Deoxypodophyllotoxin
(Synonyms: 脱氧鬼臼毒素) 目录号 : GC38564
A flavolignan with diverse biological activities
Cas No.:19186-35-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Deoxypodophyllotoxin (DPT) is a flavolignan that has been found in J. sabina and has diverse biological activities.1,2,3,4,5 It inhibits tubulin polymerization in a cell-free assay when used at a concentration of 50 nM.1 DPT in also inhibits COX-2 and 5-lipoxygenase (5-LO) in isolated mouse bone marrow-derived mast cells stimulated with KL, IL-10, and LPS (IC50s = 1.89 and 0.37 ?M, respectively).2 It reduces viral yield in the supernatant of MRC-5 cells infected with herpes simplex virus 1 (HSV-1) or HSV-2 when used at a concentration of 0.02 ?g/ml.3 DPT inhibits aggregation of rabbit platelets induced by platelet-activating factor (PAF), collagen, or arachidonic acid in a concentration-dependent manner.4 It induces mortality in P. rapae fifth instar larvae (LC50 = 0.02 g/L).5 DPT (70 ?g/kg) reduces tumor growth in a CT26 murine colon cancer model.1
1.Gamage, C.D.B., Park, S.-Y., Yang, Y., et al.Deoxypodophyllotoxin exerts anti-cancer effects on colorectal cancer cells through induction of apoptosis and suppression of tumorigenesisInt. J. Mol. Sci.20(11)2612(2019) 2.Lee, S.H., Son, M.J., Ju, H.K., et al.Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin in mouse bone marrow-derived mast cellsBiol. Pharm. Bull.27(6)786-788(2004) 3.Sudo, K., Konno, K., Shigeta, S., et al.Inhibitory effects of podophyllotoxin derivatives on herpes simplex virus replicationAntivir. Chem. Chemother.9(3)263-267(1998) 4.Chen, J.-J., Chang, Y.-L., Teng, C.-M., et al.Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifoliaPlanta Med.66(3)251-256(1999) 5.Gao, R., Gao, C., Tian, X., et al.Insecticidal activity of deoxypodophyllotoxin, isolated from Juniperus sabina L, and related lignans against larvae of Pieris rapae LPest Manag. Sci.60(11)1131-1136(2004)
| Cas No. | 19186-35-7 | SDF | |
| 别名 | 脱氧鬼臼毒素 | ||
| Canonical SMILES | O=C1[C@]2([H])[C@H](C3=CC(OC)=C(OC)C(OC)=C3)C4=CC(OCO5)=C5C=C4C[C@@]2([H])CO1 | ||
| 分子式 | C22H22O7 | 分子量 | 398.41 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at 2-8°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 | 2.51 mL | 12.5499 mL | 25.0998 mL |
| 5 mM | 0.502 mL | 2.51 mL | 5.02 mL |
| 10 mM | 0.251 mL | 1.255 mL | 2.51 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。
A comprehensive insight into the antineoplastic activities and molecular mechanisms of Deoxypodophyllotoxin: Recent trends, challenges, and future outlook
Eur J Pharmacol 2022 Aug 5;928:175089.PMID:35688183DOI:10.1016/j.ejphar.2022.175089.
Lignans constitute an important group of polyphenols, which have been demonstrated to potently suppress cancer cell proliferation. Numerous in vitro and in vivo studies indicate that Deoxypodophyllotoxin as a natural lignan possesses potent anticancer activities against various types of human cancer. The purpose of current review is to provide the reader with the latest findings in understanding the anticancer effects and molecular mechanisms of Deoxypodophyllotoxin. This review comprehensively describes the influence of Deoxypodophyllotoxin on signaling cascades and molecular targets implicated in cancer cell proliferation and invasion. A number of various signaling molecules and pathways, including apoptosis, necroptosis, cell cycle, angiogenesis, vascular disruption, ROS, MMPs, glycolysis, and microtubules as well as NF-κB, PI3K/Akt/mTOR, and MAPK cascades have been reported to be responsible for the anticancer activities of Deoxypodophyllotoxin. The results of present review suggest that the cyclolignan Deoxypodophyllotoxin can be developed as a novel and potent anticancer agent, especially as an alternative option for treatment of resistant tumors to chemotherapy.
Deoxypodophyllotoxin: a promising therapeutic agent from herbal medicine
J Ethnopharmacol 2013 Aug 26;149(1):24-34.PMID:23792585DOI:10.1016/j.jep.2013.06.021.
Background: Recently, biologically active compounds isolated from plants used in herbal medicine have been the center of interest. Deoxypodophyllotoxin (DPT), structurally closely related to the lignan podophyllotoxin, is a potent antitumor and anti-inflammatory agent. However, DPT has not been used clinically yet. Also, DPT from natural sources seems to be unavailable. Hence, it is important to establish alternative resources for the production of such lignan; especially that it is used as a precursor for the semi-synthesis of the cytostatic drugs etoposide phosphate and teniposide. Aims and objectives: The update paper provides an overview of DPT as an effective anticancer natural compound and a leader for cytotoxic drugs synthesis and development in order to highlight the gaps in our knowledge and explore future research needs. Approach and methods: The present review covers the literature available from 1877 to 2012. The information was collected via electronic search using Chinese papers and the major scientific databases including PubMed, Sciencedirect, Web of Science and Google Scholar using the keywords. All abstracts and full-text articles reporting database on the history and current status of DPT were gathered and analyzed. Results: Plants containing DPT have played an important role in traditional medicine. In light of the in vitro pharmacological investigations, DPT is a high valuable medicinal agent that has anti-tumor, anti-proliferative, anti-inflammatory and anti-allergic properties. Further, DPT is an important precursor for the cytotoxic aryltetralin lignan, podophyllotoxin, which is used to obtain semisynthetic derivatives like etoposide and teniposide used in cancer therapy. However, most studies have focused on the in vitro data. Therefore, DPT has not been used clinically yet. Conclusions: DPT has emerged as a potent chemical agent from herbal medicine. Therefore, in vivo studies are needed to carry out clinical trials in humans and enable the development of new anti-cancer agents. In addition, DPT from commercial sources seems to be unavailable due to its rarity from natural sources and cumbersome extraction procedures. Hence, it is important to establish alternative, cost-effective and renewable resources, such plant cell cultures and (semi-) synthesis strategies for the production of DPT.
Derivatives of Deoxypodophyllotoxin Induce Apoptosis through Bcl-2/Bax Proteins Expression
Anticancer Agents Med Chem 2021;21(5):611-620.PMID:32748757DOI:10.2174/1871520620999200730160952.
Background: Deoxypodophyllotoxin, isolated from the Traditional Chinese Medicine Anthriscus sylvestris, is well-known because of its significant anti-tumor activity with strong toxicity in vitro and in vivo. Objective: In this article, a series of Deoxypodophyllotoxin derivatives were synthesized and their anti-tumor effectiveness was evaluated. Methods: The anti-tumor activity of Deoxypodophyllotoxin derivatives was investigated by the MTT assay method. Apoptosis percentage was measured by flow cytometer analysis using Annexin-V-FITC. Results: The derivatives revealed obvious cytotoxicity in the MTT assay by decreasing the number of late cancer cells. The decrease of Bcl-2/Bax could be observed in MCF-7, HepG2, HT-29, and MG-63 using Annexin V-FITC. The ratio of Bcl-2/Bax in the administration group was decreased, which was determined by the ELISA kit. Conclusion: The derivatives of Deoxypodophyllotoxin could induce apoptosis in tumor cell lines by influencing Bcl-2/Bax.
Mechanistic analysis of carbon-carbon bond formation by Deoxypodophyllotoxin synthase
Proc Natl Acad Sci U S A 2022 Jan 4;119(1):e2113770119.PMID:34969844DOI:10.1073/pnas.2113770119.
Deoxypodophyllotoxin contains a core of four fused rings (A to D) with three consecutive chiral centers, the last being created by the attachment of a peripheral trimethoxyphenyl ring (E) to ring C. Previous studies have suggested that the iron(II)- and 2-oxoglutarate-dependent (Fe/2OG) oxygenase, Deoxypodophyllotoxin synthase (DPS), catalyzes the oxidative coupling of ring B and ring E to form ring C and complete the tetracyclic core. Despite recent efforts to deploy DPS in the preparation of Deoxypodophyllotoxin analogs, the mechanism underlying the regio- and stereoselectivity of this cyclization event has not been elucidated. Herein, we report 1) two structures of DPS in complex with 2OG and (±)-yatein, 2) in vitro analysis of enzymatic reactivity with substrate analogs, and 3) model reactions addressing DPS's catalytic mechanism. The results disfavor a prior proposal of on-pathway benzylic hydroxylation. Rather, the DPS-catalyzed cyclization likely proceeds by hydrogen atom abstraction from C7', oxidation of the benzylic radical to a carbocation, Friedel-Crafts-like ring closure, and rearomatization of ring B by C6 deprotonation. This mechanism adds to the known pathways for transformation of the carbon-centered radical in Fe/2OG enzymes and suggests what types of substrate modification are likely tolerable in DPS-catalyzed production of Deoxypodophyllotoxin analogs.
Deoxypodophyllotoxin Induces ROS-Mediated Apoptosis by Modulating the PI3K/AKT and p38 MAPK-Dependent Signaling in Oral Squamous Cell Carcinoma
J Microbiol Biotechnol 2022 Sep 28;32(9):1103-1109.PMID:36039387DOI:10.4014/jmb.2207.07012.
Deoxypodophyllotoxin (DPT), a naturally occurring flavonolignan, possesses several pharmacological properties, including anticancer property. However, the mechanisms underlying DPT mode of action in oral squamous cell carcinoma (OSCC) remain unknown. This study aimed to investigate the anticancer effects of DPT on OSCC and the underlying mechanisms. Results of the MTT assay revealed that DPT significantly reduced the cell viability in a time- and dose-dependent manner. Flow cytometry analysis revealed that DPT induces apoptosis in OSCC cells in a dose-dependent manner. Moreover, DPT enhanced the production of mitochondrial reactive oxygen species (ROS) in OSCC cells. Mechanistically, DPT induced apoptosis in OSCC cells by suppressing the PI3K/AKT signaling pathway while activating the p38 MAPK signaling to regulate the expression of apoptotic proteins. Treatment with SC79, an AKT activator, reversed the effects of DPT on AKT signaling in OSCC cells. Taken together, these results provide the basis for the use of DPT in combination with conventional chemotherapy for the treatment of oral cancer.