Deazaflavin

Description

Deazaflavin
CAS Number	CAS 3326-21-4
Molar Mass	227.22 g/mol (aglycone)
Chemical Formula	C11H7N3O2
IUPAC Name	benzo[g]pteridine-2,4(3H,10H)-dione (deazaisoalloxazine core ring system;

Introduction

Deazaflavin is a flavin analog and heterocyclic coenzyme scaffold supplied strictly for laboratory research use. It is studied by researchers investigating redox biochemistry, ubiquitin ligase inhibition, and enzyme cofactor mechanisms. Deazaflavin is not intended for human consumption, veterinary use, or any application outside of a controlled research setting.

Note: The research literature on this scaffold predominantly involves either substituted deazaflavin derivatives (bearing substituents at the N10 and C9 positions) or its naturally occurring analog, coenzyme F420, rather than the unsubstituted parent molecule itself. The Research Benefits below reflect the deazaflavin core structure’s documented mechanisms across this body of research.

Key Characteristics

Deazaflavin is manufactured to a high standard of chemical purity to support reproducible research outcomes. Each batch is formulated with attention to structural precision and lot-to-lot consistency, allowing researchers to rely on stable results across independent experiments.

Research Applications

Deazaflavin is used in biochemistry and cancer cell biology research as the core scaffold underlying a class of synthetic ubiquitin ligase inhibitors and as the structural basis of the naturally occurring redox cofactor coenzyme F420. It serves as a mechanistic tool for probing how this heterocyclic ring system supports electron transfer reactions and modulates protein degradation pathways in model systems.

Research Benefits

Deazaflavin and HDM2-p53 Ubiquitination Inhibition

Research indicates that structural modification of the 5-deazaflavin template produces compounds capable of inhibiting the ubiquitin E3 ligase HDM2, which normally targets the tumor suppressor protein p53 for degradation. Studies have investigated the structure-activity relationships of this template using molecular docking against an HDM2 RING domain receptor model, finding that HDM2-inhibitory activity depended on specific substituent patterns at the deazaflavin core.

Deazaflavin-Derived p53 Stabilization

Studies propose that a water-soluble deazaflavin derivative lacking the 10-aryl substituent shows greater potency in stabilizing HDM2 and p53 protein levels, activating p53-dependent transcription, and inducing cell death in transformed cell lines. Researchers use this model to explore how deazaflavin-based Hdm2 inhibitors relate to selective effects in cells expressing wild-type p53, particularly in combination with DNA-damaging agents.

Deazaflavin Cofactor Enzymatic Redox Function

Research suggests that the deazaflavin ring system, in the form of the natural cofactor F420, supports obligatory hydride transfer reactions in certain bacterial enzymes, including F420-dependent glucose-6-phosphate dehydrogenase. Studies have investigated the crystal structure and cofactor-binding mechanism of this enzyme class, finding that the deazaflavin cofactor’s low redox potential supports its role in central catabolic and xenobiotic degradation pathways in these organisms.

Summary

Deazaflavin is a heterocyclic coenzyme scaffold supplied exclusively for laboratory research. It supports investigation into three distinct areas: HDM2-p53 ubiquitination inhibition, p53 stabilization mechanisms, and enzymatic redox cofactor function. As with all research compounds in this catalog, deazaflavin is intended strictly for research use and not for human or veterinary application.

Disclaimer

This content is presented exclusively for educational purposes and should not be construed as medical advice. THE MATERIALS REFERENCED HEREIN ARE EXCLUSIVELY INTENDED FOR LABORATORY AND RESEARCH USE.

Any clinical research initiatives must be conducted under the guidance of the relevant Institutional Review Board (IRB). Similarly, preclinical research involving animals must comply with the directives of the Institutional Animal Care and Use Committee (IACUC), adhering to the standards delineated by the Animal Welfare Act (AWA).

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References

1. Dickens MP, Roxburgh P, Hock A, Mezna M, Kellam B, Vousden KH, Fischer PM. 5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2. Bioorg Med Chem. 2013 Nov 15;21(22):6868-77. doi: 10.1016/j.bmc.2013.09.038. PMID: 24113239. Read More
2. Kitagaki J, Agama KK, Pommier Y, Yang Y, Weissman AM. Targeting tumor cells expressing p53 with a water-soluble inhibitor of Hdm2. Mol Cancer Ther. 2008 Aug;7(8):2445-54. doi: 10.1158/1535-7163.MCT-08-0063. PMID: 18723490. Read More
3. Nguyen QT, Trinco G, Binda C, Mattevi A, Fraaije MW. Discovery and characterization of an F420-dependent glucose-6-phosphate dehydrogenase (Rh-FGD1) from Rhodococcus jostii RHA1. Appl Microbiol Biotechnol. 2016 Dec 13;101(7):2831-2842. doi: 10.1007/s00253-016-8038-y. PMID: 27966048. Read More