MMP-2/MMP-9 Inhibitor I - Moligand™,≥99% , CAS No.193807-58-8

CAS: 193807-58-8 Cat. No.: M276513 Molecular Weight: 381.44

GRADE & PURITY Moligand™, ≥99%

Synonyms

N-[(1,1'-Biphenyl)-4-ylsulfonyl]-D-phenylalanine | (R)-2-([1,1'-Biphenyl]-4-ylsulfonamido)-3-phenylpropanoic acid

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Overview

MMP-2/MMP-9-IN-1 is a potent bioavailable inhibitor of type IV collagenases (MMP-9 and MMP-2) with an IC50 of 0.24 and 0.3 1 μM for MMP-9 and MMP-2, respectively. activity, which can be used to study cancer.

Specifications

Synonyms

N-[(1, 1'-Biphenyl)-4-ylsulfonyl]-D-phenylalanine | (R)-2-([1, 1'-Biphenyl]-4-ylsulfonamido)-3-phenylpropanoic acid

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Matrix metalloproteinase inhibitor of MMP-2/MMP-9. Synergizes with TNF-α to induce apoptosis in cancer cells. Active in vitro .

Storage

Store at 2-8°C, Protected from light, Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: S(N[C@H](CC1=CC=CC=C1)C(O)=O)(=O)(=O)C2=CC=C(C=C2)C3=CC=CC=C3
• IUPAC Name: 3-phenyl-2-[(4-phenylphenyl)sulfonylamino]propanoic acid
• InChIKey: JBYHBQIDTNHWJF-UHFFFAOYSA-N
• INCHI: 1S/C21H19NO4S/c23-21(24)20(15-16-7-3-1-4-8-16)22-27(25,26)19-13-11-18(12-14-19)17-9-5-2-6-10-17/h1-14,20,22H,15H2,(H,23,24)
• Isomeric SMILES: C1=CC=C(C=C1)CC(C(=O)O)NS(=O)(=O)C2=CC=C(C=C2)C3=CC=CC=C3
• Molecular Weight: 381.44
• Reaxy-Rn: 13916496
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=13916496&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Phenylalanine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Phenylalanine and derivatives
• Alternative Parents: Biphenyls and derivatives Phenylpropanoic acids Benzenesulfonamides Amphetamines and derivatives Benzenesulfonyl compounds Organosulfonamides Aminosulfonyl compounds Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenylalanine or derivatives - Biphenyl - 3-phenylpropanoic-acid - Amphetamine or derivatives - Benzenesulfonamide - Benzenesulfonyl group - Monocyclic benzene moiety - Benzenoid - Organosulfonic acid amide - Aminosulfonyl compound - Sulfonyl - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Carboxylic acid - Monocarboxylic acid or derivatives - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organosulfur compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 25 mM
• Sensitivity: Light sensitive
• Molecular Weight: 381.400 g/mol
• XLogP3: 4.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 381.103 Da
• Monoisotopic Mass: 381.103 Da
• Topological Polar Surface Area: 91.900 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 565.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xinming Wang, Haonan Zhang, Weichang Xie, Bei Qian, Shixing Huang, Qiang Zhao, Xiaofeng Ye.  (2025)  Development of a decellularized extracellular matrix-derived wet adhesive for sustained drug delivery and enhanced wound healing.  Materials Today Bio,      [PMID:40255583] [10.1016/j.mtbio.2025.101734]

2. Mingye Chen, Junjie Tang, Binfa Liang, Gang Feng, Zefeng Deng, Simin Chen, Qing Sun, Jie Liu, Xian Chen.  (2025)  In situ pro-regenerative and repair capabilities of human umbilical mesenchymal stem cells and collagen hydrogel complex in mice with thin endometrium.  Acta Biomaterialia,      [PMID:41106758] [10.1016/j.actbio.2025.10.026]

3. Yunxia Du, Di Xiao, Changle Ren, Zhenlan Li, Xiaofeng Wang, Yantao Zhao, Yongmei Jiang.  (2026)  pH-responsive polydopamine-shelled 3D-printed chitosan/collagen hydrogel integrating exosomes and an enzyme/peptide cascade for diabetic wound healing.  Biomaterials Science,      [PMID:41685930] [10.1039/D5BM01823D]

4. HaoRan Jiang, Yang Qu, Qi Meng, Chenyujun Hu, Haoran Zhang, Jinqiu Tian, Bohan Xing, Bojiang Wang, Zhihao Lin, Meng Zhang, Peixun Zhang.  (2026)  Biomimetic Bamboo-Inspired Bone Repair Scaffold: Reversing Degraded States and Promoting Mesenchymal Stem Cell Differentiation.  ACS Applied Bio Materials,      [PMID:] [10.1021/acsabm.6c00387]