IPA-3 | CAS#42521-82-4 | PAK1 inhibitor

IPA-3
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 407179

CAS#: 42521-82-4

Description: IPA-3 is a potent and selective PAK1 inhibitor. IPA-3 inhibits the growth of liver cancer cells by suppressing PAK1 and NF-κB activation. IPA-3 treatment significantly inhibited the growth of HCC cells. The mechanisms through which IPA-3 treatment suppresses HCC cell growth are enhancement of apoptosis and blockage of activation of NF-κB. IPA-3 not only inhibits the HCC cell growth, but also suppresses the metastatic potential of HCC cells. Nude mouse xenograft assay demonstrated that IPA-3 treatment significantly reduced the tumor growth rate and decreased tumor volume, indicating that IPA-3 can suppress the in vivo tumor growth of HCC cells. Hepatocellular carcinoma (HCC) is one of the major malignancies worldwide and is associated with poor prognosis due to the high incidences of metastasis and tumor recurrence. Overexpression of p21-activated protein kinase 1 (PAK1) is frequently observed in HCC and is associated with a more aggressive tumor behavior, suggesting that PAK1 is a potential therapeutic target in HCC.

Chemical Structure

IPA-3

CAS# 42521-82-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407179
Name: IPA-3
CAS#: 42521-82-4
Chemical Formula: C20H14O2S2
Exact Mass: 350.04
Molecular Weight: 350.450
Elemental Analysis: C, 68.55; H, 4.03; O, 9.13; S, 18.30

Price and Availability

Size	Price	Availability
10mg	USD 285	2 Weeks
25mg	USD 500	2 Weeks
50mg	USD 850	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: IPA-3; IPA 3; IPA3.

IUPAC/Chemical Name: 1,1'-disulfanediylbis(naphthalen-2-ol)

InChi Key: RFAXLXKIAKIUDT-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H14O2S2/c21-17-11-9-13-5-1-3-7-15(13)19(17)23-24-20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H

SMILES Code: OC1=CC=C2C=CC=CC2=C1SSC3=C4C=CC=CC4=CC=C3O

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, 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).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

Instruction:

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Biological target:	IPA-3 is a selective non-ATP competitive PAK1 inhibitor with IC50 of 2.5 μM, and shows no inhibition to group II PAKs (PAKs 4-6).
In vitro activity:	IPA‐3 suppressed the proliferation of MEC‐1 in a dose‐dependent manner (Fig. S3A). Of note, IPA‐3 suppressed the viability of ibrutinib‐resistant cells (MEC‐1R) in the same manner (Fig. 6A). Annexin V and PI staining was then performed to investigate whether IPA‐3 triggered cell apoptosis. Incubation of MEC‐1R cells with higher doses of IPA‐3 led to a higher percentage of apoptotic cells, suggesting that cells underwent apoptosis under IPA‐3 treatment (Fig. 6B,C). Reference: Mol Oncol. 2022 Aug;16(16):2920-2935. https://pubmed.ncbi.nlm.nih.gov/35811334/
In vivo activity:	Twice-weekly administration of SSL-IPA3 (5 mg/kg) inhibited the growth of PC-3 tumor xenografts compared with that in the control group (Fig. 1A-C). Reference: Oncol Lett. 2020 Nov;20(5):179. https://pubmed.ncbi.nlm.nih.gov/32934746/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	5.0	14.27
	DMF:PBS (pH 7.2) (1:4)	0.2	0.57
	DMSO	35.7	101.98
	Ethanol	7.0	19.97

Preparing Stock Solutions

The following data is based on the product molecular weight 350.45 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. Wu Z, Wang L, Fan L, Tang H, Zuo X, Gu D, Lu X, Li Y, Wu J, Qin S, Xia Y, Zhu H, Wang L, Xu W, Li J, Jin H. Exploring the significance of PAK1 through chromosome conformation signatures in ibrutinib-resistant chronic lymphocytic leukaemia. Mol Oncol. 2022 Aug;16(16):2920-2935. doi: 10.1002/1878-0261.13281. Epub 2022 Jul 22. PMID: 35811334; PMCID: PMC9394240. 2. Li H, Li T, Zou W, Ni M, Hu Q, Qiu X, Yao Z, Fan J, Li L, Huang Q, Zhou R. IPA-3: An Inhibitor of Diadenylate Cyclase of Streptococcus suis with Potent Antimicrobial Activity. Antibiotics (Basel). 2022 Mar 21;11(3):418. doi: 10.3390/antibiotics11030418. PMID: 35326881; PMCID: PMC8944544. 3. Verma A, Najahi-Missaoui W, Cummings BS, Somanath PR. Sterically stabilized liposomes targeting P21 (RAC1) activated kinase-1 and secreted phospholipase A2 suppress prostate cancer growth and metastasis. Oncol Lett. 2020 Nov;20(5):179. doi: 10.3892/ol.2020.12040. Epub 2020 Aug 31. PMID: 32934746; PMCID: PMC7471734. 4. Møller LLV, Jaurji M, Kjøbsted R, Joseph GA, Madsen AB, Knudsen JR, Lundsgaard AM, Andersen NR, Schjerling P, Jensen TE, Krauss RS, Richter EA, Sylow L. Insulin-stimulated glucose uptake partly relies on p21-activated kinase (PAK)2, but not PAK1, in mouse skeletal muscle. J Physiol. 2020 Dec;598(23):5351-5377. doi: 10.1113/JP280294. Epub 2020 Sep 17. PMID: 32844438; PMCID: PMC7771197.
In vitro protocol:	1. Wu Z, Wang L, Fan L, Tang H, Zuo X, Gu D, Lu X, Li Y, Wu J, Qin S, Xia Y, Zhu H, Wang L, Xu W, Li J, Jin H. Exploring the significance of PAK1 through chromosome conformation signatures in ibrutinib-resistant chronic lymphocytic leukaemia. Mol Oncol. 2022 Aug;16(16):2920-2935. doi: 10.1002/1878-0261.13281. Epub 2022 Jul 22. PMID: 35811334; PMCID: PMC9394240. 2. Li H, Li T, Zou W, Ni M, Hu Q, Qiu X, Yao Z, Fan J, Li L, Huang Q, Zhou R. IPA-3: An Inhibitor of Diadenylate Cyclase of Streptococcus suis with Potent Antimicrobial Activity. Antibiotics (Basel). 2022 Mar 21;11(3):418. doi: 10.3390/antibiotics11030418. PMID: 35326881; PMCID: PMC8944544.
In vivo protocol:	1. Verma A, Najahi-Missaoui W, Cummings BS, Somanath PR. Sterically stabilized liposomes targeting P21 (RAC1) activated kinase-1 and secreted phospholipase A2 suppress prostate cancer growth and metastasis. Oncol Lett. 2020 Nov;20(5):179. doi: 10.3892/ol.2020.12040. Epub 2020 Aug 31. PMID: 32934746; PMCID: PMC7471734. 2. Møller LLV, Jaurji M, Kjøbsted R, Joseph GA, Madsen AB, Knudsen JR, Lundsgaard AM, Andersen NR, Schjerling P, Jensen TE, Krauss RS, Richter EA, Sylow L. Insulin-stimulated glucose uptake partly relies on p21-activated kinase (PAK)2, but not PAK1, in mouse skeletal muscle. J Physiol. 2020 Dec;598(23):5351-5377. doi: 10.1113/JP280294. Epub 2020 Sep 17. PMID: 32844438; PMCID: PMC7771197.

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1: Ji X, Zhang W, Zhang L, Zhang L, Zhang Y, Tang P. Inhibition of p21-activated
kinase 1 by IPA-3 attenuates secondary injury after traumatic brain injury in
mice. Brain Res. 2014 Oct 17;1585:13-22. doi: 10.1016/j.brainres.2014.08.026.
Epub 2014 Aug 20. PubMed PMID: 25148711.

2: Kuželová K, Grebeňová D, Holoubek A, Röselová P, Obr A. Group I PAK inhibitor
IPA-3 induces cell death and affects cell adhesivity to fibronectin in human
hematopoietic cells. PLoS One. 2014 Mar 24;9(3):e92560. doi:
10.1371/journal.pone.0092560. eCollection 2014. PubMed PMID: 24664099; PubMed
Central PMCID: PMC3963893.

3: Wong LL, Lam IP, Wong TY, Lai WL, Liu HF, Yeung LL, Ching YP. IPA-3 inhibits
the growth of liver cancer cells by suppressing PAK1 and NF-κB activation. PLoS
One. 2013 Jul 19;8(7):e68843. doi: 10.1371/journal.pone.0068843. Print 2013.
PubMed PMID: 23894351; PubMed Central PMCID: PMC3716906.

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