UniProtKB O08561 (Rn) , Q8BKC8 (Mm) , Q9UBF8 (Hs)
RefSeq Nucleotide NM_001198773 (Hs) , NM_031083 (Rn) , NM_175356 (Mm)
RefSeq Protein NP_002642 (Hs) , NP_112345 (Rn) , NP_780565 (Mm)
Protein GI 4505809 (Hs) , 256000773 (Mm) , 14389295 (Rn)
CATH/Gene3D 1.10.1070.11 (N/A)
ChEMBL Target CHEMBL3268 (Hs)
Target ID 2153
名称 phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha
缩写名 PI3Kα
家族 Phosphatidylinositol-4,5-bisphosphate 3-kinase family
别名 Thyroid-Stimulating Hormone Receptor
基因和蛋白信息
Species Transmembrane Domains Amino Acids Chromosomal Location Gene Symbol Gene Name
Human 2 1068 3q26.32 PIK3CA phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha
Mouse 2 1068 3 15.7 cM Pik3ca phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha
Rat 2 1068 2 q25 Pik3ca phosphatidylinositol-4,5-bisphosphate 3-kinase, catalytic subunit alpha
Ensembl Gene ENSG00000121879 (Hs) , ENSMUSG00000027665 (Mm) , ENSRNOG00000056371 (Rn)
Entrez Gene 5290 (Hs) , 18706 (Mm) , 170911 (Rn)
OMIM 171834 (Hs)
UniProtKB P42336 (Hs) , P42337 (Mm)
RefSeq Nucleotide NM_006218 (Hs) , NM_008839 (Mm) , NM_133399 (Rn)
RefSeq Protein NP_006209 (Hs) , NP_032865 (Mm) , NP_596890 (Rn)
Orphanet 117820 (Hs)
Protein GI 54792082 (Hs) , 254540080 (Mm) , 282158067 (Rn)
CATH/Gene3D 1.10.1070.11 (N/A) , 2.60.40.150 (N/A)
ChEMBL Target CHEMBL4005 (Hs) , CHEMBL2499 (Mm)
Target ID 2154
名称 phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta
缩写名 PI3Kβ
家族 Phosphatidylinositol-4,5-bisphosphate 3-kinase family
别名 Thyroid-Stimulating Hormone Receptor
基因和蛋白信息
Species Transmembrane Domains Amino Acids Chromosomal Location Gene Symbol Gene Name
Human 2 1070 3q22.3 PIK3CB phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta
Mouse 2 1064 9 E3.3 Pik3cb phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta
Rat 2 1070 8q31 Pik3cb phosphatidylinositol-4,5-bisphosphate 3-kinase, catalytic subunit beta
Ensembl Gene ENSG00000051382 (Hs) , ENSMUSG00000032462 (Mm) , ENSRNOG00000016384 (Rn)
Entrez Gene 5291 (Hs) , 74769 (Mm) , 85243 (Rn)
OMIM 602925 (Hs)
UniProtKB P42338 (Hs) , Q8BTI9 (Mm) , Q9Z1L0 (Rn)
RefSeq Nucleotide NM_001256045 (Hs) , NM_029094 (Mm) , NM_053481 (Rn)
RefSeq Protein NP_006210 (Hs) , NP_083370 (Mm) , NP_445933 (Rn)
Protein GI 5453894 (Hs) , 269914109 (Mm) , 16758236 (Rn)
CATH/Gene3D 1.10.1070.11 (N/A) , 2.60.40.150 (N/A)
ChEMBL Target CHEMBL3145 (Hs) , CHEMBL4739696 (Mm) , CHEMBL3608198 (Rn)
Target ID 2155
名称 phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta
缩写名 PI3Kδ
家族 Phosphatidylinositol-4,5-bisphosphate 3-kinase family
别名 Thyroid-Stimulating Hormone Receptor
基因和蛋白信息
Species Transmembrane Domains Amino Acids Chromosomal Location Gene Symbol Gene Name
Human 2 1044 1p36.22 PIK3CD phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta
Mouse 2 1043 4 E2 Pik3cd phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta
Rat 2 944 5q36 Pik3cd phosphatidylinositol-4,5-bisphosphate 3-kinase, catalytic subunit delta
Ensembl Gene ENSG00000171608 (Hs) , ENSMUSG00000039936 (Mm) , ENSRNOG00000016846 (Rn)
Entrez Gene 5293 (Hs) , 18707 (Mm) , 366508 (Rn)
OMIM 602839 (Hs)
UniProtKB O00329 (Hs) , O35904 (Mm)
RefSeq Nucleotide NM_001029837 (Mm) , NM_001108978 (Rn) , NM_005026 (Hs)
RefSeq Protein NP_001025008 (Mm) , NP_001102448 (Rn) , NP_005017 (Hs)
Protein GI 156564405 (Hs) , 255708437 (Mm) , 157822959 (Rn)
CATH/Gene3D 1.10.1070.11 (N/A) , 2.60.40.150 (N/A)
ChEMBL Target CHEMBL3130 (Hs) , CHEMBL2216745 (Mm)
Target ID 2156
名称 phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma
缩写名 PI3Kγ
家族 Phosphatidylinositol-4,5-bisphosphate 3-kinase family
别名 Thyroid-Stimulating Hormone Receptor
基因和蛋白信息
Species Transmembrane Domains Amino Acids Chromosomal Location Gene Symbol Gene Name
Human 2 1102 7q22.3 PIK3CG phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma
Mouse 2 1102 12 A3 Pik3cg phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma
Rat 2 1102 6 q16 Pik3cg phosphatidylinositol-4,5-bisphosphate 3-kinase, catalytic subunit gamma
Ensembl Gene ENSG00000105851 (Hs) , ENSMUSG00000020573 (Mm) , ENSRNOG00000009385 (Rn)
Entrez Gene 5294 (Hs) , 30955 (Mm) , 298947 (Rn)
OMIM 601232 (Hs)
UniProtKB P48736 (Hs) , Q9JHG7 (Mm)
RefSeq Nucleotide NM_001146200 (Mm) , NM_002649 (Hs) , XM_003750140 (Rn)
RefSeq Protein NP_001139672 (Mm) , NP_002640 (Hs) , XP_003750188 (Rn)
Protein GI 21237725 (Hs) , 226246569 (Mm) , 392348758 (Rn)
CATH/Gene3D 1.10.1070.11 (N/A) , 2.60.40.150 (N/A)
ChEMBL Target CHEMBL2189158 (Mm) , CHEMBL3267 (Hs)
Target ID 2800
名称 protein kinase, DNA-activated, catalytic subunit
缩写名 SHP2
家族 Other PIKK family kinases
别名 LERGU2
基因和蛋白信息
Species Transmembrane Domains Amino Acids Chromosomal Location Gene Symbol Gene Name
Human 2 4128 8q11.21 PRKDC protein kinase, DNA-activated, catalytic subunit
Mouse 2 4128 16 A2 Prkdc protein kinase, DNA activated, catalytic polypeptide
Rat 2 147 11q23 Prkdc protein kinase, DNA-activated, catalytic subunit
Protein GI 13654237 (Hs) , 124517706 (Mm)
RefSeq Protein NP_008835 (Hs) , NP_001075109 (Hs) , NP_035289 (Mm)
RefSeq Nucleotide NM_006904 (Hs) , NM_001081640 (Hs) , NM_011159 (Mm)
UniProtKB P78527 (Hs) , P97313 (Mm)
OMIM 600899 (Hs)
Entrez Gene 5591 (Hs) , 19090 (Mm) , 360748 (Rn)
Ensembl Gene ENSG00000253729 (Hs) , ENSMUSG00000022672 (Mm) , ENSRNOG00000025028 (Rn)
CATH/Gene3D 1.10.1070.11 (N/A) , 1.25.10.10 (N/A) , 1.25.40.10 (N/A)
ChEMBL Target CHEMBL2176779 (Mm) , CHEMBL3142 (Hs)

关联配体

Ligand ID 6060
名称 wortmannin
别名 antibiotic SL-2052
类别 Natural product
学名 (1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate
生物活性评价 Wortmannin has antifungal properties but does not demonstrate antibacterial activity .
评价 Wortmannin is extracted from Penicillium funiculosum. The compound is a specific, covalent inhibitor of phosphoinositide 3-kinases (PI3Ks).

参考文献

1. Singh V, Praveen V, Tripathi D, Haque S, Somvanshi P, Katti SB, Tripathi CK.  (2015)  Isolation, characterization and antifungal docking studies of wortmannin isolated from Penicillium radicum..  Sci Rep,  5  (13):  (11948).  [PMID:26159770]
2. Mizwicki MT et al..  (2013)  1a,25-dihydroxyvitamin D3 and resolvin D1 retune the balance between amyloid-? phagocytosis and inflammation in Alzheimer's disease patients..  J Alzheimers Dis,  34  ():  (155-70).  [PMID:23186989]
3. Zhang MH & Liu J.  (2022)  Cleavage stimulation factor 2 promotes malignant progression of liver hepatocellular carcinoma by activating phosphatidylinositol 3'-kinase/protein kinase B/mammalian target of rapamycin pathway..  Bioengineered,  13  (4):  (10047-10060).  [PMID:35412944]
4. Cao Y et al..  (2015)  Rescue of homeostatic regulation of striatal excitability and locomotor activity in a mouse model of Huntington's disease..  Proc Natl Acad Sci U S A,  112  (7):  (2239-44).  [PMID:25646456]
5. Inozume T et al..  (2018)  Acquisition of resistance to vemurafenib leads to interleukin-10 production through an aberrant activation of Akt in a melanoma cell line..  J Dermatol,  45  (12):  (1434-1439).  [PMID:30222203]
6. Kadir R et al..  (2016)  ALFY-Controlled DVL3 Autophagy Regulates Wnt Signaling, Determining Human Brain Size..  PLoS Genet,  12  (3):  (e1005919).  [PMID:27008544]
7. Joung EJ et al..  (2012)  Anti-inflammatory effect of ethanolic extract from Myagropsis myagroides on murine macrophages and mouse ear edema..  BMC Complement Altern Med,  12  ():  (171).  [PMID:23031211]
8. Martin-Gallausiaux C et al..  (2020)  Fusobacterium nucleatum Extracellular Vesicles Modulate Gut Epithelial Cell Innate Immunity via FomA and TLR2..  Front Immunol,  11  ():  (583644).  [PMID:33408714]
9. Chen S et al..  (2020)  Ginsenoside metabolite 20(S)-protopanaxadiol promotes neural stem cell transition from a state of proliferation to differentiation by inducing autophagy and cell cycle arrest..  Mol Med Rep,  22  ():  (353-361).  [PMID:32319663]
10. Zhang C et al..  (2016)  Gli1 promotes colorectal cancer metastasis in a Foxm1-dependent manner by activating EMT and PI3K-AKT signaling..  Oncotarget,  7  (52):  (86134-86147).  [PMID:27863385]
11. Fischer B et al..  (2012)  Inhibition of phosphoinositide-3 kinase pathway down regulates ABCG2 function and sensitizes malignant pleural mesothelioma to chemotherapy..  Lung Cancer,  78  ():  (23-9).  [PMID:22857894]
12. Liu Y et al..  (2016)  KRASG12 mutant induces the release of the WSTF/NRG3 complex, and contributes to an oncogenic paracrine signaling pathway..  Oncotarget,  7  (33):  (53153-53164).  [PMID:27449290]
13. Yue HY & Xu J.  (2014)  Myosin light chain kinase accelerates vesicle endocytosis at the calyx of Held synapse..  J Neurosci,  34  ():  (295-304).  [PMID:24381290]
14. Lee JH et al..  (2021)  n-Butylidenephthalide Modulates Autophagy to Ameliorate Neuropathological Progress of Spinocerebellar Ataxia Type 3 through mTOR Pathway..  Int J Mol Sci,  22  (12):  ().  [PMID:34199295]
15. Tulio AZ et al..  (2014)  Phenolic composition, antioxidant properties, and endothelial cell function of red and white cranberry fruits..  Food Chem,  157  ():  (540-52).  [PMID:24679816]
16. Gamero-Estevez E et al..  (2019)  Temporal Effects of Quercetin on Tight Junction Barrier Properties and Claudin Expression and Localization in MDCK II Cells..  Int J Mol Sci,  20  (19):  ().  [PMID:31581662]

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