NNZ-2591, a novel diketopiperazine, prevented scopolamine-induced acute memory impairment in the adult rat

Guan, Jian; Zhang, Rong; Dale-Gandar, Linden; Hodgkinson, S. C.; Vickers, Mark H.

doi:10.1016/j.bbr.2010.02.039

Cited by 25 publications

(16 citation statements)

References 35 publications

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“…Products were purified by column chromatography and packed with silica gel of 230-400 mesh. Scanning electron microscopy (SEM, EVO18 Ziess) was used for morphological analysis of F-CD-BF 4 and Selectfluor. UV-visible spectra were recorded by UV-visible spectrophotometer (Varian Cary 4000).…”

Section: Methodsmentioning

confidence: 99%

“…The asymmetric version of reaction is also explored with new chiral N-fluoro quaternary ammonium salt of cinchonidine (1e; F-CD-BF 4 , Figure 2). As per limited reports, F-CD-BF 4 and Selectfluor have been reagent of choice for electrophilic fluorination. [23][24][25][26] The only example pertains to Selectfluor-mediated allystannation of aldehydes and imines was studied by Wong in 2002.…”

Section: Introductionmentioning

confidence: 96%

“…Stereoselective allylation of imines and aldehydes is the common building block for chiral organic compounds in agrochemicals and pharmaceutical . For instance, chiral homoallylic amines are the synthetic intermediate of naturally occurring compounds and chiral drugs such as (−)‐quinolizidine 207I, (−)‐histrionicotoxin 259A, NNZ 2591, and ORG 34167 (Figure ). Recently, development of mild synthetic methods has been the focus area to prepare optically active homoallylic amines (Table S1).…”

Section: Introductionmentioning

confidence: 99%

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Electrophilic [N—F]⁺ catalysed asymmetric allylation of (E)‐N,1‐diphenylmethanimine

Sharma

2018

Chirality

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New efficient catalysts based on electrophilic N‐fluoro quaternary ammonium salts are reported for catalytic allylation of (E)‐N,1‐diphenylmethanimine. The chiral version of the catalyst based on cinchonidine (F‐CD‐BF4) shows high catalytic activity with approximately 94% ee and TOF (>800 h−1). The F‐CD‐BF4 is prepared from cinchonidine and Selectfluor by one‐step transfer fluorination.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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Electrophilic [N—F]⁺ catalysed asymmetric allylation of (E)‐N,1‐diphenylmethanimine

Sharma

2018

Chirality

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“…A role for cG-2allylP in neuroplasticity was also suggested by improved memory in a rat model with scopolamine-induced acute memory impairment. This improvement was associated with evidence of improved cholinergic neurotransmission [72]. …”

Section: Other Neurological Conditionsmentioning

confidence: 98%

The role for IGF-1-derived small neuropeptides as a therapeutic target for neurological disorders

Guan

Harris

Brimble

et al. 2015

Expert Opinion on Therapeutic Targets

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These small neuropeptides provide effective neuroprotection by offering an improved pharmacokinetic profile and more practical route of administration compared with IGF-1 administration. Developing modified neuropeptides to overcome the limitations of their endogenous counterparts represents a novel strategy of pharmaceutical discovery for neurological disorders. The mechanism of action may involve a regulation of IGF-1 bioavailability.

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“…For instance, cGP is shown to inhibit or promote IGF‐1 function under pathological conditions when IGF‐1 function is relatively increased or diminished, respectively (Guan et al, ). Previous studies have only investigated the roles of cGP in brain development and functional recovery from brain injuries (Guan et al, ; Guan, Zhang, Dale‐Gandar, Hodgkinson, & Vickers, ; Guan et al, ; Gudasheva et al, , Gudasheva et al, ; Singh‐Mallah et al, ), with one study showing the efficacy of cGP in inhibiting IGF‐1‐dependent tumour growth (Guan et al, ). However, the role of cGP in mammary involution, more specifically, in modulating the physiological changes in IGF‐1 function during involution, is not known.…”

Section: Introductionmentioning

confidence: 99%

Cyclic‐glycine‐proline accelerates mammary involution by promoting apoptosis and inhibiting IGF‐1 function

Singh-Mallah

McMahon

Guan

et al. 2017

Journal Cellular Physiology

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In rodents, post-lactational involution of mammary glands is characterized by the loss of mammary epithelial cells via apoptosis, which is associated with a decline in the expression of insulin-like growth factor-1 (IGF-1). Overexpression of IGF-1 delays involution by inhibiting apoptosis of epithelial cells and preserving the remaining secretory alveoli. Cyclic-glycine-proline (cGP), a metabolite of IGF-1, normalizes IGF-1 function under pathological conditions by regulating the bioavailability of IGF-1. The present study investigated the effect of cGP on the physiological decline in IGF-1 function during post-lactational mammary involution. Rat dams were gavaged with either cGP (3 mg/kg) or saline once per day from post-natal d8-22. Before collecting tissue on post-natal d23, a pair of mammary glands were sealed on d20 (72 hr-engorgement, thus representative of late-involution) and d22 (24 hr-engorgement, thus representative of mid-involution), while the remaining glands were allowed to involute naturally (early-involution). During early-involution, cGP accelerated the loss of mammary cells through apoptosis, resulting in an earlier clearance of intact secretory alveoli compared with the control group. This coincided with an earlier up-regulation of the cell survival factors, Bcl-xl and IGF-1R, in the early-involution cGP glands compared with the control glands. During late-involution, cGP reduced the bioactivity of IGF-1, which was evident through decreased phosphorylation of IGF-1R in the regressed alveoli. Maternal administration of cGP did not alter milk production and composition during early-, peak-, or late-stage of lactation. These data show that cGP accelerates post-lactational involution by promoting apoptosis and the physiological decline in IGF-1 function.

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NNZ-2591, a novel diketopiperazine, prevented scopolamine-induced acute memory impairment in the adult rat

Cited by 25 publications

References 35 publications

Electrophilic [N—F]⁺ catalysed asymmetric allylation of (E)‐N,1‐diphenylmethanimine

Electrophilic [N—F]⁺ catalysed asymmetric allylation of (E)‐N,1‐diphenylmethanimine

The role for IGF-1-derived small neuropeptides as a therapeutic target for neurological disorders

Cyclic‐glycine‐proline accelerates mammary involution by promoting apoptosis and inhibiting IGF‐1 function

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NNZ-2591, a novel diketopiperazine, prevented scopolamine-induced acute memory impairment in the adult rat

Cited by 25 publications

References 35 publications

Electrophilic [N—F]+ catalysed asymmetric allylation of (E)‐N,1‐diphenylmethanimine

Electrophilic [N—F]+ catalysed asymmetric allylation of (E)‐N,1‐diphenylmethanimine

The role for IGF-1-derived small neuropeptides as a therapeutic target for neurological disorders

Cyclic‐glycine‐proline accelerates mammary involution by promoting apoptosis and inhibiting IGF‐1 function

Contact Info

Product

Resources

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Electrophilic [N—F]⁺ catalysed asymmetric allylation of (E)‐N,1‐diphenylmethanimine

Electrophilic [N—F]⁺ catalysed asymmetric allylation of (E)‐N,1‐diphenylmethanimine