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[ CAS No. 17261-28-8 ] {[proInfo.proName]}

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Chemical Structure| 17261-28-8
Chemical Structure| 17261-28-8
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Product Citations

Product Citations

Marion H. Emmert ; Cuixian Yang ; Eugene E. Kwan , et al. DOI:

Abstract: This manuscript describes the detailed evaluation of more than 40 phosphine reductants via automated and nonautomated high-throughput experimentation approaches with the goal of identifying selective reductants for cleaving the disulfide bonds of capped, engineered cysteines in a proprietary monoclonal antibody (mAb). As a point of reference, this study included phosphines that have previously been documented in the literature [4-diphenylphosphino benzoic acid (DPPBA), tris(3-sulfophenyl)phosphine (TSPP), and 3-(diphenylphosphino)benzenesulfonate (diPPBS)]; however, all known reductants showed the formation of undesired side products upon reduction (detectable by IEX), especially at higher phosphine loadings. The high_x005f_x0002_throughput study also revealed several phosphines with potential for selective reduction that had not been previously studied for this type of transformation. These initial hits were further evaluated with regard to the phosphine/mAb ratio, solubility in aqueous media, and air oxidation behavior. The best phosphine identified (1-(4-(diphenylphosphanyl)benzyl)-1-methylpyrrolidin-1-ium bromide (P10)) was then employed in a sequence of high-throughput studies that established efficient one-pot reduction/conjugation reaction conditions. Overall, the work detailed herein demonstrates how high-throughput experimental design enables rapid and resource-sparing insights into mAb reduction and conjugation reactivity with phosphine-based reductants.

Keywords: high-throughput experimentation (HTE) ; monoclonal antibody (mAb) ; disulfide bond reduction ; mAb decapping ; phosphines ; one-pot reduction/conjugation

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Product Details of [ 17261-28-8 ]

CAS No. :17261-28-8 MDL No. :MFCD00674024
Formula : C19H15O2P Boiling Point : No data available
Linear Structure Formula :C6H4(P(C6H5)2)(COOH) InChI Key :UYRPRYSDOVYCOU-UHFFFAOYSA-N
M.W : 306.30 Pubchem ID :87021
Synonyms :

Calculated chemistry of [ 17261-28-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 92.11
TPSA : 50.89 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.76
Log Po/w (XLOGP3) : 4.13
Log Po/w (WLOGP) : 3.14
Log Po/w (MLOGP) : 4.4
Log Po/w (SILICOS-IT) : 4.87
Consensus Log Po/w : 3.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.68
Solubility : 0.00636 mg/ml ; 0.0000208 mol/l
Class : Moderately soluble
Log S (Ali) : -4.91
Solubility : 0.00381 mg/ml ; 0.0000124 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.9
Solubility : 0.0000385 mg/ml ; 0.000000126 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.64

Safety of [ 17261-28-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 17261-28-8 ]

* 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 [ 17261-28-8 ]
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