Synonym
ZPCK, Z-L-Phe chloromethyl ketone; ZLPhe chloromethyl ketone; Z-Phe-chloromethylketone; Z L Phe chloromethyl ketone; NSC-251810; SL-01; SL 01; SL01.
IUPAC/Chemical Name
Benzyl N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate
InChi Key
OYHLRJGDELITAF-INIZCTEOSA-N
InChi Code
InChI=1S/C18H18ClNO3/c19-12-17(21)16(11-14-7-3-1-4-8-14)20-18(22)23-13-15-9-5-2-6-10-15/h1-10,16H,11-13H2,(H,20,22)/t16-/m0/s1
SMILES Code
O=C(OCC1=CC=CC=C1)N[C@H](C(CCl)=O)CC2=CC=CC=C2
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, DMF, and ethanol
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).
HS Tariff Code
2934.99.9001
Biological target:
SL-01 is an inhibitor of SARS-CoV main protease (Mpro), also known as 3C-like protease (3CLpro; Ki = 306 nM). It is selective for SARS-CoV Mpro over calpain, trypsin, and thrombin (Kis = 10, >100, and >100 µM, respectively). SL-01 (20 µM) also inhibits the protein-protein interaction between p53 and MDM2 in U2OS osteosarcoma cells.
In vitro activity:
SL-01 possessed similar activity against human breast cancer growth with gemcitabine, but with lower toxicity than gemcitabine. SL-01 significantly inhibited MCF-7 proliferation as estimated by colorimetric assay. Flow cytometry assay indicated the apoptotic induction and cell cycle arrest in G1 phase. SL-01 modulated the expressions of p-ATM, p53 and p21 and decrease of cyclin D1 in MCF-7 cells.
Reference: Biochem Biophys Res Commun. 2013 Aug 23;438(2):402-9. https://pubmed.ncbi.nlm.nih.gov/23899521/
In vivo activity:
SL-01 is proposed as a potent oral anticancer agent that may supplant the use of gemcitabine. In nude mice bearing human cancer xenografts, SL-01 effectively delayed the growth of NCI-H460 and HCT-116 without significant loss of body weight. Molecular analysis indicated that the high efficacy of SL-01 was associated with its ability to induce apoptosis. The biological activities of SL-01 were more potential than that of gemcitabine.
Reference: Toxicol Appl Pharmacol. 2012 Aug 1;262(3):293-300. https://pubmed.ncbi.nlm.nih.gov/22617428/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
33.0 |
99.46 |
|
| DMSO |
33.0 |
99.46 |
|
| Ethanol |
2.0 |
6.03 |
|
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
331.79
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. Li YY, Qin YZ, Wang RQ, Li WB, Qu XJ. SL-01, an oral derivative of gemcitabine, inhibited human breast cancer growth through induction of apoptosis. Biochem Biophys Res Commun. 2013 Aug 23;438(2):402-9. doi: 10.1016/j.bbrc.2013.07.087. Epub 2013 Jul 27. PMID: 23899521.
2. Zhao C, Li Y, Qin Y, Wang R, Li G, Sun C, Qu X, Li W. Pharmacokinetics and metabolism of SL-01, a prodrug of gemcitabine, in rats. Cancer Chemother Pharmacol. 2013 Jun;71(6):1541-50. doi: 10.1007/s00280-013-2153-6. Epub 2013 Apr 6. PMID: 23564376.
3. Zhao C, Yue B, Liu H, Sun C, Li W, Qu X. SL-01, an oral gemcitabine derivative, inhibited human cancer growth more potently than gemcitabine. Toxicol Appl Pharmacol. 2012 Aug 1;262(3):293-300. doi: 10.1016/j.taap.2012.05.006. Epub 2012 May 19. PMID: 22617428.
In vitro protocol:
1. Li YY, Qin YZ, Wang RQ, Li WB, Qu XJ. SL-01, an oral derivative of gemcitabine, inhibited human breast cancer growth through induction of apoptosis. Biochem Biophys Res Commun. 2013 Aug 23;438(2):402-9. doi: 10.1016/j.bbrc.2013.07.087. Epub 2013 Jul 27. PMID: 23899521.
In vivo protocol:
1. Zhao C, Li Y, Qin Y, Wang R, Li G, Sun C, Qu X, Li W. Pharmacokinetics and metabolism of SL-01, a prodrug of gemcitabine, in rats. Cancer Chemother Pharmacol. 2013 Jun;71(6):1541-50. doi: 10.1007/s00280-013-2153-6. Epub 2013 Apr 6. PMID: 23564376.
2. Zhao C, Yue B, Liu H, Sun C, Li W, Qu X. SL-01, an oral gemcitabine derivative, inhibited human cancer growth more potently than gemcitabine. Toxicol Appl Pharmacol. 2012 Aug 1;262(3):293-300. doi: 10.1016/j.taap.2012.05.006. Epub 2012 May 19. PMID: 22617428.
1: Zhao C, Li Y, Qin Y, Wang R, Li G, Sun C, Qu X, Li W. Pharmacokinetics and metabolism of SL-01, a prodrug of gemcitabine, in rats. Cancer Chemother Pharmacol. 2013 Jun;71(6):1541-50. doi: 10.1007/s00280-013-2153-6. Epub 2013 Apr 6. PubMed PMID: 23564376.
2: Li YY, Qin YZ, Wang RQ, Li WB, Qu XJ. SL-01, an oral derivative of gemcitabine, inhibited human breast cancer growth through induction of apoptosis. Biochem Biophys Res Commun. 2013 Aug 23;438(2):402-9. doi: 10.1016/j.bbrc.2013.07.087. Epub 2013 Jul 27. PubMed PMID: 23899521.
3: Zhao C, Yue B, Liu H, Sun C, Li W, Qu X. SL-01, an oral gemcitabine derivative, inhibited human cancer growth more potently than gemcitabine. Toxicol Appl Pharmacol. 2012 Aug 1;262(3):293-300. doi: 10.1016/j.taap.2012.05.006. Epub 2012 May 19. PubMed PMID: 22617428.
4: Baptista CJ, Dourado I, de Andrade TM, Brignol S, Bertoni N, Bastos FI; Brazilian Multicity Study Group on Drug Misuse. HIV Prevalence, Knowledge, Attitudes, and Practices Among Polydrug Users in Brazil: A Biological Survey Using Respondent Driven Sampling. AIDS Behav. 2017 May 31. doi: 10.1007/s10461-017-1812-8. [Epub ahead of print] PubMed PMID: 28567550.
