DCG04
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MedKoo CAT#: 530629

CAS#: 314263-42-8

Description: DCG04 is a multivalent ligand for the mannose-6-phosphate receptor for endolysosomal targeting of an activity-based probe. DCG-04 is an activity-based probe for cysteine cathepsins, enabled fluorescent readout of its receptor-targeting properties. The resulting M6P-cluster-BODIPY-DCG-04 probe was shown to efficiently label cathepsins in cell lysates as well as in live cells.


Price and Availability

Size
Price

200mg
USD 5950
Size
Price

500mg
USD 7950
Size
Price

1g
USD 14650

DCG04, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530629
Name: DCG04
CAS#: 314263-42-8
Chemical Formula: C43H66N8O11S
Exact Mass: 902.4572
Molecular Weight: 903.106
Elemental Analysis: C, 57.19; H, 7.37; N, 12.41; O, 19.49; S, 3.55


Synonym: DCG04; DCG-04; DCG 04.

IUPAC/Chemical Name: ethyl 3-(((4S,7S,17S)-17-carbamoyl-7-(4-hydroxybenzyl)-2-methyl-5,8,15,23-tetraoxo-27-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-6,9,16,22-tetraazaheptacosan-4-yl)carbamoyl)oxirane-2-carboxylate

InChi Key: MHOVYDVXSWUHAZ-NNBHGYTGSA-N

InChi Code: InChI=1S/C43H66N8O11S/c1-4-61-42(59)37-36(62-37)41(58)49-29(22-25(2)3)40(57)48-30(23-26-16-18-27(52)19-17-26)39(56)46-21-10-5-6-15-34(54)47-28(38(44)55)12-9-11-20-45-33(53)14-8-7-13-32-35-31(24-63-32)50-43(60)51-35/h16-19,25,28-32,35-37,52H,4-15,20-24H2,1-3H3,(H2,44,55)(H,45,53)(H,46,56)(H,47,54)(H,48,57)(H,49,58)(H2,50,51,60)/t28-,29-,30-,31?,32?,35?,36?,37?/m0/s1

SMILES Code: O=C(C1OC1C(N[C@H](C(N[C@@H](CC2=CC=C(O)C=C2)C(NCCCCCC(N[C@H](C(N)=O)CCCCNC(CCCCC3SCC(C3N4)NC4=O)=O)=O)=O)=O)CC(C)C)=O)OCC


Technical Data

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).

Harmonized System Code:
293490


References

1: Hoogendoorn S, van Puijvelde GH, Kuiper J, van der Marel GA, Overkleeft HS. A multivalent ligand for the mannose-6-phosphate receptor for endolysosomal targeting of an activity-based probe. Angew Chem Int Ed Engl. 2014 Oct 6;53(41):10975-8. doi: 10.1002/anie.201406842. Epub 2014 Aug 27. PubMed PMID: 25163608.

2: Greenbaum D, Medzihradszky KF, Burlingame A, Bogyo M. Epoxide electrophiles as activity-dependent cysteine protease profiling and discovery tools. Chem Biol. 2000 Aug;7(8):569-81. PubMed PMID: 11048948.

3: Hillaert U, Verdoes M, Florea BI, Saragliadis A, Habets KL, Kuiper J, Van Calenbergh S, Ossendorp F, van der Marel GA, Driessen C, Overkleeft HS. Receptor-mediated targeting of cathepsins in professional antigen presenting cells. Angew Chem Int Ed Engl. 2009;48(9):1629-32. doi: 10.1002/anie.200805529. Erratum in: Angew Chem Int Ed Engl. 2009;48(14):2442.. Saragliadis, Anastasios [corrected to Saragliadis, Athanasios]. PubMed PMID: 19156780.

4: Kasný M, Mikes L, Dalton JP, Mountford AP, Horák P. Comparison of cysteine peptidase activities in Trichobilharzia regenti and Schistosoma mansoni cercariae. Parasitology. 2007 Oct;134(Pt 11):1599-609. Epub 2007 May 22. PubMed PMID: 17517170.

5: Kocks C, Maehr R, Overkleeft HS, Wang EW, Iyer LK, Lennon-Dumenil AM, Ploegh HL, Kessler BM. Functional proteomics of the active cysteine protease content in Drosophila S2 cells. Mol Cell Proteomics. 2003 Nov;2(11):1188-97. Epub 2003 Sep 16. PubMed PMID: 13130081.

6: Shah PP, Wang T, Kaletsky RL, Myers MC, Purvis JE, Jing H, Huryn DM, Greenbaum DC, Smith AB 3rd, Bates P, Diamond SL. A small-molecule oxocarbazate inhibitor of human cathepsin L blocks severe acute respiratory syndrome and ebola pseudotype virus infection into human embryonic kidney 293T cells. Mol Pharmacol. 2010 Aug;78(2):319-24. doi: 10.1124/mol.110.064261. Epub 2010 May 13. PubMed PMID: 20466822; PubMed Central PMCID: PMC2917856.

7: Mirković B, Sosič I, Gobec S, Kos J. Redox-based inactivation of cysteine cathepsins by compounds containing the 4-aminophenol moiety. PLoS One. 2011;6(11):e27197. doi: 10.1371/journal.pone.0027197. Epub 2011 Nov 4. PubMed PMID: 22073285; PubMed Central PMCID: PMC3208577.

8: Lampl N, Budai-Hadrian O, Davydov O, Joss TV, Harrop SJ, Curmi PM, Roberts TH, Fluhr R. Arabidopsis AtSerpin1, crystal structure and in vivo interaction with its target protease RESPONSIVE TO DESICCATION-21 (RD21). J Biol Chem. 2010 Apr 30;285(18):13550-60. doi: 10.1074/jbc.M109.095075. Epub 2010 Feb 24. PubMed PMID: 20181955; PubMed Central PMCID: PMC2859516.

9: Pungercar JR, Caglic D, Sajid M, Dolinar M, Vasiljeva O, Pozgan U, Turk D, Bogyo M, Turk V, Turk B. Autocatalytic processing of procathepsin B is triggered by proenzyme activity. FEBS J. 2009 Feb;276(3):660-8. doi: 10.1111/j.1742-4658.2008.06815.x. PubMed PMID: 19143833; PubMed Central PMCID: PMC4551429.

10: Martínez DE, Bartoli CG, Grbic V, Guiamet JJ. Vacuolar cysteine proteases of wheat (Triticum aestivum L.) are common to leaf senescence induced by different factors. J Exp Bot. 2007;58(5):1099-107. Epub 2007 Jan 11. PubMed PMID: 17218544.

11: Vasiljeva O, Papazoglou A, Krüger A, Brodoefel H, Korovin M, Deussing J, Augustin N, Nielsen BS, Almholt K, Bogyo M, Peters C, Reinheckel T. Tumor cell-derived and macrophage-derived cathepsin B promotes progression and lung metastasis of mammary cancer. Cancer Res. 2006 May 15;66(10):5242-50. PubMed PMID: 16707449.

12: Hoogendoorn S, Habets KL, Passemard S, Kuiper J, van der Marel GA, Florea BI, Overkleeft HS. Targeted pH-dependent fluorescent activity-based cathepsin probes. Chem Commun (Camb). 2011 Sep 7;47(33):9363-5. doi: 10.1039/c1cc12947c. Epub 2011 Jul 18. PubMed PMID: 21769329.

13: Chandramohanadas R, Davis PH, Beiting DP, Harbut MB, Darling C, Velmourougane G, Lee MY, Greer PA, Roos DS, Greenbaum DC. Apicomplexan parasites co-opt host calpains to facilitate their escape from infected cells. Science. 2009 May 8;324(5928):794-7. doi: 10.1126/science.1171085. Epub 2009 Apr 2. PubMed PMID: 19342550; PubMed Central PMCID: PMC3391539.

14: Reich M, van Swieten PF, Sommandas V, Kraus M, Fischer R, Weber E, Kalbacher H, Overkleeft HS, Driessen C. Endocytosis targets exogenous material selectively to cathepsin S in live human dendritic cells, while cell-penetrating peptides mediate nonselective transport to cysteine cathepsins. J Leukoc Biol. 2007 Apr;81(4):990-1001. Epub 2007 Jan 29. PubMed PMID: 17261546.

15: Rooney HC, Van't Klooster JW, van der Hoorn RA, Joosten MH, Jones JD, de Wit PJ. Cladosporium Avr2 inhibits tomato Rcr3 protease required for Cf-2-dependent disease resistance. Science. 2005 Jun 17;308(5729):1783-6. Epub 2005 Apr 21. Erratum in: Science. 2005 Oct 7;310(5745):54. PubMed PMID: 15845874.

16: Hazell AS, Pannunzio P, Rama Rao KV, Pow DV, Rambaldi A. Thiamine deficiency results in downregulation of the GLAST glutamate transporter in cultured astrocytes. Glia. 2003 Aug;43(2):175-84. PubMed PMID: 12838509.

17: Zheng F, Johnson SW. Dual modulation of gabaergic transmission by metabotropic glutamate receptors in rat ventral tegmental area. Neuroscience. 2003;119(2):453-60. PubMed PMID: 12770559.

18: Lennon-Duménil AM, Bakker AH, Maehr R, Fiebiger E, Overkleeft HS, Rosemblatt M, Ploegh HL, Lagaudrière-Gesbert C. Analysis of protease activity in live antigen-presenting cells shows regulation of the phagosomal proteolytic contents during dendritic cell activation. J Exp Med. 2002 Aug 19;196(4):529-40. PubMed PMID: 12186844; PubMed Central PMCID: PMC2196045.