caffeic acid phenethyl ester, caffeic acid phenyl ester, CAPE compound, CAPEEE, phenethyl caffeate, phenyl caffeate

| Name | Caffeic acid phenethyl ester | ||
| PubChem CID | 5281787 | ||
| Molecular Weight | 284.31g/mol | ||
| Synonyms |
caffeic acid phenethyl ester, caffeic acid phenyl ester, CAPE compound, CAPEEE, phenethyl caffeate, phenyl caffeate |
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| Formula | C₁₇H₁₆O₄ | ||
| SMILES | C1=CC=C(C=C1)CCOC(=O)C=CC2=CC(=C(C=C2)O)O | ||
| InChI | 1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7+ | ||
| InChIKey | SWUARLUWKZWEBQ-VQHVLOKHSA-N | ||
| CAS Number | 115610-29-2 | ||
| ChEMBL ID | CHEMBL319244 | ||
| ChEBI ID | CHEBI:8062 | ||
| KEGG ID | C10484 | ||
| Structure |
Download
2D
MOL
3D
MOL
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| Chineses Pinyin | FengJiao | ||
| Use Part | Bee glue | ||
| Habitat | Shandong, Beijing, Henan, Jiangsu, Hangzhou, Xinjiang | ||
| Flavor | Pungent; Bitter | ||
| Meridian Tropism | Spleen; Stomach | ||
| Species |
>Kingdom: Metazoa
-->Phylum: Arthropoda
-->Class: Insecta
-->Order: Hymenoptera
-->Family: Apidae
-->Genus: Apis
-->Species: Apis mellifera
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| Pair Name | Caffeic acid phenethyl ester, Fluorouracil | |||
| Partner Name | Fluorouracil | |||
| Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Up-regulation | Expression | CASP3 | hsa836 |
| Up-regulation | Expression | BAX | hsa581 | |
| In Vitro Model | MCF-7 | Invasive breast carcinoma of no special type | Homo sapiens (Human) | CVCL_0031 |
| Result | This study demonstrated the cytotoxicity of CAPE potential to induce apoptosis of breast cancer MCF-7 cell line single and cytotoxic-cytostatic combination with 5-FU. Therefore, further studies to develop CAPE and its derivatives will be required to discover new candidates for breast cancer agents. | |||
| Pair Name | Caffeic acid phenethyl ester, Cisplatin | |||
| Partner Name | Cisplatin | |||
| Disease Info | [ICD-11: 2C73] | Ovarian cancer | Investigative | |
| Gene Regulation | Down-regulation | Expression | USP8 | hsa9101 |
| Up-regulation | Expression | PSMD9 | hsa5715 | |
| Up-regulation | Expression | TP53 | hsa7157 | |
| Up-regulation | Cleavage | CASP3 | hsa836 | |
| In Vitro Model | TOV-112D | Ovarian endometrioid adenocarcinoma | Homo sapiens (Human) | CVCL_3612 |
| IGROV-1/Pt1 | Ovarian endometrioid adenocarcinoma | Homo sapiens (Human) | CVCL_EQ62 | |
| In Vivo Model | Exponentially growing cells (1×10⁷/mouse) were inoculated i.p. or s.c. into the right flank on day 0 forming experimental groups of 7 animals. | |||
| Result | This study reveals the therapeutic potential of CAPE in cisplatin-resistant ovarian tumors as well as in tumors expressing USP8. | |||
| Pair Name | Caffeic acid phenethyl ester, Bortezomib | |||
| Partner Name | Bortezomib | |||
| Disease Info | [ICD-11: 2A83.1] | Multiple myeloma | Investigative | |
| Gene Regulation | Down-regulation | Expression | IL6 | hsa3569 |
| Down-regulation | Activity | NFKB1 | hsa4790 | |
| In Vitro Model | ARH-77 | Plasma cell myeloma | Homo sapiens (Human) | CVCL_1072 |
| In Vivo Model | Female BALB/c mice (5–6 weeks old) were use in this study. | |||
| Result | We think that our study, which is the first to demonstrate the in vitro and in vivo effectiveness of the.combined use of CAPE and bortezomib, will be a pioneer for future human applications of CAPE in MM. | |||
| Pair Name | Caffeic acid phenethyl ester, Paclitaxel | |||
| Partner Name | Paclitaxel | |||
| Disease Info | [ICD-11: 2C73] | Ovarian cancer | Investigative | |
| Biological Phenomena | Inhibition-->Cell migration | |||
| In Vitro Model | OV7 | Ovarian carcinoma | Homo sapiens (Human) | CVCL_2675 |
| Result | The simultaneous administration of PTX and CAPE enhanced the anti-migration activity of the chemotherapeutic used in this study. | |||
| Pair Name | Caffeic acid phenethyl ester, Doxorubicin | |||
| Partner Name | Doxorubicin | |||
| Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
| Biological Phenomena | Inhibition-->Lipid metabolism | |||
| Gene Regulation | Down-regulation | Expression | SREBF1 | hsa6720 |
| Down-regulation | Expression | ACACA | hsa31 | |
| Down-regulation | Expression | FASN | hsa2194 | |
| Down-regulation | Expression | SCD | hsa6319 | |
| Down-regulation | Phosphorylation | AKT1 | hsa207 | |
| Down-regulation | Phosphorylation | MTOR | hsa2475 | |
| In Vitro Model | MCF-7 | Invasive breast carcinoma of no special type | Homo sapiens (Human) | CVCL_0031 |
| Result | Our results suggest that CAPE treatment reversed DOX resistance in breast cancer cells, at least in part by inhibiting Akt/mTOR/SREBP1 pathway-mediated lipid metabolism, indicating that CAPE may be an effective substance to assist in the treatment of breast cancer. | |||
| No. | Title | Href |
|---|---|---|
| 1 | Caffeic Acid Phenethyl Ester as a DHODH Inhibitor and Its Synergistic Anticancer Properties in Combination with 5-Fluorouracil in a Breast Cancer Cell Line. J Exp Pharmacol. 2022 Jul 23;14:243-253. doi: 10.2147/JEP.S365159. | Click |
| 2 | Caffeic acid phenethyl ester targets ubiquitin-specific protease 8 and synergizes with cisplatin in endometrioid ovarian carcinoma cells. Biochem Pharmacol. 2022 Mar;197:114900. doi: 10.1016/j.bcp.2021.114900. | Click |
| 3 | An in vitro and in vivo investigation of the cytotoxic effects of caffeic acid (3,4-dihydroxycinnamic acid) phenethyl ester and bortezomib in multiple myeloma cells. Turk J Med Sci. 2015;45(1):38-46. doi: 10.3906/sag-1401-127. | Click |
| 4 | Caffeic Acid Phenethyl Ester (CAPE) Synergistically Enhances Paclitaxel Activity in Ovarian Cancer Cells. Molecules. 2023 Aug 1;28(15):5813. doi: 10.3390/molecules28155813. | Click |
| 5 | Caffeic acid phenethyl ester reverses doxorubicin resistance in breast cancer cells via lipid metabolism regulation at least partly by suppressing the Akt/mTOR/SREBP1 pathway. Kaohsiung J Med Sci. 2023 Jun;39(6):605-615. doi: 10.1002/kjm2.12675. | Click |