Effect of double substitution in cationic chitosan derivatives on dna transfection efficiency was written by Badazhkova, Veronika D.;Raik, Sergei V.;Polyakov, Dmitry S.;Poshina, Daria N.;Skorik, Yury A.. And the article was included in Polymers (Basel, Switzerland) in 2020.Safety of 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride The following contents are mentioned in the article:
In this work, chitosan was chem. modified by a reaction with 4-formyl-N,N,N-trimethylanilinium iodide and pyridoxal hydrochloride and subsequent reduction of the imine bond with NaBH4. This reaction yielded three novel derivatives, N-[4-(N ‘,N’,N’-trimethylammonium)benzyl]chitosan chloride (TMAB-CS), N-[(3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridine)methyl]chitosan chloride (Pyr-CS), and N-[4-(N’,N’,N”-trimethylammonium)benzyl]-N-[(3-hydroxy-5-(hydroxymethyl)-2-methyl-4- pyridine)methyl]chitosan chloride (PyrTMAB-CS). Their structures and degrees of substitution were established by 1H NMR spectroscopy as DS1 = 0.22 for TMAB-CS, DS2 = 0.28 for Pyr-CS, and DS1 = 0.21, DS2 = 0.22 for PyrTMAB-CS. Dynamic light scattering measurements revealed that the new polymers formed stable polyplexes with plasmid DNA encoding the green fluorescent protein (pEGFP-N3) and that the particles had the smallest size (110-165 nm) when the polymer:DNA mass ratio was higher than 5:1. Transfection experiments carried out in the HEK293 cell line using the polymer:DNA polyplexes demonstrated that Pyr-CS was a rather poor transfection agent at polymer:DNA mass ratios less than 10:1, but it was still more effective than the TMAB-CS and PyrTMAB-CS derivatives that contained a quaternary ammonium group. Overall, the results show the possibility of combining substituent effects in a single carrier, thereby increasing its efficacy. This study involved multiple reactions and reactants, such as 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride (cas: 65-22-5Safety of 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride).
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride (cas: 65-22-5) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Safety of 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts