Synthesis and Antitumor Activity of a Novel Series of 6-Substituted Pyrrolo[2,3-d]pyrimidine Thienoyl Antifolate Inhibitors of Purine Biosynthesis with Selectivity for High Affinity Folate Receptors and the Proton-Coupled Folate Transporter over the Reduced Folate Carrier for Cellular Entry

Lei Wang; Christina Cherian; Sita Kugel Desmoulin; Lisa Polin; Yijun Deng; Jianmei Wu; Zhanjun Hou; Kathryn White; Juiwanna Kushner; Larry H. Matherly; Aleem Gangjee

doi:10.1021/jm9015729

Synthesis and Antitumor Activity of a Novel Series of 6-Substituted Pyrrolo[2,3-d]pyrimidine Thienoyl Antifolate Inhibitors of Purine Biosynthesis with Selectivity for High Affinity Folate Receptors and the Proton-Coupled Folate Transporter over the Reduced Folate Carrier for Cellular Entry

Journal of Medicinal Chemistry ◽

10.1021/jm9015729 ◽

2010 ◽

Vol 53 (3) ◽

pp. 1306-1318 ◽

Cited By ~ 44

Author(s):

Lei Wang ◽

Christina Cherian ◽

Sita Kugel Desmoulin ◽

Lisa Polin ◽

Yijun Deng ◽

...

Keyword(s):

Antitumor Activity ◽

Purine Biosynthesis ◽

Reduced Folate Carrier ◽

Folate Receptors ◽

High Affinity ◽

Cellular Entry

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Synthesis and Biological Activity of a Novel Series of 6-Substituted Thieno[2,3-d]pyrimidine Antifolate Inhibitors of Purine Biosynthesis with Selectivity for High Affinity Folate Receptors over the Reduced Folate Carrier and Proton-Coupled Folate Transporter for Cellular Entry†

Journal of Medicinal Chemistry ◽

10.1021/jm8011323 ◽

2009 ◽

Vol 52 (9) ◽

pp. 2940-2951 ◽

Cited By ~ 57

Author(s):

Yijun Deng ◽

Xilin Zhou ◽

Sita Kugel Desmoulin ◽

Jianmei Wu ◽

Christina Cherian ◽

...

Keyword(s):

Biological Activity ◽

Purine Biosynthesis ◽

Reduced Folate Carrier ◽

Folate Receptors ◽

High Affinity ◽

Cellular Entry

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Discovery of Novel Antifolate Inhibitors of De Novo Purine Nucleotide Biosynthesis with Selectivity for High Affinity Folate Receptors and the Proton-Coupled Folate Transporter Over the Reduced Folate Carrier for Cellular Entry

Targeted Drug Strategies for Cancer and Inflammation ◽

10.1007/978-1-4419-8417-3_6 ◽

2011 ◽

pp. 119-134 ◽

Cited By ~ 3

Author(s):

Larry H. Matherly ◽

Aleem Gangjee

Keyword(s):

De Novo ◽

Reduced Folate Carrier ◽

Purine Nucleotide ◽

Nucleotide Biosynthesis ◽

Folate Receptors ◽

High Affinity ◽

Cellular Entry

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Synthesis and Biological Activity of 6-Substituted Pyrrolo[2,3-d]pyrimidine Thienoyl Regioisomers as Inhibitors of de Novo Purine Biosynthesis with Selectivity for Cellular Uptake by High Affinity Folate Receptors and the Proton-Coupled Folate Transporter over the Reduced Folate Carrier

Journal of Medicinal Chemistry ◽

10.1021/jm201688n ◽

2012 ◽

Vol 55 (4) ◽

pp. 1758-1770 ◽

Cited By ~ 34

Author(s):

Lei Wang ◽

Christina Cherian ◽

Sita Kugel Desmoulin ◽

Shermaine Mitchell-Ryan ◽

Zhanjun Hou ◽

...

Keyword(s):

Biological Activity ◽

Cellular Uptake ◽

De Novo ◽

Purine Biosynthesis ◽

Reduced Folate Carrier ◽

Folate Receptors ◽

High Affinity ◽

De Novo Purine Biosynthesis

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Design, synthesis and biological evaluation of novel pyrrolo[2,3-d]pyrimidine as tumor-targeting agents with selectivity for tumor uptake by high affinity folate receptors over the reduced folate carrier

Bioorganic & Medicinal Chemistry ◽

10.1016/j.bmc.2020.115544 ◽

2020 ◽

Vol 28 (12) ◽

pp. 115544 ◽

Cited By ~ 1

Author(s):

Lalit K. Golani ◽

Farhana Islam ◽

Carrie O'Connor ◽

Aamod S. Dekhne ◽

Zhanjun Hou ◽

...

Keyword(s):

Tumor Targeting ◽

Biological Evaluation ◽

Reduced Folate Carrier ◽

Tumor Uptake ◽

Design Synthesis ◽

Folate Receptors ◽

High Affinity ◽

Synthesis And Biological Evaluation

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Epitope and Fc-Mediated Cross-linking, but Not High Affinity, Are Critical for Antitumor Activity of CD137 Agonist Antibody with Reduced Liver Toxicity

Molecular Cancer Therapeutics ◽

10.1158/1535-7163.mct-19-0608 ◽

2020 ◽

Vol 19 (4) ◽

pp. 1040-1051 ◽

Cited By ~ 3

Author(s):

Sun K. Ho ◽

Zhenghai Xu ◽

Archana Thakur ◽

Melvin Fox ◽

Siu Sze Tan ◽

...

Keyword(s):

Antitumor Activity ◽

Liver Toxicity ◽

Cross Linking ◽

High Affinity ◽

Agonist Antibody

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Further studies on the interaction of nonpolyglutamatable aminopterin analogs with dihydrofolate reductase and the reduced folate carrier as determinants of in vitro antitumor activity

Biochemical Pharmacology ◽

10.1016/s0006-2952(03)00102-3 ◽

2003 ◽

Vol 65 (9) ◽

pp. 1427-1433 ◽

Cited By ~ 5

Author(s):

Joel E Wright ◽

Gregory K Yurasek ◽

Ying-Nan Chen ◽

Andre Rosowsky

Keyword(s):

Antitumor Activity ◽

Dihydrofolate Reductase ◽

Reduced Folate Carrier

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Antitumor Activity of Clomiphene Analogsin Vitro: Relationship to Affinity for the Estrogen Receptor and Another High Affinity Antiestrogen-Binding Site

The Journal of Clinical Endocrinology & Metabolism ◽

10.1210/jcem-57-2-373 ◽

1983 ◽

Vol 57 (2) ◽

pp. 373-379 ◽

Cited By ~ 27

Author(s):

LEIGH C. MURPHY ◽

ROBERT L. SUTHERLAND

Keyword(s):

Estrogen Receptor ◽

Antitumor Activity ◽

Binding Site ◽

High Affinity

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Effects of C7 substitutions in a high affinity microtubule-binding taxane on antitumor activity and drug transport

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2011.06.034 ◽

2011 ◽

Vol 21 (16) ◽

pp. 4852-4856 ◽

Cited By ~ 6

Author(s):

Xi Xiao ◽

Ju Wu ◽

Chiara Trigili ◽

Hui Chen ◽

Joseph W.K. Chu ◽

...

Keyword(s):

Antitumor Activity ◽

Drug Transport ◽

Microtubule Binding ◽

High Affinity

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Characterization of a Folate Transporter in HeLa Cells with a Low pH Optimum and High Affinity for Pemetrexed Distinct from the Reduced Folate Carrier

Clinical Cancer Research ◽

10.1158/1078-0432.ccr-04-0645 ◽

2004 ◽

Vol 10 (18) ◽

pp. 6256-6264 ◽

Cited By ~ 59

Author(s):

Yanhua Wang ◽

Rongbao Zhao ◽

I. David Goldman

Keyword(s):

Hela Cells ◽

Low Ph ◽

Reduced Folate Carrier ◽

Ph Optimum ◽

High Affinity

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Synthesis, Biological, and Antitumor Activity of a Highly Potent 6-Substituted Pyrrolo[2,3-d]pyrimidine Thienoyl Antifolate Inhibitor with Proton-Coupled Folate Transporter and Folate Receptor Selectivity over the Reduced Folate Carrier That Inhibits β-Glycinamide Ribonucleotide Formyltransferase

Journal of Medicinal Chemistry ◽

10.1021/jm200739e ◽

2011 ◽

Vol 54 (20) ◽

pp. 7150-7164 ◽

Cited By ~ 48

Author(s):

Lei Wang ◽

Sita Kugel Desmoulin ◽

Christina Cherian ◽

Lisa Polin ◽

Kathryn White ◽

...

Keyword(s):

Antitumor Activity ◽

Folate Receptor ◽

Reduced Folate Carrier ◽

Receptor Selectivity ◽

Glycinamide Ribonucleotide Formyltransferase

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