Synonym
UAMC-1110; UAMC 1110; UAMC1110; SP-13786; SP 13786; SP13786;
IUPAC/Chemical Name
(S)-N-(2-(2-Cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)quinoline-4-carboxamide
InChi Key
PUOOCZVRHBHJRS-NSHDSACASA-N
InChi Code
InChI=1S/C17H14F2N4O2/c18-17(19)7-11(8-20)23(10-17)15(24)9-22-16(25)13-5-6-21-14-4-2-1-3-12(13)14/h1-6,11H,7,9-10H2,(H,22,25)/t11-/m0/s1
SMILES Code
O=C(C1=CC=NC2=CC=CC=C12)NCC(N3[C@H](C#N)CC(F)(F)C3)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Novel potent and selective inhibitor of fibroblast activation protein (FAP).
In vitro activity:
The synthesis, biochemical characterization, and application of three different activity-based probes (biotin-, Cy3-, and Cy5-labeled) were described based on the FAP-inhibitor UAMC1110, an in-house developed molecule considered to be the most potent and selective FAP inhibitor available. The three probes have subnanomolar FAP affinity and pronounced selectivity with respect to the related S9 family members were demonstrated. Furthermore, the fluorescent Cy3- and Cy5-labeled probes were reported to be capable of selectively detecting FAP in a cellular context, making these chemical probes highly suitable for further biological studies. Moreover, proof of concept is provided for in situ FAP activity staining in patient-derived cryosections of urothelial tumors.
Ref: Van Rymenant Y, Tanc M, Van Elzen R, Bracke A, De Wever O, Augustyns K, Lambeir AM, Kockx M, De Meester I, Van Der Veken P. In Vitro and In Situ Activity-Based Labeling of Fibroblast Activation Protein with UAMC1110-Derived Probes. Front Chem. 2021 Apr 14;9:640566. doi: 10.3389/fchem.2021.640566. PMID: 33996747; PMCID: PMC8114891.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
344.32
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
Van Rymenant Y, Tanc M, Van Elzen R, Bracke A, De Wever O, Augustyns K, Lambeir AM, Kockx M, De Meester I, Van Der Veken P. In Vitro and In Situ Activity-Based Labeling of Fibroblast Activation Protein with UAMC1110-Derived Probes. Front Chem. 2021 Apr 14;9:640566. doi: 10.3389/fchem.2021.640566. PMID: 33996747; PMCID: PMC8114891.
In vitro protocol:
Van Rymenant Y, Tanc M, Van Elzen R, Bracke A, De Wever O, Augustyns K, Lambeir AM, Kockx M, De Meester I, Van Der Veken P. In Vitro and In Situ Activity-Based Labeling of Fibroblast Activation Protein with UAMC1110-Derived Probes. Front Chem. 2021 Apr 14;9:640566. doi: 10.3389/fchem.2021.640566. PMID: 33996747; PMCID: PMC8114891.
1: De Decker A, Vliegen G, Van Rompaey D, Peeraer A, Bracke A, Verckist L, Jansen K, Geiss-Friedlander R, Augustyns K, De Winter H, De Meester I, Lambeir AM, Van der Veken P. Novel Small Molecule-Derived, Highly Selective Substrates for Fibroblast Activation Protein (FAP). ACS Med Chem Lett. 2019 Jul 9;10(8):1173-1179. doi: 10.1021/acsmedchemlett.9b00191. PMID: 31413802; PMCID: PMC6691567.
2: Moon ES, Elvas F, Vliegen G, De Lombaerde S, Vangestel C, De Bruycker S, Bracke A, Eppard E, Greifenstein L, Klasen B, Kramer V, Staelens S, De Meester I, Van der Veken P, Rösch F. Targeting fibroblast activation protein (FAP): next generation PET radiotracers using squaramide coupled bifunctional DOTA and DATA5m chelators. EJNMMI Radiopharm Chem. 2020 Jul 29;5(1):19. doi: 10.1186/s41181-020-00102-z. PMID: 32728930; PMCID: PMC7391456.
3: Gunderson AJ, Yamazaki T, McCarty K, Phillips M, Alice A, Bambina S, Zebertavage L, Friedman D, Cottam B, Newell P, Gough MJ, Crittenden MR, Van der Veken P, Young KH. Blockade of fibroblast activation protein in combination with radiation treatment in murine models of pancreatic adenocarcinoma. PLoS One. 2019 Feb 6;14(2):e0211117. doi: 10.1371/journal.pone.0211117. PMID: 30726287; PMCID: PMC6364920.
