For the neurotic chemical language fanatics: radiotracer nomenclature

[Function]

Hello everyone

The ones following my posts regularly will know that I'm writing my thesis on, among other things, nuclear imaging of primary brain tumours.

Finding accepted, standardised nomenclature for radiotracers, however, is driving me crazy. I found the Molecular Imaging and Contrast Agent Database on the NCBI website, which offers some abbreviated and full chemical names of radiotracers I'm discussing. However ... I can't seem to agree with the chemical name they give to the substance which has the INN of fludeoxyglucose (¹⁸F). Here are some of the names given in the MICAD I need evaluated by some real chemical-linguistic purists here (I'm a bit of a perfectionist and I don't like the discrepancy in ways that fludeoxyglucose (¹⁸F) can be written, among other tracers) (abbreviations are given after the hyphen):

• O-(2-[¹⁸F]Fluoroethyl)-L-tyrosine - [¹⁸F]FET
• 3'-Deoxy-3'-[¹⁸F]fluorothymidine - [¹⁸F]FLT
• [¹⁸F]Fluorocholine - [¹⁸F]FCH
• L-[methyl-¹¹C]Methionine - [¹¹C]MET
• p-(2-[¹⁸F]fluoroethyl)-L-phenylalanine - [¹⁸F]FEP

And then this:

• [¹⁸F]Fluoro-2-deoxy-2-D-glucose - [¹⁸F]FDG
• In the text beneath the table containing this chemical name, however, they describe "2-[¹⁸F]Fluoro-2-deoxy-D-glucose", which itself is already in discrepancy with the earlier reported name above.
• Additionally, a more commonly used name for this radiotracer, by almost every author, seems to be "2-Deoxy-2-[¹⁸F]fluoro-D-glucose".

Can someone please give some feedback on the nomenclature of these 6 radiotracers? Also mind the italics where given (by the MICAD). What would be the most correct full name for [¹⁸F]FDG? I acknowledge that these names are not fully fundamentally chemical (else there would be something with "ethylammonium" in [¹⁸F]FCH), but let's ignore that nonetheless.

A possible solution could've been to go with the INN of every tracer, however, it seems like only [¹⁸F]FDG has an approved INN ...

Thanks!

Function

EDIT: Can this thread be moved to Organic Chemistry or Applied Chemistry?

Edited November 12, 2017 by Function

[John Cuthber]

Well, according to WIKI fludeoxyglucose (¹⁸F) is 

2-deoxy-2-(¹⁸F)fluoro-D-glucose

and I agree with them.

I think 3'-Deoxy-3'-[18F]fluorothymidine is correct chemically.

 

What are you actually looking for here?

[Function]

Consensus and insights by experts in the field 

Thanks, John!

[John Cuthber]

Good luck with herding cats.

Make a point early on in the thesis of citing the IUPAC names and the INN where it exists  then use an abbreviation that makes sense to you. That way you will (probably) be consistent.

Anyone who knows the field well enough to "judge" your thesis will be aware of the variations available. As long as you are consistent they can't complain much.

If you happen to know who will be looking at your work, find a paper they wrote, and use the same abreviations they use.

[Function]

1 hour ago, John Cuthber said:

Good luck with herding cats.

Make a point early on in the thesis of citing the IUPAC names and the INN where it exists  then use an abbreviation that makes sense to you. That way you will (probably) be consistent.

Anyone who knows the field well enough to "judge" your thesis will be aware of the variations available. As long as you are consistent they can't complain much.

If you happen to know who will be looking at your work, find a paper they wrote, and use the same abreviations they use.

You state IUPAC and INN. However, 3'-Deoxy-3'-[18F]fluorothymidine is neither of both. The IUPAC name for that would be 1-[4-fluoranyl-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione.

Then what is 3'-deoxy-3'-[18F]fluorothymidine?

[John Cuthber]

It's a bit awkward with sugar derivatives like ribose to work out where to start counting; especially when they have two conformations.

I'd find the IUPAC name, check it carefully, and use it.

[Function]

Thanks!

For the following: "1-[(2S,4S,5R)-2-[¹⁸F]fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione"

Should the S's and the H's be in italics?