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Saturday, 11 June 2016

Dr. Martin Schnermann

Dr. Martin Schnermann
Organic Synthesis

Dr. Schnermann attended Colby College and graduated in 2002 with degrees in Chemistry and Physics. At Colby, he worked with Prof. Dasan Thamattoor in the areas of physical organic chemistry and photochemistry. After a year at Pfizer Research and Development (Groton, CT) as an associate in the medicinal chemistry division, he moved to the Scripps Research Institute. During his graduate studies, he performed research on the total synthesis and biological evaluation of anticancer natural products with Prof. Dale Boger and obtained a Ph.D. in 2008. He then completed an NIH-postdoctoral fellowship with Prof. Larry Overman at the University of California, Irvine. At Irvine, he developed light-mediated reactions to enable the synthesis of complex natural products. In addition, working with Prof. Christine Suetterlin, he pursued chemical biology and imaging studies of organelle specific probes. In 2012, Dr. Schnermann joined the NCI where his research focuses on the synthesis and development of new small-molecule imaging agents for cancer treatment and diagnosis.
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Research Summary

Near-IR Uncaging Chemistry: Discovery and Applications
Many key fundamental and applied questions in biology require unraveling issues relating to the spatial and temporal organization of multi-cellular systems. The combination of photocaged small molecule probes and the spatially controlled application of light could in principle provide key insights. However, existing photoremovable caging groups are often not suitable, particularly for organismal applications. This is due to the general requirement of UV or blue light, which suffers from associated toxicity and poor tissue penetration. By contrast, light between 650 and 900 nm, often referred to as the near-IR window, is cytocompatible and has significant tissue penetration (~centimeters). My group develops new single photon near-IR uncaging methods. This is a challenging chemistry problem because these wavelengths have only modest photonic energy. Our approach is been to define and then take advantage of photochemical reactions of long-wavelength fluorophores. In our most advanced project, we have shown that the photooxidative reactivity of heptamethine cyanines can be used for small molecule drug delivery. We have also shown that the photoredox ligand exchange of silicon phthalocyanines can be used for hypoxia-selective drug delivery. We use our methods towards two key unmet challenges in biology: (1) the development of a general theranostic approach for site-specific optical imaging and drug delivery and (2) the spatial and temporal regulation of gene expression to track and control cell fate.

Modern Synthetic Approaches for Small Molecule Imaging
There is a significant need for improved near-IR fluorophores for emerging applications in basic and applied biomedical science. Existing molecules are often prepared through inefficient classical synthetic methods that suffer from poor substrate scope and harsh reaction conditions. The limitations of existing methodologies dictate that researchers must choose from a small collection of probes whose chemical and physical properties are not ideal. We create reactions that enable the efficient preparation of novel near-IR fluorophores. We then use this chemistry to develop molecules with excellent chemical and photochemical stability and improved optical properties. These molecules are then applied towards several key cancer-related imaging applications. In related efforts, we are mining the structural diversity of natural products for light emitting scaffolds to develop broadly useful optical probes. Key to this work is the development of concise total syntheses to access compounds of interest.
1 - 5 of 11 results
1)  Nani RR, Shaum JB, Gorka AP, Schnermann MJ.
Electrophile-integrating smiles rearrangement provides previously inaccessible c4"-o-alkyl heptamethine cyanine fluorophores.
Org. Lett. 17: 302-5, 2015. [Journal]
2)  Chan Susanna T S, Patel Paresma R, Ransom Tanya R, Henrich Curtis J, McKee Tawnya C, Goey Andrew K L, Cook Kristina M, Figg William D, McMahon James B, Schnermann Martin J, Gustafson Kirk R.
Structural Elucidation and Synthesis of Eudistidine A: An Unusual Polycyclic Marine Alkaloid that Blocks Interaction of the Protein Binding Domains of p300 and HIF-1α.
J.+Am.+Chem.+Soc. 137: 5569-75, 2015. [Journal]
3)  Gorka AP, Nani RR, Zhu J, Mackem S, Schnermann MJ.
A Near-IR Uncaging Strategy Based on Cyanine Photochemistry.
J. Am. Chem. Soc. 136: 14153-14159, 2014. Full Text Article. [Journal]
4)  Schnermann MJ, Shenvi RA.
Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.
Nat Prod Rep. 2014. [Journal]
5)  Schnermann MJ, Overman LE.
A Concise Synthesis of (-)-Aplyviolene Facilitated by a Strategic Tertiary Radical Conjugate Addition.
Angew. Chem. Int. Ed. Engl. 2012. [Journal]

1) Schnermann MJ, Gorka AJ, Kobayashi HJ, Nani RJ (submitted in 2015) Near-ir Light-cleavable Conjugates And Conjugate Precursors.
Patent pending: 62/204,381 (US application).
Patent pending: 62/204,381 (US application).

2) Gustafson KR, Chan SR, Figg WR, McMahon JR, Patel PR, Schnermann MR (submitted in 2015) Hypoxia-inducible Factor 1 Hif-1 Inhibitors.
Patent pending: 62/144,182 (US application).
Patent pending: 62/144,182 (US application).


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