Z-LLNle-CHO
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MedKoo CAT#: 526397

CAS#: 133407-83-7

Description: Z-LLNle-CHO, also known as gamma-Secretase Inhibitor I, is a cell permeable inhibitor of gamma-secretase, inducing apoptosis of human glioblastoma tumor-initiating cells by proteasome inhibition and mitotic arrest response.

Chemical Structure

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Z-LLNle-CHO
CAS# 133407-83-7
Instruction

Theoretical Analysis

MedKoo Cat#: 526397
Name: Z-LLNle-CHO
CAS#: 133407-83-7
Chemical Formula: C26H41N3O5
Exact Mass: 475.30
Molecular Weight: 475.630
Elemental Analysis: C, 65.66; H, 8.69; N, 8.83; O, 16.82

Price and Availability

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5mg USD 350
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Synonym: Z-LLNle-CHO; gamma-Secretase Inhibitor I. Z-Leu-Leu-Nle-CHO (Nle = Norleucine).

IUPAC/Chemical Name: Benzyl N-[(2S)-4-methyl-1-[[(2S)-4-methyl-1-oxo-1-[[(2S)-1-oxohexan-2-yl]amino]pentan-2-yl]amino]-1-oxopentan-2-yl]carbamate

InChi Key: RNPDUXVFGTULLP-VABKMULXSA-N

InChi Code: InChI=1S/C26H41N3O5/c1-6-7-13-21(16-30)27-24(31)22(14-18(2)3)28-25(32)23(15-19(4)5)29-26(33)34-17-20-11-9-8-10-12-20/h8-12,16,18-19,21-23H,6-7,13-15,17H2,1-5H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1

SMILES Code: CCCC[C@@H](C=O)NC([C@H](CC(C)C)NC([C@H](CC(C)C)NC(OCC1=CC=CC=C1)=O)=O)=O

Appearance: 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:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 475.63 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:
In vitro protocol:
In vivo protocol:

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1: Ikezawa Y, Sakakibara-Konishi J, Mizugaki H, Oizumi S, Nishimura M. Inhibition of Notch and HIF enhances the antitumor effect of radiation in Notch expressing lung cancer. Int J Clin Oncol. 2017 Feb;22(1):59-69. doi: 10.1007/s10147-016-1031-8. Epub 2016 Aug 23. PubMed PMID: 27553958.

2: Han B, Liu SH, Guo WD, Zhang B, Wang JP, Cao YK, Liu J. Notch1 downregulation combined with interleukin-24 inhibits invasion and migration of hepatocellular carcinoma cells. World J Gastroenterol. 2015 Sep 7;21(33):9727-35. doi: 10.3748/wjg.v21.i33.9727. PubMed PMID: 26361419; PubMed Central PMCID: PMC4562956.

3: Lee HW, Kim SJ, Choi IJ, Song J, Chun KH. Targeting Notch signaling by γ-secretase inhibitor I enhances the cytotoxic effect of 5-FU in gastric cancer. Clin Exp Metastasis. 2015 Aug;32(6):593-603. doi: 10.1007/s10585-015-9730-5. Epub 2015 Jul 2. PubMed PMID: 26134677.

4: Yao M, Wang X, Wang X, Zhang T, Chi Y, Gao F. The Notch pathway mediates the angiotensin II-induced synthesis of extracellular matrix components in podocytes. Int J Mol Med. 2015 Jul;36(1):294-300. doi: 10.3892/ijmm.2015.2193. Epub 2015 Apr 22. PubMed PMID: 25902289.

5: Yang L, Zhang S, George SK, Teng R, You X, Xu M, Liu H, Sun X, Amin HM, Shi W. Targeting Notch1 and proteasome as an effective strategy to suppress T-cell lymphoproliferative neoplasms. Oncotarget. 2015 Jun 20;6(17):14953-69. PubMed PMID: 25879451; PubMed Central PMCID: PMC4558128.

6: Kim SJ, Lee HW, Baek JH, Cho YH, Kang HG, Jeong JS, Song J, Park HS, Chun KH. Activation of nuclear PTEN by inhibition of Notch signaling induces G2/M cell cycle arrest in gastric cancer. Oncogene. 2016 Jan 14;35(2):251-60. doi: 10.1038/onc.2015.80. Epub 2015 Mar 30. PubMed PMID: 25823029.

7: Na T, Liu J, Zhang K, Ding M, Yuan BZ. The notch signaling regulates CD105 expression, osteogenic differentiation and immunomodulation of human umbilical cord mesenchymal stem cells. PLoS One. 2015 Feb 18;10(2):e0118168. doi: 10.1371/journal.pone.0118168. eCollection 2015. PubMed PMID: 25692676; PubMed Central PMCID: PMC4334899.

8: Xu ZS, Zhang JS, Zhang JY, Wu SQ, Xiong DL, Chen HJ, Chen ZZ, Zhan R. Constitutive activation of NF-κB signaling by NOTCH1 mutations in chronic lymphocytic leukemia. Oncol Rep. 2015 Apr;33(4):1609-14. doi: 10.3892/or.2015.3762. Epub 2015 Jan 29. PubMed PMID: 25633905; PubMed Central PMCID: PMC4358086.

9: Kikuta J, Yamaguchi M, Shimizu M, Yoshino T, Kasai K. Notch signaling induces root resorption via RANKL and IL-6 from hPDL cells. J Dent Res. 2015 Jan;94(1):140-7. doi: 10.1177/0022034514555364. Epub 2014 Nov 5. PubMed PMID: 25376720.

10: Chen BY, Zheng MH, Chen Y, Du YL, Sun XL, Zhang X, Duan L, Gao F, Liang L, Qin HY, Luo ZJ, Han H. Myeloid-Specific Blockade of Notch Signaling by RBP-J Knockout Attenuates Spinal Cord Injury Accompanied by Compromised Inflammation Response in Mice. Mol Neurobiol. 2015 Dec;52(3):1378-1390. doi: 10.1007/s12035-014-8934-z. Epub 2014 Oct 26. PubMed PMID: 25344316.

11: Epigenetic mechanisms underlie resistance to NOTCH inhibition in T-ALL. Cancer Discov. 2014 May;4(5):OF11. doi: 10.1158/2159-8290.CD-RW2014-060. Epub 2014 Mar 13. PubMed PMID: 24795015.

12: Cai WX, Liang L, Wang L, Han JT, Zhu XX, Han H, Hu DH, Zhang P. Inhibition of Notch signaling leads to increased intracellular ROS by up-regulating Nox4 expression in primary HUVECs. Cell Immunol. 2014 Feb;287(2):129-35. doi: 10.1016/j.cellimm.2013.12.009. Epub 2014 Jan 10. Erratum in: Cell Immunol. 2014 May-Jun;289(1-2):191. PubMed PMID: 24491913.

13: Wang XM, Yao M, Liu SX, Hao J, Liu QJ, Gao F. Interplay between the Notch and PI3K/Akt pathways in high glucose-induced podocyte apoptosis. Am J Physiol Renal Physiol. 2014 Jan;306(2):F205-13. doi: 10.1152/ajprenal.90005.2013. Epub 2013 Nov 13. PubMed PMID: 24226527.

14: Singh A, Zapata MC, Choi YS, Yoon SO. GSI promotes vincristine-induced apoptosis by enhancing multi-polar spindle formation. Cell Cycle. 2014;13(1):157-66. doi: 10.4161/cc.26951. Epub 2013 Oct 29. PubMed PMID: 24200971; PubMed Central PMCID: PMC3925728.

15: Fukuzaki Y, Sugawara H, Yamanoha B, Kogure S. 532 nm low-power laser irradiation recovers γ-secretase inhibitor-mediated cell growth suppression and promotes cell proliferation via Akt signaling. PLoS One. 2013 Aug 7;8(8):e70737. doi: 10.1371/journal.pone.0070737. eCollection 2013. PubMed PMID: 23950991; PubMed Central PMCID: PMC3737144.

16: Dimova I, Hlushchuk R, Makanya A, Styp-Rekowska B, Ceausu A, Flueckiger S, Lang S, Semela D, Le Noble F, Chatterjee S, Djonov V. Inhibition of Notch signaling induces extensive intussusceptive neo-angiogenesis by recruitment of mononuclear cells. Angiogenesis. 2013 Oct;16(4):921-37. doi: 10.1007/s10456-013-9366-5. Epub 2013 Jul 24. PubMed PMID: 23881168.

17: Marshall AD, Picchione F, Geltink RI, Grosveld GC. PAX3-FOXO1 induces up-regulation of Noxa sensitizing alveolar rhabdomyosarcoma cells to apoptosis. Neoplasia. 2013 Jul;15(7):738-48. PubMed PMID: 23814486; PubMed Central PMCID: PMC3689237.

18: Kamstrup MR, Biskup E, Gjerdrum LM, Ralfkiaer E, Niazi O, Gniadecki R. The importance of Notch signaling in peripheral T-cell lymphomas. Leuk Lymphoma. 2014 Mar;55(3):639-44. doi: 10.3109/10428194.2013.807510. Epub 2013 Aug 5. PubMed PMID: 23697875.

19: Xie J, Wang W, Si JW, Miao XY, Li JC, Wang YC, Wang ZR, Ma J, Zhao XC, Li Z, Yi H, Han H. Notch signaling regulates CXCR4 expression and the migration of mesenchymal stem cells. Cell Immunol. 2013 Jan;281(1):68-75. doi: 10.1016/j.cellimm.2013.02.001. Epub 2013 Feb 13. PubMed PMID: 23474530.

20: Biskup E, Kamstrup MR, Manfé V, Gniadecki R. Proteasome inhibition as a novel mechanism of the proapoptotic activity of γ-secretase inhibitor I in cutaneous T-cell lymphoma. Br J Dermatol. 2013 Mar;168(3):504-12. doi: 10.1111/bjd.12071. PubMed PMID: 23445313.