Phorbol (4β-Phorbol)
(Synonyms: 佛波醇,4β-Phorbol) 目录号 : GC32859
A starting material in the semisynthesis of phorbol diesters
Cas No.:17673-25-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Phorbol is a diterpene originally isolated from croton oil.1 It is used as a starting material for the semisynthesis of various phorbol diesters, which are structurally analogous to diacylglycerol and activate PKC isoforms by associating with their C1 domains.2
1.Bohm, R., Flaschentrager, B., and Lendle, L.The activity of substances from croton oilArchiv fuer Experimentelle Pathologie und Pharmakologie177212-220(1935) 2.Hurley, J.H., Newton, A.C., Parker, P.J., et al.Taxonomy and function of C1 protein kinase C homology domainsProtein Sci.6(2)477-480(1997)
| Cas No. | 17673-25-5 | SDF | |
| 别名 | 佛波醇,4β-Phorbol | ||
| Canonical SMILES | O=C1C(C)=C[C@@]2([H])[C@]3(O)[C@@]([C@@](C4(C)C)([H])[C@@]4(O)[C@H](O)[C@H]3C)([H])C=C(CO)C[C@]12O | ||
| 分子式 | C20H28O6 | 分子量 | 364.43 |
| 溶解度 | DMSO : 66.67 mg/mL (182.94 mM);Water : ≥ 20 mg/mL (54.88 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.744 mL | 13.7201 mL | 27.4401 mL |
| 5 mM | 0.5488 mL | 2.744 mL | 5.488 mL |
| 10 mM | 0.2744 mL | 1.372 mL | 2.744 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Phorbol Rearrangements
J Nat Prod 2018 Sep 28;81(9):2134-2137.PMID:30216064DOI:10.1021/acs.jnatprod.8b00607.
An alternative procedure for isolation of 4β-phorbol from seeds of Croton tiglium has been developed, and an artifact containing a furan ring formed by rearrangement of 12,13,20- O-triacylated Phorbol derivatives into (6b S,7 R,8 R,8a S)-2-(hydroxymethyl)-5,7,9,9-tetramethyl-3,7,8,9,9a,9b-hexahydrocyclopropa[3',4']benzo[1',2':3,4]cyclohepta[1,2- b]furan-6b,8,8a-triol (8a) has been characterized. A mechanism involving an oxidative rearrangement and a decarboxylation for formation of the artifact is proposed.
Effect of Phorbol 12-myristate 13-acetate and its analogue 4 alpha-phorbol 12,13-didecanoate on protein phosphorylation and lysosomal enzyme release in rabbit neutrophils
J Biol Chem 1984 Jul 10;259(13):8605-11.PMID:6429145doi
The co-carcinogenic compound Phorbol 12-myristate 13-acetate but not its inactive analogue 4 alpha-phorbol 12,13-didecanoate causes the phosphorylation of several rabbit neutrophil polypeptides whose molecular weights and isoelectric points (pI) are as follows: Mr = 40,000, pI = 6.4; Mr = 50,000, pI = 4.9; Mr = 55,000, pI = 6.3; Mr = 64,000, pI = 6.0; Mr = 70,000, pI = 5.6; Mr = 90,000, pI = 6.0. Most of these phosphorylated proteins are located exclusively in the cytosol; the 64,000 molecular weight protein is found both in the cytosol and the cytoskeleton, and the 40,000 molecular weight protein is found in the nuclear pellet. The 50,000 molecular weight protein is also phosphorylated in whole cells by the chemotactic peptide fMet-Leu-Phe and in cell-free systems by protein kinase C. Using limited proteolysis, one phosphopeptide fragment was phosphorylated by the three stimuli. In addition, Phorbol 12-myristate 13-acetate but not 4 alpha-phorbol 12,13-didecanoate causes cell aggregation and the exocytotic release of the specific granules of rabbit neutrophils. In contrast, both compounds increase the amount of actin associated with the cytoskeleton. The divalent cation ionophore A23187 at low concentration and the compound Phorbol 12-myristate 13-acetate act synergistically in causing neutrophil degranulation. Lysosomal enzyme release and the phosphorylation of the 50,000 molecular weight polypeptide produced by phorbl 12-myristate 13-acetate are inhibited by trifluoperazine, and these two responses seem to be causally related. These results are discussed in terms of the role of 1,2-diacylglycerol and activation of protein kinase C in specific granule release from rabbit neutrophils.
Relationship between ornithine decarboxylase-inducing activity and configuration at C-4 in Phorbol ester derivatives
J Cancer Res Clin Oncol 1980;98(1):9-13.PMID:7451556DOI:10.1007/BF00413172.
Measurements were made of induction of ornithine decarboxylase activity after painting mouse skin with 12-O-hexadecanoyl-16-hydroxyphorbol-13-acetate and its two epimeric 4-deoxy-analogs, 12-O-hexadecanoyl-4-deoxy-16-hydroxyphorbol-13-acetate and 12-O-hexadecanoyl-4-deoxy-4 alpha-16-hydroxyphorbol-13 acetate. The inductive activities of HHPA and 4-deoxy-HHPA were similar, but 4-deoxy-4 alpha HHPA had no inductive activity. These findings on natural Phorbol esters confirm that both the 4 beta-hydrogen and the 4 beta-hydroxyl in Phorbol esters are essential for ODC-inducing activity. The interactions of 4-deoxy-HHPA and 4-deoxy-4 alpha-HHPA with a possible receptor are discussed.
Differential phosphorylation of multiple sites in protein 4.1 and protein 4.9 by Phorbol ester-activated and cyclic AMP-dependent protein kinases
J Biol Chem 1985 Aug 5;260(16):9073-6.PMID:2991234doi
The phosphorylation of the membrane skeleton components protein 4.1 and protein 4.9 in intact erythrocytes is shown to increase in the presence of either 1 microM 12-O-tetradecanoyl Phorbol 13-acetate or 2 mM dibutyryl cAMP. The phosphorylation induced by these protein kinase activators is compared by two-dimensional tryptic peptide mapping. In both proteins, the pattern of peptides phosphorylated in the presence of 12-O-tetradecanoyl Phorbol 13-acetate differs from the pattern of peptides phosphorylated in the presence of dibutyryl cAMP. The relative locations of the phosphorylated sites on protein 4.1 have been determined using limited proteolysis by alpha-chymotrypsin.
Specific binding of Phorbol ester tumor promoters
Proc Natl Acad Sci U S A 1980 Jan;77(1):567-71.PMID:6965793DOI:10.1073/pnas.77.1.567.
[20-(3)H]Phorbol 12,13-dibutyrate bound to particulate preparations from chicken embryo fibroblasts in a specific, saturable, reversible fashion. Equilibrium binding occurred with a K(d) of 25 nM; this value is very close to the 50% effective dose (ED(50)), 50 nM, previously determined for the biological response (induction of fibronectin loss) in growing chicken embryo fibroblasts. At saturation, 1.4 pmol of [20-(3)H]Phorbol 12,13-dibutyrate was bound per mg of protein (approximately 7 x 10(4) molecules per cell). Binding was inhibited by Phorbol 12-myristate 13-acetate (K(i) = 2 nM), mezerein (K(i) = 180 nM), Phorbol 12,13-dibenzoate (K(i) = 180 nM), Phorbol 12,13-diacetate (K(i) = 1.7 muM), Phorbol 12,13,20-triacetate (K(i) = 39 muM), and Phorbol 13-acetate (K(i) = 120 muM). The measured K(i) values are all within a factor of 3.5 of the ED(50) values of these derivatives for inducing loss of fibronectin in intact cells. Binding was not inhibited by the inactive compounds Phorbol (10 mug/ml) and 4alpha-phorbol 12,13-didecanoate (10 mug/ml) or by the inflammatory but nonpromoting phorbol-related diterpene esters resiniferatoxin (100 ng/ml) and 12-deoxyphorbol 13-isobutyrate 20-acetate (100 ng/ml). These data suggest that biological responses to the Phorbol esters in chicken embryo fibroblasts are mediated by this binding activity and that the binding activity corresponds to the Phorbol ester target in mouse skin involved in tumor promotion. Binding was not inhibited by the nonphorbol promoters anthralin (1 muM), phenol (1 mM), iodoacetic acid (1.7 muM), and cantharidin (75 muM), or by epidermal growth factor (100 ng/ml), dexamethasone acetate (2 muM), retinoic acid (10 muM), or prostaglandin E(2) (1 muM). These agents thus appear to act at a target distinct from that of the Phorbol esters.