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[ CAS No. 1122-62-9 ] {[proInfo.proName]}

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Chemical Structure| 1122-62-9
Chemical Structure| 1122-62-9
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Pilling, Darrell ; Martinez, Trevor C ; Gomer, Richard H DOI: PubMed ID:

Abstract: Sialic acids are located on the ends of many glycoconjugates and are cleaved off by enzymes called sialidases (neuraminidases). Upregulation of neuraminidase 3 (NEU3) is associated with intestinal inflammation and colitis, neuroinflammation, and lung fibrosis. Genetic ablation of NEU3 or pharmacological inhibition of NEU3 reduces lung fibrosis in mice. To determine if inhibiting NEU3 can inhibit liver fibrosis in the commonly-used CCl4 model, in this report, we examined the effects of injections of the NEU3 inhibitor 2-acetyl pyridine (2AP). 2AP inhibited CCl4-induced weight loss in female but not male mice. 2AP atten_x005f_x0002_uated CCl4-induced liver inflammation and fibrosis in male and female mice, but did not affect CCl4-induced steatosis. After CCl4 treatment, female but not male mice had significant increases in liver neutrophils, and 2AP attenuated this response. 2AP also reversed CCl4-induced liver desialylation and CCl4-induced increased expression of NEU3. Patients with pulmonary fibrosis have increased desialylation of some serum proteins, and elevated serum levels of NEU3. We find that sera from patients with nonalcoholic fatty liver disease (NAFLD) and nonalcoholic steatohepatitis (NASH) have elevated desialylation of a serum protein and patients with NAFLD have increased levels of NEU3. These data suggest that elevated levels of NEU3 may be associated with liver inflammation and fibrosis, and that in mice this is ameliorated by injections of a NEU3 inhibitor.

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Morse, Jared ; Ofodum, Nnamdi ; Tang, Fung-Kit , et al. DOI:

Abstract: Chloride is the most abundant anion in cell physiology and plays many critical roles in maintaining cellular homeostasis. However, current chloride sensors are rare, with inherent sensitivity in their emission properties, such as vulnerability to pH changes or short emission lifetimes. These limitations restrict theirapplication in aqueous media and imaging. In this work, we employed a transition metal complex bearing pyridinium as a recognition unit for chloride and studied the phosphorescence emission properties. Iridium(III) complex 1 was synthesized as an alternative chloride-sensitive luminophore. The conjugable design also allows customization for desired applications. Complex 1 exhibited high sensitivity and selectivity in chloride sensing across different physiological environments, regardless of pH fluctuation and ionic strength. Additionally, complex 1 featured a long microsecond emission lifetime. The chloride sensing ability of complex 1 can be measured through both luminescence intensity and long-lived phosphorescent lifetime simultaneously, providing an alternative potential route for chloride imaging.

Keywords: Chloride ; chloride detection ; chloride-sensitive luminophore ; iridium complex

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Kirolos, Sara A. ; Pilling, Darrell ; Gomer, Richard H. DOI: PubMed ID:

Abstract: Some extracellular glycoconjugates have sialic acid as the terminal sugar, and sialidases are enzymes that remove this sugar. Mammals have 4 sialidases and can be elevated in inflammation and fibrosis. In this report, we show that incubation of human neutrophils with the extracellular human sialidase NEU3, but not NEU1, NEU2 or NEU4, induces human male and female neutrophils to change from a round to a more amoeboid morphol., causes the primed human neutrophil markers CD11b, CD18, and CD66a to localize to the cell cortex, and decreases the localization of the unprimed human neutrophil markers CD43 and CD62-L at the cell cortex. NEU3, but not the other 3 sialidases, also causes human male and female neutrophils to increase their F-actin content. Human neutrophils treated with NEU3 show a decrease in cortical levels of Sambucus nigra lectin staining and an increase in cortical levels of peanut agglutinin staining, indicating a NEU3-induced desialylation. The inhibition of NEU3 by the NEU3 inhibitor 2-acetylpyridine attenuated the NEU3 effect on neutrophil morphol., indicating that the effect of NEU3 is dependent on its enzymic activity. Together, these results indicate that NEU3 can prime human male and female neutrophils, and that NEU3 is a potential regulator of inflammation.

Keywords: Neutrophil ; priming ; sialidase ; NEU1 ; NEU2 ; NEU3 ; NEU4 ; fibrosis ; activation ; sialic acid ; desialylation ; glycoconjugate ; adhesion ; aggregation

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Sara A. Kirolos ; Richard H. Gomer ; DOI: PubMed ID:

Abstract: Some extracellular glycoconjugates have sialic acid as the terminal sugar, and sialidases are enzymes that remove this sugar. Mammals have four sialidases, but their biological functions are unclear. In this report, we show that incubation of human neutrophils with the human sialidase NEU3, but not NEU1, NEU2 or NEU4, inducess human male and female neutrophils to change from a round to a more amoeboid morphology, causes the primed neutrophil markers CD66, CD11B, and CD18 to localize to the cell cortex, and decreases the localization of the unprimed neutrophil markers CD43 and CD62L at the cell cortex. NEU3, but not the other 3 sialidases, also causes human male and female neutrophils to increase their F-actin content. The inhibition of NEU3 by the NEU3 inhibitor 2-acetylpyridine attenuated the NEU3 effect on neutrophil morphology, indicating that the effect of NEU3 is dependent on its enzymatic activity. Together, these results indicate that NEU3 can prime human male and female neutrophils, and that NEU3 is a potential regulator of inflammation.

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Milligan, Sara Ann ;

Abstract: Chemorepulsion is the movement of cells away from a chemical signal and is a fundamental process in developmental biology and immune responses. The ability to manipulate chemorepulsion could lead to new therapeutics for neutrophil driven diseases such as acute respiratory distress syndrome (ARDS). However, little is known about eukaryotic chemorepulsion. Autocrine proliferation repressor protein A (AprA) is a protein that acts as an endogenous chemorepellent continuously secreted by Dictyostelium cells. AprA has structural and functional similarity to human dipeptidyl peptidase IV (DPPIV). DPPIV acts as a chemorepellent for neutrophils by activating protease activated receptor 2 (PAR2). In this dissertation, my work on Dictyostelium showed that some of the key proteins that appear to mediate AprA chemorepulsion include Ras GTPases. I have also identified proteins that are involved in regulating the distribution of active Ras protein during chemorepulsion. To identify novel proteins, I utilized restriction enzyme mediated integration, and found 17 proteins that appear to be required for AprA-induced chemorepulsion. One of these proteins is phosphatidylinositol phosphate kinase A (PIPkinA). I showed that PIPkinA is required for both AprA-induced chemorepulsion and proliferation inhibition, and that PipKinA regulates PIP and PIP3 levels in Dictyostelium. In this dissertation, while working with human neutrophils to study how a chemorepellent could also induces apoptosis of activated neutrophils, I have also explored the effect of human iii sialidases NEU1-4 on neutrophil priming. I found that NEU3, previously shown to be upregulated in fibrosis, primes neutrophils and increases expression of neutrophil markers CD11b, CD18, and CD66a to localize to the cell cortex, and decreases the localization of the unprimed neutrophil markers CD43 and CD62-L at the cell cortex. The inhibition of NEU3 by the NEU3 inhibitor 2- acetylpyridine attenuated the NEU3 effect on neutrophil morphology, indicating that the effect of NEU3 is dependent on its enzymatic activity. Together, these data expand the crucial regulation of Ras GTPases and the role of novel proteins in eukaryotic chemorepulsion. This furthers our understanding of the underlying chemorepulsion mechanism in eukaryotes, and facilitates the development of therapeutics for ARDS and neutrophil-driven diseases.

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Product Details of [ 1122-62-9 ]

CAS No. :1122-62-9 MDL No. :MFCD00006303
Formula : C7H7NO Boiling Point : -
Linear Structure Formula :(C5H4N)C(O)CH3 InChI Key :AJKVQEKCUACUMD-UHFFFAOYSA-N
M.W : 121.14 Pubchem ID :14286
Synonyms :

Calculated chemistry of [ 1122-62-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.43
TPSA : 29.96 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 0.85
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.13
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.55
Solubility : 3.38 mg/ml ; 0.0279 mol/l
Class : Very soluble
Log S (Ali) : -1.06
Solubility : 10.5 mg/ml ; 0.0866 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.589 mg/ml ; 0.00486 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 1122-62-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1122-62-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1122-62-9 ]
  • Downstream synthetic route of [ 1122-62-9 ]

[ 1122-62-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 1122-62-9 ]
  • [ 159307-02-5 ]
Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 36, p. 10890 - 10893[2] Angew. Chem., 2017, vol. 129, p. 11030 - 11033,4
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