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MedKoo Cat#: 206765 | Name: Ubenimex
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ubenimex, also known as NK 421 and Bestatin, is a CD13 inhibitor. Ubenimex attenuates acquired sorafenib resistance in renal cell carcinoma by inhibiting Akt signaling in a lipophagy associated mechanism. Ubenimex synergistically enhances the effects of anticancer drugs in hepatocellular carcinoma. Ubenimex inhibits cell proliferation, migration and invasion by inhibiting the expression of APN and inducing autophagic cell death in prostate cancer cells.

Chemical Structure

Ubenimex
Ubenimex
CAS#58970-76-6 (free base)

Theoretical Analysis

MedKoo Cat#: 206765

Name: Ubenimex

CAS#: 58970-76-6 (free base)

Chemical Formula: C16H24N2O4

Exact Mass: 308.1736

Molecular Weight: 308.38

Elemental Analysis: C, 62.32; H, 7.84; N, 9.08; O, 20.75

Price and Availability

Size Price Availability Quantity
50mg USD 150.00 Ready to ship
100mg USD 225.00 Ready to ship
250mg USD 450.00 Ready to ship
500mg USD 750.00 Ready to ship
1g USD 1,250.00 Ready to ship
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Related CAS #
58970-76-6 (free base) 65391-42-6 (HCl)
Synonym
Ubenimex, NK 421, NK-421, NK421, Bestatin, NSC 265489, NSC265489, NSC-265489
IUPAC/Chemical Name
((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)-L-leucine
InChi Key
VGGGPCQERPFHOB-RDBSUJKOSA-N
InChi Code
InChI=1S/C16H24N2O4/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22)/t12-,13+,14+/m1/s1
SMILES Code
CC(C)C[C@@H](C(O)=O)NC([C@@H](O)[C@H](N)CC1=CC=CC=C1)=O
Appearance
White 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
>2 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
Biological target:
Ubenimex is an aminopeptidase-B and leukotriene (LT) A4 hydrolase inhibitor.
In vitro activity:
The role of ubenimex in inhibiting migration and invasion was investigated by downregulating APN (Aminopeptidase N) expression levels to induce autophagic cell death and apoptosis in bladder cancer cells. Treatment with ubenimex was accompanied by decreased Akt expression, indicating that ubenimex may have similar functions to Akt inhibitors. Results also indicated that ubenimex inhibited cell migration and invasion in bladder cancer cells. Furthermore, ubenimex also induced autophagic cell death and apoptosis, which suggested that mixed programmed cell death occurred in ubenimex‑treated bladder cancer cells. Reference: Mol Med Rep. 2018 Mar;17(3):4531-4539. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5802231/
In vivo activity:
The antitumor growth effect of ubenimex was evaluated in vivo. Tumors were induced by the injection of PC-3 cells into nude mice. The body weights of the mice were measured weekly. Fig. 7A shows that none of the treatments produced any loss in body weight, which would constitute a sign of toxicity. The tumor weight in the nude mice was significantly reduced in a dose-dependent manner following ubenimex treatment (Fig. 7B and C). Thus, it can be demonstrated that ubenimex inhibited PC-3 cell proliferation in vivo. Reference: Oncol Rep. 2016 Apr;35(4):2121-30. https://www.spandidos-publications.com/or/35/4/2121
Solvent mg/mL mM
Solubility
DMSO 6.2 20.01
PBS (Ph 7.2) 0.2 0.52
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 308.38 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. Guo Q, Jing FJ, Xu W, Li X, Li X, Sun JL, Xing XM, Zhou CK, Jing FB. Ubenimex induces autophagy inhibition and EMT suppression to overcome cisplatin resistance in GC cells by perturbing the CD13/EMP3/PI3K/AKT/NF-κB axis. Aging (Albany NY). 2019 Dec 31;12(1):80-105. doi: 10.18632/aging.102598. Epub 2019 Dec 31. PMID: 31895687; PMCID: PMC6977684. 2. Wang X, Liu Y, Liu W, Zhang Y, Guo F, Zhang L, Cui M, Liu S, Wu R. Ubenimex, an APN inhibitor, could serve as an anti‑tumor drug in RT112 and 5637 cells by operating in an Akt‑associated manner. Mol Med Rep. 2018 Mar;17(3):4531-4539. doi: 10.3892/mmr.2018.8402. Epub 2018 Jan 9. PMID: 29328441; PMCID: PMC5802231.
In vitro protocol:
1. Guo Q, Jing FJ, Xu W, Li X, Li X, Sun JL, Xing XM, Zhou CK, Jing FB. Ubenimex induces autophagy inhibition and EMT suppression to overcome cisplatin resistance in GC cells by perturbing the CD13/EMP3/PI3K/AKT/NF-κB axis. Aging (Albany NY). 2019 Dec 31;12(1):80-105. doi: 10.18632/aging.102598. Epub 2019 Dec 31. PMID: 31895687; PMCID: PMC6977684. 2. Wang X, Liu Y, Liu W, Zhang Y, Guo F, Zhang L, Cui M, Liu S, Wu R. Ubenimex, an APN inhibitor, could serve as an anti‑tumor drug in RT112 and 5637 cells by operating in an Akt‑associated manner. Mol Med Rep. 2018 Mar;17(3):4531-4539. doi: 10.3892/mmr.2018.8402. Epub 2018 Jan 9. PMID: 29328441; PMCID: PMC5802231.
In vivo protocol:
1. Wang X, Niu Z, Jia Y, Cui M, Han L, Zhang Y, Liu Z, Bi D, Liu S. Ubenimex inhibits cell proliferation, migration and invasion by inhibiting the expression of APN and inducing autophagic cell death in prostate cancer cells. Oncol Rep. 2016 Apr;35(4):2121-30. doi: 10.3892/or.2016.4611. Epub 2016 Feb 3. PMID: 26846372.
1: Toviwek B, Koonawootrittriron S, Suwanasopee T, Jattawa D, Pongprayoon P. Why Bestatin Prefers Human Carnosinase 2 (CN2) to Human Carnosinase 1 (CN1). J Phys Chem B. 2024 Dec 5;128(48):11876-11884. doi: 10.1021/acs.jpcb.4c05571. Epub 2024 Nov 22. PMID: 39574306; PMCID: PMC11626516. 2: Yu Z, Li Y, Bai L, Zheng Y, Liu X, Zhen Y. The triple combination DBDx alleviates cytokine storm and related lung injury. Int Immunopharmacol. 2024 Dec 25;143(Pt 2):113431. doi: 10.1016/j.intimp.2024.113431. Epub 2024 Oct 25. PMID: 39454409. 3: Deng W, Xiong X, Lu M, Huang S, Luo Y, Wang Y, Ying Y. Curcumin suppresses colorectal tumorigenesis through restoring the gut microbiota and metabolites. BMC Cancer. 2024 Sep 12;24(1):1141. doi: 10.1186/s12885-024-12898-z. PMID: 39267014; PMCID: PMC11395590. 4: Dong S, Yang F, Zhang Y, Teng Y, Tang W, Liu J, Fan H. Effect of X-ray irradiation on renal excretion of bestatin through down-regulating organic anion transporters via the vitamin D receptor in rats. Chem Biol Interact. 2024 Aug 25;399:111123. doi: 10.1016/j.cbi.2024.111123. Epub 2024 Jul 2. PMID: 38964638. 5: Jamdar SN, Yadav P, Kulkarni BS, Sudesh, Kumar A, Makde RD. Crystal structure of a newly identified M61 family aminopeptidase with broad substrate specificity that is solely responsible for recycling acidic amino acids. FEBS J. 2024 Jul;291(14):3211-3232. doi: 10.1111/febs.17133. Epub 2024 Apr 22. PMID: 38646733. 6: Zhou Z, Huayu M, Mu Y, Tang F, Ge RL. Ubenimex combined with Albendazole for the treatment of Echinococcus multilocularis-induced alveolar echinococcosis in mice. Front Vet Sci. 2024 Mar 15;11:1320308. doi: 10.3389/fvets.2024.1320308. PMID: 38585297; PMCID: PMC10995866. 7: Nieradko-Iwanicka B, Piasecki J, Borzęcki A. Treatment with bestatin (the exogenous synthetic inhibitor of metalloproteinases) reduces the activity of metalloproteinase 2 and 12 in the spleen and lung tissues of rats in a model of lipopolysaccharide-induced sepsis. Biomed Pharmacother. 2024 May;174:116480. doi: 10.1016/j.biopha.2024.116480. Epub 2024 Mar 27. PMID: 38547765. 8: Nakamichi S, Kubota K, Matsuyama K, Misumi T, Kozuki T, Sugawara S, Naoki K, Kobayashi N, Shukuya T, Shimokawa T, Ishihara M, Wakui H, Hosomi Y, Tanaka H, Saito H, Hosokawa S, Takiguchi Y, Kasai T, Nokihara H, Morita R, Aono H, Furuya N, Okamoto H. A Phase Ⅱ Study of Ubenimex Combined With Pembrolizumab, Nab- Paclitaxel, and Carboplatin for Previously Untreated Advanced Squamous Non- Small-Cell Lung Cancer: TORG2241 (UBE-Q). Clin Lung Cancer. 2024 Jan;25(1):85-90. doi: 10.1016/j.cllc.2023.09.006. Epub 2023 Oct 4. PMID: 37981477. 9: Shi Y, Guo Q, Jing F, Shang X, Zhou C, Jing F. Ubenimex suppresses glycolysis mediated by CD13/Hedgehog signaling to enhance the effect of cisplatin in liver cancer. Transl Cancer Res. 2023 Oct 31;12(10):2823-2836. doi: 10.21037/tcr-23-435. Epub 2023 Sep 28. PMID: 37969369; PMCID: PMC10643970. 10: Zhang J, Sun S, Liu J, Zhang L, Guo D, Zhang N, Zhao J, Kong D, Xu T, Wang X, Xu W, Li X, Jiang Y. Discovery of a Novel Ubenimex Derivative as a First-in- Class Dual CD13/Proteasome Inhibitor for the Treatment of Cancer. Molecules. 2023 Aug 30;28(17):6343. doi: 10.3390/molecules28176343. PMID: 37687169; PMCID: PMC10489073. 11: Zhang T, Lin Q, Liu Z, Yang H. Effect of laparoscopic complete mesocolic excision combined with immunotherapy and its impact on immune function and tumor markers in elderly patients with colon cancer. Pak J Med Sci. 2023 Sep- Oct;39(5):1473-1477. doi: 10.12669/pjms.39.5.7090. PMID: 37680796; PMCID: PMC10480738. 12: Ariefta NR, Pagmadulam B, Hatano M, Ikeda N, Isshiki K, Matoba K, Igarashi M, Nihei CI, Nishikawa Y. Antiplasmodial Activity Evaluation of a Bestatin- Related Aminopeptidase Inhibitor, Phebestin. Antimicrob Agents Chemother. 2023 Jul 18;67(7):e0160622. doi: 10.1128/aac.01606-22. Epub 2023 Jun 14. PMID: 37314349; PMCID: PMC10353437. 13: Kaminska M, Benedyk-Machaczka M, Adamowicz K, Aliko A, Drzazga K, Słysz K, Bielecka E, Potempa J, Mydel P. Bestatin as a treatment modality in experimental periodontitis. J Periodontol. 2023 Nov;94(11):1338-1350. doi: 10.1002/JPER.22-0614. Epub 2023 Apr 25. PMID: 37021727. 14: Hassan AHE, Mahmoud K, Phan TN, Shaldam MA, Lee CH, Kim YJ, Cho SB, Bayoumi WA, El-Sayed SM, Choi Y, Moon S, No JH, Lee YS. Bestatin analogs-4-quinolinone hybrids as antileishmanial hits: Design, repurposing rational, synthesis, in vitro and in silico studies. Eur J Med Chem. 2023 Mar 15;250:115211. doi: 10.1016/j.ejmech.2023.115211. Epub 2023 Feb 14. PMID: 36827952. 15: Ni J, Shang Y, Wang WD, Wang C, Wang AM, Li GJ, Chen SZ. FASN Inhibitors Enhance Bestatin-Related Tumor Cell Apoptosis Through Upregulating PEPT1. Curr Mol Pharmacol. 2023;16(7):771-786. doi: 10.2174/1874467216666221121121549. PMID: 36411574. 16: Zhou Z, Zhou P, Mu Y, Wang L, Cao Z, Dong S, Bao H, Yang B, Xin M, Li R, Ge RL, Tang F. Therapeutic effect on Alveolar echinococcosis by targeting EM- Leucine aminopeptidase. Front Immunol. 2022 Oct 14;13:1027500. doi: 10.3389/fimmu.2022.1027500. PMID: 36311709; PMCID: PMC9614657. 17: Xiu T, Guo Q, Jing F, Shi Y, Jing F. CD13 downregulation mediated by ubenimex inhibits autophagy to overcome 5-FU resistance by disturbing the EMP3/FAK/NF-κB pathway in gastric cancer cells. Transl Cancer Res. 2022 Aug;11(8):2487-2500. doi: 10.21037/tcr-22-345. PMID: 36093528; PMCID: PMC9459635. 18: Wang A, Shang Y, Ni J, Wang W, Wang C, Li G, Chen SZ. Thymidine Kinase 1 Mediates the Synergistic Antitumor Activity of Ubenimex and Celecoxib via Regulation of Cell Cycle in Colorectal Cancer. J Pharmacol Exp Ther. 2022 Aug;382(2):188-198. doi: 10.1124/jpet.122.001118. Epub 2022 Jul 22. PMID: 35868865. 19: Vourloumis D, Mavridis I, Athanasoulis A, Temponeras I, Koumantou D, Giastas P, Mpakali A, Magrioti V, Leib J, van Endert P, Stratikos E, Papakyriakou A. Discovery of Selective Nanomolar Inhibitors for Insulin-Regulated Aminopeptidase Based on α-Hydroxy-β-amino Acid Derivatives of Bestatin. J Med Chem. 2022 Jul 28;65(14):10098-10117. doi: 10.1021/acs.jmedchem.2c00904. Epub 2022 Jul 14. PMID: 35833347. 20: Shao LJ, Wang HJ, Wang JR, Yuan XF, Sha Q. Clinical efficacy of intravesical gemcitabine combined with ubenimex in patients with non-muscle-invasive bladder carcinoma after transurethral resection of bladder tumor. Pak J Med Sci. 2022 May-Jun;38(5):1243-1249. doi: 10.12669/pjms.38.5.4599. PMID: 35799745; PMCID: PMC9247758.

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