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[ CAS No. 102-32-9 ] {[proInfo.proName]}

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Chemical Structure| 102-32-9
Chemical Structure| 102-32-9
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Yee Yee Khine ; Han Nguyen ; Favour Afolabi , et al. DOI:

Abstract: The mechanics of the tumor microenvironment (TME) significantly impact disease progression and the efficacy of anti-cancer therapeutics. While it is recognized that advanced in vitro cancer models will benefit cancer research, none of the current engineered extracellular matrices (ECM) adequately recapitulate the highly dynamic TME. Through integrating reversible boronate-ester bonding and dithiolane ring-opening polymerization, we fabricated synthetic polymer hydrogels with tumor-mimetic fast relaxation and reversibly tunable elastic moduli. Importantly, the crosslinking and dynamic stiffening of matrix mechanics were achieved in the absence of a photoinitiator, often the source of cytotoxicity. Central to this strategy was Poly(PEGA-co-LAA-co-AAPBA) (PELA), a highly defined polymer synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization. PELA contains dithiolane for initiator-free gel crosslinking, stiffening, and softening, as well as boronic acid for complexation with diol-containing to give rise to tunable viscoelasticity. PELA hydrogels were highly cytocompatible for dynamic culture of patient-derived pancreatic cancer cells. It was found that the fast-relaxing matrix induced mesenchymal phenotype of cancer cells, and dynamic matrix stiffening restricted tumor spheroid growth. Moreover, this new dynamic viscoelastic hydrogel system permitted sequential stiffening and softening to mimic the physical changes of TME.

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Lin, Fang-Yi ; Chang, Chun-Yi ; Nguyen, Han , et al. DOI: PubMed ID:

Abstract: The tumor microenvironment (TME) is known to direct cancer cell growth, migration, invasion into the matrix and distant tissues, and to confer drug resistance in cancer cells. While multiple aspects of TME have been studied using in vitro, ex vivo, and in vivo tumor models and engineering tools, the influence of matrix viscoelasticity on pancreatic cancer cells and its associated TME remained largely unexplored. In this contribution, we synthesized a new biomimetic hydrogel with tunable matrix stiffness and stress-relaxation for evaluating the effect of matrix viscoelasticity on pancreatic cancer cell (PCC) behaviors in vitro. Using three simple monomers and Reverse-Addition Fragmentation Chain-Transfer (RAFT) polymerization, we synthesized a new class of phenylboronic acid containing polymers (e.g., poly (OEGA-s-HEAA-s-APBA) or PEHA). Norbornene group was conjugated to HEAA on PEHA via carbic anhydride, affording a new NB and BA dually modified polymer - PEHNBA amenable for orthogonal thiol-norbornene photopolymerization and boronate ester diol complexation. The former provided tunable matrix elasticity, while the latter gave rise to matrix stress-relaxation (or viscoelasticity). The new PEHNBA polymers were shown to be highly cytocompatible for in situ encapsulation of PCCs and cancer-associated fibroblasts (CAFs). Furthermore, we demonstrated that hydrogels with high stress-relaxation promoted spreading of CAFs, which in turns promoted PCC proliferation and spreading in the viscoelastic matrix. Compared with elastic matrix, viscoelastic gels upregulated the secretion of soluble proteins known to promote epithelial-mesenchymal transition (EMT). This study demonstrated the crucial influence of matrix viscoelasticity on pancreatic cancer cell fate and provided an engineered viscoelastic matrix for future studies and applications related to TME.

Keywords: Hydrogels ; Viscoelasticity ; Pancreatic cancer ; RAFT ; Cancer associated fibroblasts

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Product Details of [ 102-32-9 ]

CAS No. :102-32-9 MDL No. :MFCD00004338
Formula : C8H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :CFFZDZCDUFSOFZ-UHFFFAOYSA-N
M.W : 168.15 Pubchem ID :547
Synonyms :
3,4-Dihydroxyphenylacetic Acid;NSC 73191;DOPAC
Chemical Name :3,4-Dihydroxyphenylacetic acid

Calculated chemistry of [ 102-32-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 42.03
TPSA : 77.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.8
Log Po/w (XLOGP3) : 0.98
Log Po/w (WLOGP) : 0.72
Log Po/w (MLOGP) : 0.47
Log Po/w (SILICOS-IT) : 0.59
Consensus Log Po/w : 0.71

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.74
Solubility : 3.07 mg/ml ; 0.0183 mol/l
Class : Very soluble
Log S (Ali) : -2.2
Solubility : 1.06 mg/ml ; 0.00629 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.02
Solubility : 16.1 mg/ml ; 0.0957 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 102-32-9 ]

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 [ 102-32-9 ]

* 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.

  • Downstream synthetic route of [ 102-32-9 ]

[ 102-32-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 619-60-3 ]
  • C8H7O4 [ No CAS ]
  • [ 102-32-9 ]
  • [ 54737-34-7 ]
  • 2
  • [ 102-32-9 ]
  • [ 54737-34-7 ]
  • [ 619-60-3 ]
  • C8H7O4 [ No CAS ]
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