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What do all these things have in common
What do all these things have in common
And even…
And even…
And even…
And even…
History of Porphyrins
History of Porphyrins
As the basic building block of hemoglobin, and as a hemoglobin
As the basic building block of hemoglobin, and as a hemoglobin
As the basic building block of hemoglobin, and as a hemoglobin
As the basic building block of hemoglobin, and as a hemoglobin
Chlorophyll – yes, porphyrins are important in plants, too
Chlorophyll – yes, porphyrins are important in plants, too
Cytochrome C – a molecule responsible for transporting an electron
Cytochrome C – a molecule responsible for transporting an electron
As water-splitting molecule in fuel cells – they produce hydrogen gas
As water-splitting molecule in fuel cells – they produce hydrogen gas
Photodynamic Therapy
Photodynamic Therapy
Photodynamic Therapy
Photodynamic Therapy
Polymeric Photovoltaics
Polymeric Photovoltaics
Polymeric Photovoltaics
Polymeric Photovoltaics
The Truth about Vampires
The Truth about Vampires
As a selective catalyst
As a selective catalyst
Porphyrin Variation 3
Porphyrin Variation 3
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1Porphyrins Super-molecules of the 24may allow the origins of environmental
Future and the Sinister Molecules of the contaminants (e.g. oil spills) to be
Past. Paul Goodland Kim Fields Peter Zhang ascertained.
University of South Florida. 25In Conducting Polymers. “Photovoltaic
2What do all these things have in coatings that gather light and emit
common? This……. electricity could be used to power your
3And…. house or your vehicle. If your vehicle was
4AND……. painted with a photovoltaic coating it
5AND……. could gather sun light and emit the
6And. electricity needed to power itself. This
7and. would be environmentally friendly and in
8And…. most cases cheaper than petroleum
9and. products. “ History & Coating
10And even….. Applications of Conductive Polymers Report
11They all involve a class of chemical for Chemistry 446, Spring 2002 by Jason
compounds known as porphyrins. Shaw & Derek Marin.
12History of Porphyrins. The pathway to 26Polymeric Photovoltaics. A house that
porphyrins begins with dyes extracted from generates it's own electricity and
plants such as the indigo plant. They were clothing that can power a lap top computer
so brilliantly colored and colorfast that will soon become a reality. One may ask
they quickly became a luxury. “Royal how this is possible? The answer is
Purple”. polymeric photovoltaics. While
13Porphyrins were discovered by photovoltaic clothing products are almost
accident! In 1897, a new German company here the photovoltaic structural coatings
(BASF) began manufacturing synthetic are still a ways off. Things are
indigo dye, which was cheaper and easier developing quickly in the field. All that
than the extraction process. Another remains is to make the coatings more
company, ICI, trying to make a modified efficient and cheaper to manufacture. One
indigo, kept getting a purple by-product major area of research is photovoltaic
that contaminated their desired product. pigments to augment coatings. A popular
These impurities were also brilliantly choice are the porphyrins, which are
colored dyes, which could withstand chemically similar to chlorophyll.
temperatures up to 500C! Most other dyes 27Porphyria. What made King Geoge III so
would fade or turn colors at high very mad? The British ruler who presided
temperatures. over the loss of the American colonies in
14Voila! – le Porphyrin. 1776 was diagnosed about two centuries too
15Why Porphyrins are Cool. They’re late with porphyria — a genetic disorder
really big. They can contain many that causes psychiatric disturbances,
different metal atoms in their centers. among other things. Abdominal pain.
The are very stable due to their vomiting. acute neuropathy. seizures.
conjugation (alternating single and double hallucinations. depression. anxiety.
bonds). They can take on an amazing cardiac arrhythmias. fast heart rate
variety of roles in the real world, which (tachycardia). Chronic and acute pain.
is why they are widely utilized and paranoia. Constipation and/or diarrhea.
researched…… Multiple enzymes are needed for the body
16Uses of Porphyrins. Because of the to produce heme. If any one of the enzymes
unique chemistry of porphyrins, they are is abnormal, the process cannot continue
able to serve in several ways: As a metal and the intermediate products, porphyrin
binder (ligands) As a solar cell (convert or its precursors, may build up and be
light or chemical energy) As an oxygen excreted in the urine and stool. As a
transport medium (hemoglobin) As an result of feedback, the decreased
electron transfer medium (conducting production of heme leads to increased
polymers) Gene regulation Drug metabolism production of precursors, PBG, being one
Iron metabolism Hormone synthesis. of the first substances in the porphyrin
17As the basic building block of synthesis pathway. The hepatic porphyrias
hemoglobin, and as a hemoglobin modeling primarily affect the nervous system,
molecule. Heme – a cross-coupled porphyrin resulting in…….
used in the larger molecule hemoglobin. 28The Truth about Vampires?
18Chlorophyll – yes, porphyrins are Photosensitivity? Crazy behavior? Pale
important in plants, too! Chlorophyll as a skin? Anemic? “Involuntary tranfusions”?
Photoreceptor Chlorophyll is the molecule Stories of vampires date back thousands of
that traps this 'most elusive of all years. Our modern concept stems from Bram
powers' - and is called a photoreceptor. Stoker's quirky classic Dracula and
It is found in the chloroplasts of green Hollywood's Bela Lugosi--the romantic,
plants, and is what makes green plants, sexually charged, blood-sucking outcast
green. The basic structure of a with a fatal susceptibility to sunlight
chlorophyll molecule is a porphyrin ring, and an abhorrence of garlic and crosses.
coordinated to a central atom. This is In contrast, vampires of folklore cut a
very similar in structure to the heme pathetic figure and were also known as the
group found in hemoglobin, except that in undead. In searching for some underlying
heme the central atom is iron, whereas in truth in vampire stories, researchers have
chlorophyll it is magnesium. speculated that the tales may have been
http://departments.colgate.edu/chemistry/i inspired by real people who suffered from
ages/geier-fig1.gif. porphyria. Did they seek the blood of
19Cytochrome C – a molecule responsible others because they were unable to
for transporting an electron used to manufacture their own? Hmmmm…..
provide energy to the organism. These 29Werewolf?
molecules are identical, or very similar, http://www.geocities.com/RainForest/Canopy
for related species of plants or animals. 5322/molybdenum.html.
For example, chickens and pigs have 30As a selective catalyst. Porphyrins,
identical cytochrome C, and ducks differ especially those with special groups known
only by a few atoms. as chiral centers as part of the
20As water-splitting molecule in fuel structure, have a special ability to help
cells – they produce hydrogen gas from chemical reactions to proceed to very
water. The continuous system, during the specific products. Chiral centers are
daytime porphyrin-based photovoltaics are carbons atoms with four different groups
used directly for power needs. Some of the attached to it.
fuel cells are also run backwards for 31A Quick Organic Chemistry Lesson.
water splitting, which is then stored Organic chemistry – the chemistry of
chemically as hydrogen and oxygen. carbon-containing compounds Shortcut
Chemical storage is a more viable option formula – draw lines instead of
compared to batteries in terms of carbon-carbon bonds. R – a letter used to
efficiency and weight. The stored hydrogen represent a variety of carbon-chains from
and oxygen is fed into the fuel cells at one carbon to many.
night for continued use. 32Synthesis of Porphyrins Simplified.
21Photodynamic Therapy. Porphyrins are 33The Porphyrin Synthesis Process.
commonly used as light-absorbing compounds Reaction: Pyrrole and aldehyde Separate
which are “switched on” by photons of product (porphyrin) from leftover
light and then react with cells in a reactants and by-products Purify (by
desired way. chromatography) and remove water and/or
22Photodynamic Therapy. Photodynamic other impurities Wash and filter as needed
therapy (PDT) -fiber optic surgery A to isolate product.
photosensitive drug absorbed by cancer 34Porphyrin Research. What is there to
cells can be activated by a laser beam research? Aren’t they all pretty much the
guided through optical fibers to same? Well, no. There are lots of
selectively destroy a tumor. These drugs variations. There is the “base model? And
are also used to treat other conditions, then there are lots of substituted
such as acne. John Crawford—National porphyrins. So you can change the groups
Cancer Institute "photodynamic attached to it, and when you do, it gets
therapy." Online Photograph. new characteristics.
Britannica Student Encyclopedia. 9 July 35Porphyrin Variation 1 – the Center.
2008 The center of the porphyrin can be empty
<http://student.britannica.com/eb/art-9 (left) or hold a metal ion (right). This
509>. is called coordination. The porphyrin on
23As an anticancer agent in photodynamic the left is empty, while the one on the
therapy. Cancer type. Gross incidence pa. right contains a cobalt atom.
Suitable for PDT. Head and neck (oral 36Porphyrin Variation 2 The Meso
cavity, larynx, pharynx and oesophagus. Positions. Different functional groups
Lung cancer. Bladder. Gastric. Cervical. (“R”) can be attached to one or more
Non melanoma skin. Barrett's sides. Imagine all the different
oesophagus(pre-cancerous). 150,000 w/w combinations of many possible functional
based upon a US incidence of 17.7 per groups mixed and matched at these four
100,000. Estimated 10% = 15,000. 500,000 locations.
w/w based upon a US incidence of 37Porphyrin Variation 2 The Beta
approximately 170,000. Estimated 10% = Positions. The beta positions are the
50,0000. 150,000 based upon a US incidence corner positions.
of 53,000. 5% = 7,500. Second most common 38Porphyrin Variation 3. Combinations of
cancer in Far East 120,000 pa in Japan. these combinations! Coordinated Metals
Less common in West but w/w incidence must and/or Meso-substituents and/or
exceed 300,000 pa. Estimated 10% = 30,000. alpha-substituents and/or
40,000 based upon a US incidence of around beta-substituents. Heme B.
13,000. Estimated 10% = 4000. 500,000. 39Chemical Research Is…. Discover new
Estimated 80,000. 1 million US. 5% compounds and their properties Discover
=50,000. Total potential patients. = how the new compounds function Publish
164,500 patients. . Table: potential PDT findings worldwide so others doing similar
cancer market. Table: potential PDT cancer work can learn from it, question it,
market. Table: potential PDT cancer collaborate, etc. Research sometimes leads
market. Sources: PDT Inc, SEER Cancer to recognition, advancement, and other
stats and various others. Estimates by perks. But even when it doesn’t, it always
First Instar other percentages PDT. adds to the collective body of knowledge,
Sources: PDT Inc, SEER Cancer stats and some of which may be valuable later. For
various others. Estimates by First Instar example, (late discovery example).
other percentages PDT. Sources: PDT Inc, 40USF Leadership in Porphyrin Research.
SEER Cancer stats and various others. Synthesis of new porphyrin catalysts –
Estimates by First Instar other introducing new groups to the porphyrin
percentages PDT. periphery Use of synthesized novel
24As chemical markers in oil exploration porphyrin catalysts in various
- Petroporphyrins. The presence of highly-specific synthesis reactions.
metalloporphyrins in organic-rich 41What Does it Take to Be a Research
sediments such oil shales and petroleum, Chemist. Graduate high school – take as
generally known as petroporphyrins or much science as you can, especially AP
geoporphyrins, was first established in courses Get a bachelor’s (4-year) degree
the 1930's. in a major such as chemistry, chemical
Deoxophylloerythroetioporphyrin (DPEP) and engineering, biology, or anything else
etioporphyrin-III, which usually occur as with a good chemistry foundation Apply to
the nickel(II) or vanadyl chelates, are Grad school… they usually will pay you to
commonly found in oil and oil shale. DPEP go! (don’t get excited though, it’s not a
is considered to be a ‘molecular fossil’ lot) Pick a program and do teaching,
of the chlorophylls due to the presence of research, and probably a few other duties
a five-membered exocyclic ring In the Defend your doctoral thesis and they make
1960's, mass spectrometric investigations you a doctor!
demonstrated that sedimentary porphyrin 42Benefits - PhD Degree in Chemistry.
fractions contain complex mixtures of You will in your lifetime earn about
metalloporphyrins. Indeed, more than significantly more than the master’s and
eighty porphyrin structures have been bachelor’s degreed people alongside you.
identified in organic-rich sediments by You will most likely be a specialist or
mass spectrometry and NMR spectroscopy. manager or other similar lofty position
These geoporphyrins fall into several You likely will get to travel but not too
major families, the most prevalent being much You will live to an old age…..
the DPEP series which are structurally (really) Your job will be interesting and
related to chlorophyll. The structures of ever-changing.
the porphyrins in fossil fuels can provide 43Thank You! Any questions?
insights into the origins of these 44Acknowledgements. REST Program,
materials and their sedimentary history, Florida Department of Education USF
as well as being useful chemical markers Department of Chemistry School District of
for petroleum exploration. In addition, Hillsborough County NSF CAREER Award
the porphyrins associated with a given (CHE-0711024).
sediment provide a unique fingerprint and
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