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MedKoo Cat#: 597868 | Name: Goralatide

Description:

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

Goralatide is isolated from fetal calf bone marrow; exerts a high inhibitory activity on the proliferation of hematopoietic pluripotent stem cells.

Chemical Structure

Goralatide
Goralatide
CAS#120081-14-3

Theoretical Analysis

MedKoo Cat#: 597868

Name: Goralatide

CAS#: 120081-14-3

Chemical Formula: C20H33N5O9

Exact Mass: 487.2278

Molecular Weight: 487.51

Elemental Analysis: C, 49.27; H, 6.82; N, 14.37; O, 29.54

Price and Availability

Related CAS #
No Data
Synonym
Goralatide;
IUPAC/Chemical Name
acetyl-L-seryl-L-aspartyl-L-lysyl-L-proline
InChi Key
HJDRXEQUFWLOGJ-AJNGGQMLSA-N
InChi Code
InChI=1S/C20H33N5O9/c1-11(27)22-14(10-26)18(31)24-13(9-16(28)29)17(30)23-12(5-2-3-7-21)19(32)25-8-4-6-15(25)20(33)34/h12-15,26H,2-10,21H2,1H3,(H,22,27)(H,23,30)(H,24,31)(H,28,29)(H,33,34)/t12-,13-,14-,15-/m0/s1
SMILES Code
O=C(O)[C@H]1N(C([C@H](CCCCN)NC([C@H](CC(O)=O)NC([C@H](CO)NC(C)=O)=O)=O)=O)CCC1
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 487.51 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: Li Z, Lebedyeva I, Zhao D, Myers L, Pillai GG, Hall CD, Katritzky AR. Synthesis of L-Lys-Aminoxy-Goralatide. J Pept Sci. 2014 Dec;20(12):923-7. doi: 10.1002/psc.2702. Epub 2014 Oct 20. PubMed PMID: 25331328. 2: Li Z, Lebedyeva IO, Golubovskaya VM, Cance WG, Alamry KA, Faidallah HM, Dennis Hall C, Katritzky AR. Synthesis and bioactivity of a Goralatide analog with antileukemic activity. Bioorg Med Chem. 2015 Aug 1;23(15):5056-60. doi: 10.1016/j.bmc.2015.04.061. Epub 2015 May 14. PubMed PMID: 26048023. 3: Bogden AE, Moreau JP, Gamba-Vitalo C, Deschamps de Paillette E, Tubiana M, Frindel E, Carde P. Goralatide (AcSDKP), a negative growth regulator, protects the stem cell compartment during chemotherapy, enhancing the myelopoietic response to GM-CSF. Int J Cancer. 1998 Mar 30;76(1):38-46. PubMed PMID: 9533760. 4: Wierenga PK, Konings AW. Goralatide (AcSDKP) selectively protects murine hematopoietic progenitors and stem cells against hyperthermic damage. Exp Hematol. 1996 Feb;24(2):246-52. PubMed PMID: 8641348. 5: Wierenga PK, Dillingh JH, Konings AW. Reduction of heat-induced haemotoxicity in a hyperthermic purging protocol of murine acute myeloid leukaemic stem cells by AcSDKP. Br J Haematol. 1997 Dec;99(3):692-8. PubMed PMID: 9401086. 6: Comte L, Lorgeot V, Bignon J, Volkov L, Dupuis F, Wdzieczak-Bakala J, Praloran V. In vivo modifications of AcSDKP metabolism and haematopoiesis in mice treated with 5-fluorouracil and Goralatide. Eur J Clin Invest. 1998 Oct;28(10):856-63. PubMed PMID: 9793000. 7: Wierenga PK, Brenner MK, Konings AW. Enhanced selectivity of hyperthermic purging of human progenitor cells using Goralatide, an inhibitor of cell cycle progression. Bone Marrow Transplant. 1998 Jan;21(1):73-8. PubMed PMID: 9486498. 8: Cappelaere P, Hecquet B, Rolland F, Meeus L, Domenge C, Krakowski I, De Gislain C, Chauvergne J, Dufour-Esquerré F, Carde P. [Randomized placebo trial of myeloprotection with goralatide in patients with squamous cell carcinoma of the upper respiratory and digestive tracts or esophagus, treated with a carboplatin-fluorouracil combination]. Bull Cancer. 1995 Sep;82(9):732-7. French. PubMed PMID: 8535033. 9: Massé A, Ramirez LH, Bindoula G, Grillon C, Wdzieczak-Bakala J, Raddassi K, Deschamps de Paillette E, Mencia-Huerta JM, Koscielny S, Potier P, Sainteny F, Carde P. The tetrapeptide acetyl-N-Ser-Asp-Lys-Pro (Goralatide) protects from doxorubicin-induced toxicity: improvement in mice survival and protection of bone marrow stem cells and progenitors. Blood. 1998 Jan 15;91(2):441-9. PubMed PMID: 9427696. 10: Hrenak J, Paulis L, Simko F. N-acetyl-seryl-aspartyl-lysyl-proline (Ac-SDKP): Potential target molecule in research of heart, kidney and brain. Curr Pharm Des. 2015;21(35):5135-43. Review. PubMed PMID: 26350537. 11: Worou ME, Liao TD, D'Ambrosio M, Nakagawa P, Janic B, Peterson EL, Rhaleb NE, Carretero OA. Renal protective effect of N-acetyl-seryl-aspartyl-lysyl-proline in dahl salt-sensitive rats. Hypertension. 2015 Oct;66(4):816-22. doi: 10.1161/HYPERTENSIONAHA.115.05970. PubMed PMID: 26324505; PubMed Central PMCID: PMC4658233. 12: Srivastava SP, Shi S, Kanasaki M, Nagai T, Kitada M, He J, Nakamura Y, Ishigaki Y, Kanasaki K, Koya D. Effect of Antifibrotic MicroRNAs Crosstalk on the Action of N-acetyl-seryl-aspartyl-lysyl-proline in Diabetes-related Kidney Fibrosis. Sci Rep. 2016 Jul 18;6:29884. doi: 10.1038/srep29884. PubMed PMID: 27425816; PubMed Central PMCID: PMC4947922. 13: Nitta K, Shi S, Nagai T, Kanasaki M, Kitada M, Srivastava SP, Haneda M, Kanasaki K, Koya D. Oral Administration of N-Acetyl-seryl-aspartyl-lysyl-proline Ameliorates Kidney Disease in Both Type 1 and Type 2 Diabetic Mice via a Therapeutic Regimen. Biomed Res Int. 2016;2016:9172157. doi: 10.1155/2016/9172157. Epub 2016 Mar 20. PubMed PMID: 27088094; PubMed Central PMCID: PMC4818806. 14: Nagai T, Nitta K, Kanasaki M, Koya D, Kanasaki K. The biological significance of angiotensin-converting enzyme inhibition to combat kidney fibrosis. Clin Exp Nephrol. 2015 Feb;19(1):65-74. doi: 10.1007/s10157-014-1000-3. Epub 2014 Jul 1. Review. PubMed PMID: 24975544. 15: Masuyer G, Douglas RG, Sturrock ED, Acharya KR. Structural basis of Ac-SDKP hydrolysis by Angiotensin-I converting enzyme. Sci Rep. 2015 Sep 25;5:13742. doi: 10.1038/srep13742. PubMed PMID: 26403559; PubMed Central PMCID: PMC4585900. 16: Sharp S, Poglitsch M, Zilla P, Davies NH, Sturrock ED. Pharmacodynamic effects of C-domain-specific ACE inhibitors on the renin-angiotensin system in myocardial infarcted rats. J Renin Angiotensin Aldosterone Syst. 2015 Dec;16(4):1149-58. doi: 10.1177/1470320314568438. Epub 2015 Mar 9. PubMed PMID: 25757657. 17: Mei Wang PH, Andrade MC, Quinto BM, Di Marco G, Mortara RA, Vio CP, Casarini DE. N-domain angiotensin-I converting enzyme is expressed in immortalized mesangial, proximal tubule and collecting duct cells. Int J Biol Macromol. 2015 Jan;72:380-90. doi: 10.1016/j.ijbiomac.2014.07.043. Epub 2014 Sep 1. PubMed PMID: 25193099. 18: Mnguni AT, Engel ME, Borkum MS, Mayosi BM. The Effects of Angiotensin Converting Enzyme Inhibitors (ACE-I) on Human N-Acetyl-Seryl-Aspartyl-Lysyl-Proline (Ac-SDKP) Levels: A Systematic Review and Meta-Analysis. PLoS One. 2015 Dec 11;10(12):e0143338. doi: 10.1371/journal.pone.0143338. eCollection 2015. Review. PubMed PMID: 26656271; PubMed Central PMCID: PMC4686106. 19: Chan GC, Yiu WH, Wu HJ, Wong DW, Lin M, Huang XR, Lan HY, Tang SC. N-Acetyl-seryl-aspartyl-lysyl-proline Alleviates Renal Fibrosis Induced by Unilateral Ureteric Obstruction in BALB/C Mice. Mediators Inflamm. 2015;2015:283123. doi: 10.1155/2015/283123. Epub 2015 Oct 5. PubMed PMID: 26508815; PubMed Central PMCID: PMC4609855. 20: Liao TD, Nakagawa P, Janic B, D'Ambrosio M, Worou ME, Peterson EL, Rhaleb NE, Yang XP, Carretero OA. N-Acetyl-Seryl-Aspartyl-Lysyl-Proline: mechanisms of renal protection in mouse model of systemic lupus erythematosus. Am J Physiol Renal Physiol. 2015 May 15;308(10):F1146-54. doi: 10.1152/ajprenal.00039.2015. Epub 2015 Mar 4. PubMed PMID: 25740596; PubMed Central PMCID: PMC4436999.

View History

Scillabiose

Scillabiose