Standing

Undergraduate

Type of Proposal

Oral Research Presentation

Faculty

Faculty of Science

Faculty Sponsor

Dr. Trant

Abstract/Description of Original Work

Self-immolative polymers (SIPs) are degradable polymers that have the ability to use a specific bond cleavage to initiate a cascade of reactions which ultimately result in complete depolymerization.[1] The cascade occurs from the polymer’s response to certain stimuli that selectively remove a stabilizing endcap of the polymer.[2] When the endcap is detached, elimination reactions of the polymer are initiated, which causes the SIP backbone to break down to smaller units.

There has been an increasing interest in the therapeutic potential of benzimidazole-based compounds in anticancer drugs due to their high effectiveness and target specificity. Cancer cells generally disturb cell signalling pathways in the body, and current anticancer drugs act on these rapidly replicating cells with poor selectivity, which is why benzimidazole-based structures are of great interest in medicinal chemistry.[3]. Benzamidazoles are potentially useful in SIP applications because their multifunctional properties such as pH sensitivity and electron accepting ability would allow degradation under biocompatible conditions selective to targeted cells, potentially used as a drug delivery system.

In this presentation I will discuss the Trant Team’s work on developing a benzimidazole-based SIP[4]. The polymers have been synthesized through the preparation of various starting materials and synthetic intermediates to produce two different benzimidazole derived self-immolative polymers. Along with the synthesis of such intermediates, spectroscopic techniques were applied to characterize and confirm the presence of each compound. This presentation will introduce the first known benzimidazole-backbone SIP created and discuss the synthesis and associated challenges of producing these materials during the COVID-19 pandemic.

References:

  1. Sirianni, Q. E.A., Gillies, E. R. The Architectural Evolution of Self-Immolative Polymers. Polymer. 2020, 202, pp. 122638.
  2. Sagi, A., Weinstain, R., Karton, N., Shabat, D. Self-Immolative Polymers. J. Am. Chem. 2008, 130, pp. 5434-5435.
  3. Goud, N. A., Kumar, P., Bharath, R. D. Recent Developments of Target-Based Benzimidazole Derivatives as Potential Anticancer Agents. IntechOpen. 2022. Benzimidazole [Working Volume], pp. 1-18.
  4. Taimoory, S. Maryamdokht, Xiao Yu, John F. Trant. Highly optically responsive divalent benzimidazolium-based axles with pseudorotaxane potential. 2021.

Availability

March 29: 12-3 pm; March 31: 12-1pm; April 1: 12-3pm

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Synthesizing Multifunctional Benzimidazole-Based Self-Immolative Polymers

Self-immolative polymers (SIPs) are degradable polymers that have the ability to use a specific bond cleavage to initiate a cascade of reactions which ultimately result in complete depolymerization.[1] The cascade occurs from the polymer’s response to certain stimuli that selectively remove a stabilizing endcap of the polymer.[2] When the endcap is detached, elimination reactions of the polymer are initiated, which causes the SIP backbone to break down to smaller units.

There has been an increasing interest in the therapeutic potential of benzimidazole-based compounds in anticancer drugs due to their high effectiveness and target specificity. Cancer cells generally disturb cell signalling pathways in the body, and current anticancer drugs act on these rapidly replicating cells with poor selectivity, which is why benzimidazole-based structures are of great interest in medicinal chemistry.[3]. Benzamidazoles are potentially useful in SIP applications because their multifunctional properties such as pH sensitivity and electron accepting ability would allow degradation under biocompatible conditions selective to targeted cells, potentially used as a drug delivery system.

In this presentation I will discuss the Trant Team’s work on developing a benzimidazole-based SIP[4]. The polymers have been synthesized through the preparation of various starting materials and synthetic intermediates to produce two different benzimidazole derived self-immolative polymers. Along with the synthesis of such intermediates, spectroscopic techniques were applied to characterize and confirm the presence of each compound. This presentation will introduce the first known benzimidazole-backbone SIP created and discuss the synthesis and associated challenges of producing these materials during the COVID-19 pandemic.

References:

  1. Sirianni, Q. E.A., Gillies, E. R. The Architectural Evolution of Self-Immolative Polymers. Polymer. 2020, 202, pp. 122638.
  2. Sagi, A., Weinstain, R., Karton, N., Shabat, D. Self-Immolative Polymers. J. Am. Chem. 2008, 130, pp. 5434-5435.
  3. Goud, N. A., Kumar, P., Bharath, R. D. Recent Developments of Target-Based Benzimidazole Derivatives as Potential Anticancer Agents. IntechOpen. 2022. Benzimidazole [Working Volume], pp. 1-18.
  4. Taimoory, S. Maryamdokht, Xiao Yu, John F. Trant. Highly optically responsive divalent benzimidazolium-based axles with pseudorotaxane potential. 2021.