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[ CAS No. 134-03-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 134-03-2
Chemical Structure| 134-03-2
Structure of 134-03-2 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Ang, Charles G ; Hyatt, Nadia L ; Le Minh, Giang , et al. DOI: PubMed ID:

Abstract: Disulfide exchange is underexplored as a mechanism influencing HIV-1 entry. Prior studies demonstrated that redox enzyme inhibition can prevent HIV-1 infection but with limited mechanistic explanation. We hypothesize that ligand-driven rearrangement (“conformational activation”) enables enzyme-mediated disulfide exchange in Env residues (“disulfide trigger”) that promotes fusion transformations, enhancing virus entry. We tested soluble CD4 and CD4-binding site entry inhibitors as conformational activators and the ubiquitous redox enzyme thioredoxin-1 (Trx1) as disulfide trigger. We found that combination treatment caused fusion-like Env transformation and pseudovirus lysis, independent of cells. Notably, only compounds associated with gp120 shedding caused lysis when paired with Trx1. In each case, lysis was prevented by adding the fusion inhibitor T20, demonstrating that six-helix bundle formation is required as in virus-cell fusion. In contrast to conformationally activating ligands, neither the ground state stabilizer BMS-806 with Trx1 nor Trx1 alone caused lysis. Order of addition experiments reinforced conformational activation/disulfide trigger as a sequential process, with virus/activator preincubation transiently enhancing lysis and virus/Trx1 preincubation reducing lysis. Lastly, addition of exogenous Trx1 to typical pseudovirus infections exhibited dose-dependent enhancement of infection. Altogether, these data support conformational activation and disulfide triggering as a mechanism that can induce and enhance the fusogenic transformation of Env.

Keywords: HIV-1 ; Env ; thioredoxins ; allosteric disulfides ; virus entry ; entry inhibitors ; thiols ; disulfide exchange

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Product Details of [ 134-03-2 ]

CAS No. :134-03-2 MDL No. :MFCD00082340
Formula : C6H7NaO6 Boiling Point : -
Linear Structure Formula :- InChI Key :PPASLZSBLFJQEF-RXSVEWSESA-M
M.W : 198.11 Pubchem ID :23667548
Synonyms :
Sodium ascorbate;Sodium L-ascorbate;Sodium Vitamin C;Vitamin C sodium salt
Chemical Name :Sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate

Calculated chemistry of [ 134-03-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 33.18
TPSA : 110.05 ?2

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) : -8.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : -9.01
Log Po/w (XLOGP3) : -1.64
Log Po/w (WLOGP) : -1.53
Log Po/w (MLOGP) : -2.6
Log Po/w (SILICOS-IT) : -1.15
Consensus Log Po/w : -3.19

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.1
Solubility : 248.0 mg/ml ; 1.25 mol/l
Class : Highly soluble
Log S (Ali) : -0.16
Solubility : 137.0 mg/ml ; 0.691 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 1.49
Solubility : 6140.0 mg/ml ; 31.0 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.48

Safety of [ 134-03-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 134-03-2 ]

* 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.

  • Upstream synthesis route of [ 134-03-2 ]

[ 134-03-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 134-03-2 ]
  • [ 17465-86-0 ]
  • [ 129499-78-1 ]
Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 92, p. 19 - 23
  • 2
  • [ 134-03-2 ]
  • [ 10016-20-3 ]
  • [ 129499-78-1 ]
Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 92, p. 19 - 23
  • 3
  • [ 134-03-2 ]
  • [ 7585-39-9 ]
  • [ 129499-78-1 ]
Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 92, p. 19 - 23
  • 4
  • [ 133-99-3 ]
  • [ 134-03-2 ]
  • [ 129499-78-1 ]
Reference： [1] Agricultural and Biological Chemistry, 1990, vol. 54, # 7, p. 1697 - 1703
  • 5
  • [ 134-03-2 ]
  • [ 129499-78-1 ]
Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 11, p. 3020 - 3023
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