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m ‐Nitrocinnamic Acid Containing Lipophilic Peptide Exhibits Selective Growth Inhibition Activity against Leishmania major
Author(s) -
Debnath Mintu,
Abbasi Mazharul,
Sasmal Supriya,
Datta Rupak,
Haldar Debasish
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803229
Subject(s) - peptide , hydrogen bond , chemistry , lipophilicity , stereochemistry , biochemistry , organic chemistry , molecule
A series of peptides ( 1 ‐ 3 ) containing m ‐nitrocinnamic acid, α‐aminoisobutyric acid (Aib) and L‐leucine has been synthesized and their antileishmanial propensities have been studied. The compound 1 was synthesized by condensation reaction of 3‐nitrobenzaldehyde and malonic acid. The compound 1 forms duplex by intermolecular hydrogen bonding interactions in solid state and finally self‐assemble to form supramolecular helix through C‐H⋅⋅⋅O hydrogen bonds. The peptide 2 shows antiparallel sheet‐like assembly through intermolecular N‐H⋅⋅⋅O and C‐H⋅⋅⋅O hydrogen bonding interactions. The peptide 3 adopts extended conformation and self‐assemble to form bowl‐like morphology. Moreover, the peptide 3 exhibits significant growth inhibition property on Leishmania major promastigotes with an IC 50 value of 13 μg/ml. But compound 1 and peptide 2 have IC 50 values 100 μg/ml and 41 μg/ml respectively. The higher lipophilicity of peptide 3 may increase the chances of reaching this intracellular parasite. Thus peptide 3 shows selective toxicity towards Leishmania (IC 50 =13 μg/ml) and compared to several existing standard antileishmanial drugs like pentastam (IC 50 > 64 μg/ml), sodium stibogluconate (IC 50 > 64 μg/ml) or ketoconazole (IC 50 =72 μg/ml), peptide 3 shows at least 2–6 times higher potency.