1. Membrane Transporter/Ion Channel Neuronal Signaling Apoptosis
  2. Potassium Channel Sodium Channel Na+/K+ ATPase Calcium Channel Apoptosis
  3. Annonacin

Annonacin is an acetylgenin that is toxic by inhibiting the pathway of the mitochondrial complex. Annonacin increases tau phosphorylation in R406W+/+ mice. Annonacin acts as an inhibitor of the sodium/potassium and sarcoplasmic reticulum (SERCA) ATPase pumps. Annonacin has significant killing effect on ovarian cancer cell, cervical cancer cell, breast cancer cell, bladder cancer cell and skin cancer cell. Annonacin induces apoptosis through Bax and Caspase-3-related pathways.

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Annonacin Chemical Structure

Annonacin Chemical Structure

CAS No. : 111035-65-5

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Based on 1 publication(s) in Google Scholar

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Description

Annonacin is an acetylgenin that is toxic by inhibiting the pathway of the mitochondrial complex. Annonacin increases tau phosphorylation in R406W+/+ mice. Annonacin acts as an inhibitor of the sodium/potassium and sarcoplasmic reticulum (SERCA) ATPase pumps. Annonacin has significant killing effect on ovarian cancer cell, cervical cancer cell, breast cancer cell, bladder cancer cell and skin cancer cell. Annonacin induces apoptosis through Bax and Caspase-3-related pathways[1][2][3][4].

In Vitro

Annonacin (1-10 μg/mL; 0-72 h) induces the death of a variety of cancer cell lines, and blocks cancer cells in G1 phase [2].
Annonacin 10 μg/mL; 0-24 h) induces apoptosis of T24 cells and enhance the expression of pro-apoptosis-related genes [2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay[2]

Cell Line: T24 cells
Concentration: 1 μg/mL
Incubation Time: 0, 24, 48 and 72 h
Result: Significantly reduced cell viability. Compared with untreated controls, only 56.0%, 34.2% and 35.3% of T24 cells were alive at 24, 48 and 72 hours, respectively.

Western Blot Analysis[2]

Cell Line: T24 cells
Concentration: 10 μg/mL
Incubation Time: 1, 4, 8, 12 and 24 h
Result: Increased the levels of Bax and Bad.
Inhibited the levels of procaspase-3.
In Vivo

Annonacin (0-9 mg/kg; Subcutaneous osmotic pump; 3 days) increases tau phosphorylation in R406W+/+ mice [3].
Annonacin (85 nM/100 μL; Topical application; Twice a week for 22 weeks) has anti-cancer effect in mouse model of skin tumor [4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: R406W+/+ transgenic mice[3]
Dosage: 0, 6 and 9 mg/kg/day
Administration: Subcutaneous osmotic pump; 3 days
Result: Increased the number of neurons with phosphorylated tau in the somatodendritic compartment in several brain areas.
Increased the levels of phosphorylated tau protein.
Increased in total tau protein without increase in tau mRNA, but reduced proteasomal proteolytic activity.
Increased the levels of different tau kinases.
Significantly increased the ratio of p25/p35.
Animal Model: DMBA (HY-W011845)/TPA treated female ICR mice aged 6-7 weeks old[4]
Dosage: 85 nM/100 uL
Administration: Topical application; Twice a week for 22 weeks
Result: Significantly increased the tumor latency period and reduced the tumor incidence, tumor burden and tumor volume, respectively.
Suppressed tumorigenesis manifested by significant reduction of hyperkeratosis, dermal papillae and number of keratin pearls on skin tissues.
Showed no toxicity to the liver and kidneys.
Molecular Weight

596.88

Formula

C35H64O7

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

O=C1O[C@@H](C)C=C1C[C@H](O)CCCCC[C@@H](O)CCCC[C@@H](O)[C@@H]2O[C@@H]([C@H](O)CCCCCCCCCCCC)CC2

Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility
In Vitro: 

DMSO : ≥ 20 mg/mL (33.51 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 1.6754 mL 8.3769 mL 16.7538 mL
5 mM 0.3351 mL 1.6754 mL 3.3508 mL
View the 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, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation

Purity: ≥97.0%

References

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, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 1.6754 mL 8.3769 mL 16.7538 mL 41.8845 mL
5 mM 0.3351 mL 1.6754 mL 3.3508 mL 8.3769 mL
10 mM 0.1675 mL 0.8377 mL 1.6754 mL 4.1884 mL
15 mM 0.1117 mL 0.5585 mL 1.1169 mL 2.7923 mL
20 mM 0.0838 mL 0.4188 mL 0.8377 mL 2.0942 mL
25 mM 0.0670 mL 0.3351 mL 0.6702 mL 1.6754 mL
30 mM 0.0558 mL 0.2792 mL 0.5585 mL 1.3961 mL
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  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Annonacin
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