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[ CAS No. 17435-72-2 ] {[proInfo.proName]}

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Chemical Structure| 17435-72-2
Chemical Structure| 17435-72-2
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Product Citations

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Mueller, Mikala C ; Blomberg, Rachel ; Tanneberger, Alicia E , et al. DOI: PubMed ID:

Abstract: Pulmonary arterial hypertension (PAH) impacts male and female patients in different ways. Female patients exhibit a greater susceptibility to disease (4:1 female-to-male ratio) but live longer after diagnosis than male patients. This complex sexual dimorphism is known as the estrogen paradox. Prior studies suggest that estrogen signaling may be pathologic in the pulmonary vasculature and protective in the heart, yet the mechanisms underlying these sex-differences in PAH remain unclear. PAH is a form of a pulmonary vascular disease that results in scarring of the small blood vessels, leading to impaired blood flow and increased blood pressure. Over time, this increase in blood pressure causes damage to the heart. Many previous studies of PAH relied on male cells or cells of undisclosed origin for in vitro modeling. Here we present a dynamic, 3D-bioprinted model that incorporates cells and circulating sex hormones from female patients to specifically study how female patients respond to changes in microenvironmental stiffness and sex hormone signaling. Poly(ethylene glycol)-alpha methacrylate (PEGαMA)-based hydrogels containing female human pulmonary artery adventitia fibroblasts (hPAAFs) from idiopathic PAH (IPAH) or control donors were 3D bioprinted to mimic pulmonary artery adventitia. These biomaterials were initially soft, like healthy blood vessels, and then stiffened using light to mimic vessel scarring in PAH. These 3D-bioprinted models showed that stiffening the microenvironment around female IPAH hPAAFs led to hPAAF activation. On both the protein and gene-expression levels, cellular activation markers significantly increased in stiffened samples and were highest in IPAH patient-derived cells. Treatment with a selective estrogen receptor modulator reduced expression hPAAF activation markers, demonstrating that hPAAF activation is a one pathologic response mediated by estrogen signaling in the vasculature, validating that drugs currently in clinical trials could be evaluated in sexspecific 3D-bioprinted pulmonary artery adventitia models.

Keywords: Sex-differences ; pulmonary arterial hypertension ; estrogen signaling ; bioprinting ; biomaterials

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Mueller, Mikala Clair ; Yanmei Du ; Lori A. Walker , et al. DOI:

Abstract: Respiratory diseases like pulmonary arterial hypertension (PAH) frequently exhibit sexual dimorphism. Female PAH patients are more susceptible to the disease but have increased survival rates. This phenomenon is known as the estrogen paradox, and the underlying mechanisms are not fully understood. During PAH progression in vivo, human pulmonary arterial adventitial fibroblasts (hPAAFs) differentiate into an activated phenotype. These cells produce excess, aberrant extracellular matrix proteins that stiffen the surrounding pulmonary arterial tissues. Here, we employed dynamic poly(ethylene glycol)-alpha methacrylate (PEGαMA)-based biomaterials to study how the age and sex of human serum influenced hPAAF activation in response to microenvironmental stiffening in vitro. Results showed female and male cells responded differently to increases in microenvironmental stiffness and serum composition. Male hPAAFs were less activated than female cells on soft hydrogels and more responsive to increases in microenvironmental stiffness regardless of serum composition. Female hPAAF activation followed this pattern only when cultured in younger (age < 50) female serum or when older (age ≥ 50) female serum was supplemented with estradiol. Otherwise, female hPAAF activation was relatively high on both soft and stiffened hydrogels, with little difference in activation between the two conditions. Collectively, these results suggest that it may be possible to model the estrogen paradox observed in PAH in vitro and that it is critical for researchers to report cell sex and serum source when conducting in vitro experimentation.

Keywords: Pulmonary arterial hypertension ; hydrogel ; biomaterial ; sex-differences ; sex hormones

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Saleh ; Kamiel ; Hewawasam , et al. DOI: PubMed ID:

Abstract: Introduction. Idiopathic pulmonary fibrosis is a chronic disease characterized by progressive lung scarring that inhibits gas exchange. Evidence suggests fibroblast-matrix interactions are a prominent driver of disease. However, available preclinical models limit our ability to study these interactions. We present a technique for synthesizing phototunable poly(ethylene glycol) (PEG)-based hybrid-hydrogels comprising healthy or fibrotic decellularized extracellular matrix (dECM) to decouple mechanical properties from composition and elucidate their roles in fibroblast activation. Methods. Here, we engineered and characterized phototunable hybrid-hydrogels using molecular techniques, such as ninhydrin and Ellman’s assays, to assess dECM functionalization and parallel-plate rheology to measure hydrogel mechanical properties. These biomaterials were employed to investigate the activation of fibroblasts from dual-transgenic Col1a1-GFP and αSMA-RFP reporter mice in response to changes in composition and mechanical properties. Results. We show that reacting functionalized dECM from healthy or bleomycin-injured mouse lungs with PEG alpha-methacrylate (αMA) in an off-stoichiometry Michael-addition reaction created soft hydrogels mimicking a healthy lung elastic modulus (4.99 ± 0.98 kPa). Photoinitiated stiffening increased the material modulus to fibrotic values (11.48 ± 1.80 kPa). Percent activation of primary murine fibroblasts expressing Col1a1 and αSMA increased by approximately 40% following dynamic stiffening of both healthy and bleomycin hybrid-hydrogels. There were no significant differences between fibroblast activation on stiffened healthy versus stiffened bleomycin-injured hybrid-hydrogels. Conclusions. Phototunable hybrid-hydrogels provide an important platform for probing cell-matrix interactions and developing a deeper understanding of fibrotic activation in pulmonary fibrosis. Our results suggest that mechanical properties are a more significant contributor to fibroblast activation than biochemical composition.

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Product Details of [ 17435-72-2 ]

CAS No. :17435-72-2 MDL No. :MFCD00031518
Formula : C6H9BrO2 Boiling Point : -
Linear Structure Formula :CH2C(CO2C2H5)CH2Br InChI Key :MTCMFVTVXAOHNQ-UHFFFAOYSA-N
M.W : 193.04 Pubchem ID :310620
Synonyms :

Calculated chemistry of [ 17435-72-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.64
TPSA : 26.3 ?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) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 1.5
Log Po/w (MLOGP) : 1.69
Log Po/w (SILICOS-IT) : 1.57
Consensus Log Po/w : 1.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.81
Solubility : 3.02 mg/ml ; 0.0156 mol/l
Class : Very soluble
Log S (Ali) : -1.81
Solubility : 3.02 mg/ml ; 0.0157 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.07
Solubility : 1.65 mg/ml ; 0.00855 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.24

Safety of [ 17435-72-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378-P403+P233-P501 UN#:3265
Hazard Statements:H227-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 17435-72-2 ]

* 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.

  • Downstream synthetic route of [ 17435-72-2 ]

[ 17435-72-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 6940-80-3 ]
  • [ 17435-72-2 ]
  • [ 172034-96-7 ]
  • 2
  • (E)-tert-butyl([2-(2-phenylethynyl)phenyl]methylidene})amine [ No CAS ]
  • [ 17435-72-2 ]
  • [ 37993-76-3 ]
  • ethyl 2-[(3-phenylisoquinolin-4-yl)methyl]propenoate [ No CAS ]
  • 3
  • [ 54589-54-7 ]
  • [ 17435-72-2 ]
  • [ 1187442-31-4 ]
  • 4
  • [ 66217-56-9 ]
  • [ 17435-72-2 ]
  • [ 84515-42-4 ]
  • 5
  • [ 253-66-7 ]
  • [ 17435-72-2 ]
  • [ 1562367-32-1 ]
  • 6
  • [ 18207-47-1 ]
  • [ 613-94-5 ]
  • [ 17435-72-2 ]
  • N-(2-(furan-2-yl)-4-methylene-5-oxo-2-(trifluoromethyl)pyrrolidin-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% General procedure: Trifluoromethyl ketones (1; 0.30 mmol, 1 equiv), acylhydrazines (2; 0.45 mmol, 1.5 equiv) and TsOH (20 mol%) were added to a dried round-bottom flask (50 mL) fitted with a magnetic bar. 1,4-Dioxane 4 mL) was then added and the mixture was stirred and heated to reflux. After the formation of acylhydrazones (monitored by TLC), tin powder (1.35 mmol, 4.5 equiv) and ethyl 2-(bromomethyl)acrylate (3; 1.20 mmol, 4 equiv) were added to the flask. When acylhydrazones had essentially disappeared (monitored by TLC), the reaction mixture was cooled to r.t., then 1,4-dioxane was removed under vacuum. Saturated NH4Cl solution (10 mL) was added and the mixture was stirred for 10 min. The mixture was extracted with EtOAc (3 × 10 mL) and the combined organic phases were dried (MgSO4) and concentrated. Purification of the residue by silica gel column chromatography (petroleum ether-EtOAc, 4:1) furnished the pure products 4.
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