Erratum: Structure-Activity Profiles of Novel 6-Substituted Pyrrolo[2,3-d]pyrimidine Thienoyl Antifolates with Modified Amino Acids for Cellular Uptake by Folate Receptors α and β and the Proton-Coupled Folate Transporter (Journal of Medicinal Chemistry (2014) 57 (8152-8166) DOI: 10.1021/jm501113m);Structure-activity profiles of novel 6-substituted pyrrolo[2,3- d ]pyrimidine thienoyl antifolates with modified amino acids for cellular uptake by folate receptors α and β and the proton-coupled folate transporter

Journal of Medicinal Chemistry

Volumn 57, Issue 19, 2014, Pages 8152-8166

  Golani, Lalit K ^a   George, Christina ^b   Zhao, Sai ^a   Raghavan, Sudhir ^a   Orr, Steven ^b   Wallace, Adrianne ^b   Wilson, Mike R ^c   Hou, Zhanjun ^b   Matherly, Larry H ^b,c   Gangjee, Aleem ^a  

^a DUQUESNE UNIVERSITY   (United States)

^b KARMANOS CANCER INSTITUTE   (United States)

^c WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [[5 [3 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)PROPYL]THIOPHENE 2 CARBONYL]AMINO]BUTANEDIOIC ACID; 2 [[5 [3 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)PROPYL]THIOPHENE 2 CARBONYL]AMINO]HEXANEDIOIC ACID; 2 [[5 [3 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)PROPYL]THIOPHENE 2 CARBONYL]AMINO]PENTANEDIOIC ACID; 2 [[5 [3 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)PROPYL]THIOPHENE 2 CARBONYL]AMINO]PENTANOIC ACID; 4 [[5 [3 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)PROPYL]THIOPHENE 2 CARBONYL]AMINO]BUTANOIC ACID; 5 [3 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)PROPYL]THIOPHENE 2 CARBOXYLIC ACID; AMINO ACID; ANTINEOPLASTIC AGENT; CARBOXYLIC ACID; FOLATE RECEPTOR 1; FOLATE RECEPTOR 2; FOLIC ACID ANTAGONIST; GLUTAMIC ACID; METHOTREXATE; PEMETREXED; PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE; PROTON COUPLED FOLATE TRANSPORTER; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; RALTITREXED; UNCLASSIFIED DRUG; FOLATE TRANSPORTER; PYRIMIDINE DERIVATIVE;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CANCER CELL LINE; CHEMICAL MODIFICATION; CHO CELL LINE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG POTENCY; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; IC50; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; PROTEIN EXPRESSION; PURINE SYNTHESIS; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMICAL STRUCTURE; CRICETULUS; HAMSTER; KB CELL LINE; PHYSIOLOGY; SYNTHESIS;

ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; FOLATE RECEPTOR 1; FOLATE RECEPTOR 2; FOLIC ACID ANTAGONISTS; FOLIC ACID TRANSPORTERS; HUMANS; KB CELLS; MODELS, MOLECULAR; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84907907191     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.6b00502     Document Type: Erratum

References (36)

1. Elnakat, H.; Ratnam, M. Distribution, functionality and gene regulation of folate receptor isoforms: Implications in targeted therapy Adv. Drug Delivery Rev. 2004, 56, 1067-1084
2. Matherly, L. H.; Hou, Z.; Deng, Y. Human reduced folate carrier: Translation of basic biology to cancer etiology and therapy Cancer Metastasis Rev. 2007, 26, 111-128
3. Zhao, R.; Diop-Bove, N.; Visentin, M.; Goldman, I. D. Mechanisms of membrane transport of folates into cells and across epithelia Annu. Rev. Nutr. 2011, 31, 177-201
4. Kugel Desmoulin, S.; Hou, Z.; Gangjee, A.; Matherly, L. H. The human proton-coupled folate transporter: Biology and therapeutic applications to cancer Cancer Biol. Ther. 2012, 13, 1355-1373
5. Matherly, L. H.; Wilson, M. R.; Hou, Z. The major facilitative folate transporters solute carrier 19A1 and solute carrier 46A1: Biology and role in antifolate chemotherapy of cancer Drug Metab. Dispos. 2014, 42, 632-649
6. Zhao, R.; Matherly, L. H.; Goldman, I. D. Membrane transporters and folate homeostasis: Intestinal absorption and transport into systemic compartments and tissues Expert Rev. Mol. Med. 2009, 11, e4
7. Nunez, M. I.; Behrens, C.; Woods, D. M.; Lin, H.; Suraokar, M.; Kadara, H.; Hofstetter, W.; Kalhor, N.; Lee, J. J.; Franklin, W.; Stewart, D. J.; Wistuba, II. High expression of folate receptor alpha in lung cancer correlates with adenocarcinoma histology and EGFR [corrected] mutation J. Thorac. Oncol. 2012, 7, 833-840
8. Visentin, M.; Zhao, R.; Goldman, I. D. The antifolates Hematol. Oncol. Clin. North Am. 2012, 26, 629-648
9. Gonen, N.; Assaraf, Y. G. Antifolates in cancer therapy: Structure, activity and mechanisms of drug resistance Drug Resist. Update 2012, 15, 183-210
10. Yang, J.; Vlashi, E.; Low, P. Folate-linked drugs for the treatment of cancer and inflammatory diseases Subcell. Biochem. 2012, 56, 163-179
11. Reddy, J. A.; Dorton, R.; Westrick, E.; Dawson, A.; Smith, T.; Xu, L. C.; Vetzel, M.; Kleindl, P.; Vlahov, I. R.; Leamon, C. P. Preclinical evaluation of EC145, a folate-vinca alkaloid conjugate Cancer Res. 2007, 67, 4434-4442
12. Naumann, R. W.; Coleman, R. L.; Burger, R. A.; Sausville, E. A.; Kutarska, E.; Ghamande, S. A.; Gabrail, N. Y.; Depasquale, S. E.; Nowara, E.; Gilbert, L.; Gersh, R. H.; Teneriello, M. G.; Harb, W. A.; Konstantinopoulos, P. A.; Penson, R. T.; Symanowski, J. T.; Lovejoy, C. D.; Leamon, C. P.; Morgenstern, D. E.; Messmann, R. A. PRECEDENT: A randomized phase II trial comparing vintafolide (EC145) and pegylated liposomal doxorubicin (PLD) in combination versus PLD alone in patients with platinum-resistant ovarian cancer J. Clin. Oncol. 2013, 31, 4400-4406
13. Deng, Y.; Wang, Y.; Cherian, C.; Hou, Z.; Buck, S. A.; Matherly, L. H.; Gangjee, A. Synthesis and discovery of high affinity folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity J. Med. Chem. 2008, 51, 5052-5063
14. Kugel Desmoulin, S.; Wang, Y.; Wu, J.; Stout, M.; Hou, Z.; Fulterer, A.; Chang, M. H.; Romero, M. F.; Cherian, C.; Gangjee, A.; Matherly, L. H. Targeting the proton-coupled folate transporter for selective delivery of 6-substituted pyrrolo[2,3- d ]pyrimidine antifolate inhibitors of de novo purine biosynthesis in the chemotherapy of solid tumors Mol. Pharmacol. 2010, 78, 577-587
15. Wang, Y.; Cherian, C.; Orr, S.; Mitchell-Ryan, S.; Hou, Z.; Raghavan, S.; Matherly, L. H.; Gangjee, A. Tumor-targeting with novel non-benzoyl 6-substituted straight chain pyrrolo[2,3- d ]pyrimidine antifolates via cellular uptake by folate receptor alpha and inhibition of de novo purine nucleotide biosynthesis J. Med. Chem. 2013, 56, 8684-8695
16. Deng, Y.; Zhou, X.; Kugel Desmoulin, S.; Wu, J.; Cherian, C.; Hou, Z.; Matherly, L. H.; Gangjee, A. 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 J. Med. Chem. 2009, 52, 2940-2951
17. Wang, L.; Cherian, C.; Desmoulin, S. K.; Polin, L.; Deng, Y.; Wu, J.; Hou, Z.; White, K.; Kushner, J.; Matherly, L. H.; Gangjee, A. 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 J. Med. Chem. 2010, 53, 1306-1318
18. Wang, L.; Kugel Desmoulin, S.; Cherian, C.; Polin, L.; White, K.; Kushner, J.; Fulterer, A.; Chang, M. H.; Mitchell-Ryan, S.; Stout, M.; Romero, M. F.; Hou, Z.; Matherly, L. H.; Gangjee, A. 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 beta-glycinamide ribonucleotide formyltransferase J. Med. Chem. 2011, 54, 7150-7164
19. Kugel Desmoulin, S.; Wang, L.; Hales, E.; Polin, L.; White, K.; Kushner, J.; Stout, M.; Hou, Z.; Cherian, C.; Gangjee, A.; Matherly, L. H. Therapeutic targeting of a novel 6-substituted pyrrolo [2,3- d ]pyrimidine thienoyl antifolate to human solid tumors based on selective uptake by the proton-coupled folate transporter Mol. Pharmacol. 2011, 80, 1096-1107
20. Cherian, C.; Kugel Desmoulin, S.; Wang, L.; Polin, L.; White, K.; Kushner, J.; Stout, M.; Hou, Z.; Gangjee, A.; Matherly, L. H. Therapeutic targeting malignant mesothelioma with a novel 6-substituted pyrrolo[2,3- d ]pyrimidine thienoyl antifolate via its selective uptake by the proton-coupled folate transporter Cancer Chemother. Pharmacol. 2013, 71, 999-1011
21. Wong, S. C.; Proefke, S. A.; Bhushan, A.; Matherly, L. H. Isolation of human cDNAs that restore methotrexate sensitivity and reduced folate carrier activity in methotrexate transport-defective Chinese hamster ovary cells J. Biol. Chem. 1995, 270, 17468-17475
22. Flintoff, W. F.; Davidson, S. V.; Siminovitch, L. Isolation and partial characterization of three methotrexate-resistant phenotypes from Chinese hamster ovary cells Somatic Cell Genet. 1976, 2, 245-261
23. Wang, L.; Cherian, C.; Kugel Desmoulin, S.; Mitchell-Ryan, S.; Hou, Z.; Matherly, L. H.; Gangjee, A. 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 J. Med. Chem. 2012, 55, 1758-1770
24. Zhao, R.; Goldman, I. D. The molecular identity and characterization of a proton-coupled folate transporter - PCFT: Biological ramifications and impact on the activity of pemetrexed Cancer Metastasis Rev. 2007, 26, 129-139
25. Webb, B. A.; Chimenti, M.; Jacobson, M. P.; Barber, D. L. Dysregulated pH: A perfect storm for cancer progression Nature Rev. Cancer 2011, 11, 671-677
26. Rosowsky, A.; Bader, H.; Wright, J. E.; Keyomarsi, K.; Matherly, L. H. Synthesis and biological activity of N-omega-hemiphthaloyl-alpha,omega-diaminoalkanoic acid analogues of aminopterin and 3′,5-dichloroaminopterin J. Med. Chem. 1994, 37, 2167-2174
27. Chen, C.; Ke, J.; Zhou, X. E.; Yi, W.; Brunzelle, J. S.; Li, J.; Yong, E.-L.; Xu, H. E.; Melcher, K. Structural basis for molecular recognition of folic acid by folate receptors Nature 2013, 500, 486-489
28. Wibowo, A. S.; Singh, M.; Reeder, K. M.; Carter, J. J.; Kovach, A. R.; Meng, W.; Ratnam, M.; Zhang, F.; Dann, C. E. Structures of human folate receptors reveal biological trafficking states and diversity in folate and antifolate recognition Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 15180-15188
29. Zhang, Y.; Desharnais, J.; Marsilje, T. H.; Li, C.; Hedrick, M. P.; Gooljarsingh, L. T.; Tavassoli, A.; Benkovic, S. J.; Olson, A. J.; Boger, D. L.; Wilson, I. A. Rational design, synthesis, evaluation, and crystal structure of a potent inhibitor of human GARTfase: 10-(Trifluoroacetyl)-5,10-dideazaacyclic-5,6,7,8-tetrahydrofolic acid Biochemistry 2003, 42, 6043-6056
30. Kugel Desmoulin, S.; Wang, L.; Polin, L.; White, K.; Kushner, J.; Stout, M.; Hou, Z.; Cherian, C.; Gangjee, A.; Matherly, L. H. Functional loss of the reduced folate carrier enhances the antitumor activities of novel antifolates with selective uptake by the proton-coupled folate transporter Mol. Pharmacol. 2012, 82, 591-600
31. Moran, R. G.; Colman, P. D.; Rosowsky, A. Structural requirements for the activity of antifolates as substrates for mammalian folylpolyglutamate synthetase NCI Monogr. 1987, 133-138
32. Moran, R. G.; Colman, P. D.; Rosowsky, A.; Forsch, R. A.; Chan, K. K. Structural features of 4-amino antifolates required for substrate activity with mammalian folylpolyglutamate synthetase Mol. Pharmacol. 1985, 27, 156-166
33. LeadIT 2.1.6; BioSolveIT GmbH: Sankt Augustin, Germany, 2013; www.biosolveit.de.
34. Molecular Operating Environment (MOE), 2013.08; Chemical Computing Group Inc.: 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7, 2013.
35. McNicholas, S.; Potterton, E.; Wilson, K. S.; Noble, M. E. M. Presenting your structures: The CCP4mg molecular-graphics software Acta Crystallogr., Sect. D: Biol. Crystallogr. 2011, 67, 386-394
36. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. Protein measurement with the folin phenol reagent J. Biol. Chem. 1951, 193, 265-275