La Idea Qumica

ACS UPR Aguadilla

Green Chemistry Division

JanuaryMay 2016

10th edition

Camouflage Pigmentation
By Christian Montes Castillo | Active member of ACS UPR-Ag

Cristina C. Torres Cabn, Editor

Hello! The tenth edition celebrates
chemistry in colors. You'll find articles
explaining how chemistry gives color
to the world around us.
Advisor: Dr. Brenda J. Ramos Santana

In this edition:

Camouflage Pigmentation

Chemistry of bioluminescence
and bio-fluorescence

Chemistry in our atmosphere

4-5

Optics and Silk

What is synesthesia?

Anticancer activity

Pigmentation in plants

by Cristina C. Torres Cabn, Eds.

Prof. Brenda J. Ramos Santana, Ph.D., Eds.

Camouflage is a
biological adaptation acquired by many organisms
during evolution. This adaptation can help them
hide from predators and
stay alive in situations that
can cause their death. This
adaptation is variable, because it can be expressed as
a changing color mechanism or seen as physical
appearance of the organism. In addition, organism
that are susceptible to be
hunted are not the only
ones who develop these
traits; predators also developed this during evolution.
These traits allowed them
not to be seen by their prey.
Also, it increases the probability of finding food. From
this perspective we can see
that both organisms; the
predator and prey had to
develop these traits and
mechanism for environmental adaptation and
survival.
One
organism
that uses this mechanism
for protection is the octopus. The octopus is a mollusk that belongs to the
cephalopods family. These
creatures are characterized
by having their extremities
attached to their head and
the ability to change colors
quickly. In addition, octopus are capable of altering
skin texture to assimilate
their surroundings. This
action can be done by the
presence of specialized cells
found within their skin.
This cells are chromatophores (Fig. 1) and they
have an organelle within

them known as the elastic

saccule; which possess the
pigments. Unlike other
organism, the octopus has
a more complex chromatophore cell, because this cell
has muscular fibers for
stretching. Through this
mechanism the organelle
stretches and the pigments
inside is reflected in the
skin surface. This process is
known as mimicry and it
consists in changing the
appearance and texture of
this amazing creature.
Figure 2 shows a camouflaged octopus in comparison to its original color.
There are many
types of pigmentation depending on the color that is
reflected under the presence of white light. The
chromatophore cells are
classified in two different
types. One are the biocromes which are real pigments like carotenoids and
pteridines and the other
one is a reflecting structure
that can exhibit different
colors in the visible spectrum. The most common
colors in the chromatophore are: yellow, brown,
and red. Also, blue and
white are reflected. One
mechanism used to change
the color is reorienting the
refraction surface of the
chromatophore cell. By this
mechanism, the octopus is
able to communicate, hide
and hunt. Actually, the
melanophores (brown pigments) are studied with the
purpose of understanding
some human diseases, because these cells are related

to the melanocytes found in mammals. In addition, they are used as a

tool for the designing of new drugs.
Finally, the chemistry of colors is
fascinating and abundant in nature.
Through the study of pigments we
can appreciate how the organisms in
this planet have adapted to survive
and defend themselves from predators. The study of pigments can be
helpful for the understanding of
some diseases and the development
of new medical treatment for conditions.

Fig. 1 Cromatophore. Fransaval

Fig. 2 Camouflaged octopus .Telegraph

La Idea Qumica

Page 2

Chemistry of Bioluminescence and Bio-fluorescence: Applications in Science and Discoveries

By Kelly A. Vega Pagn | Active member of ACS UPR-Ag
Bioluminescence
Bioluminescence is the phenomenon in which a living organism produces and emits light. This occurs
through a chemical reaction catalyzed by the enzyme luciferase, in
which luciferin is oxidized by oxygen (O2). As part of the reaction, it
requires the energy molecule ATP
(adenosine triphosphate), which
provides energy for the transformation of luciferin to oxidized luciferin. The excess energy that arises
from this reaction is released in the
form of light, what we can observe.
There are different types of light
depending on the composition of
the reactants, although the most
common emitted is blue light.
Bio-fluorescence
The bio-fluorescence, on the other hand, is when an organism
absorbs, transforms, and radiates
light.
It occurs when a specific molecule that the bio-fluorescent organism possesses, after being
electronically excited by light, for
example, returns to its ground
state.
The light increases the energy
of the electrons of the molecule
or pigment to an excited state,
from a lower to a higher energy
level. Then, as they lose energy
because of the vibrations in the
molecule, is released in the form
of electromagnetic radiation that
may be within the visible spectrum; in other words, it emits
light and then returns to its
ground state. However, it re-

quires the light received to be of

greater energy than the light
emitted by the fluorescence, and
that the molecule or pigment is
able to absorb it in the first place.

Marine Species
Bioluminescence, like biofluorescence is found in diverse
organisms. These may be microscopic like some bacteria
and bioluminescent protists
that maintain symbiotic relationships with other organisms, bioluminescent insects
such as fireflies and even corals, fish, algae and, for the first
time evidenced bioluminescent
reptiles.
The bio-fluorescent reptile is
known as the Hawksbill sea
turtle; recently found near the
Salomon islands by marine
biologist David Gruberfound.
In this case, the Hawksbill sea
turtle, Eretmochelys imbricata,
critically endangered species,
absorbs the light reflected by
the sea and emits it as green
and or red light.
Findings like these have led
scientists to the use of mechanisms of bio-fluorescence and
of the reactions of bioluminescence in broad fields of Science
and Medicine, for example in

cellular and molecular biology

that implements the chemistry of
these two phenomenon as laboratory techniques for the study of
the cell and the developing of
many more advances.

Medicine
A recent study, for example,
published by a team of scientists under the name "Dynamic
bioluminescence and fluorescence imaging of the effects of
the antivascular agent Combretastatin-A4P (CA4P) on
brain tumor xenografts", reveals the use of scanning of
bioluminescent and fluorescent images for the study of
the responses of tumors to
therapies. According to the
study, the technology allowed
to obtain more concise results
using less laboratory rats, resulted to be validate and less
expensive when compared to
other methods.
The observation of the world
that surrounds us, and of all
the processes and reactions
that take place in it, keeps inspiring scientists to study
chemistry on whole new levels
and in nature in search of
knowledge, findings and their
application.

Page 3

10th edition

Color of Metals

Metals burn in different colors.CompoundInterest 2014

The ACS Student Chapter at the University of

Puerto Rico in Aguadilla demonstrates different colors seen in metals (Figure 3) by burning sodium, copper and potassium with ethanol during their Initiation Acts 2015-2016 .

Figure 3. Cristina Torres and Milton Torres during the

demonstration of different colors in metals.

Chemistry in our atmosphere

Aurora borealis
By Brian O. Acevedo Fuentes | Active member of ACS UPR-Ag

The Aurora Borealis,

known as the northern lights, are a series
of bright lights produced in the atmosphere of the Earth,
thanks to the excitation of certain molecules.
This wonderful phenomenon occurs in a
very interesting way
which is explained as
follows: when the
packet of photons of
sunlight radiates and
penetrates our atmosphere it excites
the atoms and the
gas particles causing
them to collide and to
enter in the excited
state, generating a
palette. The color of
the aurora depends
mainly on the molecule that is being irradiated and depending
the altitude at which
it is being radiate. The
colors most frequently seen are a greenish
-yellow tone that is
produced by the excitation of the molecule

of oxygen at an altitude of 60 miles

above the Earth. The
oxygen molecule also
has another tone,
which is red, at an altitude of 150 miles
above the Earth, this
color is not usually
seen, and its really
rare. The nitrogen
atom as the oxygen
atom is excited by the
photons, producing
blue and violet tones,
usually nitrogen is
excited at altitudes of
60 miles above the
Earth.
How do we know
this? Well, scientists
are studying the aurora by launching rockets that measure the
quantities of particles; they estimate
the amount of these
particles and the altitude at which they
collide. They also obtain information with
images of ultraviolet
and X-rays taken by
satellites.
Did you know that

these wonders can be

artificially created?
How? Thanks to the
particle accelerator,
as this may emit an
energy powerful
enough to excite molecules; or by using a
radio frequency with
high energy.
Auroras are not just a
bright light in the atmosphere, this phenomena indicate the
climate of certain region in which its visible; indeed the emergence of the Aurora
doesnt mean the
same everywhere. In
some places the
emergence means
there will be lots of
rain and storm, while
elsewhere indicates a
calmer climate and
warm and vice versa.
If the phenomenon
did not occur generally indicated that the
weather would be less
steep for places
where storms and
rain appeared; and for
places where the

weather is calm and warm

indicated that it would be
colder than usual.
Maybe you wonder if it is
possible to occur on other
planets... the answer is yes.
This occurs on Saturn, Uranus and Jupiter because
these planets, like our planet, own a magnetic field
with the respective atoms
to be excited and be able to
show bright patterns in the
atmosphere.

La Idea Qumica

Page 5

Aurora australis
By Deyaneira Vargas | Active member of ACS UPR-Ag

Aurora australis is a
phenomenon found
in the southern hemisphere of structural
form with a brightness that allows the
emission of light rays
without raising the
temperature on the
night sky. At night
the aurora begins
with a very isolated
elongated arc that is
spreading on the horizon and goes eastwest.
During the
midnight, the bow
can increase in brightness. In addition, it
possesses very different
colors
that
change rapidly with
time. They begin to
form each of the elevations which are
formed on the surface
along an arc with vertical structures that
resemble light rays
very long and thin.
The sky can fill intervals of spirals and
light rays move rapidly from horizon to
horizon and can last a
few minutes or last
for hours. As dawn
approaches the whole
process is gradually
subsiding and only
small areas of the sky
looks bright until the

morning comes. The

colors of the aurora
depends on a set of
similar things together by having one or
more common molecules of very small
parts or small bodies
of the solar wind and
the energy level that
these atoms or molecules reach. Oxygen is
what ensures that the
primary colors of the
auroras look; green,
yellow and red being
the least common.
The sun constantly
emits all kinds of particles that some simply pass through the
atmosphere; some hit
the ground and others with the Earth's
magnetic field so that
the positive and negative charges take
opposite directions.
Due to the arrangement of the Earth's
magnetic field both
particles flow from
reaching the pole to
finally hitting the
magnetosphere producing beautiful luminous phenomena. Auroras are produced by
the collision of protons and electrons
from the sun trapped

in the magnetic field

of the pole. Because
of the duplication
that occurs between
positive and negative
particles the same
luminescence occurs
at the North Pole and
the South Pole at the
same time. The polar
auroras are one of the
most amazing phenomena that can be
seen in the Antarctic
sky. They occur at
high altitudes and can
only be observed near
the poles into the
ground. It is a physical
phenomenon that can
be compared to the
principle of operation
of the fluorescent
tubes.
Observing
auroras
require very specific
weather conditions
that only occur near
the poles during the
polar night. Auroras
can be seen in the
dark. Although the
scientific instruments
can detect disturbances in the magnetic
field that human eyes
cannot see them during the day. It highlights
that
even
though there was a
disturbance in the

magnetic field it could not

be observed because light
does not help to see it. Only
with the dark elements of
magnetic studies can be
detected, but still it wouldnt be seen.

Comparison between Aurora borealis

and Aurora australis

Name:

Aurora
borealis

Aurora
australis

Effect:

Charged
particles excite
atmospheric
molecules

Charged
particles
excite
atmospheric
molecules

Location:

Northern
Southern
hemisphere hemisphere

Pge 6

La Idea Qumica

Optics and Silk

By Luis Acevedo Soto | Active member of ACS UPR-Ag
When we think
about optics, we probably
think about eyesight and
glasses. The truth is, optics deals with much more
than that. Optics is all
around us and we employ
it in many of our everyday
activities. To be more specific, optics is the field of
science which studies phenomenon and technology
associated with the generation, transmission, utilization, detection, and
manipulation of light. In
other words, optics studies the behavior and properties of light. It is a very
broad field, from our very
small phone, to the cumbersome X-ray machines.

Ophthalmology, telecommunications, quantum

optics, spectroscopy,
among many others are
just some of the different
applications which involve
optics. In such a progressing world where nearly
almost everything is digital, optics becomes more
important each day and at
the same time, innovative
ways of putting it to use
keep developing, such as
manufacturing optic devices from silk using photolithography, which is a
method of impression
using light and chemicals
to imprint a geometric
pattern in the making of
circuits, semiconductors,

and other electrical devices.

Using fibers from
the Bombyx Mori (Fig. 4)
cocoon, which have been
previously used in the
elaboration of medical
sutures and textiles, researchers have concluded
that these fibers have the
potential to make optic
devices such as lenses,
making them flexible and
most importantly biodegradable. In 2013, Vamsi
K. Yadavalli, a scientist
from the Virginia Commonwealth University,
introduced photolithography in order to fabricate
with silk. Using photolithography, this process of
fabrication is faster and
less expensive. Since pho-

tolithography is not typically

used with biological compounds
such as silk, scientists add acrylate groups (acrylic) to the silk
proteins in order to make the silk
photoreactive. Yadavalli and his
team concocted two optical devices: a Fresnel Zone Plate and a
silk iridescent pattern (Fig. 5 & 6).
Currently, Yadavalli and his team
are still investigating this technique in pursuance of bettering
the resolution, thus hoping to
work with this technology in the
future which will generate biodegradable products. This practice
complies with the green chemistry principle #10: Design for degradation. These products are
being designed so at the end of
their function or utilization they
are broken down and hold no
repercussion to our environment.

Fig. 4 Bombyx mori. Magorzata

Fig. 6 A microstructured pattern of silk proteins diffract sunlight

to producer a rainbow of colors. ACS Appl. Mater. Interfaces

Fig. 5 A Fresnel plate made of silk proteins using

photolithography. ACS Appl.Mater.Interfaces

La Idea Qumica

Page 7

What is Synesthesia?
By Widaliz Vega Rodrguez | Active member of ACS UPR-Ag
Synesthesia is
when 2 unrelated senses
are activated concurrently.
People with synesthesia are
called synesthetes. Synesthesia occurs involuntarily
and is irrepressible; it happens on its own response to
stimuli. For example, a non
-synesthete will experience
a smell and then apply a
picture from its memory to
it, unless he has never experienced that smell before.
In contrast, a synesthete
will experience the smell,
and the mental picture they
will see are unrelated textures and colors assigned to
that experience, they will
experience the same mental picture, even if they
have never experienced the
smell. Its seen in 1:100,000

people to 1:5,000 people

depending on the subtype
of the synesthesia. There
are around 35 subtypes of
synesthesia, from tastehearing to sound-touch.
Some of these subtypes are
different from each other.
The most common being,
color-graphemic, in which
letters and numbers produce colors and simple patterns (Fig. 7). Synesthetic
percepts are variable as
well, some of them see flat
colors, and other may see
more complex patterns in
3D. There are also some
that taste food and nonfood alike.
Sometimes synesthetic are confused with
drug users, because of their
synesthetic-like experienc-

es. The difference is that

this experiences only last
while being under the influence, once sober, they disappear. True synethetes
have their synesthesia since
a young age, being females,
mostly affected in a 2:1
ratio. Synesthesia is not
considered a disease, this is
why we can say that it does
not affect people with it.
Studies have shown that
synesthetes can perform
better on test of memory
and intelligence. They are
not mentally ill; they test
negative on scales that
check for schizophrenia,
delusions and psychosis.
There are some synesthesias that may be induces by
the loss of a limb, such as
the phantom limb, which is

a remapping of the cortex after an

amputation phenomenon. For
synethetes it is not a distraction of
the everyday life, because they
have grown used to it. In fact, they
seem to enjoy having this sensations, and sometimes pity nonsynesthetes for having as 1D sensory experience, as they call it. The
only time that a synesthetes is
bothered by it is when the stimulus
produces an adversive synesthetic
experience. For example, some
words make taste like sour milk or
cigarette smoke, or when the
name of a person has a vibrant or
exciting hue compared to how his
personality is like.

Fig. 7 Vision of a person with synesthesia. Sci@StAnd

ACS UPRAg celebrates colors at the Chemistry Festival on

October 18, 2015.

Chemistry in colors experiments!

Page 8

La Idea Qumica

Pigment produced by Serratia marcescens shows anticancer activity

By Arlyn V. Padn Lpez | Active member of ACS UPR-Ag
There are a variety of or-

promising pigment to cre-

ganisms that are capable

ate cancer treatments,

of producing pigments.

because it attacks cancer

Among these is Serratia

cells without damaging

marcescens (Fig. 8), a bac-

non-malignant cells. The

terium cocobacillus

mechanisms of action to

shaped, Gram negative

combat cancer cells is

and facultative anaerobic.

apoptosis, which is de-

It is known mostly for pro-

fined as programmed cell

ducing a red pigment,

death induced by extra or

called prodigiosin (Fig. 9).

intracellular signals.

This is also produced by

Apoptosis includes ex-

other microorganisms,

pression of genes encod-

but S. marcescens is the

ing apoptotic proteins.

main producer of this pig-

This mechanism acts

ment. Prodigiosin belongs

against cells MCF-7 breast

to the family of prodi-

cancer, which are the

ginines, which is charac-

most used (among other

terized by three pyrrole

cell types, such as MDA-

rings in its structure. It is

MB-231 and T47D) for

also a secondary metabo-

studies of hormonal re-

lite, which means that its

sponses. This is due to

synthesized by the bacte-

their high sensitivity to

rium, but does not have a

hormones for expressing

direct role in their growth

the estrogen receptor. In

or reproduction.

this mechanism, PG activates expression of NAG-1

Prodigiosin (PG) is a

gene, which encodes an

apoptotic protein. It also
activates the enzyme
"kinase-3 glycogen synthase" (GSK-3) (Fig. 10),
which is involved in the
expression of NAG-1 gene
and apoptosis. In turn,

Fig. 8 Serratia marcescens

NAG-1 and GSK-3 death

receptors activate DR-4
and DR-5 in cancer cells.
The substrate of these
receptors is caspase-8, a
protein mediating apoptotic processes, and noticed that PG increases
the levels of this protein.
Furthermore, PG-induced
apoptosis in MCF-7 cells is
blocked by treatment PG
and AR-A014418 (GSK3), implying that the activity of GSK-3 is required for apoptosis to
occur.

Fig. 9 Structure of prodigiosin.

In an in vitro study, Sruthy

and

colleagues

deter-

mined that if cancer cells

are exposed to a concentration of increasing prodigiosin, the percent inhibition of the cells also increases. In addition, it was
observed that the anticancer activity of prodigiosin is higher in breast
cancer cells MCF-7, MDAcells and T47D MB-231,
also studied.

However,

they must perform an in

vivo analysis to determine
the exact cytotoxic potential of prodigiosin.

Fig. 10 Ribbon model of GSK-3.

Page 9

10th edition

Pigmentation in plants: flowers and fruits

By Loyda M. Morales Rodrguez | Vice-President 2015-2016
Have you ever wondered what makes a
flower or plant to produce its color? For example, what pigments
makes us see a yellow
sunflower or a violet
Petunia? The color observed in flowers is the
result of light reflected
from different plant pigments. In general, a pigment is any molecule or
chemical that absorbs
radiation between
380nm ultraviolet
(violet) -760nm (red)
and produces color.
Pigmentation in
plants, vegetables and
flowers has important
functions. Some are
used as reusable cata-

lysts that facilitate and

accelerate chemical reactions; thus promoting the
principle of green chemistry: "Enhancing catalysis". Carotenoids are catalysts; these (red, orange
and yellow) pigments are
related to the synthesis
of vitamin A and have an
important role in vision
and growth.
Other pigments serve
to camouflage plants and
are involved in photosynthesis. In nature, chlorophyll is involved in the
absorption of light energy and production of sugars and oxygen.

Pollination and reproduction processes are

also influenced
by the pigmentation. The
flower color attracts pollinators such as bees (Fig.
11), butterflies and hummingbirds, that carry pollen and facilitate fertilization. Pigmentation of
fruits and seeds attracts

biotechnological developments that focus primarily on

the role of pigments in attracting insects or visual preference. Several of these investigations in pigments found in
crops, vegetables, fruits aims
to improve the nutritional
properties of crops (i.e. Golden Rice, Fig. 12), and also its
ornamental characteristics
(i.e. the blue rose).

Fig. 11 Pollinator bee. John Kimbler

consumer animals that

then disperse them to new
areas. On the other hand,
the pigmentation is of
great importance to new

Fig. 12 Golden rice. CaseforGoldenRice

Our chapter celebrates CCED at the Festival!

ACS UPRAg Earth Day at the Chemistry Festival on April 24, 2016.

Earth Day Festival celebrated April 24, 2016.

La Idea Qumica
Visit us on the web!
facebook.com/upragacs || acsuprag.com || acsuprag@gmail.com

Second Environmental and Green Chemistry Symposium, Resource: Lic. Anbal

Hernndez Vega, Title: Sostenibilidad y Ambiente: El rol protagnico de las
macroalgas marinas, celebrated Nov. 24, 2015 at UPR Aguadilla.

ACS UPR-Ag Chapter receives Outstanding Chapter Award and

Green Chemistry Award at the 251st ACS National Meeting
celebrated on March 13-17, 2016 in San Diego, California.

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Optics and Silk

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Salviati, D. El color y los pigmentos
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http://
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Perry, L. Color in Flowers OH 24. Jan
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http://pss.uvm.edu/ppp/pubs/
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