Bioanalytical screening of riboflavin antagonists for targeted drug delivery - A thermodynamic and kinetic study

ACS Medicinal Chemistry Letters

Volumn 2, Issue 5, 2011, Pages 363-367

  Plantinga, Anna ^a   Witte, Amanda ^a   Li, Ming Hsin ^b,c   Harmon, Andrew ^a   Choi, Seok Ki ^c   Banaszak Holl, Mark M ^b,c   Orr, Bradford G ^b,c   Baker, James R ^b,c   Sinniah, Kumar ^a  

^a CALVIN COLLEGE   (United States)

^b UNIVERSITY OF MICHIGAN HEALTH SYSTEM   (United States)

^c UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROQUINE; CHLORPROMAZINE; DRUG RECEPTOR; LIGAND; LUMIFLAVINE; MEPACRINE; PERPHENAZINE; RIBOFLAVIN; RIBOFLAVIN BINDING PROTEIN;

ARTICLE; DRUG ANTAGONISM; DRUG DELIVERY SYSTEM; DRUG IDENTIFICATION; DRUG SCREENING; DRUG TARGETING; ISOTHERMAL TITRATION CALORIMETRY; KINETICS; MICROCALORIMETRY; PRIORITY JOURNAL; SPECTROSCOPY; SURFACE PLASMON RESONANCE; THERMODYNAMICS;

EID: 79956071463     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml100296z     Document Type: Article

References (26)

1. White, H. B.; Merrill, A. H. Riboflavin-Binding Proteins Annu. Rev. Nutr. 1988, 8 (1) 279-299
2. Karande, A. A.; Sridhar, L.; Gopinath, K. S.; Adiga, P. R. Riboflavin carrier protein: A serum and tissue marker for breast carcinoma Int. J. Cancer (Pred. Oncol.) 2001, 95, 277-281 (Pubitemid 32847035)
3. Johnson, T.; Ouhtit, A.; Gaur, R.; Fernando, A.; Schwarzenberger, P.; Su, J.; Ismail, M. F.; El-Sayyad, H. I.; Karande, A.; Elmageed, Z. A.; Rao, P.; Raj, M. Biochemical characterization of riboflavin carrier protein (RCP) in prostate cancer Front. Biosci. 2009, 14, 3534-3640
4. Phelps, M. A.; Foraker, A. B.; Gao, W.; Dalton, J. T.; Swaan, P. W. A Novel Rhodamine-Riboflavin Conjugate Probe Exhibits Distinct Fluorescence Resonance Energy Transfer that Enables Riboflavin Trafficking and Subcellular Localization Studies Mol. Pharm. 2004, 1, 257-266
5. Holladay, S. R.; Yang, Z.-f.; Kennedy, M. D.; Leamon, C. P.; Lee, R. J.; Jayamani, M.; Mason, T.; Low, P. S. Riboflavin-mediated delivery of a macromolecule into cultured human cells Biochim. Biophys. Acta, Gen. Subj. 1999, 1426 (1) 195-204 (Pubitemid 29027882)
6. Huang, S.-N.; Phelps, M. A.; Swaan, P. W. Involvement of Endocytic Organelles in the Subcellular Trafficking and Localization of Riboflavin J. Pharmacol. Exp. Ther. 2003, 306 (2) 681-687 (Pubitemid 36886168)
7. Thomas, T. P.; Choi, S. K.; Li, M.-H.; Kotlyar, A.; Baker, J. R. Design of Riboflavin-presenting PAMAM Dendrimers as a New Nanoplatform for Cancer-targeted Delivery Bioorg. Med. Chem. Lett. 2010, 20, 5191-5194
8. Becvar, J.; Palmer, G. The binding of flavin derivatives to the riboflavin-binding protein of egg white. A kinetic and thermodynamic study J. Biol. Chem. 1982, 257 (10) 5607-5617
9. Chu, C. K.; Bardos, T. J. Synthesis and inhibition analysis of 2(4)-imino-4(2)-amino-2,4-dideoxyriboflavin, a dual antagonist of riboflavin and folinic acid J. Med. Chem. 1977, 20 (2) 312-314 (Pubitemid 8032294)
10. O'Brien, D. E.; Baiocchi, F.; Robins, R. K.; Cheng, C. C. Pyrimidines. IX. 4- and 5-(Substituted-anilino)pyrimidines J. Med. Pharm. Chem. 1962, 5 (6) 1085-1103
11. Monaco, H. L. Crystal structure of chicken riboflavin-binding protein EMBO J. 1997, 16, 1475-1483 (Pubitemid 27151942)
12. Galat, A. Interaction of riboflavin binding protein with riboflavin, quinacrine, chlorpromazine and daunomycin Int. J. Biochem. 1988, 20 (9) 1021-1029
13. Choi, J. D.; McCormick, D. B. The interaction of flavins with egg white riboflavin-binding protein Arch. Biochem. Biophys. 1980, 204 (1) 41-51
14. Zhou, X.; Sun, Q.; Kini, R. M.; Sivaraman, J. A universal method for fishing target proteins from mixtures of biomolecules using isothermal titration calorimetry Protein Sci. 2008, 17 (10) 1798-1804
15. Caelen, I.; Kalman, A.; Wahlstrom, L. Biosensor-Based Determination of Riboflavin in Milk Samples Anal. Chem. 2003, 76 (1) 137-143
16. Hong, S.; Leroueil, P. R.; Majoros, I. J.; Orr, B. G.; Baker, J. J. R.; Banaszak Holl, M. M. The Binding Avidity of a Nanoparticle-Based Multivalent Targeted Drug Delivery Platform Chem. Biol. 2007, 14 (1) 107-115 (Pubitemid 46124068)
17. Attie, A. D.; Raines, R. T. Analysis of Receptor-Ligand Interactions J. Chem. Educ. 1995, 72 (2) 119-124
18. Chavalitshewinkoon, P.; Wilairat, P.; Gamage, S.; Denny, W.; Figgitt, D.; Ralph, R. Structure-activity relationships and modes of action of 9-anilinoacridines against chloroquine-resistant Plasmodium falciparum in vitro Antimicrob. Agents Chemother. 1993, 37 (3) 403-406 (Pubitemid 23072580)
19. Wallace, D. J. The use of quinacrine (Atabrine) in rheumatic diseases: A reexamination Semin. Arthritis Rheum. 1989, 18 (4) 282-296
20. Wilson, W. D.; Jones, R. L. Interaction of actinomycin D, ethidium quinacrine daunorubicin, and tetralysine with DNA: 31P NMR chemical shift and relaxation investigation Nucleic Acids Res. 1982, 10 (4) 1399-1410
21. Harle, D. G.; Baldo, B. A. Structural features of potent inhibitors of rat kidney histamine N-methyltransferase Biochem. Pharmacol. 1988, 37 (3) 385-388 (Pubitemid 18027345)
22. Stuhlmeier, K. M.; Pollaschek, C. Quinacrine but not chloroquine inhibits PMA induced upregulation of matrix metalloproteinases in leukocytes: quinacrine acts at the transcriptional level through a PLA2-independent mechanism J. Rheumatol. 2006, 33 (3) 472-480 (Pubitemid 43334567)
23. Orzáez, M.; Mondragón, L.; García-Jareño, A.; Mosulén, S.; Pineda-Lucena, A.; Pérez-Payá, E. Deciphering the antitumoral activity of quinacrine: Binding to and inhibition of Bcl-xL Bioorg. Med. Chem. Lett. 2009, 19 (6) 1592-1595
24. Dey, A.; Tergaonkar, V.; Lane, D. P. Double-edged swords as cancer therapeutics: simultaneously targeting p53 and NF-[kappa]B pathways Nat. Rev. Drug Discovery 2008, 7 (12) 1031-1040
25. Gurova, K. V.; Hill, J. E.; Guo, C.; Prokvolit, A.; Burdelya, L. G.; Samoylova, E.; Khodyakova, A. V.; Ganapathi, R.; Ganapathi, M.; Tararova, N. D.; Bosykh, D.; Lvovskiy, D.; Webb, T. R.; Stark, G. R.; Gudkov, A. V. Small molecules that reactivate p53 in renal cell carcinoma reveal a NF-k'-dependent mechanism of p53 suppression in tumors Proc. Natl. Acad. Sci. U.S.A. 2005, 102 (48) 17448-17453 (Pubitemid 41740886)
26. Mammen, M.; Choi, S. K.; Whitesides, G. M. Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors Angew. Chem., Int. Ed. 1998, 37, 2755