Cat. No.: HY-W714183

Dinitramine

Dinitramine is a herbicide. Dinitramine activates the Erk/P38/JNK/MAPK pathway and inactivates the PI3k/Akt pathway in testicular cells. Dinitramine induces endoplasmic reticulum stress, dysregulation of calcium homeostasis in the cytoplasm and mitochondria, apoptosis, and downregulated expression of cell cycle genes in testicular cells. Dinitramine reduces the viability and proliferation capacity of testicular cells, and inhibits cell division by suppressing the synthesis of tubulin. Dinitramine induces abnormal heart development, inhibited angiogenesis, inflammatory responses, apoptosis, and impaired embryonic growth in zebrafish embryos.

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CAS No.: 29091-05-2
Formula: C₁₁H₁₃F₃N₄O₄
Molecular Weight:322.24

Storage:

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

Dinitramine Chemical Structure

CAS No.: 29091-05-2

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

Biological Activity

Description

All ERK Isoforms :

All p38 MAPK Isoforms :

All JNK Isoforms :

All PI3K Isoforms :

All Akt Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
HFF	IC₅₀	0.045 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	0.089 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235V mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235V mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	0.32 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235L mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235L mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	0.33 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R243C mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R243C mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	0.37 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin F24H mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin F24H mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	0.42 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin S6I mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin S6I mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	0.51 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin H28Q mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin H28Q mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	12.5 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin L136F mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin L136F mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	18.4 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R243S mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R243S mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	26.6 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin T239I mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin T239I mutation infected in HFF cells by plaque assay	[PMID: 20145086]
HFF	IC₅₀	3.4 μM Compound: 4	Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin V4L mutation infected in HFF cells by plaque assay Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin V4L mutation infected in HFF cells by plaque assay	[PMID: 20145086]

In Vitro

Dinitramine (2-20 μM; 24 h) reduces the viability and proliferative potential of TM3 and TM4 cells. Treatment with 20 μM dinitramine decreases the viability of TM3 cells to 78.7% and that of TM4 cells to 84.7%, and reduces the proliferative potential of both cell lines to below 50%^[1].
Dinitramine (10-20 μM; 6 days) reduces the spheroid density and area of TM3 and TM4 cells in 3D culture systems; treatment with 20 μM decreases the spheroid density of TM3 cells by 22% and the area by 12%, while treatments with both 10 μM and 20 μM significantly reduce the spheroid density and area of TM4 cells^[1].
Dinitramine (0-20 μM; 24 h) induces cell cycle arrest and cell death in TM3 and TM4 cells, inhibits the mRNA expression of cell cycle progression genes *Ccnd1*, *Cdk4* and *Ccne1* in cells, and activates endoplasmic reticulum stress in cells^[1].
Dinitramine (0-20 μM) increases cytosolic and mitochondrial matrix calcium levels in TM3 and TM4 cells; treatment with 20 μM elevates the cytosolic calcium level to 230% in TM3 cells and to 300% in TM4 cells, while increasing the mitochondrial matrix calcium level to 230% in both cell lines^[1].
Dinitramine (5-20 μM; 30 min) activates the Mapk signaling pathway and inactivates the Pi3k/Akt signaling pathway in TM3 and TM4 cells; treatment with 20 μM for 30 min upregulates the levels of phosphorylated Erk1/2, P38 and Jnk, while downregulates the levels of phosphorylated Akt and Rps6kb1 in both cell lines^[1].
Combined treatment with dinitramine (20 μM; 24 h) and calcium regulators restores the proliferative potential of dinitramine-treated TM4 cells, but fails to restore that of TM3 cells^[1].

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

Cell Viability Assay^[1]

Cell Line:

immature murine Leydig (TM3) cells, immature murine Sertoli (TM4) cells
Concentration:

0, 2, 5, 10, and 20 μM
Incubation Time:

24 h
Result:

Reduced relative viability of TM3 cells to 78.7% and TM4 cells to 84.7% at 20 μM.
Reduced relative proliferative potential of TM3 and TM4 cells in a concentration-dependent manner to below 50% at 20 μM.

Cell Cycle Analysis^[1]

Cell Line:

immature murine Leydig (TM3) cells, immature murine Sertoli (TM4) cells
Concentration:

0, 2, 5, 10, and 20 μM
Incubation Time:

24 h
Result:

Increased the number of TM3 and TM4 cells in the sub-G1 phase by approximately 2-fold compared to vehicle controls.
Reduced the number of TM4 cells in the G0/G1 phase by approximately 10%, with no remarkable changes in TM3 cell cycle phase distribution.

Real Time qPCR^[1]

Cell Line:

immature murine Leydig (TM3) cells, immature murine Sertoli (TM4) cells
Concentration:

20 μM
Incubation Time:

24 h
Result:

Significantly reduced the expression of cell cycle progression-related genes Ccnd1, Cdk4, and Ccne1 in both TM3 and TM4 cells.

Western Blot Analysis^[1]

Cell Line:

immature murine Leydig (TM3) cells, immature murine Sertoli (TM4) cells
Concentration:

0, 5, 10, and 20 μM
Incubation Time:

24 h
Result:

Increased Grp78/Bip protein expression in TM3 and TM4 cells in a concentration-dependent manner.
Increased Ire1α protein levels by 1.5-fold in TM3 and 2.4-fold in TM4 cells at 20 μM.
Increased phosphorylated Eif2α levels by 2.3-fold in TM3 and 1.4-fold in TM4 cells at 20 μM.
Increased Chop protein levels by 2.3-fold in TM3 and 2-fold in TM4 cells at 20 μM.

Western Blot Analysis^[1]

Cell Line:

immature murine Leydig (TM3) cells, immature murine Sertoli (TM4) cells
Concentration:

5-20 μM
Incubation Time:

30 min
Result:

Increased phosphorylated Erk1/2 levels to 1.7-fold in TM3 and 1.9-fold in TM4 cells at 20 μM.
Increased phosphorylated P38 and Jnk levels significantly in both cell lines at 20 μM.
Reduced phosphorylated Akt levels to approximately half in TM3 cells and to 0.75-fold in TM4 cells at 20 μM.
Reduced phosphorylated Rps6kb1 levels to approximately half in TM3 cells and 0.59-fold in TM4 cells at 20 μM.
Reduced phosphorylated Rps6 levels to approximately half in TM3 cells (no significant change in TM4 cells) at 20 μM.

Cell Proliferation Assay^[1]

Cell Line:

immature murine Leydig (TM3) cells, immature murine Sertoli (TM4) cells
Concentration:

20 μM
Incubation Time:

24 h
Result:

Restored proliferative potential of TM4 cells by approximately 20% compared to dinitramine alone when co-treated with 1 μM 2-APB.
Restored proliferative potential of TM4 cells to 65% compared to dinitramine alone when co-treated with 2 μM BAPTA.
Did not alter proliferative potential of dinitramine-treated TM3 cells with co-treatment.

In Vivo

Dinitramine (1.6-6.4 mg/L; water immersion; 96 h) induces concentration-dependent developmental toxicity, cardiotoxicity, vascular injury, inflammation and apoptosis in Danio rerio (zebrafish) embryos^[2].

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

Animal Model:

wild-type; fli1:eGFP transgenic^[2]
Dosage:

1.6 mg/L; 3.2 mg/L; 6.4 mg/L
Administration:

aqueous immersion; continuous exposure for 96 hours, medium refreshed every 24 hours
Result:

Induced concentration-dependent malformations including shortened body length, reduced eye size, spinal curvature, swollen yolk sacs, and pericardial edema; increased pericardial edema to over 300% of control levels at 6.4 mg/L.
Reduced hatchability dose-dependently, reaching near 0% at 6.4 mg/L.
Decreased heart rate dose-dependently to 80 beats per minute at 6.4 mg/L (down from 184 bpm in controls); caused 3-fold enlargement of atrial long-axis diameter at 6.4 mg/L; significantly downregulated cardiac development genes (spaw, bmp4, bmp2b, erbb4b, myh6, itga5, lmna, actc1a, actc2) across all doses.
Reduced caudal vein plexus area to 80% of control and fluorescent intensity to 75% of control at 6.4 mg/L; caused abnormal formation of intersegmental vessels, dorsal longitudinal anastomotic vessel, dorsal aorta, and caudal vein; dysregulated expression of angiogenesis-related genes (kdr, vegfd, flt1, vegfaa).
Significantly upregulated inflammatory genes (il1b, nos2a, il6, tnfa, cox2a, cox2b) at 6.4 mg/L, with il1b expression increased 39-fold compared to controls.
Increased relative apoptotic cell numbers 4.8-fold (eye), 6.4-fold (brain), and 2.7-fold (tail) at 6.4 mg/L; upregulated pro-apoptotic genes (p53, casp8, casp9, casp3) and downregulated anti-apoptotic gene bcl2 across all doses.

Chemical Information

CAS No. 29091-05-2
Molecular Weight 322.24
Formula C₁₁H₁₃F₃N₄O₄
SMILES

NC1=C([N+]([O-])=O)C(N(CC)CC)=C(C=C1C(F)(F)F)[N+]([O-])=O
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]. Ham J, et al. The herbicide dinitramine affects the proliferation of murine testicular cells via endoplasmic reticulum stress-induced calcium dysregulation. Environ Pollut. 2021;272:115982. [Content Brief]

[2]. Park H, et al. Dinitramine induces cardiotoxicity and morphological alterations on zebrafish embryo development. Aquat Toxicol. 2021;240:105982. [Content Brief]

[3]. Hiroshi MATSUMOTO, et al. Differential Activity of Simetryn and Dimethametryn on Photosynthesis and Growth of Rice Cultivars and Barnyardgrass. Weed Research, Japan Vol. 32(2)123~128(1987).

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How should lyophilized recombinant proteins be reconstituted and stored?

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Dinitramine

All ERK Isoforms

All p38 MAPK Isoforms

All JNK Isoforms

All PI3K Isoforms

All Akt Isoforms

Biological Activity

Chemical Information

Purity & Documentation

References

Calculators

Help & FAQs

Dinitramine Related Classifications

HY-W714183 Related Classifications