Synthesis and Biological Activity of Novel Neuroprotective Diketopiperazines

Prakash, K. R. C.; Tang, Yanjuan; Kozikowski, Alan P.; Flippen‐Anderson, Judith L.; Knoblach, Susan M.; Faden, Alan I.

doi:10.1016/s0968-0896(02)00132-3

Cited by 48 publications

(26 citation statements)

References 31 publications

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“…This peptide was shown to have many effects on the brain where it is present in much higher concentrations than TRH and to have several properties both related and unrelated to TRH [3,6,35,41,42]. Prakash et al [43] have synthesized two isomeric compounds based on the structure of CHP in which His was replaced by 3,5-di-tert-butyltyrosine. The resulting diketopiperazines prevented neuronal death in an model of traumatic injury suggesting that they may be useful as treatments for neuronal degeneration .…”

Section: Cns Activitymentioning

confidence: 99%

Thyrotropin-Releasing Hormone Analogs

Colson

Gershengorn²

2006

MRMC

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Thyrotropin releasing hormone (TRH: pyroglutamic acid-histidine-prolineamide) regulates the activity of cells in the anterior pituitary and within the central and peripheral nervous systems. TRH, which has been the subject of much research over the past three decades, exerts its effects by acting through class A G-protein coupled receptors. The recent discovery of a second receptor subtype has generated an interest in the discovery of receptor subtype-selective TRH analogs. In this review, we describe advances in the development of TRH analogs and in the understanding of their mechanism of interaction with TRH receptors. We also describe the recent breakthrough in the identification of analogs that bind selectively at TRH-R2.

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Section: Cns Activitymentioning

confidence: 99%

Thyrotropin-Releasing Hormone Analogs

Colson

Gershengorn²

2006

MRMC

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“…Unsurprisingly, their potential for pharmacological use has not escaped attention. [9,10] Since the early 1980s, the energetics (e.g. heats of transfer between the gas, water and/or crystal phases as well as heats of dilution etc.)…”

Section: Introductionmentioning

confidence: 99%

Vibrational spectra and crystal structure of the di‐amino acid peptide cyclo(L‐Met‐L‐Met): comparison of experimental data and DFT calculations

Mendham

Potter

Palmer

et al. 2009

J Raman Spectroscopy

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Experimental Raman and FT-IR spectra of solid-state non-deuterated andN-deuterated samples of cyclo(L-Met-L-Met) are reported and discussed. The Raman and FT-IR results show characteristic amide I vibrations (Raman: 1649 cm −1 , infrared: 1675 cm −1 ) for molecules exhibiting a cis amide conformation. A Raman band, assigned to the cis amide II vibrational mode, is observed at ∼1493 cm −1 but no IR band is observed in this region. Cyclo(L-Met-L-Met) crystallises in the triclinic space group P1 with one molecule per unit cell. The overall shape of the diketopiperazine (DKP) ring displays a (slightly distorted) boat conformation. The crystal packing employs two strong hydrogen bonds, which traverse the entire crystal via translational repeats. B3-LYP/cc-pVDZ calculations of the structure of the molecule predict a boat conformation for the DKP ring, in agreement with the experimentally determined X-ray structure.

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“…Among them are the smallest cyclopeptides, 2,5-diketopiperazines derivatives, which are commonly found as natural products. [5] These compounds exhibit high-affinity binding to a large variety of receptors and show a broad range of biological acitivities, [6] including antimicrobial, antitumoral, antiviral, and neuroprotective effects. 2,5-diketopiperazine derivatives are synthesized in solution or on the solid phase from commercially available and appropriately protected chiral a-amino acids in processes that are usually not atom-economical and generate considerable amounts of waste.…”

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confidence: 99%