Elamipretide acetate | CAS#1334953-95-5 | Peptide antioxidant

MedKoo Cat#: 464194 | Name: Elamipretide acetate

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Description:

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

Elamipretide, also known as MTP 131, is a mitochondria-targeted peptide antioxidant. Elamipretide treatment during pregnancy ameliorates the progression of polycystic kidney disease in maternal and neonatal mice with PKD1 mutations. Elamipretide (SS-31) treatment attenuates age-associated post-translational modifications of heart proteins.

Chemical Structure

Elamipretide acetate

CAS#1334953-95-5 (acetate)

Theoretical Analysis

MedKoo Cat#: 464194

Name: Elamipretide acetate

CAS#: 1334953-95-5 (acetate)

Chemical Formula: C34H53N9O7

Exact Mass: 699.4068

Molecular Weight: 699.85

Elemental Analysis: C, 58.35; H, 7.63; N, 18.01; O, 16.00

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks
10mg	USD 750.00	2 Weeks

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Related CAS #

736992-21-5 (free base) 1334953-95-5 (acetate) 2244098-12-0 (3HCl)

Synonym

MTP 131 acetate; MTP131 acetate; MTP-131 acetate; Elamipretide acetate; SS-31; SS31; SS 31;

IUPAC/Chemical Name

(S)-6-amino-N-((S)-1-amino-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-((R)-2-amino-5-guanidinopentanamido)-3-(4-hydroxy-2,6-dimethylphenyl)propanamido)hexanamide acetate

InChi Key

UEYRJRBULBAAEG-NFWUDPOKSA-N

InChi Code

InChI=1S/C32H49N9O5.C2H4O2/c1-19-15-22(42)16-20(2)23(19)18-27(41-29(44)24(34)11-8-14-38-32(36)37)31(46)39-25(12-6-7-13-33)30(45)40-26(28(35)43)17-21-9-4-3-5-10-21;1-2(3)4/h3-5,9-10,15-16,24-27,42H,6-8,11-14,17-18,33-34H2,1-2H3,(H2,35,43)(H,39,46)(H,40,45)(H,41,44)(H4,36,37,38);1H3,(H,3,4)/t24-,25+,26+,27+;/m1./s1

SMILES Code

O=C(N)[C@H](CC1=CC=CC=C1)NC([C@H](CCCCN)NC([C@H](CC2=C(C)C=C(O)C=C2C)NC([C@@H](CCCNC(N)=N)N)=O)=O)=O.CC(O)=O

Appearance

Solid powder

Purity

>95% (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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

to be determined

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:

Elamipretide, also known as MTP 131, is a mitochondria-targeted peptide antioxidant.

In vitro activity:

To validate that elamipretide was influencing mitochondrial dynamics in ARPE-19 cells, they were first nucleofected with a plasmid expressing mitoBFP and cultured for 24 h. Cells were then incubated with 1 µM elamipretide or vehicle for 20 h (Additional file 1: Figure S1). By 4 and 7 h, however, cells exposed to elamipretide exhibited a significant increase in mitochondrial volume (P = 0.005 and P = 0.002, respectively) relative to untreated cells. Reference: BMC Res Notes. 2021 May 22;14(1):198. https://pubmed.ncbi.nlm.nih.gov/34022923/

In vivo activity:

This study examined renal superoxide production in a type 2 diabetes animal model, the db/db mouse, and the role of a mitochondrial protectant, MTP-131 (also called elamipretide, SS-31, or Bendavia) in restoring renal superoxide production and ameliorating DKD (diabetic kidney disease). This study found that 18-week-old db/db mice have reduced renal and cardiac superoxide levels, as measured by dihydroethidium oxidation, and increased levels of albuminuria, mesangial matrix accumulation, and urinary H2O2 Administration of MTP-131 significantly inhibited increases in albuminuria, urinary H2O2, and mesangial matrix accumulation in db/db mice and fully preserved levels of renal superoxide production in these mice. MTP-131 also reduced total renal lysocardiolipin and major lysocardiolipin subspecies and preserved lysocardiolipin acyltransferase 1 expression in db/db mice. Reference: J Biol Chem. 2020 May 22;295(21):7249-7260. https://pubmed.ncbi.nlm.nih.gov/32277051/

	Solvent	mg/mL	mM
Solubility
	PBS (pH 7.2)	10.0	14.29

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 699.85 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. Grosser JA, Fehrman RL, Keefe D, Redmon M, Nickells RW. The effects of a mitochondrial targeted peptide (elamipretide/SS31) on BAX recruitment and activation during apoptosis. BMC Res Notes. 2021 May 22;14(1):198. doi: 10.1186/s13104-021-05613-9. PMID: 34022923; PMCID: PMC8141144. 2. Petcherski A, Trudeau KM, Wolf DM, Segawa M, Lee J, Taddeo EP, Deeney JT, Liesa M. Elamipretide Promotes Mitophagosome Formation and Prevents Its Reduction Induced by Nutrient Excess in INS1 β-cells. J Mol Biol. 2018 Dec 7;430(24):4823-4833. doi: 10.1016/j.jmb.2018.10.020. Epub 2018 Oct 30. PMID: 30389435; PMCID: PMC6290358. 3. Miyamoto S, Zhang G, Hall D, Oates PJ, Maity S, Madesh M, Han X, Sharma K. Restoring mitochondrial superoxide levels with elamipretide (MTP-131) protects db/db mice against progression of diabetic kidney disease. J Biol Chem. 2020 May 22;295(21):7249-7260. doi: 10.1074/jbc.RA119.011110. Epub 2020 Apr 10. PMID: 32277051; PMCID: PMC7247302. 4. Zhang H, Chen Y, Li F, Wu C, Cai W, Ye H, Su H, He M, Yang L, Wang X, Zhou K, Ni W. Elamipretide alleviates pyroptosis in traumatically injured spinal cord by inhibiting cPLA2-induced lysosomal membrane permeabilization. J Neuroinflammation. 2023 Jan 7;20(1):6. doi: 10.1186/s12974-023-02690-4. PMID: 36609266; PMCID: PMC9825014.

In vitro protocol:

In vivo protocol:

1. Miyamoto S, Zhang G, Hall D, Oates PJ, Maity S, Madesh M, Han X, Sharma K. Restoring mitochondrial superoxide levels with elamipretide (MTP-131) protects db/db mice against progression of diabetic kidney disease. J Biol Chem. 2020 May 22;295(21):7249-7260. doi: 10.1074/jbc.RA119.011110. Epub 2020 Apr 10. PMID: 32277051; PMCID: PMC7247302. 2. Zhang H, Chen Y, Li F, Wu C, Cai W, Ye H, Su H, He M, Yang L, Wang X, Zhou K, Ni W. Elamipretide alleviates pyroptosis in traumatically injured spinal cord by inhibiting cPLA2-induced lysosomal membrane permeabilization. J Neuroinflammation. 2023 Jan 7;20(1):6. doi: 10.1186/s12974-023-02690-4. PMID: 36609266; PMCID: PMC9825014.

1: Hong S, Ghandriz R, Siddiqi S, Zhu XY, Saadiq IM, Jordan KL, Tang H, Ali KA, Lerman A, Eirin A, Lerman LO. Effects of Elamipretide on Autophagy in Renal Cells of Pigs with Metabolic Syndrome. Cells. 2022 Sep 16;11(18):2891. doi: 10.3390/cells11182891. PMID: 36139466; PMCID: PMC9496989. 2: Hornby B, Thompson WR, Almuqbil M, Manuel R, Abbruscato A, Carr J, Vernon HJ. Natural history comparison study to assess the efficacy of elamipretide in patients with Barth syndrome. Orphanet J Rare Dis. 2022 Sep 2;17(1):336. doi: 10.1186/s13023-022-02469-5. PMID: 36056411; PMCID: PMC9438322. 3: Zhang X, Bowen E, Zhang M, Szeto HH, Deng XH, Rodeo SA. SS-31 as a Mitochondrial Protectant in the Treatment of Tendinopathy: Evaluation in a Murine Supraspinatus Tendinopathy Model. J Bone Joint Surg Am. 2022 Aug 18. doi: 10.2106/JBJS.21.01449. Epub ahead of print. PMID: 35984013. 4: Zhang P, Chen Y, Zhang S, Chen G. Mitochondria-Related Ferroptosis Drives Cognitive Deficits in Neonatal Mice Following Sevoflurane Administration. Front Med (Lausanne). 2022 Jul 22;9:887062. doi: 10.3389/fmed.2022.887062. PMID: 35935755; PMCID: PMC9355652. 5: Mitchell W, Tamucci JD, Ng EL, Liu S, Birk AV, Szeto HH, May ER, Alexandrescu AT, Alder NN. Structure-activity relationships of mitochondria-targeted tetrapeptide pharmacological compounds. Elife. 2022 Aug 1;11:e75531. doi: 10.7554/eLife.75531. PMID: 35913044; PMCID: PMC9342957. 6: Zhang X, Zhang Y, Zhang M, Nakagawa Y, Caballo CB, Szeto HH, Deng XH, Rodeo SA. Evaluation of SS-31 as a Potential Strategy for Tendinopathy Treatment: An In Vitro Model. Am J Sports Med. 2022 Aug;50(10):2805-2816. doi: 10.1177/03635465221107943. Epub 2022 Jul 21. PMID: 35862638. 7: Zheng Z, Lei C, Liu H, Jiang M, Zhou Z, Zhao Y, Yu CY, Wei H. A ROS- Responsive Liposomal Composite Hydrogel Integrating Improved Mitochondrial Function and Pro-Angiogenesis for Efficient Treatment of Myocardial Infarction. Adv Healthc Mater. 2022 Jul 18:e2200990. doi: 10.1002/adhm.202200990. Epub ahead of print. PMID: 35848825. 8: Wang W, Tran PV. Mitochondrial pharmacotherapy during pregnancy and lactation in an ADPKD mouse model: a win for both mothers and their offspring. Kidney Int. 2022 May;101(5):870-872. doi: 10.1016/j.kint.2022.02.008. PMID: 35461611. 9: Whitson JA, Johnson R, Wang L, Bammler TK, Imai SI, Zhang H, Fredrickson J, Latorre-Esteves E, Bitto A, MacCoss MJ, Rabinovitch PS. Age-related disruption of the proteome and acetylome in mouse hearts is associated with loss of function and attenuated by elamipretide (SS-31) and nicotinamide mononucleotide (NMN) treatment. Geroscience. 2022 Jun;44(3):1621-1639. doi: 10.1007/s11357-022-00564-w. Epub 2022 Apr 13. PMID: 35416576; PMCID: PMC9213586. 10: Mason SA, Wadley GD, Keske MA, Parker L. Effect of mitochondrial-targeted antioxidants on glycaemic control, cardiovascular health, and oxidative stress in humans: A systematic review and meta-analysis of randomized controlled trials. Diabetes Obes Metab. 2022 Jun;24(6):1047-1060. doi: 10.1111/dom.14669. Epub 2022 Mar 3. PMID: 35165982; PMCID: PMC9314850. 11: Schwemmlein J, Maack C, Bertero E. Mitochondria as Therapeutic Targets in Heart Failure. Curr Heart Fail Rep. 2022 Apr;19(2):27-37. doi: 10.1007/s11897-022-00539-0. Epub 2022 Feb 11. PMID: 35147851; PMCID: PMC9023431. 12: Nhu NT, Xiao SY, Liu Y, Kumar VB, Cui ZY, Lee SD. Neuroprotective Effects of a Small Mitochondrially-Targeted Tetrapeptide Elamipretide in Neurodegeneration. Front Integr Neurosci. 2022 Jan 17;15:747901. doi: 10.3389/fnint.2021.747901. PMID: 35111001; PMCID: PMC8801496. 13: Obi C, Smith AT, Hughes GJ, Adeboye AA. Targeting mitochondrial dysfunction with elamipretide. Heart Fail Rev. 2022 Sep;27(5):1925-1932. doi: 10.1007/s10741-021-10199-2. Epub 2022 Jan 17. PMID: 35037146. 14: Daneshgar N, Liang PI, Lan RS, Horstmann MM, Pack L, Bhardwaj G, Penniman CM, O'Neill BT, Dai DF. Elamipretide treatment during pregnancy ameliorates the progression of polycystic kidney disease in maternal and neonatal mice with PKD1 mutations. Kidney Int. 2022 May;101(5):906-911. doi: 10.1016/j.kint.2021.12.006. Epub 2021 Dec 22. PMID: 34953771; PMCID: PMC9038630. 15: Alam NM, Douglas RM, Prusky GT. Treatment of age-related visual impairment with a peptide acting on mitochondria. Dis Model Mech. 2022 Mar 1;15(3):dmm048256. doi: 10.1242/dmm.048256. Epub 2022 Feb 21. PMID: 34766182; PMCID: PMC8891924. 16: Shankland SJ, Wang Y, Shaw AS, Vaughan JC, Pippin JW, Wessely O. Podocyte Aging: Why and How Getting Old Matters. J Am Soc Nephrol. 2021 Nov;32(11):2697-2713. doi: 10.1681/ASN.2021050614. PMID: 34716239; PMCID: PMC8806106. 17: Thompson R, Jefferies J, Wang S, Pu WT, Takemoto C, Hornby B, Heyman A, Chin MT, Vernon HJ. Current and future treatment approaches for Barth syndrome. J Inherit Metab Dis. 2022 Jan;45(1):17-28. doi: 10.1002/jimd.12453. Epub 2021 Nov 10. PMID: 34713454. 18: Sabbah HN. Elamipretide for Barth syndrome cardiomyopathy: gradual rebuilding of a failed power grid. Heart Fail Rev. 2022 Sep;27(5):1911-1923. doi: 10.1007/s10741-021-10177-8. Epub 2021 Oct 8. PMID: 34623544; PMCID: PMC9388406. 19: Nashine S. Potential Therapeutic Candidates for Age-Related Macular Degeneration (AMD). Cells. 2021 Sep 19;10(9):2483. doi: 10.3390/cells10092483. PMID: 34572131; PMCID: PMC8464988. 20: Whitson JA, Martín-Pérez M, Zhang T, Gaffrey MJ, Merrihew GE, Huang E, White CC, Kavanagh TJ, Qian WJ, Campbell MD, MacCoss MJ, Marcinek DJ, Villén J, Rabinovitch PS. Elamipretide (SS-31) treatment attenuates age-associated post- translational modifications of heart proteins. Geroscience. 2021 Oct;43(5):2395-2412. doi: 10.1007/s11357-021-00447-6. Epub 2021 Sep 4. PMID: 34480713; PMCID: PMC8599536.