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Thursday, August 18, 2016

Crystallography as a Drug Design and Delivery Tool Vincent Stoll, Research Fellow and Associate Director of Structural Biology, Abbvie

Robert Wenslow, Vice President Business Development, Crystal Pharmatech

Andrew Brunskill, Associate Principal Scientist, Merck



Chemophobia: How We Became Afraid of Chemicals and What to Do About It

James Kennedy, Chemistry Teacher and Blogger, Haileybury, Australia

Darren Griffin, Professor of Genetics, University of Kent, UK

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www.acs.org/acswebinars Slides available now! Recordings will be available to ACS members in a few weeks

2016 Material Science Series “The Chemistry of Power Free Wearable Sensors: Smart Polymeric Materials”

The 2016 Material Science Series is co-produced with ACS Industry Member Programs, C&EN, and the ACS POLY Division

Mark Jones Executive External Strategy and

Communications Fellow,

Dow Chemical

Michele Lee Ph.D. Student, Dept. of Chemical

Engineering and Materials Science,

University of Southern California Andrea Armani

Fluor Early Career Chair and Associate

Professor, Dept. of Chemical Engineering

and Materials Science,

University of Southern California

The Chemistry of Power

Free Wearable Sensors:

Smart Polymeric Materials

Thursday, August 4th 2016, 2 – 3 pm EST

facebook.com/ArmaniResearchLab

@ArmaniLab

www.armani.usc.edu

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Outline

• History of wearable technology

• Smart polymers

• Responsive functional groups

• Smart polymers in wearable sensors

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“Wearable” Technology designed to be worn on the body

Past: Bulky/ wired Power-source dependent Singular functionality

1983

Ioannou, K., Ignaszewski, M., Macdonald, I. 2014, BCMJ, 56, 86-89.

1947

1923

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Portable Multifunctional Connected

2015 2013 2008

Present:

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2017 2018

Seamless integration Battery-free Expanded functionality

2016

Future:


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Audience Survey Question ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT

• $500 million

• $5 billion

• $30 billion

• $100 billion

How much is the wearable tech industry predicted to be worth by 2020?

Smart Polymers

light

heat chemical environment

pH

saltcityoptics.com 33rdsquare.com

voltage

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Smart Polymeric Materials Functionality depends on where modification occurs

backbone modification

pendant group modification

cross-link modification

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Ayer, M. A.; Simon, Y. C.; Weder, C. 2016, Macromolecules, 49, 2917-2927.

Graded mechanical properties after T or UV

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PTHPMA conversion to PMAA releases THP Modify environmental pH

Wang, J., Pelletier, M., Zhang, H, et al. 2009, Langmuir, 25, 13201-205. 25


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PEG-based photolabile hydrogel

2D & 3D cell culture matrix Cell morphology, cytoskeleton changes with environment

Kloxin, A., Tibbitt, M., Anseth, K. 2010, Nat. Protocols, 5, 1867-87.


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Secondary structure

brush layer

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Secondary structure

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Secondary structure

hydrogel

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Secondary structure

hydrogel

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Secondary structure

micelle

hydrogel

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Secondary structure

micelle

hydrogel

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Secondary structure

micelle

hydrogel

multilayer film

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Secondary structure

micelle

hydrogel

multilayer film

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Secondary structure

micelle

hydrogel

multilayer film

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Audience Survey Question ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT

• Transition lenses

• Dental night guard

• Self-healing paint

• Anti-fogging glass

Which of these is not made with a smart polymeric material?

Stimuli-responsive groups

Temperature - triggered

Light - triggered

pH - triggered

Electrically - triggered

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poly(N-isopropylacrylamide) (PNIPAM)

Low Critical Solution Temperature (LCST) = 32°C Close to body temperature

Below LCST Above LCST

Swollen Hydrophilic surface

Compacted Hydrophobic surface

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Bagherifard, S., Tamayol, A., et al. 2015, Adv. Healthcare Mater., 5, 175-184.

Crosslinked PNIPAM to synthesize responsive microparticles

As T increases, microparticles shrink

Thermoresponsive drug release


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Particle shrinkage results in drug release during heating

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Release rate is temperature dependent



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• Integrated drug release capsules into a biocompatible flexible platform (hydrogel patch)

alginate patch with loaded microparticles

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Beverina, L., Pagani, G.A., Sassi, M. 2014, Chem. Commun., 50, 5413-30.

Conjugated polymers: poly(heterocycles)

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Chou, H., Nguyen, A., et al. 2015, Nat. Comm., 6, 1-10.


poly(3-hexylthiophene-2,3-diyl) (P3HT)

• Voltage induces change in P3HT oxidation state

• Oxidation state changes absorbance & color appearance of P3HT


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Pressure-sensitive layer

• Pyramidal microstructured PDMS spray-coated with single walled carbon nanotubes (SWNT) act as pressure-sensitive layer


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Electrochromic pressure sensor


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Electrochromic pressure sensor


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pH - triggered

polyaniline (PANI)

leucoemeraldine pernigraniline

low pH high pH

emeraldine

pH changes lead to changes in color & conductivity 50

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Bandodkar, A., Hung, V., et al. 2013, Analyst, 138, 123–128.

Temporary tattoo pH indicator

• Integrated PANI into tattoo-based sweat sensor

• Screen-printed carbon reference electrode and insulator, patterned PANI onto release-agent coated base paper to transfer to skin

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pH - triggered

Bandodkar, A., Hung, V., et al. 2013, Analyst, 138, 123–128.

Temporary tattoo pH indicator

• Monitored changes in pH while cycling matched with commercial pH meter

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pH - triggered

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Lee, M., Gungor, E., Armani, A. 2015, Macromolecules., 48, 8746-8751.

Light - triggered

o-nitrobenzyl (ONB) λ = 300-380

• Photocleavage occurs upon exposure to UVA, UVB light

• Cleaving causes formation of new functional groups

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UV-responsive polymer

• Incorporate ONB into a bifunctional ATRP initiator

• Post-synthesis, ONB is located directly in center of the chain

ONB, ortho-nitrobenzyl ATRP, atom transfer radical polymerization

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Light - triggered

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UV-responsive polymer

• Photocleavage reduces polymer molecular weight by half

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Light - triggered


Environment-dependent response

• UV-dose dependent photocleavage

• Rate of photocleavage is environment-dependent

% c

lea

ve

d

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Light - triggered

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Environment-dependent response

• UV-dose dependent photocleavage

• Rate of photocleavage is environment-dependent

% c

lea

ve

d

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Light - triggered


Colorimetric UV detection

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Light - triggered

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References

Smart material sensors

• Ayer, M. A.; Simon, Y. C.; Weder, C. 2016, Macromolecules, 49, 2917-2927.

• Wang, J., Pelletier, M., Zhang, H, et al. 2009, Langmuir, 25, 13201-205.

• Kloxin, A., Tibbitt, M., Anseth, K. 2010, Nat. Protocols, 5, 1867-87.

• Bagherifard, S., Tamayol, A., et al. 2015, Adv. Healthcare Materials, 5, 175-184.

• Chou, H., Nguyen, A., et al. 2015, Nat. Comm., 6, 1-10.

• Bandodkar, A., Hung, V., et al. 2013, Analyst, 138, 123–128.

• Lee, M., Gungor, E., Armani, A. 2015, Macromolecules., 48, 8746-8751.

Reviews

• Schattling, P., Jochum, F., et al. 2014, Polymer Chemistry, 5, 25-36.

• Stuart, M., Huck, W., et al. 2010, Nature Materials, 9, 101-113.

• Xia, F., Jiang, L.. 2008, Adv. Mat., 15, 2842-2858.

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facebook.com/ArmaniResearchLab

@ArmaniLab

www.armani.usc.edu www-scf.usc.edu/~lee853/

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Dow Chemical








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2016 Material Science Series http://bit.ly/2016MaterialScienceSeries

The 2016 Material Science Series is co-produced with

ACS Industry Member Programs, C&EN, and the ACS POLY Division

Discover the material science innovations that make life more comfortable!

8/3/2016

32


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Dow Chemical








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“Fantastic ACS Webinar. I have one intraocular lens because of cataract surgery and occasionally wear a contact lens in the other eye, so this topic affects me personally. I also self-administered LOTS of eye drops after the cataract surgery, so the drug delivery info is appreciated as well. It is good to know that so much great work is being done in this field.”

Daniel A. Green, Principal Investigator, DuPont

Quote in reference to: http://bit.ly/ContactsChemistry

Be a featured fan on an upcoming webinar! Write to us @ [email protected]

How has ACS Webinars benefited you?

®

66

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Benefits of ACS Membership


Chemical & Engineering News (C&EN) The preeminent weekly news source.

NEW! Free Access to ACS Presentations on Demand® ACS Member only access to over 1,000 presentation recordings from recent ACS meetings and select events.

NEW! ACS Career Navigator Your source for leadership development, professional education, career services, and much more.

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ACS Webinars does not endorse any products or services. The views expressed in this presentation are those of the presenter and do not necessarily reflect the views or policies of the American Chemical Society.

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American Chemical Society - The Chemistry of …...2016/08/04 · • Support for Student Chapters, student symposia, and student awards Become a Member of POLY to enjoy these benefits!