PicropodophyllotoxinCAS# 17434-18-3 |
- 5-Hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Catalog No.:BCC8350
CAS No.:4354-76-1
- Podophyllotoxin
Catalog No.:BCN5957
CAS No.:518-28-5
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 17434-18-3 | SDF | Download SDF |
| PubChem ID | 72435 | Appearance | Cryst. |
| Formula | C22H22O8 | M.Wt | 414.4 |
| Type of Compound | Lignans | Storage | Desiccate at -20°C |
| Synonyms | AXL1717;Picropodophyllin;477-47-4 | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one | ||
| SMILES | COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O | ||
| Standard InChIKey | YJGVMLPVUAXIQN-HAEOHBJNSA-N | ||
| Standard InChI | InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Picropodophyllotoxin shows highly antifeeding and toxic activities against the 3rd-instar larve of Mythimna separate W.and the 4th-instar larvae of Pieris rapae L.and the 3rd-instar larve of Plutella xylostella L. |
| In vitro | Study on 6 insecticidal podophyllotoxin compounds from the berries of Sabina vulgaris Ant.[Reference: WebLink]《Journal of Northwest A & F University(Natural Science Edition)》 2007-09In order to isolate other insecticidal podophyllotoxin compounds from the berries of Sabina vulgaris Ant.,six podophyllotoxin compounds were isolated by tracing with insecticidal activity.They were identified as acetyl Picropodophyllotoxin,deoxyPicropodophyllotoxin,acetyl epipodophyllotoxin,podophyllotoxin,deoxypodophyllotoxin and Picropodophyllotoxin. |
| Structure Identification | Bioprocess Biosyst Eng. 2009 Aug;32(5):663-71.Novel biotransformation process of podophyllotoxin to produce podophyllic acid and picropodophyllotoxin by Pseudomonas aeruginosa CCTCC AB93066. Part I: process development.[Pubmed: 19115065]A novel biotransformation process of podophyllotoxin (1) to produce Picropodophyllotoxin (2) and podophyllic acid (3) was developed in this work. |
Picropodophyllotoxin Dilution Calculator
Picropodophyllotoxin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.4131 mL | 12.0656 mL | 24.1313 mL | 48.2625 mL | 60.3282 mL |
| 5 mM | 0.4826 mL | 2.4131 mL | 4.8263 mL | 9.6525 mL | 12.0656 mL |
| 10 mM | 0.2413 mL | 1.2066 mL | 2.4131 mL | 4.8263 mL | 6.0328 mL |
| 50 mM | 0.0483 mL | 0.2413 mL | 0.4826 mL | 0.9653 mL | 1.2066 mL |
| 100 mM | 0.0241 mL | 0.1207 mL | 0.2413 mL | 0.4826 mL | 0.6033 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
AXL1717 (Picropodophyllotoxin) is a selective inhibitor of IGF-1R with IC50 value rangs from 0.24-0.33 μM [1].
IGF-1R (type 1 insulin-like growth factor receptor) is a transmembrane receptor that activated by IGF-1 and plays an important role in cell growth and anabolic effects in adults. It has been reported that over-expression of IGF-1R is correlated with a variety of cancers and its inhibitors has been revealed to anti-cancer in clinical study [1] [2].
AXL 1717 is a potent IGF-1RTK inhibitor and has ability to inhibit tumor cells combined with HDAC inhibitor LBH589. When tested with 4 human myeloma cells (RPMI 8226, Karpas707, LP-1, and OPM-2) and 1 murine cell (5T33MM), AXL1717 treatment markedly decreased cell survival in a dose-dependent manner, arrested cell cycle in G2-M phase and induced cell apoptosis by inhibiting IGF-1RTK [1]. In four colon carcinoma cell lines (HT-29, HCT-116, DLD-1 and CaCO-2), AXL1717 treatment showed high ability to inhibit cell proliferation and migration in a dose-dependent manner [2].
In mouse model with 5TMM subcutaneous xenograft, administration of AXL 1717 (1.5 mg/d) resulted in a prolonged survival in combination with LBH (2.5 mg/kg/d) compared with control group [1].
AXL1717 has been tested to treat non-small cell lung cancer patients in a Phase I/II clinically [3].
References:
[1].Lemaire, M., et al., The HDAC inhibitor LBH589 enhances the antimyeloma effects of the IGF-1RTK inhibitor picropodophyllin. Clin Cancer Res, 2012. 18(8): p. 2230-9.
[2].Feng, X., et al., Multiple antitumor effects of picropodophyllin in colon carcinoma cell lines: clinical implications. Int J Oncol, 2012. 40(4): p. 1251-8.
[3].Ekman, S., et al., Clinical Phase I study with an Insulin-like Growth Factor-1 receptor inhibitor: experiences in patients with squamous non-small cell lung carcinoma. Acta Oncol, 2011. 50(3): p. 441-7.
- Astragaloside
Catalog No.:BCN5959
CAS No.:17429-69-5
- Caohuoside E
Catalog No.:BCN8198
CAS No.:174286-23-8
- Epimedin K
Catalog No.:BCN8201
CAS No.:174286-13-6
- Apigenin 7-O-(2G-rhamnosyl)gentiobioside
Catalog No.:BCN1524
CAS No.:174284-20-9
- Pancixanthone A
Catalog No.:BCN7379
CAS No.:174232-30-5
- Methyl 3-(2,4-dihydroxyphenyl)propionate
Catalog No.:BCN1525
CAS No.:17422-90-1
- 3-Chloro-4-hydroxypiperidin-2-one
Catalog No.:BCN3992
CAS No.:174204-83-2
- Aristolochic acid D
Catalog No.:BCN2902
CAS No.:17413-38-6
- 3-(4-Pyridyl)-D-Alanine.2HCl
Catalog No.:BCC2650
CAS No.:174096-41-4
- Tomatine
Catalog No.:BCN2966
CAS No.:17406-45-0
- Bevirimat
Catalog No.:BCC5312
CAS No.:174022-42-5
- Dehydroabietic acid
Catalog No.:BCN1119
CAS No.:1740-19-8
- Tsugaric acid A
Catalog No.:BCN2980
CAS No.:174391-64-1
- Riluzole
Catalog No.:BCC3849
CAS No.:1744-22-5
- Amiloride HCl dihydrate
Catalog No.:BCC5068
CAS No.:17440-83-4
- Sanggenol A
Catalog No.:BCN3602
CAS No.:174423-30-4
- Tipranavir
Catalog No.:BCC2002
CAS No.:174484-41-4
- alpha-Spinasterol glucoside
Catalog No.:BCN1120
CAS No.:1745-36-4
- 2-Allylphenol
Catalog No.:BCC8518
CAS No.:1745-81-9
- SDZ 220-581
Catalog No.:BCC1939
CAS No.:174575-17-8
- SDZ 220-040
Catalog No.:BCC6992
CAS No.:174575-40-7
- SB 218795
Catalog No.:BCC7037
CAS No.:174635-53-1
- SB-222200
Catalog No.:BCC1926
CAS No.:174635-69-9
- Talnetant
Catalog No.:BCC1981
CAS No.:174636-32-9
Novel biotransformation process of podophyllotoxin to produce podophyllic acid and picropodophyllotoxin by Pseudomonas aeruginosa CCTCC AB93066. Part I: process development.[Pubmed:19115065]
Bioprocess Biosyst Eng. 2009 Aug;32(5):663-71.
A novel biotransformation process of podophyllotoxin (1) to produce Picropodophyllotoxin (2) and podophyllic acid (3) was developed in this work. Eight bacteria which could modify the structure of podophyllotoxin were screened out from the tested fourteen bacteria. The highest conversion of podophyllotoxin (i.e., 70.2 +/- 8.0%) was obtained when Pseudomonas aeruginosa CCTCC AB93066 was used as biocatalyst, so P. aeruginosa was selected as a typical biocatalyst in the following study. Product (2) and (3) were separated through D312 macroporous resin and sephadex LH-20 gel column chromatograph. On the basis of (1)H NMR, (13)C NMR, ESI-MS and Elemental Analysis, product (2) and (3) were identified as Picropodophyllotoxin (2) and podophyllic acid (3), respectively. This suggested the site-specific isomerization and hydrolization of podophyllotoxin occurred during its biotransformation process by P. aeruginosa. For the first time, podophyllotoxin was biotransformed into its hydrolytic derivate (i.e., podophyllic acid).
Phase II randomized study of the IGF-1R pathway modulator AXL1717 compared to docetaxel in patients with previously treated, locally advanced or metastatic non-small cell lung cancer.[Pubmed:27882820]
Acta Oncol. 2017 Mar;56(3):441-447.
BACKGROUND: The primary objective of this study was to compare the progression-free survival (PFS) at 12 weeks between patients treated with IGF-1R pathway modulator AXL1717 (AXL) and patients treated with docetaxel (DCT). MATERIAL AND METHODS: The study was conducted at 19 study centers in five countries. A total of 99 patients with previously treated, locally advanced or metastatic non-small cell lung cancer (NSCLC) of the squamous cell carcinoma (SCC) or adenocarcinoma (AC) subtypes in need of additional treatment were randomized and treated with either 300 or 400 mg of AXL as daily BID treatment (58 patients) or DCT given as 75 mg/m(2) in three-week cycles (41 patients) as monotherapy in a 3:2 ratio for each NSCLC subtype. Patients were treated in the primary study treatment period for a maximum of four treatment cycles. RESULTS: The 12-week PFS rate, median PFS and overall survival (OS), as well Kaplan-Meier hazard ratio for PFS and OS, did not show any statistically significant differences between the treatment groups. For the primary endpoint, the AXL group had a lower percentage of patients (25.9%) who were progression-free at Week 12 as compared to the DCT group (39.0%), although the difference was not statistically significant. The most notable difference in the incidence of treatment emergent adverse effects (TEAEs) was the lower incidence of treatment-related grade 3/4 neutropenia in patients treated with AXL. CONCLUSION: These results suggest neither of the treatments to be superior of the other when treating locally advanced or metastatic NSCLC. Considering the lower incidence of grade 3/4 neutropenia in the AXL group this treatment warrants further research.
A phase I pilot study of the insulin-like growth factor 1 receptor pathway modulator AXL1717 in combination with gemcitabine HCl and carboplatin in previously untreated, locally advanced, or metastatic non-small cell lung cancer.[Pubmed:25794491]
Med Oncol. 2015 Apr;32(4):129.
AXL1717 is an orally bioavailable IGF-1R pathway modulator that has been shown to have anti-tumoral effects. The objectives of the present study were to define maximum tolerated dose and the recommended phase II dose (RPTD) of AXL1717 in combination with gemcitabine HCl and carboplatin in non-small cell lung cancer (NSCLC). Patients with previously untreated, locally advanced, or metastatic NSCLC (squamous cell cancer or adenocarcinoma) in good performance status and with preserved major organ functions were enrolled in the study. The study was an open-label phase I study with planned cohorts of three patients per dose level of AXL1717 (215, 290, and 390 mg BID). In total, 12 patients were enrolled in the study, and of these, two were prematurely excluded. AXL1717 was administered at one dose level, 215 mg BID. A total number of 81 unique adverse events were reported. Bone marrow toxicity was reported in 10 out of 12 patients, and this organ class showed the largest number of related events. AXL1717 in combination with gemcitabine HCl and carboplatin is a possible treatment approach in previously untreated, locally advanced, or metastatic non-small cell lung cancer. However, due to the bone marrow toxicity profile shown in the present study, further dose increases of AXL1717 above 215 mg BID will probably not be feasible. Therefore, 215 mg BID constitutes maximum tolerated dose and RPTD.
