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Cat. No.: HY-N21815

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Phenoxan

Phenoxan is an inhibitor of cytochrome b and NADH: ubiquinone oxidoreductase. It exerts anti-HIV, antifungal, and cytotoxic effects by inhibiting the electron transport chain, the activity of HIV-1 Reverse Transcriptase, and viral replication. Phenoxan can be used in studies of HIV-1 infection and fungal infections.

For research use only. We do not sell to patients.

CAS No.: 134332-63-1
Formula: C₂₃H₂₅NO₄
Molecular Weight:379.45

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Please store the product under the recommended conditions in the Certificate of Analysis.

Phenoxan Chemical Structure

CAS No.: 134332-63-1

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
Chemical Information
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Biological Activity

Description

IC₅₀ & Target

HIV-1

6.6 nM (ID₅₀)

All Cytochrome P450 Isoforms :

All HIV Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
MT4	EC50	6.6 nM	Inhibition of HIV-1-induced cytopathogenicity in MT-4 cells assessed via ³H-thymidine incorporation into cellular DNA after 4 days post-infection with a 20 h thymidine incubation period. Inhibition of HIV-1-induced cytopathogenicity in MT-4 cells assessed via ³H-thymidine incorporation into cellular DNA after 4 days post-infection with a 20 h thymidine incubation period.	1429243
MT4	CC₅₀	> 6600 nM	Cytotoxicity against MT-4 cells assessed via ³H-thymidine incorporation into cellular DNA after 4 days post-infection with a 20 h thymidine incubation period. Cytotoxicity against MT-4 cells assessed via ³H-thymidine incorporation into cellular DNA after 4 days post-infection with a 20 h thymidine incubation period.	1429243
H9	CC₅₀	6600 nM	Cytotoxicity against human lymphoblastoid H9 cells assessed via ³H-thymidine incorporation measurement. Cytotoxicity against human lymphoblastoid H9 cells assessed via ³H-thymidine incorporation measurement.	1429243
MOLT-3	CC₅₀	6600 nM	Cytotoxicity against human lymphoblastoid Molt-3 cells assessed via ³H-thymidine incorporation measurement. Cytotoxicity against human lymphoblastoid Molt-3 cells assessed via ³H-thymidine incorporation measurement.	1429243
Jurkat	CC₅₀	66000 nM	Cytotoxicity against human lymphoblastoid Jurkat cells assessed via ³H-thymidine incorporation measurement. Cytotoxicity against human lymphoblastoid Jurkat cells assessed via ³H-thymidine incorporation measurement.	1429243
MOLT-4	CC₅₀	66000 nM	Cytotoxicity against human lymphoblastoid Molt-4 clone 8 cells assessed via ³H-thymidine incorporation measurement. Cytotoxicity against human lymphoblastoid Molt-4 clone 8 cells assessed via ³H-thymidine incorporation measurement.	1429243
Raji	CC₅₀	66000 nM	Cytotoxicity against human lymphoblastoid Raji cells assessed via ³H-thymidine incorporation measurement. Cytotoxicity against human lymphoblastoid Raji cells assessed via ³H-thymidine incorporation measurement.	1429243

In Vitro

Phenoxan completely inhibits HIV-1-induced cytopathogenicity in MT-4 cells at a concentration of 6.6 μM, exhibits no cytotoxicity at concentrations > 6600 nM, and has a selectivity index > 10³^[2].
Phenoxan does not inhibit HIV-1-induced syncytium formation at a concentration of 6.6 μM in a co-culture system of Molt-4 clone 8 cells and HIV-1_IIIB-infected Molt-4 cells^[2].
Phenoxan inhibits the activity of purified HIV-1_IIIB reverse transcriptase with an IC₅₀ of 376 μM, a concentration that is much higher than that required for its anti-HIV-1 activity in MT-4 cells^[2].
Phenoxan (6600-66000 nM) exhibits toxicity to H9 and Molt-3 cells at a concentration of 6600 nM, and to Jurkat, Molt-4 clone 8 and Raji cells at a concentration of 66000 nM^[2].
Phenoxan (compound 1) (40 μg) inhibits the growth of specific fungal strains, with a minimum inhibitory concentration of 19 ng/mL against Ustilago maydis, and shows no activity against the tested bacteria and yeasts^[1].
Phenoxan (2.2 ng/mL; 4 minutes) potently inhibits NADH oxidation in bovine heart submitochondrial particles, with an IC₅₀ of 5.8 nM (2.2 ng/mL)^[1].
Phenoxan (25 μg/mL) completely inhibits NADH-induced reduction of cytochromes aa₃, b, and c + c₁ in bovine heart submitochondrial particles^[1].

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

Chemical Information

CAS No. 134332-63-1
Molecular Weight 379.45
Formula C₂₃H₂₅NO₄
SMILES

CCC1=C(C2=COC(CC/C(C)=C/C3=CC=CC=C3)=N2)OC(OC)=C(C1=O)C
Structure Classification
- Alkaloids
- Other Alkaloids
Initial Source
- Microorganisms
myxobacteria
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Kunze B, et al. Phenoxan, a new oxazole-pyrone from myxobacteria: production, antimicrobial activity and its inhibition of the electron transport in complex I of the respiratory chain. J Antibiot (Tokyo). 1992 Sep;45(9):1549-52.

[2]. Jurkiewicz E, et al. Three New Potent HIV-1 Inhibitors from Myxobacteria. Antiviral Chemistry and Chemotherapy. 1992;3(4):189-193.

[3]. Serebrianyĭ AM, et al. [Stimulated repopulation as a basis of antimutagenesis and the adaptive response in plants]. Genetika. 2002 Mar;38(3):340-6.

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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Biological Activity
- Description
- IC₅₀ & Target
- In Vitro
Chemical Information
Purity & Documentation
References

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Phenoxan

All Cytochrome P450 Isoforms

All HIV Isoforms