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(1933) established that polynuclear aromatic hydrocarbons (PAHs) were carcinogenic components of pitch. ... Although less is known about their health effects than about those of PAHs, it is clear that some nitro-PAHs are potent mutagens and carcinogens.(1)

Benzene and polynuclear hydrocarbons containing more than two benzene rings fused together are toxic and said to possess cancer producing (carcinogenic) property. Such polynuclear hydrocarbons are formed on incomplete combustion of organic materials like tobacco, coal and petroleum.(2)

From the two sources cited above, I keep seeing that polybenzenoid compounds like 1,2-benzanthracene, 3-methylcholanthrene and 1,2- benzpyrene are mentioned to be carcinogens.

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In general, why are polynuclear compounds carcinogenic? I google searched on this topic and all I could find is their effects and concentrations in various substances.

My questions are:

  1. Why are they carcinogenic

  2. Is there a reason for a given organic compound to be carcinogenic?

References

  1. Potential Carcinogenic Effects of Polynuclear Aromatic Hydrocarbons and Nitroaromatics in Mobile Source Emissions, STEPHEN S.HECHT(link)
  2. pg403, NCERT Class XI part 2(pdf link)
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Haha Hahaha
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  • Search the term intercalation of DNA by polyaromatics. Not all organic compounds are carcinogens. Our whole body has thousands of organic compounds. – AChem Jan 03 '20 at 04:59
  • i meant for a given organic compound – Haha Hahaha Jan 03 '20 at 05:00
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    There is no way to predict beforehand. Experiment decides it. One can make guesses from known classes of compounds by extrapolation. For example, if PAHs are bad, aromatic amines are also powerful carcinogens. – AChem Jan 03 '20 at 05:05
  • See https://chemistry.stackexchange.com/questions/125402/how-does-one-tell-or-conclude-if-a-substance-is-carcinogenic – Aniruddha Deb Jan 03 '20 at 05:22
  • i did not find that answer satisfactory, i do not a want an answer like experiment carried, result obtained, conclusion derived, reason unknown. – Haha Hahaha Jan 03 '20 at 05:24
  • Related: https://chemistry.stackexchange.com/questions/95168/is-benzene-harmful-to-human-health/95202 – Nilay Ghosh Jan 03 '20 at 05:30
  • https://chemistry.stackexchange.com/questions/39109/does-benzenes-resonance-structure-allow-it-to-enter-dna – Nilay Ghosh Jan 03 '20 at 05:30
  • and https://chemistry.stackexchange.com/questions/75590/what-component-of-the-human-dna-reacts-with-4-5-benzoapyrene-oxide-and-7-8-ben – Nilay Ghosh Jan 03 '20 at 05:31
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    @Haha HaHaHa Reality is often very unsatisfactory. That does not make an answer, pointing to such reality, unsatisfactory as well. – Poutnik Jan 03 '20 at 05:49
  • @NilayGhosh thanks, a gem of an answer with a 130+ score of orthocresol right there, perfect. – Haha Hahaha Jan 03 '20 at 05:54
  • yaa, @Poutnik thats the only sad thing about chemistry – Haha Hahaha Jan 03 '20 at 05:54

1 Answers1

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Why are they carcinogenic?

From my point of view as a medicinal chemist, polycyclic aromatic hydrocarbons compounds tend to be metabolized by specific cytochrome P450 (CYP 450) isoforms to form highly electrophilic species, which are highly reactive and can react with the DNA of the cell and damage it. Specifically, they can react with the nucleophilic nitrogen in the DNA bases such as adenine.

Is there a reason for a given organic compound to be carcinogenic?

Mechanism for carcinogenicity can vary, in general, any compound damaging or altering the DNA can be carcinogenic. For example, highly reactive electrophiles (such as formaldehyde).

Reference

  1. https://socratic.org/questions/how-do-polycyclic-aromatic-hydrocarbons-cause-cancer
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