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MedKoo Cat#: 330166 | Name: Cenupatide free base

Description:

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

Cenupatide is an urokinase plasminogen activator receptor (uPAR) inhibitor drug candidate. Cenupatide inhibits uPAR binding to the formyl peptide receptors (FPRs) can improve kidney lesions in a rat model of streptozotocin (STZ)-induced diabetes. Cenupatide was found to revert STZ-induced up-regulation of uPA levels and activity, while uPAR on podocytes and (s)uPAR were unaffected. In glomeruli, Cenupatide inhibited FPR2 expression suggesting that the drug may act downstream uPAR, and recovered the increased activity of the αvβ3 integrin/Rac-1 pathway indicating a major role of uPAR in regulating podocyte function.

Chemical Structure

Cenupatide free base
Cenupatide free base
CAS#1006388-38-0 (free base)

Theoretical Analysis

MedKoo Cat#: 330166

Name: Cenupatide free base

CAS#: 1006388-38-0 (free base)

Chemical Formula: C28H47N11O5

Exact Mass: 617.3762

Molecular Weight: 617.76

Elemental Analysis: C, 54.44; H, 7.67; N, 24.94; O, 12.95

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
1006388-38-0 (free base) unknown (TFA)
Synonym
Cenupatide free base, Cenupatide; Ac-Arg-Aib-Arg-α(Me)Phe-NH2); UPARANT;
IUPAC/Chemical Name
(S)-2-acetamido-N-(1-(((S)-1-(((S)-1-amino-2-methyl-1-oxo-3-phenylpropan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)amino)-2-methyl-1-oxopropan-2-yl)-5-guanidinopentanamide
InChi Key
JDNFBDNDFFJJIB-JVAKCPTJSA-N
InChi Code
InChI=1S/C28H47N11O5/c1-17(40)36-19(12-8-14-34-25(30)31)21(41)38-27(2,3)24(44)37-20(13-9-15-35-26(32)33)22(42)39-28(4,23(29)43)16-18-10-6-5-7-11-18/h5-7,10-11,19-20H,8-9,12-16H2,1-4H3,(H2,29,43)(H,36,40)(H,37,44)(H,38,41)(H,39,42)(H4,30,31,34)(H4,32,33,35)/t19-,20-,28-/m0/s1
SMILES Code
O=C(NC(C)(C)C(N[C@@H](CCCNC(N)=N)C(N[C@](CC1=CC=CC=C1)(C)C(N)=O)=O)=O)[C@@H](NC(C)=O)CCCNC(N)=N
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 617.76 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
1: Dal Monte M, Cammalleri M, Pecci V, Carmosino M, Procino G, Pini A, De Rosa M, Pavone V, Svelto M, Bagnoli P. Inhibiting the urokinase-type plasminogen activator receptor system recovers STZ-induced diabetic nephropathy. J Cell Mol Med. 2018 Nov 13. doi: 10.1111/jcmm.14004. [Epub ahead of print] PubMed PMID: 30426662. 2: Cammalleri M, Dal Monte M, Locri F, Marsili S, Lista L, De Rosa M, Pavone V, Rusciano D, Bagnoli P. Diabetic Retinopathy in the Spontaneously Diabetic Torii Rat: Pathogenetic Mechanisms and Preventive Efficacy of Inhibiting the Urokinase-Type Plasminogen Activator Receptor System. J Diabetes Res. 2017;2017:2904150. doi: 10.1155/2017/2904150. Epub 2017 Dec 31. PubMed PMID: 29464181; PubMed Central PMCID: PMC5804371. 3: Cammalleri M, Locri F, Marsili S, Dal Monte M, Pisano C, Mancinelli A, Lista L, Rusciano D, De Rosa M, Pavone V, Bagnoli P. The Urokinase Receptor-Derived Peptide UPARANT Recovers Dysfunctional Electroretinogram and Blood-Retinal Barrier Leakage in a Rat Model of Diabetes. Invest Ophthalmol Vis Sci. 2017 Jun 1;58(7):3138-3148. doi: 10.1167/iovs.17-21593. PubMed PMID: 28632880. 4: Boccella S, Panza E, Lista L, Belardo C, Ianaro A, De Rosa M, de Novellis V, Pavone V. Preclinical evaluation of the urokinase receptor-derived peptide UPARANT as an anti-inflammatory drug. Inflamm Res. 2017 Aug;66(8):701-709. doi: 10.1007/s00011-017-1051-5. Epub 2017 Apr 29. PubMed PMID: 28456844. 5: Rezzola S, Corsini M, Chiodelli P, Cancarini A, Nawaz IM, Coltrini D, Mitola S, Ronca R, Belleri M, Lista L, Rusciano D, De Rosa M, Pavone V, Semeraro F, Presta M. Inflammation and N-formyl peptide receptors mediate the angiogenic activity of human vitreous humour in proliferative diabetic retinopathy. Diabetologia. 2017 Apr;60(4):719-728. doi: 10.1007/s00125-016-4204-0. Epub 2017 Jan 13. PubMed PMID: 28083635. 6: Motta C, Lupo G, Rusciano D, Olivieri M, Lista L, De Rosa M, Pavone V, Anfuso CD. Molecular Mechanisms Mediating Antiangiogenic Action of the Urokinase Receptor-Derived Peptide UPARANT in Human Retinal Endothelial Cells. Invest Ophthalmol Vis Sci. 2016 Oct 1;57(13):5723-5735. doi: 10.1167/iovs.16-19909. PubMed PMID: 27787560. 7: Cammalleri M, Dal Monte M, Locri F, Lista L, Aronsson M, Kvanta A, Rusciano D, De Rosa M, Pavone V, André H, Bagnoli P. The Urokinase Receptor-Derived Peptide UPARANT Mitigates Angiogenesis in a Mouse Model of Laser-Induced Choroidal Neovascularization. Invest Ophthalmol Vis Sci. 2016 May 1;57(6):2600–2611. doi: 10.1167/iovs.15-18758. Erratum in: Invest Ophthalmol Vis Sci. 2016 Jul 1;57(8):3891. PubMed PMID: 27168367. 8: Dal Monte M, Rezzola S, Cammalleri M, Belleri M, Locri F, Morbidelli L, Corsini M, Paganini G, Semeraro F, Cancarini A, Rusciano D, Presta M, Bagnoli P. Antiangiogenic Effectiveness of the Urokinase Receptor-Derived Peptide UPARANT in a Model of Oxygen-Induced Retinopathy. Invest Ophthalmol Vis Sci. 2015 Apr;56(4):2392-407. doi: 10.1167/iovs.14-16323. PubMed PMID: 25766585. 9: Carriero MV, Bifulco K, Minopoli M, Lista L, Maglio O, Mele L, Di Carluccio G, De Rosa M, Pavone V. UPARANT: a urokinase receptor-derived peptide inhibitor of VEGF-driven angiogenesis with enhanced stability and in vitro and in vivo potency. Mol Cancer Ther. 2014 May;13(5):1092-104. doi: 10.1158/1535-7163.MCT-13-0949. Epub 2014 Apr 4. PubMed PMID: 24705350.