SMIP004 | CAS#143360-00-3

SMIP004
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 406809

CAS#: 143360-00-3

Description: 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

CAS# 143360-00-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406809
Name: SMIP004
CAS#: 143360-00-3
Chemical Formula: C13H19NO
Exact Mass: 205.15
Molecular Weight: 205.301
Elemental Analysis: C, 76.06; H, 9.33; N, 6.82; O, 7.79

Price and Availability

Size	Price	Availability
10mg	USD 500	2 Weeks
50mg	USD 1550	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	20.5	100.00

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.

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.

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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.
PubMed PMID: 23902736; PubMed Central 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.
PubMed PMID: 21182779; PubMed Central PMCID: PMC3025922.

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