L 709049 | CAS#143313-51-3| ICE inhibitor

MedKoo Cat#: 341129 | Name: L 709049

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Description:

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

L-709049, also known as Ac-YVAD-CHO, is a potent and selective inhibitor of interleukin-1β converting enzyme (ICE), also known as caspase-1, with Ki values of 3.0 nM in mice and 0.76 nM in humans. It functions by reversibly binding to caspase-1, thereby suppressing the production of mature interleukin-1β (IL-1β), a key pro-inflammatory cytokine. This compound has demonstrated anti-inflammatory activity and the ability to inhibit cancer cell growth in preclinical studies.

Chemical Structure

L 709049

CAS#143313-51-3

Theoretical Analysis

MedKoo Cat#: 341129

Name: L 709049

CAS#: 143313-51-3

Chemical Formula: C23H32N4O8

Exact Mass: 492.2220

Molecular Weight: 492.53

Elemental Analysis: C, 56.09; H, 6.55; N, 11.38; O, 25.99

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 400.00	2 Weeks

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Synonym

L 709049; L-709049; L709049; Caspase-1 Inhibitor I; N-Ac-Tyr-Val-Ala-Asp-CHO; Ac-YVAD-CHO

IUPAC/Chemical Name

L-Alaninamide, N-acetyl-L-tyrosyl-L-valyl-N-((1S)-2-carboxy-1-formylethyl)-

InChi Key

KQCBPHUOVBKBPQ-SJVNDZIOSA-N

InChi Code

InChI=1S/C23H32N4O8/c1-12(2)20(23(35)27-21(33)13(3)24-16(11-28)10-19(31)32)26-22(34)18(25-14(4)29)9-15-5-7-17(30)8-6-15/h5-8,11-13,16,18,20,24,30H,9-10H2,1-4H3,(H,25,29)(H,26,34)(H,31,32)(H,27,33,35)/t13-,16-,18-,20-/m0/s1

SMILES Code

C[C@@H](C(=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)C)N[C@@H](CC(=O)O)C=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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ac-YVAD-CHO (L-709049) is a potent, reversible, specific tetrapeptide interleukin-lβ converting enzyme (ICE) inhibitor with mouse and human Ki values of 3.0 and 0.76 nM.

In vitro activity:

Pre-treatment with Ac-YVAD-CHO inhibited QA-induced internucleosomal DNA fragmentation. Ac-YVAD-CHO inhibited QA-induced increases in caspase-1 activity and p53 protein levels, but had no effect on QA-induced IkappaB-alpha degradation, NF-kappaB or AP-1 activation. Reference: Acta Pharmacol Sin. 2005 Feb;26(2):150-4. https://pubmed.ncbi.nlm.nih.gov/15663890/

In vivo activity:

These data demonstrate that administration of the caspase-1 inhibitor Ac-YVAD-CHO by inhalation is able to reduce the pulmonary and systemic release of proinflammatory mediators in rat endotoxaemia. Reference: Intensive Care Med. 2007 May;33(5):863-871. https://pubmed.ncbi.nlm.nih.gov/17384935/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	60.91
	DMSO	30.0	60.91
	Ethanol	30.0	60.91
	PBS (pH 7.2)	5.0	10.15

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 492.53 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.

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. Tamai R, Kiyoura Y. Alendronate augments lipid A-induced IL-1β release and Smad3/NLRP3/ASC-dependent cell death. Life Sci. 2018 Apr 1;198:8-17. doi: 10.1016/j.lfs.2018.02.014. Epub 2018 Feb 10. PMID: 29438662. 2. Cao Y, Gu ZL, Lin F, Han R, Qin ZH. Caspase-1 inhibitor Ac-YVAD-CHO attenuates quinolinic acid-induced increases in p53 and apoptosis in rat striatum. Acta Pharmacol Sin. 2005 Feb;26(2):150-4. doi: 10.1111/j.1745-7254.2005.00525.x. PMID: 15663890. 3. Boost KA, Hoegl S, Hofstetter C, Flondor M, Stegewerth K, Platacis I, Pfeilschifter J, Muhl H, Zwissler B. Targeting caspase-1 by inhalation-therapy: effects of Ac-YVAD-CHO on IL-1 beta, IL-18 and downstream proinflammatory parameters as detected in rat endotoxaemia. Intensive Care Med. 2007 May;33(5):863-871. doi: 10.1007/s00134-007-0588-0. Epub 2007 Mar 24. PMID: 17384935.

In vitro protocol:

In vivo protocol:

1. Boost KA, Hoegl S, Hofstetter C, Flondor M, Stegewerth K, Platacis I, Pfeilschifter J, Muhl H, Zwissler B. Targeting caspase-1 by inhalation-therapy: effects of Ac-YVAD-CHO on IL-1 beta, IL-18 and downstream proinflammatory parameters as detected in rat endotoxaemia. Intensive Care Med. 2007 May;33(5):863-871. doi: 10.1007/s00134-007-0588-0. Epub 2007 Mar 24. PMID: 17384935.

1: Yang HH, Jun HK, Jung YJ, Choi BK. Enterococcus faecalis activates caspase-1 leading to increased interleukin-1 beta secretion in macrophages. J Endod. 2014 Oct;40(10):1587-92. doi: 10.1016/j.joen.2014.06.015. Epub 2014 Aug 12. PubMed PMID: 25127933. 2: Kariya K, Demiral T, Sasaki T, Tsuchiya Y, Turkan I, Sano T, Hasezawa S, Yamamoto Y. A novel mechanism of aluminum-induced cell death involving vacuolar processing enzyme and vacuolar collapse in tobacco cell line BY-2. J Inorg Biochem. 2013 Nov;128:196-201. doi: 10.1016/j.jinorgbio.2013.07.001. Epub 2013 Jul 8. PubMed PMID: 23891542. 3: Teper-Bamnolker P, Buskila Y, Lopesco Y, Ben-Dor S, Saad I, Holdengreber V, Belausov E, Zemach H, Ori N, Lers A, Eshel D. Release of apical dominance in potato tuber is accompanied by programmed cell death in the apical bud meristem. Plant Physiol. 2012 Apr;158(4):2053-67. doi: 10.1104/pp.112.194076. Epub 2012 Feb 23. PubMed PMID: 22362870; PubMed Central PMCID: PMC3320206. 4: Boost KA, Hoegl S, Hofstetter C, Flondor M, Stegewerth K, Platacis I, Pfeilschifter J, Muhl H, Zwissler B. Targeting caspase-1 by inhalation-therapy: effects of Ac-YVAD-CHO on IL-1 beta, IL-18 and downstream proinflammatory parameters as detected in rat endotoxaemia. Intensive Care Med. 2007 May;33(5):863-871. doi: 10.1007/s00134-007-0588-0. Epub 2007 Mar 24. PubMed PMID: 17384935. 5: Husain Z, Holodick N, Day C, Szymanski I, Alper CA. Increased apoptosis of CD20+ IgA + B cells is the basis for IgA deficiency: the molecular mechanism for correction in vitro by IL-10 and CD40L. J Clin Immunol. 2006 Mar;26(2):113-25. Epub 2006 Apr 26. PubMed PMID: 16758339. 6: Wagner G, Laufer S. Small molecular anti-cytokine agents. Med Res Rev. 2006 Jan;26(1):1-62. Review. PubMed PMID: 16283677. 7: Rana SN, Li X, Chaudry IH, Bland KI, Choudhry MA. Inhibition of IL-18 reduces myeloperoxidase activity and prevents edema in intestine following alcohol and burn injury. J Leukoc Biol. 2005 May;77(5):719-28. Epub 2005 Feb 23. PubMed PMID: 15728717. 8: Cao Y, Gu ZL, Lin F, Han R, Qin ZH. Caspase-1 inhibitor Ac-YVAD-CHO attenuates quinolinic acid-induced increases in p53 and apoptosis in rat striatum. Acta Pharmacol Sin. 2005 Feb;26(2):150-4. PubMed PMID: 15663890. 9: Crowe DL, Yoon E. A common pathway for chemotherapy-induced apoptosis in human squamous cell carcinoma lines distinct from that of receptor-mediated cell death. Anticancer Res. 2003 May-Jun;23(3B):2321-8. PubMed PMID: 12894510. 10: McBride CB, McPhail LT, Vanderluit JL, Tetzlaff W, Steeves JD. Caspase inhibition attenuates transection-induced oligodendrocyte apoptosis in the developing chick spinal cord. Mol Cell Neurosci. 2003 Jul;23(3):383-97. PubMed PMID: 12837623. 11: Enomoto A, Suzuki N, Morita A, Ito M, Liu CQ, Matsumoto Y, Yoshioka K, Shiba T, Hosoi Y. Caspase-mediated cleavage of JNK during stress-induced apoptosis. Biochem Biophys Res Commun. 2003 Jul 11;306(4):837-42. PubMed PMID: 12821118. 12: Kang HJ, Soh Y, Kim MS, Lee EJ, Surh YJ, Kim HR, Kim SH, Moon A. Roles of JNK-1 and p38 in selective induction of apoptosis by capsaicin in ras-transformed human breast epithelial cells. Int J Cancer. 2003 Feb 10;103(4):475-82. PubMed PMID: 12478662. 13: Nakano H, Shinohara K. Time sequence analysis of caspase-3-independent programmed cell death and apoptosis in X-irradiated human leukemic MOLT-4 cells. Cell Tissue Res. 2002 Dec;310(3):305-11. Epub 2002 Oct 23. PubMed PMID: 12457229. 14: Ahn SG, Kim HS, Jeong SW, Kim BE, Rhim H, Shim JY, Kim JW, Lee JH, Kim IK. Sox-4 is a positive regulator of Hep3B and HepG2 cells' apoptosis induced by prostaglandin (PG)A(2) and delta(12)-PGJ(2). Exp Mol Med. 2002 Jul 31;34(3):243-9. PubMed PMID: 12216117. 15: Barna BP, Dweik RA, Farver CF, Culver D, Yen-Lieberman B, Thomassen MJ. Nitric oxide attenuates beryllium-induced IFNgamma responses in chronic beryllium disease: evidence for mechanisms independent of IL-18. Clin Immunol. 2002 May;103(2):169-75. PubMed PMID: 12027422. 16: Zou W, Zeng J, Zhuo M, Xu W, Sun L, Wang J, Liu X. Involvement of caspase-3 and p38 mitogen-activated protein kinase in cobalt chloride-induced apoptosis in PC12 cells. J Neurosci Res. 2002 Mar 15;67(6):837-43. PubMed PMID: 11891799. 17: Kögel D, Reimertz C, Mech P, Poppe M, Frühwald MC, Engemann H, Scheidtmann KH, Prehn JH. Dlk/ZIP kinase-induced apoptosis in human medulloblastoma cells: requirement of the mitochondrial apoptosis pathway. Br J Cancer. 2001 Nov 30;85(11):1801-8. PubMed PMID: 11742505; PubMed Central PMCID: PMC2363987. 18: Kwon KB, Yang JY, Ryu DG, Rho HW, Kim JS, Park JW, Kim HR, Park BH. Vibrio vulnificus cytolysin induces superoxide anion-initiated apoptotic signaling pathway in human ECV304 cells. J Biol Chem. 2001 Dec 14;276(50):47518-23. Epub 2001 Oct 8. PubMed PMID: 11591724. 19: Kühn K, Lotz M. Regulation of CD95 (Fas/APO-1)-induced apoptosis in human chondrocytes. Arthritis Rheum. 2001 Jul;44(7):1644-53. PubMed PMID: 11465715. 20: Zhao Y, Wu M, Shen Y, Zhai Z. Analysis of nuclear apoptotic process in a cell-free system. Cell Mol Life Sci. 2001 Feb;58(2):298-306. PubMed PMID: 11289311.