Otto Phanstiel

Organic Synthesis and Medicinal Chemistry

Professor of Chemistry Ph.D., University of Florida Phone: 407-823-5410 E-mail: ophansti@mail.ucf.edu Web page: Organic Songs (Fun) View Full Curriculum Vita Reviewer, The Journal of the American Chemical Society Reviewer, Journal of Medicinal Chemistry Reviewer, Journal of Organic Chemistry Reviewer, Organic Letters

August, 2005: Otto Phanstiel (PI) and Saleh Naser were awarded a grant renewal from the Broad Medical Research Program for their work on polyamines and inflammatory bowel disease ($50,000).

July, 2005: Otto Phanstiel (PI), Thomas Selby and Martin Richardson were awarded funding from Mannkind Biopharmaceuticals to study proprietary drug delivery technologies ($184,551).

April, 2005: Otto Phanstiel and Todd Meyer were each awarded the Florida Hospital Gala Endowed Award for Oncological Research ($7500).

Research

Our goals are to synthesize new drugs and drug-delivery agents to aid in the treatment of human diseases. We are currently developing new therapies for cancer, iron poisoning, tuberculosis, and malaria.

	New Drug-Targeting Methods to Fight Cancer We are synthesizing a series of multi-functional drugs, which append a polyamine vector to a DNA intercalator. The strategy involves using the polyamine portion of the drug to carry the lethal intercalator into the cell (e.g., a Trojan Horse approach).
	Metal Binding Drugs Siderophores are naturally-occurring iron binding agents biosynthesized by bacteria to acquire iron from their environment. Our group is developing new siderophore structures, which can target the iron transport system of virulent bacteria and provide a pathway for the selective delivery of antibiotic agents.
	New microcapsules for drug encapsulation We have developed technology to generate microcapsules, in which drugs can be encapsulated. Our technology allows for control of the aqueous self-assembly of small diamide diacids into microcapsule or microsphere architectures.

Selected Publications

1. "Modeling the Preferred Shapes of Polyamine Transporter Ligands and Dihydromotuporamine-C Mimics: Shovel versus Hoe," Breitbeil III, F. Kaur, N.; Delcros, J-G.; Martin,B.; Abboud, K.A.; Phanstiel IV, O. J. Med. Chem. 2006, 49, 2407-2416.
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2. "Synthesis and Biological Evaluation of Dihydromotuporamine Derivatives in Cells Containing Active Polyamine Transporters" Kaur, N.; Delcros, J-G.; Martin, B.; Phanstiel IV, O. J. Med. Chem. 2005, 48, 3832-3839.
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3. "N1-Substituent Effects in the Selective Delivery of Polyamine-Conjugates into Cells Containing Active Polyamine Transporters." Gardner, R.A.; Delcros, J-G.; Konate, F.; Breitbeil III, F.; Martin, B.; Sigman, M.; Huang, M.; Phanstiel IV, O. J. Med. Chem. 2004, 47, 6055-6069.
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4. "Synthesis and Biological Evaluation of new Acinetoferrin Homologues for use as Iron Transport Probes in Mycobacteria." Gardner, R.A.; Ghobrial, G.; Naser, S.A.; Phanstiel IV, O. J. Med. Chem. 2004, 47, 4933-4940.
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5. "Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for Marinobacter hydrocarbonoclasticus, an oil-degrading bacteria." Gardner, R.A.; Kinkade, R. ; Wang, C. ; Phanstiel IV, O. J. Org. Chem. 2004, 69, 3530-3537.
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6. "Defining the Molecular Requirements for the Selective Delivery of Polyamine-Conjugates into Cells Containing Active Polyamine Transporters," Wang, C.; Delcros, J-G.; Cannon, L.; Konate, F.; Carias, H.; Biggerstaff, J.; Gardner, R.A.; Phanstiel IV, O. J. Med. Chem. 2003, 46, 5129-5138.
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7. "Molecular Requirements for Targeting the Polyamine Transport System: Synthesis and Biological Evaluation of Polyamine-Anthracene Conjugates," Wang, C.; Delcros, J-G.; Biggerstaff, J.; Phanstiel IV, O. J. Med. Chem. 2003, 46, 2672-2682.
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8. "Synthesis and Biological Evaluation of N1-(anthracen-9-ylmethyl)triamines as Molecular Recognition Elements for the Polyamine Transporter," Wang, C.; Delcros, J-G.; Biggerstaff, J.; Phanstiel IV, O. J. Med. Chem. 2003, 46, 2663-2671.
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9. "N-(Benzoyloxyamines): an investigation of their thermal stability, synthesis and incorporation into novel peptide constructs," Nemchik, A.+; Badescu, V.*; Phanstiel IV, O. Tetrahedron 2003, 59, No. 24, 4315-4325.
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1. "Modeling the Preferred Shapes of Polyamine Transporter Ligands and Dihydromotuporamine-C Mimics: Shovel versus Hoe," Breitbeil III, F. Kaur, N.; Delcros, J-G.; Martin,B.; Abboud, K.A.; Phanstiel IV, O. J. Med. Chem. 2006, 49, 2407-2416. http://dx.doi.org/10.1021/jm050814w
    
2. "Synthesis and Biological Evaluation of Dihydromotuporamine Derivatives in Cells Containing Active Polyamine Transporters" Kaur, N.; Delcros, J-G.; Martin, B.; Phanstiel IV, O. J. Med. Chem. 2005, 48, 3832-3839. http://dx.doi.org/10.1021/jm0491288
    
3. "N1-Substituent Effects in the Selective Delivery of Polyamine-Conjugates into Cells Containing Active Polyamine Transporters." Gardner, R.A.; Delcros, J-G.; Konate, F.; Breitbeil III, F.; Martin, B.; Sigman, M.; Huang, M.; Phanstiel IV, O. J. Med. Chem. 2004, 47, 6055-6069. http://dx.doi.org/10.1021/jm0497040
    
4. "Synthesis and Biological Evaluation of new Acinetoferrin Homologues for use as Iron Transport Probes in Mycobacteria." Gardner, R.A.; Ghobrial, G.; Naser, S.A.; Phanstiel IV, O. J. Med. Chem. 2004, 47, 4933-4940.
   http://dx.doi.org/10.1021/jm049805y
    
5. "Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for Marinobacter hydrocarbonoclasticus, an oil-degrading bacteria." Gardner, R.A.; Kinkade, R. ; Wang, C. ; Phanstiel IV, O. J. Org. Chem. 2004, 69, 3530-3537. http://dx.doi.org/10.1021/jo049803l
    
6. "Defining the Molecular Requirements for the Selective Delivery of Polyamine-Conjugates into Cells Containing Active Polyamine Transporters," Wang, C.; Delcros, J-G.; Cannon, L.; Konate, F.; Carias, H.; Biggerstaff, J.; Gardner, R.A.; Phanstiel IV, O. J. Med. Chem. 2003, 46, 5129-5138.
   http://dx.doi.org/10.1021/jm030223a
    
7. "Molecular Requirements for Targeting the Polyamine Transport System: Synthesis and Biological Evaluation of Polyamine-Anthracene Conjugates," Wang, C.; Delcros, J-G.; Biggerstaff, J.; Phanstiel IV, O. J. Med. Chem. 2003, 46, 2672-2682.
   http://dx.doi.org/10.1021/jm020598g
    
8. "Synthesis and Biological Evaluation of N1-(anthracen-9-ylmethyl)triamines as Molecular Recognition Elements for the Polyamine Transporter," Wang, C.; Delcros, J-G.; Biggerstaff, J.; Phanstiel IV, O. J. Med. Chem. 2003, 46, 2663-2671.
   http://dx.doi.org/10.1021/jm030028w
    
9. "N-(Benzoyloxyamines): an investigation of their thermal stability, synthesis and incorporation into novel peptide constructs," Nemchik, A.+; Badescu, V.*; Phanstiel IV, O. Tetrahedron 2003, 59, No. 24, 4315-4325.
   http://dx.doi.org/10.1016/S0040-4020(03)00635-5
    

Graduate Students

New students will learn how to conduct multi-step organic syntheses and have an opportunity to assist with the biological evaluation of their own compounds. They will learn how to grow cancer cells, and conduct their own bio-evaluations (determine IC50 values, conduct apoptosis assays, perform confocal microscopy studies, etc).

Phanstiel's Research Group Pictures

LINK: Graduate Theses/Dissertations Supervised