Synonym
TP110; TP-110; TP 110; Tyropeptin A7.
IUPAC/Chemical Name
(2S)-2-((2S)-3-(4-methoxyphenyl)-N-(1-(4-methoxyphenyl)-3-oxopropan-2-yl)-2-(2-(naphthalen-1-yl)acetamido)propanamido)-3-methylbutanamide
SMILES Code
CC(C)[C@H](N(C(C=O)CC1=CC=C(OC)C=C1)C([C@@H](NC(CC2=C3C=CC=CC3=CC=C2)=O)CC4=CC=C(OC)C=C4)=O)C(N)=O
Appearance
white 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, not in water
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).
Preparing Stock Solutions
The following data is based on the
product
molecular weight
623.74
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 |
1: Iijima M, Momose I, Ikeda D. Increased ABCB1 expression in TP-110-resistant RPMI-8226 cells. Biosci Biotechnol Biochem. 2010;74(9):1913-9. Epub 2010 Sep 7. PubMed PMID: 20834157.
2: Iijima M, Momose I, Ikeda D. TP-110, a new proteasome inhibitor, down-regulates IAPs in human multiple myeloma cells. Anticancer Res. 2009 Apr;29(4):977-85. PubMed PMID: 19414335.
3: Watanabe T, Momose I, Abe M, Abe H, Sawa R, Umezawa Y, Ikeda D, Takahashi Y, Akamatsu Y. Synthesis of boronic acid derivatives of tyropeptin: proteasome inhibitors. Bioorg Med Chem Lett. 2009 Apr 15;19(8):2343-5. doi: 10.1016/j.bmcl.2009.02.117. Epub 2009 Mar 4. PubMed PMID: 19307118.
4: Zanzonico P, Dauer L, St Germain J. Operational radiation safety for PET-CT, SPECT-CT, and cyclotron facilities. Health Phys. 2008 Nov;95(5):554-70. doi: 10.1097/01.HP.0000327651.15794.f7. PubMed PMID: 18849690.
5: Momose I, Iijima M, Kawada M, Ikeda D. A new proteasome inhibitor, TP-110, induces apoptosis in human prostate cancer PC-3 cells. Biosci Biotechnol Biochem. 2007 Apr;71(4):1036-43. Epub 2007 Apr 7. PubMed PMID: 17420589.
6: Momose I, Umezawa Y, Hirosawa S, Iijima M, Iinuma H, Ikeda D. Synthesis and activity of tyropeptin A derivatives as potent and selective inhibitors of mammalian 20S proteasome. Biosci Biotechnol Biochem. 2005 Sep;69(9):1733-42. PubMed PMID: 16195592.
7: Momose I, Umezawa Y, Hirosawa S, Iinuma H, Ikeda D. Structure-based design of derivatives of tyropeptin A as the potent and selective inhibitors of mammalian 20S proteasome. Bioorg Med Chem Lett. 2005 Apr 1;15(7):1867-71. PubMed PMID: 15780623.
8: Spach MS, Heidlage JF, Darken ER, Hofer E, Raines KH, Starmer CF. Cellular Vmax reflects both membrane properties and the load presented by adjoining cells. Am J Physiol. 1992 Dec;263(6 Pt 2):H1855-63. PubMed PMID: 1481909.
9: Dowden SB, Cossins L, Glazebrook J, Ramsden M, Strike P. DNA-damage inducible genes on the I group plasmid TP 110. Biochimie. 1982 Aug-Sep;64(8-9):681-5. PubMed PMID: 6291638.
