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MedKoo Cat#: 406809 | Name: SMIP004
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SMIP004 is a novel inducer of cancer-cell selective apoptosis of human prostate cancer cells. SMIP004 decreased the levels of positive cell cycle regulators, upregulated cyclin-dependent kinase inhibitors, and resulted in G1 arrest, inhibition of colony formation in soft agar, and cell death. SMIP004 potently inhibits the growth of prostate and breast cancer xenografts in mice. SMIP004, by inducing mitochondrial ROS formation, targets specific sensitivities of prostate cancer cells to redox and bioenergetic imbalances that can be exploited in cancer therapy.

Chemical Structure

SMIP004
SMIP004
CAS#143360-00-3

Theoretical Analysis

MedKoo Cat#: 406809

Name: SMIP004

CAS#: 143360-00-3

Chemical Formula: C13H19NO

Exact Mass: 205.1467

Molecular Weight: 205.30

Elemental Analysis: C, 76.06; H, 9.33; N, 6.82; O, 7.79

Price and Availability

Size Price Availability Quantity
10mg USD 550.00 2 Weeks
50mg USD 1,650.00 2 weeks
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Synonym
SMIP004; SMIP-004; SMIP 004.
IUPAC/Chemical Name
N-(4-butyl-2-methylphenyl)acetamide
InChi Key
ZFVMECVBUGMWIX-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H19NO/c1-4-5-6-12-7-8-13(10(2)9-12)14-11(3)15/h7-9H,4-6H2,1-3H3,(H,14,15)
SMILES Code
CC(NC1=CC=C(CCCC)C=C1C)=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
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).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
SMIP004 upregulates p27 and activates the unfolded protein response (UPR) in LNCaP prostate cancer cells overexpressing SKP2. SMIP004 also induces oxidative stress. SMIP004 induces proteasomal degradation of cyclin D1 and acts as CDK2 inhibitor.
In vitro activity:
Results from this study suggest that SMIP004 could have potential in prostate cancer treatment. SMIP004 upregulated p21(Cip)¹, inhibited cellular CDK2 activity, induced G1 delay, inhibited colony formation in soft agar, and exhibited preferential cytotoxicity in LNCaP cells relative to normal human fibroblasts. SMIP004 was found to downregulate SKP2 and to stabilize p27, although it is not a proteasome inhibitor. Reference: BMC Biol. 2010 Dec 23;8:153. https://pubmed.ncbi.nlm.nih.gov/21182779/
In vivo activity:
SMIP004 has potential to be a novel antidepressant. In C57BL6/J mice, SMIP004 displayed obvious antidepressant-like activities in all conducted tests. The antidepressant-like activity of SMIP004 in naïve mice occurred at day 11; SMIP004 also produced antidepressant-like activities in naïve mice after three times in a 24-h administration scheme, but not before the test. Combined SMIP004-fluoxetine administration induced coordinated antidepressant-like effects in the tail suspension test and forced swim test. Reference: Eur J Pharmacol. 2019 Jan 15;843:260-267. https://pubmed.ncbi.nlm.nih.gov/30502341/
Solvent mg/mL mM comments
Solubility
DMSO 20.5 100.00
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 205.30 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
Formulation protocol:
1. Rico-Bautista E, Zhu W, Kitada S, Ganapathy S, Lau E, Krajewski S, Ramirez J, Bush JA, Yuan Z, Wolf DA. Small molecule-induced mitochondrial disruption directs prostate cancer inhibition via UPR signaling. Oncotarget. 2013 Aug;4(8):1212-29. doi: 10.18632/oncotarget.1130. PMID: 23902736; PMCID: PMC3787152. 2. Rico-Bautista E, Yang CC, Lu L, Roth GP, Wolf DA. Chemical genetics approach to restoring p27Kip1 reveals novel compounds with antiproliferative activity in prostate cancer cells. BMC Biol. 2010 Dec 23;8:153. doi: 10.1186/1741-7007-8-153. PMID: 21182779; PMCID: PMC3025922. 3. Li C, Du L, Ren Y, Liu X, Jiao Q, Cui D, Wen M, Wang C, Wei G, Wang Y, Ji A, Wang Q. SKP2 promotes breast cancer tumorigenesis and radiation tolerance through PDCD4 ubiquitination. J Exp Clin Cancer Res. 2019 Feb 13;38(1):76. doi: 10.1186/s13046-019-1069-3. PMID: 30760284; PMCID: PMC6375223. 4. Wang D, Xu X, Wu Y, Lin Y, Gao M, Hu P, Chen D, Lu X, Chen Z, Wang H, Huang C. SMIP004: A compound with antidepressant-like activities in mouse models. Eur J Pharmacol. 2019 Jan 15;843:260-267. doi: 10.1016/j.ejphar.2018.11.039. Epub 2018 Nov 29. PMID: 30502341.
In vitro protocol:
1. Rico-Bautista E, Zhu W, Kitada S, Ganapathy S, Lau E, Krajewski S, Ramirez J, Bush JA, Yuan Z, Wolf DA. Small molecule-induced mitochondrial disruption directs prostate cancer inhibition via UPR signaling. Oncotarget. 2013 Aug;4(8):1212-29. doi: 10.18632/oncotarget.1130. PMID: 23902736; PMCID: PMC3787152. 2. Rico-Bautista E, Yang CC, Lu L, Roth GP, Wolf DA. Chemical genetics approach to restoring p27Kip1 reveals novel compounds with antiproliferative activity in prostate cancer cells. BMC Biol. 2010 Dec 23;8:153. doi: 10.1186/1741-7007-8-153. PMID: 21182779; PMCID: PMC3025922.
In vivo protocol:
1. Li C, Du L, Ren Y, Liu X, Jiao Q, Cui D, Wen M, Wang C, Wei G, Wang Y, Ji A, Wang Q. SKP2 promotes breast cancer tumorigenesis and radiation tolerance through PDCD4 ubiquitination. J Exp Clin Cancer Res. 2019 Feb 13;38(1):76. doi: 10.1186/s13046-019-1069-3. PMID: 30760284; PMCID: PMC6375223. 2. Wang D, Xu X, Wu Y, Lin Y, Gao M, Hu P, Chen D, Lu X, Chen Z, Wang H, Huang C. SMIP004: A compound with antidepressant-like activities in mouse models. Eur J Pharmacol. 2019 Jan 15;843:260-267. doi: 10.1016/j.ejphar.2018.11.039. Epub 2018 Nov 29. PMID: 30502341.
1: Tang L, Zhang B, Li G, Qiu X, Dai Z, Liu H, Zhu Y, Feng B, Su Z, Han W, Huang H, Li Q, Zhang Z, Wang M, Liu H, Chen Y, Zhang Y, Wu D, Zheng X, Liu T, Zhao J, Li C, Zheng G. Upregulated SKP2 Empowers Epidermal Proliferation Through Downregulation of P27 Kip1. Ann Dermatol. 2024 Oct;36(5):282-291. doi: 10.5021/ad.23.118. PMID: 39343755; PMCID: PMC11439983. 2: Liu Q, Cheng L, Li F, Zhu H, Lu X, Huang C, Yuan X. NSC689857, an inhibitor of Skp2, produces antidepressant-like effects in mice. Behav Pharmacol. 2024 Jun 1;35(4):227-238. doi: 10.1097/FBP.0000000000000773. Epub 2024 Apr 24. PMID: 38651981. 3: Yuan J, Zhu Z, Zhang P, Ashrafizadeh M, Abd El-Aty AM, Hacımüftüoğlu A, Linnebacher CS, Linnebacher M, Sethi G, Gong P, Zhang X. SKP2 promotes the metastasis of pancreatic ductal adenocarcinoma by suppressing TRIM21-mediated PSPC1 degradation. Cancer Lett. 2024 Apr 10;587:216733. doi: 10.1016/j.canlet.2024.216733. Epub 2024 Feb 14. PMID: 38360141. 4: Reyes-Castellanos G, Carrier A. A novel anticancer pharmacological agent targeting mitochondrial complex I. Trends Pharmacol Sci. 2022 Sep;43(9):706-708. doi: 10.1016/j.tips.2022.03.007. Epub 2022 Apr 2. PMID: 35382944. 5: Jain S, Hu C, Kluza J, Ke W, Tian G, Giurgiu M, Bleilevens A, Campos AR, Charbono A, Stickeler E, Maurer J, Holinski-Feder E, Vaisburg A, Bureik M, Luo G, Marchetti P, Cheng Y, Wolf DA. Metabolic targeting of cancer by a ubiquinone uncompetitive inhibitor of mitochondrial complex I. Cell Chem Biol. 2022 Mar 17;29(3):436-450.e15. doi: 10.1016/j.chembiol.2021.11.002. Epub 2021 Nov 30. PMID: 34852219. 6: Li F, Huang C, Lu X, Xiang H, Wang D, Chen Z, Chen J, He H, Yuan X. Identification of the antidepressive properties of C1, a specific inhibitor of Skp2, in mice. Behav Pharmacol. 2021 Feb 1;32(1):62-72. doi: 10.1097/FBP.0000000000000604. PMID: 33416256. 7: Li C, Du L, Ren Y, Liu X, Jiao Q, Cui D, Wen M, Wang C, Wei G, Wang Y, Ji A, Wang Q. SKP2 promotes breast cancer tumorigenesis and radiation tolerance through PDCD4 ubiquitination. J Exp Clin Cancer Res. 2019 Feb 13;38(1):76. doi: 10.1186/s13046-019-1069-3. PMID: 30760284; PMCID: PMC6375223. 8: Wang D, Xu X, Wu Y, Lin Y, Gao M, Hu P, Chen D, Lu X, Chen Z, Wang H, Huang C. SMIP004: A compound with antidepressant-like activities in mouse models. Eur J Pharmacol. 2019 Jan 15;843:260-267. doi: 10.1016/j.ejphar.2018.11.039. Epub 2018 Nov 29. PMID: 30502341. 9: Rico-Bautista E, Zhu W, Kitada S, Ganapathy S, Lau E, Krajewski S, Ramirez J, Bush JA, Yuan Z, Wolf DA. Small molecule-induced mitochondrial disruption directs prostate cancer inhibition via UPR signaling. Oncotarget. 2013 Aug;4(8):1212-29. doi: 10.18632/oncotarget.1130. PMID: 23902736; PMCID: PMC3787152. 10: Rico-Bautista E, Yang CC, Lu L, Roth GP, Wolf DA. Chemical genetics approach to restoring p27Kip1 reveals novel compounds with antiproliferative activity in prostate cancer cells. BMC Biol. 2010 Dec 23;8:153. doi: 10.1186/1741-7007-8-153. PMID: 21182779; PMCID: PMC3025922.