Cat. No.: HY-N6674

Diazepinomicin

Name: Diazepinomicin
Brand: MedChemExpress
SKU: HY-N6674
Availability: PreOrder

(Synonyms: ECO-4601; TLN-4601; BU 4664L)

Diazepinomicin (ECO-4601) is a reagent with both anticancer and antibacterial activities.. Diazepinomicin decreases Bcl2 and BAX expression, induces dose-dependent cell death and apoptotic bodies, and inhibits Ras-MAPK signaling and tumor growth/proliferation. Diazepinomicin induces apoptosis through caspase 3 activation, PARP cleavage, cytochrome C release, loss of membrane potential, and DNA fragmentation, independent of PBR expression. Diazepinomicin binds PBR/TSPO and displaces PK11195 through its farnesyl side chain rather than the dibenzodiazepinone core. Diazepinomicin can be used in research on hepatocellular carcinoma, Gram-positive bacterial infections, and glioma.

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

CAS No.: 733035-26-2
Formula: C₂₈H₃₄N₂O₄
Molecular Weight:462.58

Storage:

-20°C, protect from light, stored under nitrogen

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

Diazepinomicin Chemical Structure

CAS No.: 733035-26-2

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Use of MCE Products

Fluorescent Dye

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

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
Chemical Information
Purity & Documentation
References
Calculators
Help & FAQs
Classifications
Bioz

Biological Activity

Description

IC₅₀ & Target

^[1]^[2]^[3]

BCL2

PBR

Bax

Ras

p38 MAPK

Caspase 3

PARP

TSPO

All Caspase Isoforms :

All PARP Isoforms :

All Bcl-2 Family Isoforms :

All Ras Isoforms :

All p38 MAPK Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
HUVEC	IC₅₀	0.43 μg/mL Compound: 1, BU-4664L	Antiinvasive activity against HUVEC assessed as inhibition of cell migration after 6 hrs by Matrigel assay Antiinvasive activity against HUVEC assessed as inhibition of cell migration after 6 hrs by Matrigel assay	[PMID: 20056543]
HUVEC	IC₅₀	0.72 μg/mL Compound: 1, BU-4664L	Antiangiogenic activity against HUVEC cells assessed as inhibition of vascular formation after 6 hrs by wound healing assay Antiangiogenic activity against HUVEC cells assessed as inhibition of vascular formation after 6 hrs by wound healing assay	[PMID: 20056543]
HUVEC	IC₅₀	2 μg/mL Compound: 1, BU-4664L	Cytotoxicity against HUVEC cells Cytotoxicity against HUVEC cells	[PMID: 20056543]
NCI-H460	GI₅₀	13.6 μM Compound: 1; BU-4664L	Antiproliferative activity against human NCI-H460 cells assessed as cell growth inhibition by MTT assay Antiproliferative activity against human NCI-H460 cells assessed as cell growth inhibition by MTT assay	[PMID: 34838651]
PC-3	GI₅₀	1.95 μM Compound: 1; BU-4664L	Antiproliferative activity against human PC-3 cells assessed as cell growth inhibition by MTT assay Antiproliferative activity against human PC-3 cells assessed as cell growth inhibition by MTT assay	[PMID: 34838651]
Renca	IC₅₀	0.78 μg/mL Compound: 1, BU-4664L	Antiinvasive activity against mouse Renca by Matrigel assay Antiinvasive activity against mouse Renca by Matrigel assay	[PMID: 20056543]
Renca	IC₅₀	8.3 μg/mL Compound: 1, BU-4664L	Cytotoxicity against mouse Renca cells Cytotoxicity against mouse Renca cells	[PMID: 20056543]

In Vitro

Anti-cancerApoptosisBacterial InfectionMitochondrial FunctionOthers

Anti-cancer

Diazepinomicin (1-25 μM; 24 h) induces dose-dependent antiproliferative activity in human hepatoma HepG2 cells^[1].

Anti-cancer

Apoptosis

Diazepinomicin (10-15 μM; 24 h) induces apoptotic nuclear changes in human hepatoma HepG2 cells^[1].
Diazepinomicin (10-15 μM; 24 h) induces apoptotic nuclear condensation and apoptotic body formation in human hepatoma HepG2 cells^[1].
Diazepinomicin (10-15 μM; 24 h) induces DNA fragmentation (a hallmark of apoptosis) in human hepatoma HepG2 cells^[1].
Diazepinomicin (10-15 μM; 24 h) downregulates the expression of 25 kDa Bcl-2 and 20 kDa BAX proteins in human hepatoma HepG2 cells^[1].

Apoptosis

Diazepinomicin (1-10 µM; 18 h) induces caspase 3 activation and PARP cleavage in Jurkat WT and Jurkat-PBR cells^[3].
Diazepinomicin (10 µM; 0-6 h) induces cytochrome C release from mitochondria to cytosol between 2 and 4 h in both Jurkat WT and Jurkat-PBR cells^[3].
Diazepinomicin (10 µM; 0-24 h) induces DNA nucleosomal fragmentation and more than 95% cell death by 24 h in both Jurkat WT and Jurkat-PBR cells^[3].

Bacterial Infection

Diazepinomicin (32 μg/mL) shows modest antimicrobial activity against selected Gram-positive bacteria with an MIC of 32 μg/mL^[2].

Mitochondrial Function

Diazepinomicin (increasing concentrations; 1 h) binds PBR in rat heart enriched mitochondrial membranes with a K_i of 1.4 µM^[3].
Diazepinomicin (10 µM; up to 6 h) decreases mitochondrial membrane potential similarly in both Jurkat WT and Jurkat-PBR cells^[3].

Others

Diazepinomicin (0.1-30 µM; 3 days) inhibits Jurkat WT and Jurkat-PBR cell growth with IC₅₀ around 10 µM^[3].

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

Cell Proliferation Assay^[1]

Cell Line:

human hepatoma HepG2 cells
Concentration:

1; 2; 5; 10; 25 μM
Incubation Time:

24 h
Result:

Induced dose-dependent decreases in HepG2 cell proliferation, with increasing cell death observed at higher concentrations.

Apoptosis Analysis^[1]

Cell Line:

human hepatoma HepG2 cells
Concentration:

10; 15 μM
Incubation Time:

24 h
Result:

Induced clumping of cells with slight distortion, as well as very condensed and fragmented nuclei (hallmark features of apoptosis).\nInduced condensed nuclei and apoptotic bodies, characteristic of apoptotic cells.\nInduced DNA fragmentation, visualized as characteristic DNA ladder bands on agarose gel electrophoresis.

Western Blot Analysis^[1]

Cell Line:

human hepatoma HepG2 cells
Concentration:

10; 15 μM
Incubation Time:

24 h
Result:

Reduced intensity of Bcl-2 (25 kDa) and BAX (20 kDa) protein bands, indicating downregulation of both anti-apoptotic Bcl-2 and pro-apoptotic BAX protein expression.

Related Protocols :

Chemical Information

CAS No. 733035-26-2
Appearance Solid
Molecular Weight 462.58
Formula C₂₈H₃₄N₂O₄
Color Off-white to gray
SMILES

O=C1C2=CC=CC(O)=C2NC3=C(O)C=C(O)C=C3N1C/C=C(C)/CC/C=C(C)/CC/C=C(C)\C
Synonyms

ECO-4601; TLN-4601; BU 4664L
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

-20°C, protect from light, stored under nitrogen

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

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (278 KB)
SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Rambabu V, et al. In vitro cytotoxicity perspective of diazepinomicin (ECO-4601) on human hepatoma cell line (HEPG2)[J]. Biomedicine & Aging Pathology, 2014, 4(1): 65-70.

[2]. Charan RD, et al. Diazepinomicin, a new antimicrobial alkaloid from a marine Micromonospora sp. J Nat Prod. 2004;67(8):1431-1433. [Content Brief]

[3]. Bertomeu T, et al. TLN-4601 peripheral benzodiazepine receptor (PBR/TSPO) binding properties do not mediate apoptosis but confer tumor-specific accumulation. Biochemical pharmacology. 2010 Nov 15;80(10):1572-9. [Content Brief]

Calculators

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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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Diazepinomicin

All Caspase Isoforms

All PARP Isoforms

All Bcl-2 Family Isoforms

All Ras Isoforms

All p38 MAPK Isoforms