WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H208437
CAS#: 1348565-08-1
Description: K11002 is a peptidyl cysteine protease inhibitor
Hodoodo Cat#: H208437
Name: K11002
CAS#: 1348565-08-1
Chemical Formula: C31H35N3O5S
Exact Mass: 561.23
Molecular Weight: 561.700
Elemental Analysis: C, 66.29; H, 6.28; N, 7.48; O, 14.24; S, 5.71
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Synonym: K-11-002, K-11002, K02
IUPAC/Chemical Name: N-((S)-1-Oxo-3-phenyl-1-(((S,E)-5-phenyl-1-(phenylsulfonyl)pent-1-en-3-yl)amino)propan-2-yl)morpholine-4-carboxamide
InChi Key: HSZIWISHLSFWJO-PRABLTMGSA-N
InChi Code: InChI=1S/C31H35N3O5S/c35-30(29(24-26-12-6-2-7-13-26)33-31(36)34-19-21-39-22-20-34)32-27(17-16-25-10-4-1-5-11-25)18-23-40(37,38)28-14-8-3-9-15-28/h1-15,18,23,27,29H,16-17,19-22,24H2,(H,32,35)(H,33,36)/b23-18+/t27-,29-/m0/s1
SMILES Code: O=C(N1CCOCC1)N[C@@H](CC2=CC=CC=C2)C(N[C@@H](CCC3=CC=CC=C3)/C=C/S(=O)(C4=CC=CC=C4)=O)=O
Appearance: To be determined
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
More Info:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 561.70 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: | |
In vitro protocol: | |
In vivo protocol: |
1: Vermeire JJ, Lantz LD, Caffrey CR. Cure of hookworm infection with a cysteine protease inhibitor. PLoS Negl Trop Dis. 2012;6(7):e1680. doi: 10.1371/journal.pntd.0001680. Epub 2012 Jul 3. PMID: 22802972; PMCID: PMC3389033.
2: Aratikatla EK, Kalamuddin M, Malhotra P, Mohmmed A, Bhattacharya AK. Enantioselective Synthesis of γ-Phenyl-γ-amino Vinyl Phosphonates and Sulfones and Their Application to the Synthesis of Novel Highly Potent Antimalarials. ACS Omega. 2020 Nov 2;5(45):29025-29037. doi: 10.1021/acsomega.0c03470. PMID: 33225134; PMCID: PMC7675543.
3: Kerr ID, Wu P, Marion-Tsukamaki R, Mackey ZB, Brinen LS. Crystal Structures of TbCatB and rhodesain, potential chemotherapeutic targets and major cysteine proteases of Trypanosoma brucei. PLoS Negl Trop Dis. 2010 Jun 8;4(6):e701. doi: 10.1371/journal.pntd.0000701. PMID: 20544024; PMCID: PMC2882330.
4: Chen YT, Lira R, Hansell E, McKerrow JH, Roush WR. Synthesis of macrocyclic trypanosomal cysteine protease inhibitors. Bioorg Med Chem Lett. 2008 Nov 15;18(22):5860-3. doi: 10.1016/j.bmcl.2008.06.012. Epub 2008 Jun 10. PMID: 18585034; PMCID: PMC2642929.
5: Chan VJ, Selzer PM, McKerrow JH, Sakanari JA. Expression and alteration of the S2 subsite of the Leishmania major cathepsin B-like cysteine protease. Biochem J. 1999 May 15;340 ( Pt 1)(Pt 1):113-7. PMID: 10229665; PMCID: PMC1220228.
6: Cummins CL, Salphati L, Reid MJ, Benet LZ. In vivo modulation of intestinal CYP3A metabolism by P-glycoprotein: studies using the rat single-pass intestinal perfusion model. J Pharmacol Exp Ther. 2003 Apr;305(1):306-14. doi: 10.1124/jpet.102.044719. PMID: 12649383.
7: Zhang Y, Hsieh Y, Izumi T, Lin ET, Benet LZ. Effects of ketoconazole on the intestinal metabolism, transport and oral bioavailability of K02, a novel vinylsulfone peptidomimetic cysteine protease inhibitor and a P450 3A, P-glycoprotein dual substrate, in male Sprague-Dawley rats. J Pharmacol Exp Ther. 1998 Oct;287(1):246-52. PMID: 9765344.
8: Shi GP, Bryant RA, Riese R, Verhelst S, Driessen C, Li Z, Bromme D, Ploegh HL, Chapman HA. Role for cathepsin F in invariant chain processing and major histocompatibility complex class II peptide loading by macrophages. J Exp Med. 2000 Apr 3;191(7):1177-86. doi: 10.1084/jem.191.7.1177. PMID: 10748235; PMCID: PMC2193169.
9: Zhang Y, Benet LZ. Characterization of P-glycoprotein mediated transport of K02, a novel vinylsulfone peptidomimetic cysteine protease inhibitor, across MDR1-MDCK and Caco-2 cell monolayers. Pharm Res. 1998 Oct;15(10):1520-4. doi: 10.1023/a:1011990730230. PMID: 9794492.