Z-FR-AMC TFA
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 464993

CAS#: unknown

Description: Z-FR-AMC is a fluorogenic substrate for cathepsin L. Upon enzymatic cleavage by cathepsin L, 7-amino-4-methylcoumarin (AMC) is released and its fluorescence can be used to quantify cathepsin L activity. AMC displays excitation/emission maxima of 340-360/440-460 nm, respectively.


Chemical Structure

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Z-FR-AMC TFA
CAS# unknown

Theoretical Analysis

MedKoo Cat#: 464993
Name: Z-FR-AMC TFA
CAS#: unknown
Chemical Formula: C35H37F3N6O8
Exact Mass: 726.2625
Molecular Weight: 726.7102
Elemental Analysis: C, 57.85; H, 5.13; F, 7.84; N, 11.56; O, 17.61

Price and Availability

Size Price Availability Quantity
10.0mg USD 230.0 2 Weeks
25.0mg USD 410.0 2 Weeks
50.0mg USD 670.0 2 Weeks
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Synonym: Z-FR-AMC TFA; ZFRAMC TFA; Z FR AMC TFA; Z-FRAMC TFA; Z-FR AMC TFA; ZFR-AMC TFA; Z FR-AMC TFA; Z-FR-7-amino-4-Methylcoumarin; Z-Phe-Arg-AMC;

IUPAC/Chemical Name: benzyl ((S)-1-(((S)-5-guanidino-1-((4-methyl-2-oxo-2H-chromen-7-yl)amino)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 2,2,2-trifluoroacetate

InChi Key: AVPSADNFAQBJBZ-WMXJXTQLSA-N

InChi Code: InChI=1S/C33H36N6O6.C2HF3O2/c1-21-17-29(40)45-28-19-24(14-15-25(21)28)37-30(41)26(13-8-16-36-32(34)35)38-31(42)27(18-22-9-4-2-5-10-22)39-33(43)44-20-23-11-6-3-7-12-23;3-2(4,5)1(6)7/h2-7,9-12,14-15,17,19,26-27H,8,13,16,18,20H2,1H3,(H,37,41)(H,38,42)(H,39,43)(H4,34,35,36);(H,6,7)/t26-,27-;/m0./s1

SMILES Code: CC(C1=CC=C(C=C1O2)NC([C@@H](NC([C@H](CC3=CC=CC=C3)NC(OCC4=CC=CC=C4)=O)=O)CCCNC(N)=N)=O)=CC2=O.OC(C(F)(F)F)=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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 1.0 1.38
DMSO 1.0 1.38
Ethanol 1.0 1.38

Preparing Stock Solutions

The following data is based on the product molecular weight 726.7102 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

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1: Zabala-Peñafiel A, Dias-Lopes G, Cysne-Finkelstein L, Conceição-Silva F, Miranda LFC, Fagundes A, Schubach AO, Fernandes Pimentel MI, Souza-Silva F, Machado LA, Alves CR. Serine proteases profiles of Leishmania (Viannia) braziliensis clinical isolates with distinct susceptibilities to antimony. Sci Rep. 2021 Jul 9;11(1):14234. doi: 10.1038/s41598-021-93665-z. PMID: 34244581; PMCID: PMC8271011.

2: Torralbo-Ramírez V, Molina-Fernández D, Malagón D, Benítez R, Adroher FJ. Differential Cleaving of Specific Substrates for Cathepsin-Like Activity Shows Cysteine and Serine Protease Activities and a Differential Profile Between Anisakis simplex s.s. and Anisakis pegreffii, Sibling Species Major Etiologic Agents of Anisakiasis. Foodborne Pathog Dis. 2019 Nov;16(11):744-751. doi: 10.1089/fpd.2019.2633. Epub 2019 Jun 19. PMID: 31215796.

3: Santos-de-Souza R, Monteiro de Castro Côrtes L, Dos Santos Charret K, Cysne- Finkelstein L, Alves CR, Souza-Silva F. Serine Proteinases in Leishmania (Viannia) braziliensis Promastigotes Have Distinct Subcellular Distributions and Expression. Int J Mol Sci. 2019 Mar 15;20(6):1315. doi: 10.3390/ijms20061315. PMID: 30875904; PMCID: PMC6471289.

4: Li M, Li Q, Yang Z, Hu G, Li T, Chen X, Ao J. Identification of cathepsin B from large yellow croaker (Pseudosciaena crocea) and its role in the processing of MHC class II-associated invariant chain. Dev Comp Immunol. 2014 Aug;45(2):313-20. doi: 10.1016/j.dci.2014.03.019. Epub 2014 Apr 3. PMID: 24705226.

5: Salas-Sarduy E, Cabrera-Muñoz A, Cauerhff A, González-González Y, Trejo SA, Chidichimo A, Chávez-Planes Mde L, Cazzulo JJ. Antiparasitic effect of a fraction enriched in tight-binding protease inhibitors isolated from the Caribbean coral Plexaura homomalla. Exp Parasitol. 2013 Nov;135(3):611-22. doi: 10.1016/j.exppara.2013.09.013. Epub 2013 Sep 30. PMID: 24090569.

6: Sudhamalla B, Kumar M, Roy KR, Kumar RS, Bhuyan AK. Cysteine endoprotease activity of human ribosomal protein S4 is entirely due to the C-terminal domain, and is consistent with Michaelis-Menten mechanism. Biochim Biophys Acta. 2013 Nov;1830(11):5342-9. doi: 10.1016/j.bbagen.2013.06.011. Epub 2013 Jun 19. PMID: 23791938.

7: Sudhamalla B, Kumar M, Kumar RS, Sashi P, Yasin UM, Ramakrishna D, Rao PN, Bhuyan AK. Enzyme dimension of the ribosomal protein S4 across plant and animal kingdoms. Biochim Biophys Acta. 2013 Nov;1830(11):5335-41. doi: 10.1016/j.bbagen.2013.06.010. Epub 2013 Jun 19. PMID: 23791937.

8: Sudhamalla B, Yadaiah M, Ramakrishna D, Bhuyan AK. Cysteine protease attribute of eukaryotic ribosomal protein S4. Biochim Biophys Acta. 2012 Oct;1820(10):1535-42. doi: 10.1016/j.bbagen.2012.05.001. Epub 2012 May 9. PMID: 22579920.

9: Rieux A, Gras S, Lecaille F, Niepceron A, Katrib M, Smith NC, Lalmanach G, Brossier F. Eimeripain, a cathepsin B-like cysteine protease, expressed throughout sporulation of the apicomplexan parasite Eimeria tenella. PLoS One. 2012;7(3):e31914. doi: 10.1371/journal.pone.0031914. Epub 2012 Mar 22. PMID: 22457711; PMCID: PMC3310820.

10: Yadaiah M, Nageswara Rao P, Sudhamalla B, Ramakrishna D, Mahammad Yasin U, Bhuyan AK. Cloning, Escherichia coli expression, purification, characterization, and enzyme assay of the ribosomal protein S4 from wheat seedlings (Triticum vulgare). Protein Expr Purif. 2012 Jan;81(1):55-62. doi: 10.1016/j.pep.2011.09.003. Epub 2011 Sep 17. PMID: 21945701.

11: Malagón D, Díaz-López M, Benítez R, Adroher FJ. Cathepsin B- and L-like cysteine protease activities during the in vitro development of Hysterothylacium aduncum (Nematoda: Anisakidae), a worldwide fish parasite. Parasitol Int. 2010 Mar;59(1):89-92. doi: 10.1016/j.parint.2009.11.001. Epub 2009 Nov 20. PMID: 19932193.

12: Liton PB, Lin Y, Luna C, Li G, Gonzalez P, Epstein DL. Cultured porcine trabecular meshwork cells display altered lysosomal function when subjected to chronic oxidative stress. Invest Ophthalmol Vis Sci. 2008 Sep;49(9):3961-9. doi: 10.1167/iovs.08-1915. Epub 2008 May 9. PMID: 18469195; PMCID: PMC3601374.

13: Muleke CI, Ruofeng Y, Lixin X, Yanming S, Xiangrui L. Characterization of HC58cDNA, a putative cysteine protease from the parasite Haemonchus contortus. J Vet Sci. 2006 Sep;7(3):249-55. doi: 10.4142/jvs.2006.7.3.249. Erratum in: J Vet Sci. 2006 Dec;7(4):405. PMID: 16871019; PMCID: PMC3242124.

14: Vasiljeva O, Dolinar M, Turk V, Turk B. Recombinant human cathepsin H lacking the mini chain is an endopeptidase. Biochemistry. 2003 Nov 25;42(46):13522-8. doi: 10.1021/bi035355k. PMID: 14621998.