2015 Mystery Molecule

December

The architects of this molecule, synthesized in order to study electron transfer, recognized its similarity to a prop which will be prominently featured in a new movie opening this month. Can you guess what it is?

December 2015 AACC Molecule Answer

Zinc naphthalocyanine-fulleropyrrolidone triad
Researchers at Wichita State University in Kansas and Tohoku University in Japan created this molecule by allowing two porphryin analogues (the flat “wings”) to self-assemble with fullerene (the spherical center). The details may be found in their report in the Journal of Porphryins and Phthalocyanines 2005; 9:698-705. The resemblance of the “super” molecule to the TIE fighter (shown to the right) used by the Empire in the Star Wars films was not lost on the scientists; they included it in the title of their report. Hoping to learn more about photosynthesis, they used the molecule to study photo-induced electron transfer from the two porphyrins to the fullerene. Interestingly, the TIE fighters are so-named because they use “twin-ion engines”. May the force be with you!


November

Turing Pharmaceuticals recently raised the price of this molecule from $13.50 to $750 overnight, stimulating discussion of the cost of drugs last month. Can you guess what it is? 

November 2015 Molecule

Pyrimethamine
This drug, also known as Daraprim ©, was first synthesized in 1953 and has been used to treat toxoplasmosis (as well as malaria) for decades. Over the past several years, the rights to manufacture and distribute it have passed from one company to another, with each transfer accompanied by slight price increases. But the huge price increase imposed by its most recent owner came in the wake of other similar price increases after sale to new companies for drugs used to treat infectious disease, heart disease and cancer – for no apparent reason other than a profit motive. 


October

This newly discovered molecule, named for a Canadian province, may be the source of the unique flavor of maple syrup. Can you guess what it is?

October Molecule 2015

Quebecol
Sugar produced in the leaves of trees has been transferred to the wood by now and will be stored there during the winter. In the spring, when temperatures start to rise above freezing, the stored sugar will start to leave the wood as sap. For some reason, maple trees produce sap with a high amount of sucrose and the maple syrup produced from the sap has a unique flavor presumed to be due to one of several phenolic compounds. A new candidate was discovered several years ago (by researchers in Rhode Island) and it was named after Quebec, the source of most of the world’s maple syrup. This phenol is not present in maple sap naturally but is believed to be formed during the manufacturing process. Investigators are looking into whether it may also be the source of the possible health benefits of maple syrup.


September

Oliver Sacks, the neurologist and author who died last month, is probably best known for having used this molecule. Can you guess what it is?

L-3,4-dihydroxyphenylalanine (L-DOPA)
This precursor to the neurotransmitters dopamine, norepinephrine and epinephrine is also used as a drug to treat Parkinson’s disease. The neurologist Oliver Sacks famously used the drug to treat people who were suffering from encephalitis following an epidemic in the early part of the 20th century. In the late 1960s, his treatment of these patients with L-DOPA produced dramatic effects which were, unfortunately, short-lived. His book describing this experimentation, “Awakenings”, was the basis of a film with Robin Williams playing Dr. Sacks.


August

Congress just passed another attempt to force the FDA to allow companies to put this molecule into the sunscreen you will be using at the beach this month. Can you guess what it is?

Ecamsule
This benzylidine derivative was first used as a sunscreen in the early 1990s and is now widely available outside the U.S. It is different from compounds used in most of the available sunscreens because it blocks ultraviolet A (UVA) rays as well as ultraviolet B (UVB) rays. Although UVB rays are primarily responsible for sunburn, it is UVA rays that are primarily responsible for skin cancer. The FDA has approved use of ecamsule at a low concentration in a few products, but it is one of eight compounds that manufacturers would like to use much more widely which are waiting for FDA approval. Last month, Congress passed a follow-up to the Sunscreen Innovation Act passed last year in an attempt to move this approval along. We hope that you had a great summer but were careful while at the beach.


July

When he saw this image flying at him in a movie theatre, Dr. Yuk-Ming Dennis Lo, who delivers the opening plenary this month at our annual meeting in Atlanta, was inspired to use a certain molecule in an innovative way. Can you guess what it is?

July Molecule

Fetal DNA

Dr. Lo was the opening plenary speaker at this year’s AACC annual meeting. He described how seeing the letter H in the title of a Harry Potter movie inspired him to look at the paternal and maternal halves of the fetal genome separately. By searching for genetic fragments with maternal and paternal markers, he and his colleagues were able to establish the detection of fetal DNA in maternal blood as a major diagnostic test for aneuploidy. Dr. Lo also described the use of DNA fragment size to distinguish fetal DNA as well as tumor DNA, making it possible to envision genomic sequencing of cell-free DNA as a screen for cancer in the not too distant future.

June

When you hit the beach this summer, you may want to pop this molecule in first. Can you guess what it is?

Nicotinamide

Last month, Australian researchers reported that taking this form of vitamin B3 protects people with a history of skin cancer from developing new lesions. They believe it may enhance the ability of skin cells to repair DNA damaged by UV irradiation. They still advise people to continue to cover up and use sun screen as well, however. Their findings were presented at the annual meeting of the American Society for Clinical Oncology. It is interesting that the addition of the amino group (which turns nicotinic acid, or niacin, into nicotinamide) seems to reduce the flushing associated with niacin therapy.

May

The Supreme Court recently heard a case that involves the use of this molecule. Can you guess what it is?

Midazolam

This benzodiazepine was substituted for sodium pentothal when availability of the latter became a problem for states using lethal injection to execute prisoners. It is the first of a three-drug protocol (inducing deep sleep, followed by muscular paralysis and, finally, heart stopping). Oklahoma's use of midazolam was botched, and the inmate, Clayton Lockett, died after the procedure was halted. Two other states (Ohio and Arizona) have used midazolam in a two-drug protocol. Both of their executions in 2014 were prolonged, accompanied by the inmate's gasping. The Supreme Court heard arguments in all three states against the use of this alternative last month. A summary of what different states use for lethal injection may be found at http://www.deathpenaltyinfo.org/state-lethal-injection. Some are considering less chemical alternatives (such as the firing squad).


April

This molecule is responsible for the bright color of the product awarded the first “Kids Eat Right” label by the Academy of Nutrition last month. Can you guess what it is?

Tartrazine

This yellow azo dye is also known as “yellow 5”. Kraft Singles, those individually wrapped single slices of bright yellow cheese, will soon bear the seal of approval from the Academy of Nutrition and Dietetics. This most recognizable form of “American” cheese was invented by James Lewis Kraft many years ago by sterilizing cheddar cheese to prevent mold. It is officially considered a “cheese product:” and many are surprised by the new endorsement. At least it’s an excellent source of calcium and vitamin D.


March

This molecule is not produced in a new genetically-modified apple recently approved by the US Department of Agriculture. Can you guess what it is?

Polyquinone

When the flesh of an apple is exposed to air, the enzyme polyphenol oxidase catalyzes the addition of hydroxyl groups to phenolic compounds, their polymerization and further oxidation of the polyphenolic groups to form polyquinones. These create the familiar brown color. Assuming that consumers would prefer apples that do not “brown”, a Canadian company used small RNA suppression technology to markedly reduce the expression of polyphenol oxidase in a new breed of apples. Although there is debate regarding whether or not these are “genetically modified”, the sale of “Arctic” apples in the U.S. was recently approved.


February

Failure to inject this molecule into young children is creating controversy in classrooms across the U.S. Can you guess what it is?

Measles virus hemagglutinin

The measles virus uses this protein to attach to human cells and it is the protein used in the vaccine. (Unlike other viruses, there is only one serotype, so production of the vaccines in use today utilizes the progenies of the original isolate.) Despite the widespread use of the vaccine, measles still causes childhood mortality worldwide. An epidemic 25 years ago was caused by a group of children visiting Disneyland who were not vaccinated because their parents were members of a religious faith which did not believe in vaccination and over 100 children died. This spurred a federal program, Vaccines for Children, which has almost eliminated measles in the US. However, recent resistance to vaccination, either because of fear of autism or religious belief, has resulted in an increase in unvaccinated children. Potential laws mandating vaccination in states which allow parents to abstain because of personal beliefs are creating controversy.


January

The FDA recently approved the use of this molecule to enhance the safety of blood transfusions. Can you guess what it is?

 

Amotosalen

This molecule belongs to the class of photoactive compounds called psoralens, used for many years to treat skin disorders such as eczema, psoriasis and even lymphoma. Psoralens combine with nucleic acids (both DNA and RNA) and they enhance the ability of ultraviolet irradiation to disrupt their structure (PUVA therapy). The FDA recently approved a new system that adds this psoralen to platelet products which are then irradiated. Since the platelets lack nuclei, only contaminating bacteria will be affected. Ultraviolet irradiation is commonly used to disinfect drinking water and other substances. Platelet products are prone to bacterial contamination because they are stored at room temperature, not in the refrigerator, to avoid clumping. This novel approach to decontamination may make platelet transfusions safer.