SID-26681509 | CAS# 958772-66-2 | Human Cathepsin L inhibitor

MedKoo Cat#: 574876 | Name: SID 26681509

Description:

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

SID 26681509 is a potent, reversible, competitive, and selective inhibitor of human cathepsin L that inhibits propagation of malaria parasite Plasmodium falciparum and inhibits Leishmania major. SID 26681509 shows no inhibitory activity against cathepsin G.

Chemical Structure

SID 26681509

CAS#958772-66-2

Theoretical Analysis

MedKoo Cat#: 574876

Name: SID 26681509

CAS#: 958772-66-2

Chemical Formula: C27H33N5O5S

Exact Mass: 539.2202

Molecular Weight: 539.65

Elemental Analysis: C, 60.09; H, 6.16; N, 12.98; O, 14.82; S, 5.94

Price and Availability

Size	Price	Availability
50mg	USD 950.00	2 Weeks
100mg	USD 1,650.00	2 Weeks
1g	USD 4,650.00	2 Weeks

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Synonym

SID-26681509; SID26681509; SID 26681509

IUPAC/Chemical Name

S-(2-((2-ethylphenyl)amino)-2-oxoethyl) 2-((tert-butoxycarbonyl)-L-tryptophyl)hydrazine-1-carbothioate

InChi Key

OTIWAYTTYNFEKL-QFIPXVFZSA-N

InChi Code

InChI=1S/C27H33N5O5S/c1-5-17-10-6-8-12-20(17)29-23(33)16-38-26(36)32-31-24(34)22(30-25(35)37-27(2,3)4)14-18-15-28-21-13-9-7-11-19(18)21/h6-13,15,22,28H,5,14,16H2,1-4H3,(H,29,33)(H,30,35)(H,31,34)(H,32,36)/t22-/m0/s1

SMILES Code

O=C(NNC(SCC(NC1=CC=CC=C1CC)=O)=O)[C@H](CC2=CNC3=CC=CC=C23)NC(OC(C)(C)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 and ethanol

Shelf Life

>3 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:

SID 26681509 is a potent, reversible, competitive, and selective inhibitor of human cathepsin L with an IC50 of 56 nM. SID 26681509 inhibits in vitro propagation of malaria parasite Plasmodium falciparum and inhibits Leishmania major with IC50s of 15.4 μM and 12.5 μM, respectively.

In vitro activity:

This study reports the discovery of SID 26681509. SID 26681509 displayed 7- to 151-fold greater selectivity toward cathepsin L than papain and cathepsins B, K, V, and S with no activity against cathepsin G. SID 26681509 demonstrated a lack of toxicity in human aortic endothelial cells and zebrafish. It inhibited in vitro propagation of Plasmodium falciparum (IC50 = 15.4 mM) and inhibited Leishmania major (IC50 = 12.5 mM). Reference: Mol Pharmacol. 2008 Jul;74(1):34-41. https://pubmed.ncbi.nlm.nih.gov/18403718/

In vivo activity:

SID 26681509 treatment significantly improved survival in murine models of sepsis and reduced liver damage following warm liver ischemia/reperfusion models, characterized by strong HMGB1-TLR4 driven pathology. Reference: Mol Med. 2015 Dec;21(1):749-757. https://pubmed.ncbi.nlm.nih.gov/26349060/

	Solvent	mg/mL	mM
Solubility
	DMSO	27.0	50.00
	Ethanol	5.4	10.00
	DMSO	27.0	50.00
	Ethanol	5.4	10.00

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 539.65 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. Campbell GR, Spector SA. Vitamin D inhibits human immunodeficiency virus type 1 and Mycobacterium tuberculosis infection in macrophages through the induction of autophagy. PLoS Pathog. 2012;8(5):e1002689. doi: 10.1371/journal.ppat.1002689. Epub 2012 May 10. PMID: 22589721; PMCID: PMC3349755. 2. Shah PP, Myers MC, Beavers MP, Purvis JE, Jing H, Grieser HJ, Sharlow ER, Napper AD, Huryn DM, Cooperman BS, Smith AB 3rd, Diamond SL. Kinetic characterization and molecular docking of a novel, potent, and selective slow-binding inhibitor of human cathepsin L. Mol Pharmacol. 2008 Jul;74(1):34-41. doi: 10.1124/mol.108.046219. Epub 2008 Apr 10. PMID: 18403718; PMCID: PMC2575030. 3. Pribis JP, Al-Abed Y, Yang H, Gero D, Xu H, Montenegro MF, Bauer EM, Kim S, Chavan SS, Cai C, Li T, Szoleczky P, Szabo C, Tracey KJ, Billiar TR. The HIV Protease Inhibitor Saquinavir Inhibits HMGB1-Driven Inflammation by Targeting the Interaction of Cathepsin V with TLR4/MyD88. Mol Med. 2015 Dec;21(1):749-757. doi: 10.2119/molmed.2015.00197. Epub 2015 Sep 2. PMID: 26349060; PMCID: PMC4749497.

In vitro protocol:

In vivo protocol:

1. Pribis JP, Al-Abed Y, Yang H, Gero D, Xu H, Montenegro MF, Bauer EM, Kim S, Chavan SS, Cai C, Li T, Szoleczky P, Szabo C, Tracey KJ, Billiar TR. The HIV Protease Inhibitor Saquinavir Inhibits HMGB1-Driven Inflammation by Targeting the Interaction of Cathepsin V with TLR4/MyD88. Mol Med. 2015 Dec;21(1):749-757. doi: 10.2119/molmed.2015.00197. Epub 2015 Sep 2. PMID: 26349060; PMCID: PMC4749497.

1: Strøm TB, Bjune K, Leren TP. Bone morphogenetic protein 1 cleaves the linker region between ligand-binding repeats 4 and 5 of the LDL receptor and makes the LDL receptor non-functional. Hum Mol Genet. 2020 May 28;29(8):1229-1238. doi: 10.1093/hmg/ddz238. PMID: 31600776. 2: Campbell GR, Spector SA. Vitamin D inhibits human immunodeficiency virus type 1 and Mycobacterium tuberculosis infection in macrophages through the induction of autophagy. PLoS Pathog. 2012;8(5):e1002689. doi: 10.1371/journal.ppat.1002689. Epub 2012 May 10. PMID: 22589721; PMCID: PMC3349755. 3: Shah PP, Myers MC, Beavers MP, Purvis JE, Jing H, Grieser HJ, Sharlow ER, Napper AD, Huryn DM, Cooperman BS, Smith AB 3rd, Diamond SL. Kinetic characterization and molecular docking of a novel, potent, and selective slow- binding inhibitor of human cathepsin L. Mol Pharmacol. 2008 Jul;74(1):34-41. doi: 10.1124/mol.108.046219. Epub 2008 Apr 10. PMID: 18403718; PMCID: PMC2575030.