Taccalonolide AJ
Based on 1 publication(s) in Google Scholar
Taccalonolide AJ is a microtubule stabilizer and antiproliferative agent with an IC50 of 4.2 nM against β-tubulin (β-tubulin) D226. Taccalonolide AJ increases cellular microtubule density, induces microtubule bundling, triggers G2/M cell cycle arrest with abnormal mitotic spindles, and inhibits cancer cell proliferation. Taccalonolide AJ can be used in the research of oral cancer, breast cancer, solid tumors, as well as tumors resistant to Paclitaxel (HY-B0015) and Doxorubicin (HY-15142A).
Nos produits utilisent uniquement pour la recherche. Nous ne vendons pas aux patients.
- Pureté: 98.6%
- CAS No.: 2230777-09-8
- Formule: C34H44O14
- Masse moléculaire:676.70
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Stockage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year
To place orders, for customer services and technical support, please contact: MedChemExpress USA
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Pureté et documentation
- Références
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Help & FAQs
Publications Citing Use of MedChemExpress (MCE) Taccalonolide AJ
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Activité biologique
Description
IC50 & Target
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β-Tubulin 4.2 nM (IC50, D226) |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HeLa | IC50 |
4.2 nM
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Antiproliferative cytotoxicity against human cervical cancer HeLa cells assessed by SRB assay.
Antiproliferative cytotoxicity against human cervical cancer HeLa cells assessed by SRB assay.
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22040100 |
| MDA-MB-435 | GI50 |
6 nM
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Antiproliferative activity against human melanoma MDA-MB-435 cells assessed by sulforhodamine B assay under 0.1% serum conditions.
Antiproliferative activity against human melanoma MDA-MB-435 cells assessed by sulforhodamine B assay under 0.1% serum conditions.
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28112516 |
| MDA-MB-435 | GI50 |
7 nM
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Antiproliferative activity against human melanoma MDA-MB-435 cells assessed by sulforhodamine B assay under 1% serum conditions.
Antiproliferative activity against human melanoma MDA-MB-435 cells assessed by sulforhodamine B assay under 1% serum conditions.
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28112516 |
| MDA-MB-435 | GI50 |
9 nM
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Antiproliferative activity against human melanoma MDA-MB-435 cells assessed by sulforhodamine B assay under 10% serum conditions.
Antiproliferative activity against human melanoma MDA-MB-435 cells assessed by sulforhodamine B assay under 10% serum conditions.
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28112516 |
| HeLa | GI50 |
8.5 nM
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Antiproliferative activity against human HeLa cervical cancer cells assessed by SRB assay after 48 h treatment.
Antiproliferative activity against human HeLa cervical cancer cells assessed by SRB assay after 48 h treatment.
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32005831 |
| SK-OV-3 | GI50 |
6.2 nM
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Antiproliferative activity against human SK-OV-3 ovarian cancer cells assessed by SRB assay after 48 h treatment.
Antiproliferative activity against human SK-OV-3 ovarian cancer cells assessed by SRB assay after 48 h treatment.
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32005831 |
| HeLa | IC50 |
4 nM
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Antiproliferative activity against human HeLa cells assessed via sulforhodamine B (SRB) assay.
Antiproliferative activity against human HeLa cells assessed via sulforhodamine B (SRB) assay.
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24048820 |
In Vitro
Taccalonolide AJ (compound 7) (20 μM; 18 h) stabilizes microtubules, increases microtubule density and induces microtubule bundling in HeLa cells, and also triggers G2/M cell cycle arrest with abnormal mitotic spindles[1].
Taccalonolide AJ (30 nM) increases interphase microtubule density, induces G2/M cell cycle arrest in HeLa cells, and promotes the formation of multiple abnormal mitotic spindles with unique morphologies[6].
Taccalonolide AJ (10 μM; 40 min) directly promotes the polymerization of purified tubulin[1].
Taccalonolide AJ directly promotes the polymerization of purified tubulin, with reduced nucleation efficiency[3].
Taccalonolide AJ (compound 2) (5-20 μM; 60 min) promotes the polymerization of purified porcine brain tubulin in a concentration-dependent manner, with the maximum activity observed at 20 μM[4].
Taccalonolide AJ binds to D226 of β-tubulin via epoxy ring opening, and interacts with the key residues K19, H229, R278, L217, L219 and T223 to stabilize the complex[4].
Taccalonolide AJ (30 nM; 16 h) induces the formation of bundled tubulin oligomers in HepG2 cells[5].
Taccalonolide AJ (10 μM; 30 min) stimulates the polymerization of purified porcine brain tubulin[5].
Taccalonolide AJ (25 μM; 3 h) inhibits GTP hydrolysis at the E-site in purified porcine brain tubulin[5].
Taccalonolide AJ (10-30 μM) increases the rate and extent of purified tubulin polymerization in a concentration-dependent manner and enhances the stability of microtubules against cold-induced depolymerization[6].
Taccalonolide AJ (10-30 μM) increases the rate and extent of purified porcine brain tubulin polymerization in a dose-dependent manner, with a persistent nucleation lag phase[7].
Taccalonolide AJ (10-30 μM; 4-60 min) slowly initiates the polymerization of purified porcine brain tubulin[7].
Taccalonolide AJ (10 μM) enhances the mechanical stability of microtubules assembled from purified porcine brain tubulin, protecting them from shear damage during vigorous pipetting[7].
Taccalonolide AJ (125 μM) covalently binds to β-tubulin peptides spanning residues 212-230 and 213-230 in purified bovine brain tubulin[7].
Taccalonolide AJ (125 μM) stabilizes the interprotofilament lateral contacts on α-tubulin in purified bovine brain tubulin microtubules without altering the stability of the β-tubulin M-loop[7].
Taccalonolide AJ (4 nM) is a potent microtubule stabilizer that inhibits cancer cell proliferation in vitro, with an IC50 of 4 nM[2].
Taccalonolide AJ (100 nM; 22 h) stabilizes microtubules in the human triple-negative breast cancer cell line HCC1937[4].
At the concentration that induces maximum G2/M phase arrest (18 h), Taccalonolide AJ induces interphase microtubule bundling and forms dense, numerous mitotic spindle asters in HeLa cells[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:HCC1937 triple-negative breast cancer cells
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Concentration:100 nM
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Incubation Time:22 h
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Result:Induced microtubule stabilization in cells expressing wild-type or mutant β-tubulin constructs.
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Cell Line:HepG2 cells
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Concentration:30 nM
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Incubation Time:16 h
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Result:Induced the formation of bundle-like tubulin oligomers in HepG2 cells.
Parmacokinetics
| Species | Dose | Route | Cmax | T1/2 | AUC |
|---|---|---|---|---|---|
| Mice[2] | 300 μg | i.v. | 19 μg/mL | 8.1 min | 3.5 μg/mL·h |
In Vivo
Taccalonolide AJ (four doses total) shows only slight antitumor activity in the MDA-MB-231 breast cancer xenograft model, which is accompanied by unacceptable toxicity at tested doses[3].
Taccalonolide AJ exhibits excellent, persistent antitumor efficacy when administered directly to MDA-MB-231 breast cancer xenografts in female athymic nude mice, but lacks an efficacy window with systemic administration[6].
Taccalonolide AJ (0.5-0.85 mg/kg; i.p.) lacks a safe effective range for antitumor activity in the MDA-MB-231 breast cancer xenograft model, as no measurable efficacy occurs at non-toxic doses, and toxic doses only yield modest antitumor effects[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:athymic nude mice (6-7 week old female; SCC-4 oral cancer cells injected subcutaneously into rear flank, tumors grown to average 200 mm3 before treatment)[2]
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Dosage:20, 40, 80 µg total
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Administration:intratumoral; 2 doses on days 0 and 3
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Result:Failed to inhibit tumor growth at 20 µg total dose.
Caused slight tumor growth inhibition relative to vehicle controls at 40 µg total dose.
Caused robust, prolonged tumor growth inhibition relative to vehicle controls at 80 µg total dose.
Doubled the median time to reach 1500 mm3 tumor volume to 42 days at 80 µg total dose, compared to 18 days for vehicle controls.
Showed no weight loss or toxicities at all tested doses.
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Animal Model:athymic nude mice (female)[7]
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Dosage:0.5, 0.85 mg/kg
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Administration:i.p.; days 1, 3, 5, 8 (0.5 mg/kg); days 1, 4, 8 (0.85 mg/kg)
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Result:Showed no measurable antitumor effects at 0.5 mg/kg despite average weight loss of greater than 10% and two mice succumbing to toxicity on days 11 and 12 (LD40).
Produced no antitumor effects at lower non-toxic dosing regimens.
Showed modest antitumor effects at 0.85 mg/kg but caused unacceptable toxicity leading to LD80.
Chemical Information
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CAS No. 2230777-09-8
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Appearance Solid
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Masse moléculaire 676.70
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Formule C34H44O14
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Color White to off-white
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SMILES
C[C@]1([C@@]2(O)C)[C@]3(OC2=O)[C@H]([C@@H](C)[C@@]4([H])[C@@]1([H])[C@@H]([C@]5([H])[C@@]4([C@H]([C@@H](OC(C)=O)[C@@]6([H])[C@@]5([H])[C@H](C([C@]7([H])[C@@]6([C@H]([C@@H](O8)[C@@H]8C7)OC(C)=O)C)=O)O)OC(C)=O)C)O)O3
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 2 years -20°C 1 year
Publications (1)
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Journal Impact Factor
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Most Recent
Solvant et solubilité
In Vitro:
DMSO : 110 mg/mL (162.55 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pureté et documentation
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Fiche technique (306 KB)
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SDS (254 KB)
- English - EN (254 KB)
- Français - FR (254 KB)
- Deutsch - DE (254 KB)
- Norwegian - NO (254 KB)
- Español - ES (254 KB)
- Swedish - SV (254 KB)
- Italian - IT (254 KB)
- Korean - KR (254 KB)
- Portuguese - PT (254 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. Li J, et al. Potent taccalonolides, AF and AJ, inform significant structure-activity relationships and tubulin as the binding site of these microtubule stabilizers. Journal of the American Chemical Society. 2011 Nov 30;133(47):19064-7. [Content Brief]
[2]. Risinger AL, et al. Pharmacokinetic Analysis and in Vivo Antitumor Efficacy of Taccalonolides AF and AJ. Journal of natural products. 2017 Feb 24;80(2):409-414. [Content Brief]
[3]. Yee SS, et al. Taccalonolide Microtubule Stabilizers. Prog Chem Org Nat Prod. 2020;112:183-206.
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 1.4778 mL | 7.3888 mL | 14.7776 mL | 36.9440 mL |
| 5 mM | 0.2956 mL | 1.4778 mL | 2.9555 mL | 7.3888 mL | |
| 10 mM | 0.1478 mL | 0.7389 mL | 1.4778 mL | 3.6944 mL | |
| 15 mM | 0.0985 mL | 0.4926 mL | 0.9852 mL | 2.4629 mL | |
| 20 mM | 0.0739 mL | 0.3694 mL | 0.7389 mL | 1.8472 mL | |
| 25 mM | 0.0591 mL | 0.2956 mL | 0.5911 mL | 1.4778 mL | |
| 30 mM | 0.0493 mL | 0.2463 mL | 0.4926 mL | 1.2315 mL | |
| 40 mM | 0.0369 mL | 0.1847 mL | 0.3694 mL | 0.9236 mL | |
| 50 mM | 0.0296 mL | 0.1478 mL | 0.2956 mL | 0.7389 mL | |
| 60 mM | 0.0246 mL | 0.1231 mL | 0.2463 mL | 0.6157 mL | |
| 80 mM | 0.0185 mL | 0.0924 mL | 0.1847 mL | 0.4618 mL | |
| 100 mM | 0.0148 mL | 0.0739 mL | 0.1478 mL | 0.3694 mL |
Taccalonolide AJ Related Classifications
HY-N4208 Related Classifications
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