NBDHEX
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MedKoo CAT#: 462531

CAS#: 787634-60-0

Description: 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

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NBDHEX
CAS# 787634-60-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 462531
Name: NBDHEX
CAS#: 787634-60-0
Chemical Formula: C12H15N3O4S
Exact Mass: 297.08
Molecular Weight: 297.329
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 2 Weeks
10mg USD 440 2 Weeks
50mg USD 900 2 Weeks
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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:
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 125.0 420.41

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.

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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