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5.04314

Bortezomib

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

Sinónimos:

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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Fórmula empírica (notación de Hill):
C19H25BN4O4
Número CAS:
179324-69-7
Peso molecular:
384.24
MDL number:
MFCD09056737
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (LC/MS)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, desiccated (hygroscopic), protect from light
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Nombre del producto

Bortezomib,

assay

≥98% (LC/MS)

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, desiccated (hygroscopic), protect from light

color

off-white

solubility

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

storage temp.

−20°C

SMILES string

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

InChI key

GXJABQQUPOEUTA-RDJZCZTQSA-N

General description

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.

Biochem/physiol Actions

Cell permeable: yes
Reversible: yes

Features and Benefits

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

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C.) Stock solutions are stable for up to 6 months at -20°C.
Use only fresh DMSO or Ethanol for reconstitution.

Other Notes

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.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

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Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2

target_organs

Gastro-intestinal system,Nervous system,Blood,Liver,Kidney

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
J Adams et al.
Cancer research, 59(11), 2615-2622 (1999-06-11)
The ubiquitin-proteasome pathway plays a critical role in the regulated degradation of proteins involved in cell cycle control and tumor growth. Dysregulating the degradation of such proteins should have profound effects on tumor growth and cause cells to undergo apoptosis.
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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SKUGTIN
5.04314.000104055977263923