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Chemical Structure| 520-36-5 Chemical Structure| 520-36-5

Structure of Apigenin
CAS No.: 520-36-5

Chemical Structure| 520-36-5

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Apigenin is a natural flavonoid compound with anti-inflammatory, antioxidant, and anticancer activities. Apigenin is primarily used in cancer research, anti-inflammatory studies, and as a dietary supplement for antioxidant and chronic disease prevention research. Apigenin (Standard) is an analytical standard of Apigenin, used for research and analytical applications.

Synonyms: 4',5,7-Trihydroxyflavone; Apigenol; 457Trihydroxyflavone

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Scott, Jared Lee ;

Abstract: Breast cancer (BC) is the second greatest contributor to the death of women, second only to heart disease, and is the most common type of cancer. BC treatments involve the administration of adjuvant chemotherapies which often have side effects that prevent patients from completing the full course of drugs or the refusal to take these potentially lifesaving treatments. Many chemotherapy drugs are developed from plants, and some plant extracts can exhibit significant anticancer activities while also having less toxic side effects. However, these potential "plant therapeutics" suffer from poor oral bioavailability. The Apiaceae plant family consists of several species that are used as culinarily spices including anise, celery, cumin, and coriander, all of which have demonstrated antioxidant, chemopreventive, and anticancer activities. One method to improve the systemic distribution of anticancer phytochemicals is their encapsulation in naturally produced membrane bound nanoparticles known as exosomes. Exosomes are produced by most eukaryotic organisms, as well as some prokaryotes, and are involved in cell-to-cell communication through the delivery of proteins, nucleic acids, and small molecules from one cell to another. Exosomes are found in many extracellular fluids including blood, urine, and milk. Bovine milk exosomes represent a scalable source of exosomes that are already present in the human diet and have been explored as a drug delivery system that can increase effectiveness and improve bioavailability. To enhance the loading potential and anticancer bioactivity of Apiaceae phytochemicals, an acid hydrolysis (AH) of the glycoside compounds present in ethanolic spice extracts was performed on eight ethanolic spice extracts. The antiproliferative effects of AH extracts and exosomal formulations were assayed with three model types of BC cells. Cumin was characterized in greater detail as these extracts had the highest concentration of terpenoids and alkaloids while also having significant concentrations of phenolics and responded well to AH with increased antiproliferative activity and exosomal loading. Extracts and exosomal formulations exhibited broad antiproliferative effects with lower IC50s in the extracts delivered with exosomes. The phytochemical contents of AH-cumin extracts and exosomal formulations were assayed with HPLC-DAD, LC-MS/MS, and GC-MS, while the potential anticancer mechanisms of these treatments were investigated in triple negative BC (TNBC). AHcumin extracts were determined to have numerous phenolic compounds, many of which have known anticancer mechanisms, in addition to several alkaloids and lipid compounds, some of which have activities that could contribute to the anticancer effects observed. Mechanistically, AH-cumin extracts and exosomal formulations were shown to interact with multidrug resistance proteins and inhibit lipid metabolism in TNBC cells. These results indicate that acid hydrolyzed cumin extracts delivered through exosome nanoparticles represent a possible avenue towards the development of novel treatments for TNBC, the hardest type of BC to treat.

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Amin, Faiq ; Ibrahim, Mahmoud AA ; Rizwan-ul-Hasan, Syed ; Khaliq, Saima ; Gabr, Gamal A ; Muhammad , et al.

Abstract: Background: The current study utilizes in silico molecular docking/molecular dynamics to evaluate the binding affinity of apigenin and safranal with 5HT1AR/5HT2AR, followed by assessment of in vivo effects of these compounds on depressive and anxious behavior. Methods: The docking between apigenin and safranal and the 5HT1A and 5HT2A receptors was performed utilizing AutoDock Vina software, while MD and protein-lipid molecular dynamics simulations were executed by AMBER16 software. For in vivo analysis, healthy control (HC), disease control (DC), f luoxetine-, and apigenin-safranal-treated rats were tested for changes in depression and anxiety using the forced swim test (FST) and the elevated plus-maze test (EPMT), respectively. Results: The binding affinity estimations identified the superior interacting capacity of apigenin over safranal for 5HT1A/5HT2Areceptors over 200 ns MD simulations. Both compounds exhibit oral bioavailability and absorbance. In the rodent model, there was a significant increase in the overall mobility time in the FST, while in the EPMT, there was a decrease in latency and an increase in the number of entries for the treated and HC rats compared with the DC rats, suggesting a reduction in depressive/anxiety symptoms after treatment. Conclusions: Our analyses suggest apigenin and safranal as prospective medication options to treat depression and anxiety

Keywords: depression ; anxiety ; natural compounds ; molecular docking and dynamics ; serotonin receptors ; murine model

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Product Details of Apigenin

CAS No. :520-36-5
Formula : C15H10O5
M.W : 270.23
SMILES Code : O=C1C=C(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O)=C3
Synonyms :
4',5,7-Trihydroxyflavone; Apigenol; 457Trihydroxyflavone
MDL No. :MFCD00006831
InChI Key :KZNIFHPLKGYRTM-UHFFFAOYSA-N
Pubchem ID :5280443

Safety of Apigenin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Mouse embryonic fibroblasts 25 µM 24 hours Investigate the effect of xanthosine on cellular metabolome, results showed xanthosine downregulated metabolites involved in cholesterol and uric acid synthesis pathways Int J Mol Sci. 2023 Feb 17;24(4):4066

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT03365648 Allergic Rhinoconjunctivitis Not Applicable Completed - Italy ... More >> Fondazione IRCCS Policlinico San Matteo Pavia, (pv), Italy, 27100 Ospedale regionale San Salvatore - ASL 1 Avezzano Sulmona L'Aquila L'Aquila, AQ, Italy, 67100 A.O.U. Consorziale "Policlinico Giovanni XXIII" Bari, BA, Italy, 70126 A.O.U. Consorziale "Policlinico-Giovanni XXIII" Bari, BA, Italy, 70126 A.O.U. Policlinico Vittorio Emanuele Catania, CT, Italy, 95123 Istituto Giannina Gaslini Genova, GE, Italy, 16132 P.O. San Giovanni di Dio - ASP di Crotone Crotone, KR, Italy, 88900 A.O.U. Policlinico "G. Martino" Messina, ME, Italy, 98124 P.O. G. Salvini di Garbagnate Milanese - ASST Rhodense Garbagnate Milanese, MI, Italy, 20042 Ospedale Civile di Legnano - ASST Ovest Milanese Legnano, MI, Italy, 20162 Fondazione IRCCS Cà Granda Ospedale Maggiore Policlinico Milano, MI, Italy, 20122 Ospedale San Carlo Borromeo - ASST Azienda Socio Sanitaria Territoriale Santi Paolo E Carlo Milano, MI, Italy, 20157 Ospedale Città di Sesto San Giovanni - ASST Nord Milano Sesto San Giovanni, MI, Italy, 20099 Ospedale di Polistena "Santa Maria degli Ungheresi" - ASP di Reggio Calabria Polistena, RC, Italy, 89024 A.O.U. Policlinico Umberto I Roma, RM, Italy, 00161 P.O. di Busto Arsizio - ASST Valle Olona Busto Arsizio, VA, Italy, 21051 Az. Osp. Univ. dell'Università degli Studi della Campania "Luigi Vanvitelli" Napoli, Italy, 80138 Less <<
NCT01286324 Primary Insomnia ... More >> Chronic Insomnia Less << Phase 2 Completed - United States, Michigan ... More >> University of Michigan Department of Family Medicine Ann Arbor, Michigan, United States, 48105 Less <<
NCT03139227 Health Status Unknown Not Applicable Recruiting August 31, 2020 United States, Ohio ... More >> Ohio State University Comprehensive Cancer Center Recruiting Columbus, Ohio, United States, 43210 Contact: Sagar D. Sardesai, MBBS    614-293-0066    Sagar.Sardesai@osumc.edu    Principal Investigator: Sagar D. Sardesai, MBBS          Sub-Investigator: Andrea I. Doseff, PhD          Sub-Investigator: Maryam Lustberg, MD MPH Less <<
NCT01286324 - Completed - -
NCT00609310 Colorectal Cancer Phase 2 Suspended December 2016 Germany ... More >> community Hospital Darmstadt, Hesse, Germany Less <<
NCT03526081 Healthy Not Applicable Active, not recruiting December 31, 2018 United States, California ... More >> Ragle Human Nutrition Research Center, Department of Nutrition at UC Davis Davis, California, United States, 95616 UC Davis Davis, California, United States, 95616 Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.70mL

0.74mL

0.37mL

18.50mL

3.70mL

1.85mL

37.01mL

7.40mL

3.70mL

References

 

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