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Mc-Val-Cit-PABC-PNP

Product Name
Mc-Val-Cit-PABC-PNP
CAS No.
159857-81-5
Chemical Name
Mc-Val-Cit-PABC-PNP
Synonyms
Mc-Val-Cit-PABC-PNP;MC-Val-Cit-PAB-PNP;MC-VC-PAB-PNP;MC-Val-Cit-PABC;L-Ornithinamide;MC-VAL-CIT-PAB-PNB;SKL361;CS-1787;AK-32171;VCMMAE linker
CBNumber
CB32667895
Molecular Formula
C35H43N7O11
Formula Weight
737.76
MOL File
159857-81-5.mol
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Mc-Val-Cit-PABC-PNP Property

Boiling point:
1034.5±65.0 °C(Predicted)
Density 
1.338±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
DMF: 25 mg/ml; DMSO: 20 mg/ml; DMSO:PBS(pH 7.2) (1:4): 0.20 mg/ml
form 
A crystalline solid
pka
13.24±0.70(Predicted)
color 
Off-white to light yellow
InChIKey
UQRQGHMQKAXOTE-DHIFEGFHSA-N
SMILES
C(N)(=O)[C@H](CCCNC(N)=O)N(C(=O)[C@H](C(C)C)NC(=O)CCCCCN1C(=O)C=CC1=O)C1=CC=C(COC(OC2=CC=C([N+]([O-])=O)C=C2)=O)C=C1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H303May be harmfulif swallowed

H320Causes eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

TCI Chemical
Product number
M3209
Product name
Mc-Val-Cit-PABC-PNP
Packaging
500MG
Price
$580
Updated
2025/07/31
Cayman Chemical
Product number
23881
Product name
Mc-Val-Cit-PABC-PNP
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
23881
Product name
Mc-Val-Cit-PABC-PNP
Purity
≥98%
Packaging
5mg
Price
$139
Updated
2024/03/01
Cayman Chemical
Product number
23881
Product name
Mc-Val-Cit-PABC-PNP
Purity
≥98%
Packaging
10mg
Price
$243
Updated
2024/03/01
Iris Biotech GmbH
Product number
ADC1110
Product name
MC-Val-Cit-PAB-PNP
Packaging
250mg
Price
$472.5
Updated
2021/12/16
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Mc-Val-Cit-PABC-PNP Chemical Properties,Usage,Production

Description

Mc-Val-Cit-PABC-PNP is a peptide linker molecule used in the synthesis of antibody-drug conjugates (ADCs). It contains a maleimidocaproyl (Mc) group that can be conjugated to an antibody and a p-nitrophenol (PNP) group that allows the peptide to be linked to anticancer compounds, such as doxorubicin or monomethyl auristatin E (MMAE; ). ADCs target specific cell populations to induce a selective response, such as cell death in cancer cells.

Uses

Mc-Val-Cit-PABC-PNP is a cathepsin cleavable ADC linker used in the synthesis of antibody-drug conjugates.

General Description

Mc-Val-Cit-PABC-PNP is chemically known as L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-, an enzymatically cleavable linker for antibody-drug conjugates (ADCs). Other ADCs linkers include MC-Val-Cit-PAB-PNP, Mc-Val-Ala-PAB-PNP, Mc-Val-Cit-PABOH, and VcMMAE.

Synthesis

159857-80-4

5070-13-3

159857-81-5

GENERAL STEPS: To a mixed solution of compound 11 (500 mg, 0.87 mmol) and bis(4-nitrophenyl) carbonate (bis-PNP, 2.64 g, 8.72 mmol) in DCM:DMF (8:2, 25 mL) was added N,N-diisopropylethylamine (DIPEA, 0.45 mL, 2.61 mmol). The reaction mixture was stirred at 23 °C for 20 h. After purification by silica gel column chromatography (eluent: DCM:CH3OH, 50:1 to 10:1), the target product, maleimidohexanoyl-L-valyl-L-citrulline p-aminobenzyl alcohol p-nitrophenyl carbonate 9 (364 mg, 57% yield) was obtained. Thin layer chromatography (TLC) Rf = 0.40 (unfolding agent: CH2Cl2:CH3OH, 9:1).1H NMR (400 MHz, CDCl3/CD3OD) δ 9.45 (s, 1H), 8.23 (d, J = 8.3 Hz, 2H), 7.59 (d, J = 8.5 Hz, 2H), 7.35 (d, J = 8.3 Hz. 2H), 7.34 (d, J = 8.5 Hz, 2H), 6.65 (s, 2H), 5.20 (s, 2H), 4.56 (dt, J = 10.5, 5.4 Hz, 1H), 4.15 (d, J = 7.2 Hz, 1H), 3.46 (dd, J = 8.0, 6.4 Hz, 2H), 3.16-2.89 (m, 2H). 2.21 (dd, J = 8.3, 6.6 Hz, 2H), 2.06-1.97 (m, 1H), 1.90-1.83 (m, 1H), 1.73-1.46 (m, 7H), 1.34-1.20 (m, 2H), 0.91 (d, J = 6.7 Hz, 3H), 0.90 (d, J = 6.7 Hz, 3H).13C NMR (125 MHz, CDCl3/CD3OD) δ 174.4, 172.4, 171.1, 170.6, 160.5, 155.5, 152.5, 145.3, 138.7, 134.1, 129.9, 129.5, 125.2, 121.8, 120.0, 70.6, 59.0, 53.2, 37.5, 35.8, 30.6, 29.6, 29.3, 28.1, 26.2, 25.1, 19.1, 18.1. ESI-MS m/z: Calculated value C34H42N6O11: 737.3; measured value: 738.3 ([M + H]+).

IC 50

Protease Cleavable Linker; Cleavable Linker

References

[1] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[2] Patent: WO2017/66668, 2017, A1. Location in patent: Paragraph 000199; 000200
[3] Patent: WO2014/191578, 2014, A1. Location in patent: Page/Page column 137-138
[4] Patent: EP2927227, 2015, A1. Location in patent: Paragraph 0051; 0052; 0053; 0054; 0055-0059
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 989 - 1000

Mc-Val-Cit-PABC-PNP Preparation Products And Raw materials

Raw materials

Preparation Products

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Mc-Val-Cit-PABC-PNP Suppliers

Americas 1 Canada 1 China 226 China Hong Kong 1 Europe 1 India 4 Japan 1 United States 16 Global 251
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View Lastest Price from Mc-Val-Cit-PABC-PNP manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
Mc-Val-Cit-PABC-PNP 159857-81-5
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-09-28
Xian confluore Biological Technology Co., Ltd.
Product
MC-Val-Cit-PAB-PNP 159857-81-5
Price
US $0.00/g
Min. Order
5g
Purity
>97.00%
Supply Ability
5g
Release date
2024-03-29
Henan Fengda Chemical Co., Ltd
Product
L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]- 159857-81-5
Price
US $50.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-22

159857-81-5, Mc-Val-Cit-PABC-PNPRelated Search:

SUC-ALA-ALA-PRO-PHE-PNA L-Tryptophan L-Valine methyl ester hydrochloride L-Valine Maleimide

  • L-Ornithinamide
  • Maleimidocaproyl-L-valine-L-citrulline-p-aminobenzyl alcohol p-nitrophenyl carbonate Mc-Val-Cit-PABC-PNP
  • MC-Val-Cit-PABC
  • L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-
  • Mc-Val-Cit-PABC-PNP
  • MC-VC-PAB-PNP
  • MC-VAL-CIT-PAB-PNB
  • MC-Val-Cit-PAB-PNP
  • Maleimidocaproyl-L-valine-L-citrulline-p-aminobenzyl alcohol p-nitrophenyl carbonate
  • MC-Val-Cit-PAB-PNP (ADC peptide linker)
  • 4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl 4-nitrophenyl carbonate
  • MC-VC-PAB-PNP,Mc-Val-Cit-PABC-PNP
  • MC-VAL-CIT-PABC-PNP;MC-VC-PAB-PNP;MC-VAL-CIT-PAB-PNB;MC-VAL-CIT-PAB-PNP
  • Mc-Val-Cit-PABC-PNP (Maleimidocaproyl-L-valine-L-citrulline-p-aminobenzyl alcohol p-nitrophenyl carbonate)
  • CS-1787
  • Mc-Val-Cit-PABC-PNP(VCMMAE linker)
  • [4-[[(2S)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methyl-butanoyl]amino]-5-ureido-pentanoyl]amino]phenyl]methyl (4-nitrophenyl) carbonate
  • N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide
  • VCMMAE linker
  • JACS-159857-81-5
  • N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-
  • L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(5-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]-
  • 4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl 4-nitrophenyl carbonate,linker
  • N-(6-Maleimidocaproyl)-L-valyl-N5-carbamoyl-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl
  • L-OrnithinaMide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aMinocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]Methyl]phenyl]- ISO 9001：2015 REACH
  • SKL361
  • AK-32171
  • [4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl (4-nitrophenyl) carbonate
  • 1H-Indene-1,3(2H)-dione,5,8-dichloro-
  • N-[6-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]-L-ornithinamide
  • Top quality 159857-81-5 MC-Val-Cit-PABC
  • (4-[(2S)-5-(carbamoylamino)-2-[(2S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido]pentanamido]phenyl)methyl 4-nitrophenyl carbonate
  • Ornithine Impurity 13
  • Inhibitor|||inhibit|||MC-Val-Cit-PABC-PNP|||Maleimidocaproyl-L-valine-L-citrulline-p-aminobenzyl alcohol p-nitrophenyl carbonate|||Maleimidocaproyl-L-valine-L-citrulline-p-aminobenzyl alcohol p-nitrophenyl carbonate|||ADC Linkers|||MC Val Cit PABC PNP|||Antibody-drug conjugate
  • 159857-81-5
  • 159857-81-6
  • C35H43N7O11
  • ADCs Linkers
  • ADCs
  • ADC-Linker
  • ADC-Linkers