Histidyl-Proline Diketopiperazine Isomers as Multipotent Anti-Alzheimer Drug Candidates

Biomolecules. 2020 May 9;10(5):737. doi: 10.3390/biom10050737.

Abstract

Cyclic dipeptides administered by both parenteral and oral routes are suggested as promising candidates for the treatment of neurodegeneration-related pathologies. In this study, we tested Cyclo (His-Pro) isomers (cHP1-4) for their anti-Alzheimer potential using a differentiated human neuroblastoma cell line (SH-SY5Y) as an Alzheimer's disease (AD) experimental model. The SH-SY5Y cell line was differentiated by the application of all-trans retinoic acid (RA) to obtain mature neuron-like cells. Amyloid-beta 1-42 (1-42) peptides, the main effector in AD, were administered to the differentiated cell cultures to constitute the in vitro disease model. Next, we performed cell viability analyses 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) release assays) to investigate the neuroprotective concentrations of cyclodipeptides using the in vitro AD model. We evaluated acetylcholinesterase (AChE), α- and β-secretase activities (TACE and BACE1), antioxidant potency, and apoptotic/necrotic properties and performed global gene expression analysis to understand the main mechanism behind the neuroprotective features of cHP1-4. Moreover, we conducted sister chromatid exchange (SCE), micronucleus (MN), and 8-hydroxy-2'-deoxyguanosine (8-OHdG) analyses to evaluate the genotoxic damage potential after applications with cHP1-4 on cultured human lymphocytes. Our results revealed that cHP1-4 isomers provide a different degree of neuroprotection against 1-42-induced cell death on the in vitro AD model. The applications with cHP1-4 isomers altered the activity of AChE but not the activity of TACE and BACE1. Our analysis indicated that the cHP1-4 increased the total antioxidant capacity without altering total oxidative status levels in the cellular AD model and that cHP1-4 modulated the alterations of gene expressions by 1-42 exposure. We also observed that cHP1-4 exhibited noncytotoxic and non-genotoxic features in cultured human whole blood cells. In conclusion, cHP1-4 isomers, especially cHP4, have been explored as novel promising therapeutics against AD.

Keywords: Alzheimer’s disease; amyloid-beta 1-42; histidyl-proline diketopiperazine; neuroprotection; novel therapeutics.

MeSH terms

  • 8-Hydroxy-2'-Deoxyguanosine / metabolism
  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / drug therapy*
  • Alzheimer Disease / pathology
  • Amyloid Precursor Protein Secretases / metabolism
  • Amyloid beta-Peptides / toxicity
  • Antioxidants / pharmacology
  • Apoptosis / drug effects
  • Cell Death / drug effects
  • Cell Line, Tumor
  • Gene Expression Regulation / drug effects
  • Humans
  • Isomerism
  • Lymphocytes / drug effects
  • Lymphocytes / metabolism
  • Metaphase / drug effects
  • Mitomycin / pharmacology
  • Models, Biological
  • Necrosis
  • Neurons / drug effects
  • Neurons / metabolism
  • Neurons / pathology
  • Neuroprotection / drug effects
  • Oxidation-Reduction
  • Oxidative Stress / drug effects
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / pharmacology
  • Peptides, Cyclic / therapeutic use*
  • Piperazines / chemistry*
  • Piperazines / pharmacology
  • Piperazines / therapeutic use*

Substances

  • Amyloid beta-Peptides
  • Antioxidants
  • Peptides, Cyclic
  • Piperazines
  • Mitomycin
  • 8-Hydroxy-2'-Deoxyguanosine
  • Acetylcholinesterase
  • Amyloid Precursor Protein Secretases
  • histidyl-proline diketopiperazine