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Showing NP-Card for 2,4-dinitrophenyl-S-glutathione (NP0339793)

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Record Information
Version2.0
Created at2024-09-11 23:35:08 UTC
Updated at2024-09-11 23:35:08 UTC
NP-MRD IDNP0339793
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,4-dinitrophenyl-S-glutathione
Description2,4-Dinitrophenyl-S-glutathione belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 2,4-dinitrophenyl-S-glutathione was first documented in 2018 (PMID: 29981893). Based on a literature review a small amount of articles have been published on 2,4-dinitrophenyl-S-glutathione (PMID: 36127061) (PMID: 35887010) (PMID: 32476256) (PMID: 29052767).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339793 (2,4-dinitrophenyl-S-glutathione)


  Mrv2104 05272302072D          

 32 32  0  0  0  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -5.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -5.5736    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2700   -4.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -3.5468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -2.6113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -2.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -2.2995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -3.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -3.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -3.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -4.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -3.5468    0.0000 N   0  3  0  0  0  1  0  0  0  0  0  0
    3.7806   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -5.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -5.5736    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -1.2082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -0.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -0.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    0.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    1.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    1.9101    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.4304    2.0660    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.0802    2.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    0.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    0.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    0.0391    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.8101   -0.7404    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0802    0.6628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 24 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 21 29  2  0  0  0  0
M  CHG  7   3  -1  15   1  18  -1  25   1  26  -1  30   1  31  -1
M  RAD  1  15   2
M  END
Download

3D MOL for NP0339793 (2,4-dinitrophenyl-S-glutathione)

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3D SDF for NP0339793 (2,4-dinitrophenyl-S-glutathione)

  Mrv2104 05272302072D          

 32 32  0  0  0  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -5.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -5.5736    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2700   -4.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -3.5468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -2.6113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -2.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -2.2995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -3.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -3.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -3.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -4.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -3.5468    0.0000 N   0  3  0  0  0  1  0  0  0  0  0  0
    3.7806   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -5.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -5.5736    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -1.2082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -0.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -0.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    0.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    1.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    1.9101    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.4304    2.0660    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.0802    2.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    0.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    0.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    0.0391    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.8101   -0.7404    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0802    0.6628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 24 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 21 29  2  0  0  0  0
M  CHG  7   3  -1  15   1  18  -1  25   1  26  -1  30   1  31  -1
M  RAD  1  15   2
M  END
> <DATABASE_ID>
NP0339793

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[N+]C(CCC(=O)NC(CSC1=C(C=C(C=C1)[N+]([O-])=O)[N+]([O-])=O)C(=O)NCC([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1/C16H17N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/q+1/p-2

> <INCHI_KEY>
LQUNHXCQYCVLGL-UHFFFAOYNA-L

> <FORMULA>
C16H15N5O10S

> <MOLECULAR_WEIGHT>
469.38

> <EXACT_MASS>
469.054511457

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
41.814883467694315

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[1-carboxylato-3-({1-[(carboxylatomethyl)carbamoyl]-2-[(2,4-dinitrophenyl)sulfanyl]ethyl}carbamoyl)propyl]azaniumyl

> <JCHEM_LOGP>
-1.7725379402092785

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.9632961207178687

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2857234707101557

> <JCHEM_PKA_STRONGEST_BASIC>
-1.938021998897374

> <JCHEM_POLAR_SURFACE_AREA>
247.79999999999995

> <JCHEM_REFRACTIVITY>
126.48419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1-carboxylato-3-{[1-(carboxylatomethylcarbamoyl)-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}propyl)ammonio

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339793 (2,4-dinitrophenyl-S-glutathione)
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PDB for NP0339793 (2,4-dinitrophenyl-S-glutathione)
HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.512  -9.531   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -1.008 -10.404   0.000  0.00  0.00           O-1
HETATM    4  C   UNK     0      -0.504  -7.785   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.504  -6.621   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000  -5.166   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.512  -4.875   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.008  -4.001   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.520  -4.292   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.024  -5.748   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.016  -6.912   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.537  -6.039   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.041  -7.494   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.553  -7.785   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       7.561  -6.621   0.000  0.00  0.00           N+1
HETATM   16  C   UNK     0       7.057  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.569  -9.531   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.049 -10.404   0.000  0.00  0.00           O-1
HETATM   19  C   UNK     0       0.504  -2.546   0.000  0.00  0.00           C+0
HETATM   20  S   UNK     0      -1.008  -2.255   0.000  0.00  0.00           S+0
HETATM   21  C   UNK     0      -1.512  -0.800   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.024  -0.509   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.529   0.946   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.520   2.110   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      -3.024   3.565   0.000  0.00  0.00           N+1
HETATM   26  O   UNK     0      -4.537   3.856   0.000  0.00  0.00           O-1
HETATM   27  O   UNK     0      -2.016   4.730   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.008   1.819   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.504   0.364   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       1.008   0.073   0.000  0.00  0.00           N+1
HETATM   31  O   UNK     0       1.512  -1.382   0.000  0.00  0.00           O-1
HETATM   32  O   UNK     0       2.016   1.237   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24   29                                                       
CONECT   29   28   30   21                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

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3D PDB for NP0339793 (2,4-dinitrophenyl-S-glutathione)
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SMILES for NP0339793 (2,4-dinitrophenyl-S-glutathione)
[N+]C(CCC(=O)NC(CSC1=C(C=C(C=C1)[N+]([O-])=O)[N+]([O-])=O)C(=O)NCC([O-])=O)C([O-])=O
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INCHI for NP0339793 (2,4-dinitrophenyl-S-glutathione)
InChI=1/C16H17N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/q+1/p-2
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View in JSmol
SynonymsNot Available
Chemical FormulaC16H15N5O10S
Average Mass469.3800 Da
Monoisotopic Mass469.05451 Da
IUPAC Name[1-carboxylato-3-({1-[(carboxylatomethyl)carbamoyl]-2-[(2,4-dinitrophenyl)sulfanyl]ethyl}carbamoyl)propyl]azaniumyl
Traditional Name(1-carboxylato-3-{[1-(carboxylatomethylcarbamoyl)-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}propyl)ammonio
CAS Registry NumberNot Available
SMILES
[N+]C(CCC(=O)NC(CSC1=C(C=C(C=C1)[N+]([O-])=O)[N+]([O-])=O)C(=O)NCC([O-])=O)C([O-])=O
InChI Identifier
InChI=1/C16H17N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/q+1/p-2
InChI KeyLQUNHXCQYCVLGL-UHFFFAOYNA-L
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentOligopeptides  
Alternative Parents
Substituents
  • Alpha-oligopeptide
    • 

  • Gamma-glutamyl alpha peptide
    • 

  • Glutamine or derivatives
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • N-acyl-alpha-amino acid
    • 

  • Alpha-amino acid amide
    • 

  • Cysteine or derivatives
    • 

  • N-substituted-alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • Nitrobenzene
    • 

  • Aryl thioether
    • 

  • Nitroaromatic compound
    • 

  • Thiophenol ether
    • 

  • Alkylarylthioether
    • 

  • Benzenoid
    • 

  • N-acyl-amine
    • 

  • Fatty acyl
    • 

  • Fatty amide
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Monocyclic benzene moiety
    • 

  • Carboxamide group
    • 

  • Carboxylic acid salt
    • 

  • Organic nitro compound
    • 

  • C-nitro compound
    • 

  • Secondary carboxylic acid amide
    • 

  • Thioether
    • 

  • Sulfenyl compound
    • 

  • Carboxylic acid
    • 

  • Organic oxoazanium
    • 

  • Organic salt
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organosulfur compound
    • 

  • Organic anion
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.8ChemAxon
pKa (Strongest Acidic)2.29ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area247.8 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity126.48 m³·mol⁻¹ChemAxon
Polarizability41.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. De Anna JS, Bieczynski F, Carcamo JG, Venturino A, Luquet CM: Chlorpyrifos stimulates ABCC-mediated transport in the intestine of the rainbow trout Oncorhynchus mykiss. Pestic Biochem Physiol. 2022 Oct;187:105222. doi: 10.1016/j.pestbp.2022.105222. Epub 2022 Sep 5. [PubMed:36127061  ] 
  2. Li P, Yang Y, Lin Z, Hong S, Jiang L, Zhou H, Yang L, Zhu L, Liu X, Liu L: Bile Duct Ligation Impairs Function and Expression of Mrp1 at Rat Blood-Retinal Barrier via Bilirubin-Induced P38 MAPK Pathway Activations. Int J Mol Sci. 2022 Jul 11;23(14):7666. doi: 10.3390/ijms23147666. [PubMed:35887010  ] 
  3. Tocchetti GN, Dominguez CJ, Zecchinati F, Arana MR, Rigalli JP, Ruiz ML, Villanueva SSM, Mottino AD: Intraluminal nutrients acutely strengthen rat intestinal MRP2 barrier function by a glucagon-like peptide-2-mediated mechanism. Acta Physiol (Oxf). 2020 Dec;230(4):e13514. doi: 10.1111/apha.13514. Epub 2020  Jun 17. [PubMed:32476256  ] 
  4. Tocchetti GN, Dominguez CJ, Zecchinati F, Arana MR, Ruiz ML, Villanueva SSM, Mottino AD, Weiss J, Rigalli JP: Inhibition of multidrug resistance-associated protein 2 (MRP2) activity by the contraceptive nomegestrol acetate in HepG2 and Caco-2 cells. Eur J Pharm Sci. 2018 Sep 15;122:205-213. doi: 10.1016/j.ejps.2018.07.017. Epub  2018 Jul 6. [PubMed:29981893  ] 
  5. Tocchetti GN, Arias A, Arana MR, Rigalli JP, Dominguez CJ, Zecchinati F, Ruiz ML, Villanueva SSM, Mottino AD: Acute regulation of multidrug resistance-associated protein 2 localization and activity by cAMP and estradiol-17beta-D-glucuronide in rat intestine and Caco-2 cells. Arch Toxicol. 2018 Feb;92(2):777-788. doi: 10.1007/s00204-017-2092-9. Epub 2017  Oct 20. [PubMed:29052767  ]