Payload Information

General Information of This Payload
Payload ID
PAY0XFCHM
Name
Pyropheophorbide-a
Synonyms
Pyropheophorbide a; Pyropheophorbide-a; 24533-72-0; Pyropheophorbide alpha; PYROPHEOPHORBIDE; CHEBI:48398; 3-[(21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid; (3S-trans)-9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid; 3-[(3S,4S)-14-ethyl-4,8,13,18-tetramethyl-20-oxo-9-vinylphorbin-3-yl]propanoic acid; 3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-, (3S-trans)-; C33H34N4O3; PpaPpa; pyrophaeophorbide; C33-H34-N4-O3; SCHEMBL378992; CHEMBL520220; CHEMBL1807359; 3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-, (3S,4S)-; IEGUQQKIFBYXLG-UWJYYQICSA-N; JUDGRMABQJKRPW-UWJYYQICSA-N; DTXSID901315902; BDBM50569289; AKOS040744355; HY-128973; CS-0102957; C18064; F87241; J-015556; 3-(ethyl-tetramethyl-oxo-vinyl-[?]yl)propanoic acid; Q27121183; 7beta-(2-Carboxyethyl)-13-ethenyl-7,8-dihydro-2,8alpha,12,17-tetramethyl-18-ethyl-3,5-(carbonylmethylene)-21H,23H-porphyrin
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Target(s) .
 Target Info 
Structure
Formula
C33H34N4O3
Isosmiles
CCC1=C(C2=NC1=CC3=C(C4=C(CC(=C5[C@H]([C@@H](C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)O)C4=N3)O)C)C
PubChem CID
161456
InChI
InChI=1S/C33H34N4O3/c1-7-19-15(3)23-12-25-17(5)21(9-10-30(39)40)32(36-25)22-11-29(38)31-18(6)26(37-33(22)31)14-28-20(8-2)16(4)24(35-28)13-27(19)34-23/h7,12-14,17,21,36,38H,1,8-11H2,2-6H3,(H,39,40)/t17-,21-/m0/s1
InChIKey
FDKRLXBXYZKWRZ-UWJYYQICSA-N
IUPAC Name
3-[(21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid
Pharmaceutical Properties
Molecule Weight
534.6
Polar area
107
Complexity
1660
xlogp Value
2.6
Heavy Count
40
Rot Bonds
5
Hbond acc
7
Hbond Donor
3
Each Antibody-drug Conjugate Related to This Payload
Full Information of The Activity Data of The ADC(s) Related to This Payload
Pyro-Linker-ZHER2 [Investigative]
 ADC Info 
Discovered Using Cell Line-derived Xenograft Model
Click To Hide/Show 1 Activity Data Related to This Level
Experiment 1 Reporting the Activity Date of This ADC [1]
Efficacy Data Tumor Growth Inhibition value (TGI) ≈ 100.00% (Day 19) High HER2 expression (HER2 +++)
Method Description
BALB/c nude mice bearing HER2-high expression NCI-N87 tumors received iv injection of 20 nmol/mouse of Pyro-Linker-ZHER2, Pyro-Linker-OH, Pyro, or PBS buffer only and then irradiated with 180 J/cm2 light 4 h (for groups of PyroLinker-ZHER2 and PBS buffer only) postinjection.
In Vivo Model NCI-N87 CDX model
In Vitro Model Gastric tubular adenocarcinoma NCI-N87 cells CVCL_1603
Revealed Based on the Cell Line Data
Click To Hide/Show 6 Activity Data Related to This Level
Experiment 1 Reporting the Activity Date of This ADC [1]
Efficacy Data Half Maximal Inhibitory Concentration (IC50)
12.50 nM
High HER2 expression (HER2 +++)
Method Description
Dark toxicity was measured without light illumination, and a HER2 receptor blocking experiment was carried out by preincubation of the cells with free ZHER2:2891 affibody (10.0 M) for 4 h before the addition of Pyro, Pyro-Linker-OH, or Pyro-Linker-ZHER2.
In Vitro Model Invasive breast carcinoma BT-474 cells CVCL_0179
Experiment 2 Reporting the Activity Date of This ADC [1]
Efficacy Data Half Maximal Inhibitory Concentration (IC50)
23.00 nM
High HER2 expression (HER2 +++)
Method Description
Dark toxicity was measured without light illumination, and a HER2 receptor blocking experiment was carried out by preincubation of the cells with free ZHER2:2891 affibody (10.0 M) for 4 h before the addition of Pyro, Pyro-Linker-OH, or Pyro-Linker-ZHER2.
In Vitro Model Gastric tubular adenocarcinoma NCI-N87 cells CVCL_1603
Experiment 3 Reporting the Activity Date of This ADC [1]
Efficacy Data Half Maximal Inhibitory Concentration (IC50) > 1000 nM Low HER2 expression (HER2 -)
Method Description
Dark toxicity was measured without light illumination, and a HER2 receptor blocking experiment was carried out by preincubation of the cells with free ZHER2:2891 affibody (10.0 M) for 4 h before the addition of Pyro, Pyro-Linker-OH, or Pyro-Linker-ZHER2.
In Vitro Model Invasive breast carcinoma MCF-7 cells CVCL_0031
Experiment 4 Reporting the Activity Date of This ADC [1]
Efficacy Data Half Maximal Inhibitory Concentration (IC50) > 1000 nM Low HER2 expression (HER2 -)
Method Description
Dark toxicity was measured without light illumination, and a HER2 receptor blocking experiment was carried out by preincubation of the cells with free ZHER2:2891 affibody (10.0 M) for 4 h before the addition of Pyro, Pyro-Linker-OH, or Pyro-Linker-ZHER2.
In Vitro Model Prostate carcinoma PC-3 cells CVCL_0035
Experiment 5 Reporting the Activity Date of This ADC [1]
Efficacy Data Half Maximal Inhibitory Concentration (IC50) > 1000 nM High HER2 expression (HER2 +++)
Method Description
Dark toxicity was measured without light illumination, and a HER2 receptor blocking experiment was carried out by preincubation of the cells with free ZHER2:2891 affibody (10.0 M) for 4 h before the addition of Pyro, Pyro-Linker-OH, or Pyro-Linker-ZHER2.
In Vitro Model Gastric tubular adenocarcinoma NCI-N87 cells (blocking) CVCL_1603
Experiment 6 Reporting the Activity Date of This ADC [1]
Efficacy Data Half Maximal Inhibitory Concentration (IC50) > 1000 nM Low HER2 expression (HER2 -)
Method Description
Dark toxicity was measured without light illumination, and a HER2 receptor blocking experiment was carried out by preincubation of the cells with free ZHER2:2891 affibody (10.0 M) for 4 h before the addition of Pyro, Pyro-Linker-OH, or Pyro-Linker-ZHER2.
In Vitro Model Prostate carcinoma PC-3 cells (blocking) CVCL_0035
References
Ref 1 Anti-HER2 Affibody-Conjugated Photosensitizer for Tumor Targeting Photodynamic Therapy. Mol Pharm. 2020 May 4;17(5):1546-1557. doi: 10.1021/acs.molpharmaceut.9b01247. Epub 2020 Apr 16.

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