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5.04314

Sigma-Aldrich

Bortezomib

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

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C19H25BN4O4
Numero CAS:
179324-69-7
Peso molecolare:
384.24
Codice UNSPSC:
12352200
NACRES:
NA.77

product name

Bortezomib,

Saggio

≥98% (LC/MS)

Livello qualitativo

100

Forma fisica

solid

Produttore/marchio commerciale

Calbiochem®

Condizioni di stoccaggio

OK to freeze
desiccated (hygroscopic)
protect from light

Colore

off-white

Solubilità

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

Temperatura di conservazione

−20°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
GXJABQQUPOEUTA-RDJZCZTQSA-N

Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

Cell permeable: yes
Reversible: yes

Caratteristiche e vantaggi

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

Confezionamento

Packaged under inert gas

Attenzione

Toxicity: Standard Handling (A)

Nota sulla preparazione

Use only fresh DMSO or Ethanol for reconstitution.

Ricostituzione

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

Altre note

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.

Note legali

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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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
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.
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
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
Philipp Beck et al.
Biological chemistry, 393(10), 1101-1120 (2012-10-24)
The 20S proteasome core particle (CP) is the proteolytically active key element of the ubiquitin proteasome system that directs the majority of intracellular protein degradation in eukaryotic cells. Over the past decade, the CP has emerged as an anticancer therapy
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