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5.04314

Sigma-Aldrich

Bortezomib

≥98% (LC/MS), solid, 20S proteasome inhibitor, Calbiochem®

Synonyme(s) :

Bortezomib, (R)-3-Methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butylboronic acid, BTZ, LDP-341, LDP341, MG341, MLN-341, MLN341, PS341, Proteasome Inhibitor XXII, PS-341, MG-341, Pyz-Phe-boroLeu, BTZ, LDP-341, LDP341, MG341, MLN-341, MLN341, PS341, Proteasome Inhibitor XXII, PS-341, MG-341, Pyz-Phe-boroLeu, (R)-3-Methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butylboronic acid

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About This Item

Formule empirique (notation de Hill):
C19H25BN4O4
Numéro CAS:
179324-69-7
Poids moléculaire :
384.24
Numéro MDL:
MFCD09056737
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Nom du produit

Bortezomib,

Essai

≥98% (LC/MS)

Niveau de qualité

100

Forme

solid

Fabricant/nom de marque

Calbiochem®

Conditions de stockage

OK to freeze
desiccated (hygroscopic)
protect from light

Couleur

off-white

Solubilité

DMSO: 100 mg/mL
ethanol: 2 mg/mL (with sonication)

Température de stockage

−20°C

Chaîne SMILES 

B(O)(O)[C@@H](NC(=O)[C@@H](NC(=O)c2nccnc2)Cc1ccccc1)CC(C)C

InChI

1S/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m0/s1

Clé InChI

GXJABQQUPOEUTA-RDJZCZTQSA-N

Description générale

Bortezomib, a cell-permeable dipeptidylboronate compound, is a proteasome inhibitor. The proteasomal system is crucial for cellular protein turnover, which is necessary for maintaining cell homeostasis. Bortezomib binds reversibly to the chymotrypsin-like subunit of the 26S proteasome, inhibiting its function and thereby preventing the degradation of multiple pro-apoptotic factors. Bortezomib selectively inhibits 20S proteasome β5 ChTL/chymotrypsin- over β1 CL/caspase- and β2 TL/trypsin-like activity (kinact/Ki = 38,000, 5,700, and <100 M-1s-1, respectively, in human 20S proteasome assays using 10 M Suc-LLVY-AMC/Cat. No. 539142, 10 M Z-LLE-AMC/Cat. No. 539141, or 50 M Boc-LRR-AMC as substrate; IC50 in 1 h = 7, 74, and 4,200 nM, respectively) via a covalent, slowly reversible, interaction between the nucleophilic Thr1 hydroxy group/Thr1Oγ of the catalytic β subunit and the inhibitor′s electrophilic boronic moiety, displaying much reduced potency against human chymotrypsin, cathepsin G, leukocyte elastase, and thrombin (Ki = 0.32, 0.63, 2.3, and 13 M, respectively, vs. 620 nM using rabbit muscle 20S). A widely used inhibitor both in cultures in vitro and in animals in vivo. Despite being the first proteasome inhibitor approved by FDA for clinical anticancer treatment, its therapeutic efficacy continues to be hampered by off-target effects and dose-limiting toxicity.

Application

Bortezomib has been used to induce aerobic glycolysis/ neuropathic pain in mice and study chemotherapy-induced painful peripheral neuropathy.

Actions biochimiques/physiologiques

Cell permeable: yes
Reversible: yes

Caractéristiques et avantages

  • Cell permeable and enables targeted action
  • Allows reversible modulation of cellular processes

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Standard Handling (A)

Notes préparatoires

Use only fresh DMSO or Ethanol for reconstitution.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C.) Stock solutions are stable for up to 6 months at -20°C.

Autres remarques

Du, X.L, and Chen, Q. 2013. Acta Haematol.129, 207.
Tamatani, T., et al. 2013. Int. J. Oncol.42, 935.
Beck, P., et al. 2012. J. Biol. Chem.393, 1101.
Fang, H.T., et al. 2012. Proc. Natl. Acad. Sci. USA.109, 2521.
Chen, D., et al. 2011. Curr. Cancer Drug Targets11, 239.
Demo, S.D., et al. 2007. Cancer Res.67, 6383.
Adams, J., et al. 1999. Cancer Res.59, 2615.
Teicher, B.A., et al. 1999. Clin. Cancer Res.5, 2638.
Adams, J., et al. 1998. Bioorg. Med. Chem. Lett.8, 333.

Informations légales

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Susan D Demo et al.
Cancer research, 67(13), 6383-6391 (2007-07-10)
Clinical studies with bortezomib have validated the proteasome as a therapeutic target for the treatment of multiple myeloma and non-Hodgkin's lymphoma. However, significant toxicities have restricted the intensity of bortezomib dosing. Here we describe the antitumor activity of PR-171, a
Panjamurthy Kuppusamy et al.
Frontiers in pain research (Lausanne, Switzerland), 5, 1424348-1424348 (2024-07-09)
Chemotherapy-induced peripheral neuropathy (CIPN) is a debilitating side effect of cancer treatment that significantly impacts patients' quality of life. This study investigated the effects of targeting metabolic pathways on bortezomib-induced neuropathic pain and tumor growth using a Lewis lung carcinoma
J Adams et al.
Bioorganic & medicinal chemistry letters, 8(4), 333-338 (1999-01-01)
Potent and selective dipeptidyl boronic acid proteasome inhibitors are described. As compared to peptidyl aldehyde compounds, boronic acids in this series display dramatically enhanced potency. Compounds such as 15 are promising new therapeutics for treatment of cancer and inflammatory diseases.
B A Teicher et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 5(9), 2638-2645 (1999-09-28)
The anticancer activity of the boronic acid dipeptide proteasome inhibitor PS-341 was examined in vitro and in vivo. PS-341 was a potent cytotoxic agent toward MCF-7 human breast carcinoma cells in culture, producing an IC90 of 0.05 microM on 24
D Chen et al.
Current cancer drug targets, 11(3), 239-253 (2011-01-21)
Targeting the ubiquitin-proteasome pathway has emerged as a rational approach in the treatment of human cancer. Based on positive preclinical and clinical studies, bortezomib was subsequently approved for the clinical use as a front-line treatment for newly diagnosed multiple myeloma
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