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MedKoo Cat#: 462531 | Name: NBDHEX
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

NBDHEX is a potent glutathione S-transferase P1-1 (GSTP1-1) inhibitor. It induces apoptosis of tumor cells. NBDHEX acts as an anticancer agent by inhibiting GSTs catalytic activity, avoiding inconvenience of the inhibitor extrusion from the cell by specific pumps and disrupting the interaction between the GSTP1-1 and key signaling effectors.

Chemical Structure

NBDHEX
NBDHEX
CAS#787634-60-0

Theoretical Analysis

MedKoo Cat#: 462531

Name: NBDHEX

CAS#: 787634-60-0

Chemical Formula: C12H15N3O4S

Exact Mass: 297.0783

Molecular Weight: 297.33

Elemental Analysis: C, 48.48; H, 5.09; N, 14.13; O, 21.52; S, 10.78

Price and Availability

Size Price Availability Quantity
5mg USD 280.00 2 Weeks
10mg USD 440.00 2 Weeks
50mg USD 900.00 2 Weeks
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Related CAS #
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Synonym
NBDHEX
IUPAC/Chemical Name
6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexan-1-ol
InChi Key
RGXYYAZGELLKDA-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H15N3O4S/c16-7-3-1-2-4-8-20-10-6-5-9(15(17)18)11-12(10)14-19-13-11/h5-6,16H,1-4,7-8H2
SMILES Code
OCCCCCCSC1=CC=C([N+]([O-])=O)C2=NON=C21
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
NBDHEX is a potent glutathione S-transferase P1-1 (GSTP1-1) inhibitor.
In vitro activity:
Interestingly, NBDHEX triggers two different types of cell death: a caspase-dependent apoptosis in the H69AR cells and a necrotic phenotype in the parental H69 cells. The apoptotic pathway triggered by NBDHEX in H69AR cells is associated with c-Jun NH(2)-terminal kinase and c-Jun activation, whereas glutathione oxidation and activation of p38(MAPK) is observed in the NBDHEX-treated H69 cells. Reference: Mol Cancer Ther. 2008 Feb;7(2):371-9. https://pubmed.ncbi.nlm.nih.gov/18281520/
In vivo activity:
The in vivo antitumour efficacy of NBDHEX was evaluated on human melanoma (Me501 and A375) mouse models. After 15 d of daily treatment, a statistically significant tumour inhibition (approximately 70%) was observed (Fig. 7, panel A). Tumours treated with NBDHEX showed a more than 50% decrease in the mitotic in-dex (Fig. 7, panel C). Reference: Eur J Cancer. 2009 Sep;45(14):2606-17. https://pubmed.ncbi.nlm.nih.gov/19665369/
Solvent mg/mL mM
Solubility
DMSO 125.0 420.41
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 297.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Liu W, Cheng L, Du Y, Liu X, Ma J, Yan L. 6-(7-Nitro-2,1,3-benzoxadiazol-4-ylthio) Hexanol Inhibits Proliferation and Induces Apoptosis of Endometriosis by Regulating Glutathione S-Transferase Mu Class 4. Reprod Sci. 2023 Mar 16. doi: 10.1007/s43032-023-01207-x. Epub ahead of print. PMID: 36928896. 2. Filomeni G, Turella P, Dupuis ML, Forini O, Ciriolo MR, Cianfriglia M, Pezzola S, Federici G, Caccuri AM. 6-(7-Nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol, a specific glutathione S-transferase inhibitor, overcomes the multidrug resistance (MDR)-associated protein 1-mediated MDR in small cell lung cancer. Mol Cancer Ther. 2008 Feb;7(2):371-9. doi: 10.1158/1535-7163.MCT-07-0487. PMID: 18281520. 3. Sha H, Dong S, Yu C, Zou R, Zhu Y, Lu Y, Zhang J, Cao H, Chen D, Wu J, Feng J. In Vitro and in Vivo Efficacy of NBDHEX on Gefitinib-resistant Human Non-small Cell Lung Cancer. J Cancer. 2020 Oct 18;11(24):7216-7223. doi: 10.7150/jca.46461. PMID: 33193885; PMCID: PMC7646187. 4. Pellizzari Tregno F, Sau A, Pezzola S, Geroni C, Lapenta C, Spada M, Filomeni G, Bonanno E, Federici G, Caccuri AM. In vitro and in vivo efficacy of 6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol (NBDHEX) on human melanoma. Eur J Cancer. 2009 Sep;45(14):2606-17. doi: 10.1016/j.ejca.2009.06.033. Epub 2009 Aug 6. PMID: 19665369.
In vitro protocol:
1. Liu W, Cheng L, Du Y, Liu X, Ma J, Yan L. 6-(7-Nitro-2,1,3-benzoxadiazol-4-ylthio) Hexanol Inhibits Proliferation and Induces Apoptosis of Endometriosis by Regulating Glutathione S-Transferase Mu Class 4. Reprod Sci. 2023 Mar 16. doi: 10.1007/s43032-023-01207-x. Epub ahead of print. PMID: 36928896. 2. Filomeni G, Turella P, Dupuis ML, Forini O, Ciriolo MR, Cianfriglia M, Pezzola S, Federici G, Caccuri AM. 6-(7-Nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol, a specific glutathione S-transferase inhibitor, overcomes the multidrug resistance (MDR)-associated protein 1-mediated MDR in small cell lung cancer. Mol Cancer Ther. 2008 Feb;7(2):371-9. doi: 10.1158/1535-7163.MCT-07-0487. PMID: 18281520.
In vivo protocol:
1. Sha H, Dong S, Yu C, Zou R, Zhu Y, Lu Y, Zhang J, Cao H, Chen D, Wu J, Feng J. In Vitro and in Vivo Efficacy of NBDHEX on Gefitinib-resistant Human Non-small Cell Lung Cancer. J Cancer. 2020 Oct 18;11(24):7216-7223. doi: 10.7150/jca.46461. PMID: 33193885; PMCID: PMC7646187. 2. Pellizzari Tregno F, Sau A, Pezzola S, Geroni C, Lapenta C, Spada M, Filomeni G, Bonanno E, Federici G, Caccuri AM. In vitro and in vivo efficacy of 6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol (NBDHEX) on human melanoma. Eur J Cancer. 2009 Sep;45(14):2606-17. doi: 10.1016/j.ejca.2009.06.033. Epub 2009 Aug 6. PMID: 19665369.
1: Sha HH, Wang Z, Dong SC, et al. 6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio) hexanol: a promising new anticancer compound. Biosci Rep. 2018;38(1):BSR20171440. Published 2018 Feb 13. doi:10.1042/BSR20171440 2: Filomeni G, Turella P, Dupuis ML, et al. 6-(7-Nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol, a specific glutathione S-transferase inhibitor, overcomes the multidrug resistance (MDR)-associated protein 1-mediated MDR in small cell lung cancer. Mol Cancer Ther. 2008;7(2):371-379. doi:10.1158/1535-7163.MCT-07-0487 3: Pellizzari Tregno F, Sau A, Pezzola S, et al. In vitro and in vivo efficacy of 6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol (NBDHEX) on human melanoma. Eur J Cancer. 2009;45(14):2606-2617. doi:10.1016/j.ejca.2009.06.033

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