PD 150606 | CAS#179528-45-1 | calpain inhibitor

PD 150606
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531245

CAS#: 179528-45-1

Description: PD 150606 is calpain inhibitor. PD150606 protects against ischemia/reperfusion injury by preventing μ-calpain-induced mitochondrial apoptosis. PD150606 attenuates glutamate induced spiral ganglion neuron apoptosis through apoptosis inducing factor pathway in vitro. PD150606) inhibits selective motor neuron death via inhibition of kainate-induced Ca2+ influx and not via calpain inhibition.

Chemical Structure

PD 150606

CAS# 179528-45-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531245
Name: PD 150606
CAS#: 179528-45-1
Chemical Formula: C9H7IO2S
Exact Mass: 305.92
Molecular Weight: 306.118
Elemental Analysis: C, 35.31; H, 2.30; I, 41.46; O, 10.45; S, 10.47

Price and Availability

Size	Price	Availability	Quantity
200mg	USD 950
500mg	USD 1850
1g	USD 2950
2g	USD 3950
5g	USD 6450
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: PD 150606; PD-150606; PD150606.

IUPAC/Chemical Name: 3-(4-iodophenyl)-2Z-mercapto-2-propenoic acid

InChi Key: DJCVSFWGKYHMKH-YVMONPNESA-N

InChi Code: InChI=1S/C9H7IO2S/c10-7-3-1-6(2-4-7)5-8(13)9(11)12/h1-5,13H,(H,11,12)/b8-5-

SMILES Code: O=C(O)/C(S)=C/C1=CC=C(I)C=C1

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:

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Biological target:	PD 150606 is a selective, cell-permeable non-peptide calpain inhibitor with Ki values of 0.21 μM and 0.37 μM.
In vitro activity:	Alpha-mercaptoacrylate derivatives (exemplified by PD150606), with potent and selective inhibitory actions against calpain, have been identified. PD150606 exhibits the following characteristics: (i) Ki values for mu- and m-calpains of 0.21 microM and 0.37 microM, respectively, (ii) high specificity for calpains relative to other proteases, (iii) uncompetitive inhibition with respect to substrate, and (iv) it does not shield calpain against inactivation by the active-site inhibitor trans-(epoxysuccinyl)-L-leucyl-amido-3-methylbutane, suggesting a nonactive site action for PD150606. The recombinant calcium-binding domain from each of the large or small subunits of mu-calpain was found to interact with PD150606. In low micromolar range, PD15O6O6 inhibited calpain activity in two intact cell systems. The neuroprotective effects of this class of compound were also demonstrated by the ability of PD150606 to attenuate hypoxic/hypoglycemic injury to cerebrocortical neurons in culture and excitotoxic injury to Purkinje cells in cerebellar slices. Reference: Proc Natl Acad Sci U S A. 1996 Jun 25;93(13):6687-92. https://pubmed.ncbi.nlm.nih.gov/8692879/
In vivo activity:	In a separate experiment, a pharmacological inhibitor of calpain PD150606 (Biomol, USA, 3 mg/kg/day, i.p.) daily for 30 days was given to mice after bleomycin injection on daily basis. Calpain activities increased in SSc-mouse lungs. Both deletion of Capns1 and administration of PD150606 attenuated dermal sclerosis as evidenced by a reduction of skin thickness and reduced interstitial fibrosis and inflammation in bleomycin model of SSc mice. Reference: Arthritis Res Ther. 2022 Jun 21;24(1):148. https://pubmed.ncbi.nlm.nih.gov/35729674/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	20.0	65.33
	DMSO	26.2	85.60
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.63
	Ethanol	8.7	28.27

Preparing Stock Solutions

The following data is based on the product molecular weight 306.12 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. Luo T, Yue R, Hu H, Zhou Z, Yiu KH, Zhang S, Xu L, Li K, Yu Z. PD150606 protects against ischemia/reperfusion injury by preventing μ-calpain-induced mitochondrial apoptosis. Arch Biochem Biophys. 2015 Nov 15;586:1-9. doi: 10.1016/j.abb.2015.06.005. Epub 2015 Jun 16. PMID: 26091952. 2. Wang KK, Nath R, Posner A, Raser KJ, Buroker-Kilgore M, Hajimohammadreza I, Probert A W Jr, Marcoux FW, Ye Q, Takano E, Hatanaka M, Maki M, Caner H, Collins JL, Fergus A, Lee KS, Lunney EA, Hays SJ, Yuen P. An alpha-mercaptoacrylic acid derivative is a selective nonpeptide cell-permeable calpain inhibitor and is neuroprotective. Proc Natl Acad Sci U S A. 1996 Jun 25;93(13):6687-92. doi: 10.1073/pnas.93.13.6687. PMID: 8692879; PMCID: PMC39087. 3. Zhang L, Zheng D, Yan Y, Yu Y, Chen R, Li Z, Greer PA, Peng T, Wang Q. Myeloid cell-specific deletion of Capns1 prevents macrophage polarization toward the M1 phenotype and reduces interstitial lung disease in the bleomycin model of systemic sclerosis. Arthritis Res Ther. 2022 Jun 21;24(1):148. doi: 10.1186/s13075-022-02833-7. PMID: 35729674; PMCID: PMC9210712. 4. Yamaguchi T, Yoneyama M, Ogita K. Calpain inhibitor alleviates permanent hearing loss induced by intense noise by preventing disruption of gap junction-mediated intercellular communication in the cochlear spiral ligament. Eur J Pharmacol. 2017 May 15;803:187-194. doi: 10.1016/j.ejphar.2017.03.058. Epub 2017 Mar 31. PMID: 28366808.
In vitro protocol:	1. Luo T, Yue R, Hu H, Zhou Z, Yiu KH, Zhang S, Xu L, Li K, Yu Z. PD150606 protects against ischemia/reperfusion injury by preventing μ-calpain-induced mitochondrial apoptosis. Arch Biochem Biophys. 2015 Nov 15;586:1-9. doi: 10.1016/j.abb.2015.06.005. Epub 2015 Jun 16. PMID: 26091952. 2. Wang KK, Nath R, Posner A, Raser KJ, Buroker-Kilgore M, Hajimohammadreza I, Probert A W Jr, Marcoux FW, Ye Q, Takano E, Hatanaka M, Maki M, Caner H, Collins JL, Fergus A, Lee KS, Lunney EA, Hays SJ, Yuen P. An alpha-mercaptoacrylic acid derivative is a selective nonpeptide cell-permeable calpain inhibitor and is neuroprotective. Proc Natl Acad Sci U S A. 1996 Jun 25;93(13):6687-92. doi: 10.1073/pnas.93.13.6687. PMID: 8692879; PMCID: PMC39087.
In vivo protocol:	1. Zhang L, Zheng D, Yan Y, Yu Y, Chen R, Li Z, Greer PA, Peng T, Wang Q. Myeloid cell-specific deletion of Capns1 prevents macrophage polarization toward the M1 phenotype and reduces interstitial lung disease in the bleomycin model of systemic sclerosis. Arthritis Res Ther. 2022 Jun 21;24(1):148. doi: 10.1186/s13075-022-02833-7. PMID: 35729674; PMCID: PMC9210712. 2. Yamaguchi T, Yoneyama M, Ogita K. Calpain inhibitor alleviates permanent hearing loss induced by intense noise by preventing disruption of gap junction-mediated intercellular communication in the cochlear spiral ligament. Eur J Pharmacol. 2017 May 15;803:187-194. doi: 10.1016/j.ejphar.2017.03.058. Epub 2017 Mar 31. PMID: 28366808.

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1: Luo T, Yue R, Hu H, Zhou Z, Yiu KH, Zhang S, Xu L, Li K, Yu Z. PD150606 protects against ischemia/reperfusion injury by preventing μ-calpain-induced mitochondrial apoptosis. Arch Biochem Biophys. 2015 Nov 15;586:1-9. doi: 10.1016/j.abb.2015.06.005. PubMed PMID: 26091952.

2: Ding ZJ, Chen X, Tang XX, Wang X, Song YL, Chen XD, Mi WJ, Wang J, Lin Y, Chen FQ, Qiu JH. Calpain inhibitor PD150606 attenuates glutamate induced spiral ganglion neuron apoptosis through apoptosis inducing factor pathway in vitro. PLoS One. 2015 Apr 15;10(4):e0123130. doi: 10.1371/journal.pone.0123130. PubMed PMID: 25874633; PubMed Central PMCID: PMC4398365.

3: Low KE, Karunan Partha S, Davies PL, Campbell RL. Allosteric inhibitors of calpains: Reevaluating inhibition by PD150606 and LSEAL. Biochim Biophys Acta. 2014 Dec;1840(12):3367-73. doi: 10.1016/j.bbagen.2014.08.014. PubMed PMID: 25196359.

4: Farkas B, Tantos A, Schlett K, Világi I, Friedrich P. Ischemia-induced increase in long-term potentiation is warded off by specific calpain inhibitor PD150606. Brain Res. 2004 Oct 22;1024(1-2):150-8. PubMed PMID: 15451377.

5: Chatterjee PK, Todorovic Z, Sivarajah A, Mota-Filipe H, Brown PA, Stewart KN, Mazzon E, Cuzzocrea S, Thiemermann C. Inhibitors of calpain activation (PD150606 and E-64) and renal ischemia-reperfusion injury. Biochem Pharmacol. 2005 Apr 1;69(7):1121-31. PubMed PMID: 15763548.

6: Xu W, Yao K, Wang KJ, Wu RY, Sun ZH. [Prevention of oxidative cataract by PD150606 - an inhibitor of calpains]. Zhonghua Yan Ke Za Zhi. 2003 Jul;39(7):400-5. Chinese. PubMed PMID: 12921669.

7: Weijun T, Zhenshun C, Qiuyue T, Ting W, Min L, Li Z. [Transforming growth factor-β1 induces epithelial-mesenchymal transition in A549 cells by up-regulating expression of calpain]. Zhonghua Jie He He Hu Xi Za Zhi. 2015 Mar;38(3):202-5. Chinese. PubMed PMID: 26269309.

8: Van den Bosch L, Van Damme P, Vleminckx V, Van Houtte E, Lemmens G, Missiaen L, Callewaert G, Robberecht W. An alpha-mercaptoacrylic acid derivative (PD150606) inhibits selective motor neuron death via inhibition of kainate-induced Ca2+ influx and not via calpain inhibition. Neuropharmacology. 2002 Apr;42(5):706-13. PubMed PMID: 11985829.

9: Ali MA, Stepanko A, Fan X, Holt A, Schulz R. Calpain inhibitors exhibit matrix metalloproteinase-2 inhibitory activity. Biochem Biophys Res Commun. 2012 Jun 22;423(1):1-5. doi: 10.1016/j.bbrc.2012.05.005. PubMed PMID: 22575511.

10: Roseblade A, Luk F, Ung A, Bebawy M. Targeting microparticle biogenesis: a novel approach to the circumvention of cancer multidrug resistance. Curr Cancer Drug Targets. 2015;15(3):205-14. PubMed PMID: 25714701.

11: Shang K, Zhang J, Amna T, Yang J, Cheng X, Zhang C, Hwang I. Attenuation of cellular toxicity by calpain inhibitor induced by bacterial endotoxin: a mechanistic study using muscle precursor cells as a model system. Mol Biol Rep. 2015 Aug;42(8):1281-8. doi: 10.1007/s11033-015-3869-7. PubMed PMID: 25813209.

12: Shenkman BS, Belova SP, Lomonosova YN, Kostrominova TY, Nemirovskaya TL. Calpain-dependent regulation of the skeletal muscle atrophy following unloading. Arch Biochem Biophys. 2015 Oct 15;584:36-41. doi: 10.1016/j.abb.2015.07.011. PubMed PMID: 26297661.

13: Colunga A, Bollino D, Schech A, Aurelian L. Calpain-dependent clearance of the autophagy protein p62/SQSTM1 is a contributor to ΔPK oncolytic activity in melanoma. Gene Ther. 2014 Apr;21(4):371-8. doi: 10.1038/gt.2014.6. PubMed PMID: 24553345; PubMed Central PMCID: PMC3975656.

14: Yamaguchi T, Yoneyama M, Hinoi E, Ogita K. Involvement of calpain in 4-hydroxynonenal-induced disruption of gap junction-mediated intercellular communication among fibrocytes in primary cultures derived from the cochlear spiral ligament. J Pharmacol Sci. 2015 Oct;129(2):127-34. doi: 10.1016/j.jphs.2015.09.005. PubMed PMID: 26499182.

15: Chang H, Sheng JJ, Zhang L, Yue ZJ, Jiao B, Li JS, Yu ZB. ROS-Induced Nuclear Translocation of Calpain-2 Facilitates Cardiomyocyte Apoptosis in Tail-Suspended Rats. J Cell Biochem. 2015 Oct;116(10):2258-69. doi: 10.1002/jcb.25176. PubMed PMID: 25820554.

16: Rothe J, Wakileh M, Dreißiger K, Weber H. The flavonoid beverage Haelan 951 induces growth arrest and apoptosis in pancreatic carcinoma cell lines in vitro. BMC Complement Altern Med. 2015 Jul 3;15:212. doi: 10.1186/s12906-015-0734-0. PubMed PMID: 26138287; PubMed Central PMCID: PMC4490641.

17: Li H, Nepal RM, Martin A, Berger SA. Induction of apoptosis in Eμ-myc lymphoma cells in vitro and in vivo through calpain inhibition. Exp Hematol. 2012 Jul;40(7):548-563.e2. doi: 10.1016/j.exphem.2012.02.002. PubMed PMID: 22366408.

18: Hossain S, Liu HN, Fragoso G, Almazan G. Agonist-induced down-regulation of AMPA receptors in oligodendrocyte progenitors. Neuropharmacology. 2014 Apr;79:506-14. doi: 10.1016/j.neuropharm.2013.12.020. PubMed PMID: 24412648.

19: Li X, Luo R, Chen R, Song L, Zhang S, Hua W, Chen H. Cleavage of IκBα by calpain induces myocardial NF-κB activation, TNF-α expression, and cardiac dysfunction in septic mice. Am J Physiol Heart Circ Physiol. 2014 Mar;306(6):H833-43. doi: 10.1152/ajpheart.00893.2012. PubMed PMID: 24441549.

20: Chang H, Zhang L, Xu PT, Li Q, Sheng JJ, Wang YY, Chen Y, Zhang LN, Yu ZB. Nuclear translocation of calpain-2 regulates propensity toward apoptosis in cardiomyocytes of tail-suspended rats. J Cell Biochem. 2011 Feb;112(2):571-80. doi: 10.1002/jcb.22947. PubMed PMID: 21268078.

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PD 150606 featured