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5.04314

Sigma-Aldrich

Bortezomib

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Synonym(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
Empirical Formula (Hill Notation):
C19H25BN4O4
CAS Number:
Molecular Weight:
384.24

assay

≥98% (LC/MS)

Quality Level

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

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

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5.040445.339165.31372
vibrant-m

5.04314

Bortezomib

vibrant-m

5.04044

PrCP Inhibitor

vibrant-m

5.33916

KIFC1 Inhibitor, AZ82

vibrant-m

5.31372

Caspase-1/4 Inhibitor, VX-765

form

solid

form

powder

form

film

form

solid

assay

≥98% (LC/MS)

assay

≥97% (HPLC)

assay

≥96% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

solubility

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

solubility

DMSO: 100 mg/mL

solubility

DMSO: 50 mg/mL

solubility

DMSO: 100 mg/mL

color

off-white

color

white

color

yellow

color

white

General description

A cell-permeable dipeptidylboronate compound that 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) via a covalent, slowly reversible manner, 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.
A cell-permeable dipeptidylboronate compound that 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.

Biochem/physiol Actions

Cell permeable: yes
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Preparation Note

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.

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
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
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.
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
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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