Davunetide

• CAT Number: I006402
• CAS Number: 211439-12-2
• Molecular Formula: C36H60N10O12
• Molecular Weight: 824.934
• Purity: ≥95%
• Synonyms: Davunetide; AL 108; AL 208; AL-108; AL-208; H2N-L-Asn-L-Ala-L-Pro-L-Val-L-Ser-L-Ile-L-Pro-L-Gln-COOH; NAP (peptide); NAPVSIPQ.;L-asparaginyl-L-alanyl-L-prolyl-L-valyl-L-seryl-L-isoleucyl-L-prolyl-L-glutamine
• Target: Cytoskeleton
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4°C for short term or -20 °C for long term
• IUPAC Name: (2S)-5-amino-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2,4-diamino-4-oxobutanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoic acid
• InChI: InChI=1S/C36H60N10O12/c1-6-18(4)28(35(56)46-14-8-9-23(46)31(52)41-21(36(57)58)11-12-25(38)48)44-30(51)22(16-47)42-33(54)27(17(2)3)43-32(53)24-10-7-13-45(24)34(55)19(5)40-29(50)20(37)15-26(39)49/h17-24,27-28,47H,6-16,37H2,1-5H3,(H2,38,48)(H2,39,49)(H,40,50)(H,41,52)(H,42,54)(H,43,53)(H,44,51)(H,57,58)/t18-,19-,20-,21-,22-,23-,24-,27-,28-/m0/s1
• InChIKey: DWLTUUXCVGVRAV-XWRHUKJGSA-N
• SMILES: CCC(C)C(C(=O)N1CCCC1C(=O)NC(CCC(=O)N)C(=O)O)NC(=O)C(CO)NC(=O)C(C(C)C)NC(=O)C2CCCN2C(=O)C(C)NC(=O)C(CC(=O)N)N

Davunetide(CAT: I006402) is an eight amino acid peptide (NAPVSIPQ) that has been shown to provide potent neuroprotection, in vitro and in vivo. Davunetide has been shown to increase memory scores in patients suffering from amnestic mild cognitive impairment, a precursor to Alzheimer/’s disease, and to enhance functional daily behaviors in schizophrenia patients.

Reference

1:Davunetide improves spatial learning and memory in Alzheimer/’s disease-associated rats. Zhang J, Wei SY, Yuan L, Kong LL, Zhang SX, Wang ZJ, Wu MN, Qi JS.Physiol Behav. 2017 May 15;174:67-73. doi: 10.1016/j.physbeh.2017.02.038. Epub 2017 Feb 28. PMID: 28257938
2:Impairment of mitochondria dynamics by human A53T α-synuclein and rescue by NAP (davunetide) in a cell model for Parkinson/’s disease. Melo TQ, van Zomeren KC, Ferrari MF, Boddeke HW, Copray JC.Exp Brain Res. 2017 Mar;235(3):731-742. doi: 10.1007/s00221-016-4836-9. Epub 2016 Nov 19. PMID: 27866262 Free PMC Article
3:NAP (davunetide) protects primary hippocampus culture by modulating expression profile of antioxidant genes during limiting oxygen conditions. Arya A, Meena R, Sethy NK, Das M, Sharma M, Bhargava K.Free Radic Res. 2015 Apr;49(4):440-52. doi: 10.3109/10715762.2015.1011153. Epub 2015 Mar 2. PMID: 25727410
4:Intranasal NAP (davunetide) decreases tau hyperphosphorylation and moderately improves behavioral deficits in mice overexpressing α-synuclein. Magen I, Ostritsky R, Richter F, Zhu C, Fleming SM, Lemesre V, Stewart AJ, Morimoto BH, Gozes I, Chesselet MF.Pharmacol Res Perspect. 2014 Oct;2(5):e00065. doi: 10.1002/prp2.65. Epub 2014 Aug 6. PMID: 25505609 Free PMC Article
5:Protein profiling reveals antioxidant and signaling activities of NAP (Davunetide) in rodent hippocampus exposed to hypobaric hypoxia. Sethy NK, Sharma NK, Das M, Bhargava K.J Mol Neurosci. 2014 Nov;54(3):414-29. doi: 10.1007/s12031-014-0381-9. Epub 2014 Jul 20. PMID: 25038875
6:Davunetide in patients with progressive supranuclear palsy: a randomised, double-blind, placebo-controlled phase 2/3 trial. Boxer AL, Lang AE, Grossman M, Knopman DS, Miller BL, Schneider LS, Doody RS, Lees A, Golbe LI, Williams DR, Corvol JC, Ludolph A, Burn D, Lorenzl S, Litvan I, Roberson ED, Höglinger GU, Koestler M, Jack CR Jr, Van Deerlin V, Randolph C, Lobach IV, Heuer HW, Gozes I, Parker L, Whitaker S, Hirman J, Stewart AJ, Gold M, Morimoto BH; AL-108-231 Investigators..Lancet Neurol. 2014 Jul;13(7):676-85. doi: 10.1016/S1474-4422(14)70088-2. Epub 2014 May 27. PMID: 24873720 Free PMC Article
7:Davunetide: Peptide therapeutic in neurological disorders. Magen I, Gozes I.Curr Med Chem. 2014;21(23):2591-8. Review. PMID: 24533805
8:Davunetide (NAP) protects the retina against early diabetic injury by reducing apoptotic death. Scuderi S, D/’Amico AG, Castorina A, Federico C, Marrazzo G, Drago F, Bucolo C, D/’Agata V.J Mol Neurosci. 2014 Nov;54(3):395-404. doi: 10.1007/s12031-014-0244-4. Epub 2014 Feb 2. PMID: 24488575
9:Microtubule-stabilizing peptides and small molecules protecting axonal transport and brain function: focus on davunetide (NAP). Magen I, Gozes I.Neuropeptides. 2013 Dec;47(6):489-95. doi: 10.1016/j.npep.2013.10.011. Epub 2013 Oct 24. Review. PMID: 24210139
10:Davunetide: a review of safety and efficacy data with a focus on neurodegenerative diseases. Morimoto BH, Fox AW, Stewart AJ, Gold M.Expert Rev Clin Pharmacol. 2013 Sep;6(5):483-502. doi: 10.1586/17512433.2013.827403. Epub 2013 Aug 24. Review. PMID: 23971871