197151-79-4Relevant academic research and scientific papers
Water-soluble closo-docecaborate-containing pteroyl derivatives targeting folate receptor-positive tumors for boron neutron capture therapy
Nakagawa, Fumiko,Kawashima, Hidehisa,Morita, Taiki,Nakamura, Hiroyuki
, p. 1 - 9 (2020)
Water-soluble pteroyl-closo-dodecaborate conjugates (PBCs 1–4), were developed as folate receptor (FRα) targeting boron carriers for boron neutron capture therapy (BNCT). PBCs 1–4 had adequately low cytotoxicity with IC50 values in the range of 1~3 mM toward selected human cancer cells, low enough to use as BNCT boron agents. PBCs 1–3 showed significant cell uptake by FRα positive cells, especially U87MG glioblastoma cells, although the accumulation of PBC 4 was low compared with PBCs 1–3 and L-4-boronophenylalanine (L-BPA). The cellular uptake of PBC 1 and PBC 3 by HeLa cells was arrested by increasing the concentration of folate in the medium, indicating that the major uptake mechanisms of PBC 1–3 are primarily through FRα receptor-mediated endocytosis.
Synthesis, characterization, and anticancer activity of folate γ-ferrocenyl conjugates
Bertuzzi, Diego L.,Braga, Carolyne B.,Ornelas, Catia,Perli, Gabriel
, p. 4694 - 4703 (2020/04/03)
The quest for alternative therapeutic agents with safe and effective profiles is one of the biggest challenges in oncology. Folate-targeted therapy can deliver drugs selectively into malignant cells via the Frα receptor, whereas bioorganometallic chemistr
Folic acid conjugates of a bleomycin mimic for selective targeting of folate receptor positive cancer cells
Geersing, Arjan,de Vries, Reinder H.,Jansen, Gerrit,Rots, Marianne G.,Roelfes, Gerard
supporting information, p. 1922 - 1927 (2019/06/05)
A major challenge in the application of cytotoxic anti-cancer drugs is their general lack of selectivity, which often leads to systematic toxicity due to their inability to discriminate between malignant and healthy cells. A particularly promising target for selective targeting are the folate receptors (FR) that are often over-expressed on cancer cells. Here, we report on a conjugate of the pentadentate nitrogen ligand N4Py to folic acid, via a cleavable disulphide linker, which shows selective cytotoxicity against folate receptor expressing cancer cells.
Design and structure activity relationship of tumor-homing histone deacetylase inhibitors conjugated to folic and pteroic acids
Sodji, Quaovi H.,Kornacki, James R.,McDonald, John F.,Mrksich, Milan,Oyelere, Adegboyega K.
, p. 340 - 359 (2015/04/27)
Histone deacetylase (HDAC) inhibition has recently emerged as a novel therapeutic approach for the treatment of various pathological conditions including cancer. Currently, two HDAC inhibitors (HDACi) - Vorinostat and Romidepsin - have been approved for t
Site-specific folate conjugation to a cytotoxic protein
Smith, Bryan D.,Higgin, Joshua J.,Raines, Ronald T.
, p. 5029 - 5032 (2011/10/09)
Conjugation to folic acid is known to enhance the uptake of molecules by human cells that over-produce folate receptors. Variants of bovine pancreatic ribonuclease (RNase A) that have attenuated affinity for the endogenous ribonuclease inhibitor protein (
The synthesis of pteroyl-lys conjugates and its application as Technetium-99m labeled radiotracer for folate receptor-positive tumor targeting
Guo, Hongjuan,Xie, Fang,Zhu, Meilin,Li, Yan,Yang, Zhi,Wang, Xuebin,Lu, Jie
, p. 2025 - 2029 (2011/05/02)
Aiming to develop a new 99mTc-labeled folate derivative for FR-positive tumor imaging, a simpler method has been established to synthesize the folate-drug conjugates with free α-carboxyl group. In this study, the conjugate pteroyl-lys-HYNIC was
Folate-modified cholesterol-bearing pullulan as a drug carrier
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Page/Page column 3, (2008/06/13)
Folate modified cholesterol-bearing pullulan (FA-CHP) was synthesized by the reaction of folic acid γ-2-aminoethylamide and 4-nitorophenyl chloroformate-activated cholesterol-bearing pullulan, wherein folate and pullulan are connected through a NH—CH
Phosphinic acid pseudopeptides analogous to glutamyl-γ-glutamate: Synthesis and coupling to pteroyl azides leads to potent inhibitors of folylpoly-γ-glutamate synthetase
Valiaeva,Bartley,Konno,Coward
, p. 5146 - 5154 (2007/10/03)
Several routes to a complex phosphinate phosphapeptide analogous to the γ-glutamyl peptide Gluγ-Glu have been investigated. Formation of γ-phosphono glutamate derivatives via addition of a phosphorus-based radical to protected vinylglycine was found to be of limited value because of the elevated temperatures required. Alkylation and conjugate addition reactions of trivalent phosphorus (PIII) species were investigated. In situ generation of bis-trimethylsilyl esters of phosphinous acids proved to be an effective route to phosphinates of modest structural complexity. However, this chemistry could not be extended to the incorporation of an amino acid moiety at the N-terminal side of the desired phosphinate. A successful synthesis of the target phosphinate phosphapeptide was effected using PIII chemistry and dehydrohalogenation to yield an α,β-unsaturated phosphinic acid ester, following which conjugate addition of diethylacetamido malonate and acid-mediated hydrolysis afforded the desired phosphinate phosphapeptide. Coupling of the unprotected phosphinate phosphapeptide with two acyl azides derived from folic acid and methotrexate led to the corresponding pteroylphosphapeptides of interest as possible mimics of tetrahedral intermediates in the reaction catalyzed by folylpolyglutamate synthetase.
Efficient syntheses of pyrofolic acid and pteroyl azide, reagents for the production of carboxyl-differentiated derivatives of folic acid
Luo, Jin,Smith, Michael D.,Lantrip, Douglas A.,Wang, Susan,Fuchs
, p. 10004 - 10013 (2007/10/03)
Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N10-(trifluoroacetyl)pyrrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from I without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.
