Aminobenzoic acid incorporated octapeptides for cation transport

Benke, Bahiru Punja; Madhavan, Nandita

doi:10.1016/j.bmc.2015.02.031

Cited by 15 publications

(9 citation statements)

References 34 publications

(30 reference statements)

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“…The selectivity inducer is slightly farther away from the C terminus in peptide 2 . Peptide 3 was designed based on our earlier success with octapeptide scaffolds [6a,c] and has the selectivity inducer at the centre of a hexapeptide alanine scaffold. Peptide 1 with the ligand at the C terminus was the most efficient Cu II transporter.…”

Section: Introductionmentioning

confidence: 99%

Ligand Induced Cu^II Transport Restricts Cancer and Mycobacterial Growth: Towards a Plug‐and‐Select Ion Channel Scaffold

et al. 2021

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Synthetic channels with high ion selectivity are attractive drug targets for diseases involving ion dysregulation. Achieving selective transport of divalent ions is highly challenging due their high hydration energies. A small tripeptide amphiphilic scaffold installed with a pybox ligand selectively transports Cu II ions across membranes. The peptide forms stable dimeric pores in the membrane and transports ions by a Cu 2 + /H + antiport mechanism. The ligand-induced excellent Cu II selectivity as well as high membrane permeability of the peptide is exploited to promote cancer cell death. The peptide's ability to restrict mycobacterial growth serves as seeds to evolve antibacterial strategies centred on selectively modulating ion homeostasis in pathogens. This simple peptide can potentially function as a universal, yet versatile, scaffold wherein the ion selectivity can be precisely controlled by modifying the ligand at the C terminus.

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Section: Introductionmentioning

confidence: 99%

Ligand Induced Cu^II Transport Restricts Cancer and Mycobacterial Growth: Towards a Plug‐and‐Select Ion Channel Scaffold

et al. 2021

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“…Anydysfunction in these processes led to various diseases such as cystic fibrosis, Dent disease, Bartter syndrome, and epilepsy [34][35][36][37][38][39][40][41]. In order to mimic the regulatory functions in living systems, a wide range of anion transporters have been investigated that include peptides [42][43][44][45][46][47][48][49][50][51], oligoureas [52][53], anion-π slides [54][55][56][57],steroids [58][59][60][61], calixpyrroles [62][63][64],calixarenes [65][66][67], and other scaffolds [68][69][70]. In particular, peptide based transmembrane anion transporters have attracted great interest.…”

Section: Ion Transport Activitymentioning

confidence: 99%

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Burade¹,

Pawar²,

Saha³

et al. 2019

Preprint

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The C3-tetrasubstituted furanoid sugar amino acid derived linear amino acid dipeptide 8 and tetrapeptide 9 on intra-molecular cyclization afforded oxazolone pseudo-peptides 1 and 2a, respectively, with formation of oxazole ring at the C-terminus. Conformational study of 2a showed seven membered intramolecular C=O×××HN (II) hydrogen bonding leading to the γ-turn conformation which is absent in the precursor tetrapeptide 9 thus indicating the role of oxazolone ring in γ-turn formation in 2a. This fact was supported by the molecular modeling studies. The oxazolone ring containing pseudo-tetrapeptide 2a was found to be better ion transporter than pseudodi-peptide1.The ion selectivity of 2a indicated Cl-anion-selective transport via the antiport mechanism.

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“…Thus, the major goal of this study is to develop a green, facile and efficient approach for a new combination of CPT-GNHs@FHQ-PUL to improve the efficacy, selectivity, and safety of these systems. The functional molecules grafted onto PUL-stabilized GNHs can not only create intermolecular interactions with CPT but also offer benefits for increasing uptake, selectivity, and efficacy [ 42 ]. For effective drug delivery, PUL was designed to contain three parts, including positive charges, hydrophobic molecules of p -aminobenzoic acid, and targeted ligands of folic acid.…”

Section: Introductionmentioning

confidence: 99%

Targeted Gold Nanohybrids Functionalized with Folate-Hydrophobic-Quaternized Pullulan Delivering Camptothecin for Enhancing Hydrophobic Anticancer Drug Efficacy

Laksee¹,

Supachettapun

Muangsin

et al. 2021

Polymers

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This study presented a green, facile and efficient approach for a new combination of targeted gold nanohybrids functionalized with folate-hydrophobic-quaternized pullulan delivering hydrophobic camptothecin (CPT-GNHs@FHQ-PUL) to enhance the efficacy, selectivity, and safety of these systems. New formulations of spherical CPT-GNHs@FHQ-PUL obtained by bio-inspired strategy were fully characterized by TEM, EDS, DLS, zeta-potential, UV-vis, XRD, and ATR-FTIR analyses, showing a homogeneous particles size with an average size of approximately 10.97 ± 2.29 nm. CPT was successfully loaded on multifunctional GNHs@FHQ-PUL via intermolecular interactions. Moreover, pH-responsive CPT release from newly formulated-CPT-GNHs@FHQ-PUL exhibited a faster release rate under acidic conditions. The intelligent CPT-GNHs@FHQ-PUL (IC50 = 6.2 μM) displayed a 2.82-time higher cytotoxicity against human lung cancer cells (Chago-k1) than CPT alone (IC50 = 2.2 μM), while simultaneously exhibiting less toxicity toward normal human lung cells (Wi-38). These systems also showed specific uptake by folate receptor-mediated endocytosis, exhibited excellent anticancer activity, induced the death of cells by increasing apoptosis pathway (13.97%), and arrested the cell cycle at the G0-G1 phase. The results of this study showed that the delivery of CPT by smart GNHs@FHQ-PUL systems proved to be a promising strategy for increasing its chemotherapeutic effects.

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Aminobenzoic acid incorporated octapeptides for cation transport

Cited by 15 publications

References 34 publications

Ligand Induced Cu^II Transport Restricts Cancer and Mycobacterial Growth: Towards a Plug‐and‐Select Ion Channel Scaffold

Ligand Induced Cu^II Transport Restricts Cancer and Mycobacterial Growth: Towards a Plug‐and‐Select Ion Channel Scaffold

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Targeted Gold Nanohybrids Functionalized with Folate-Hydrophobic-Quaternized Pullulan Delivering Camptothecin for Enhancing Hydrophobic Anticancer Drug Efficacy

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Aminobenzoic acid incorporated octapeptides for cation transport

Cited by 15 publications

References 34 publications

Ligand Induced CuII Transport Restricts Cancer and Mycobacterial Growth: Towards a Plug‐and‐Select Ion Channel Scaffold

Ligand Induced CuII Transport Restricts Cancer and Mycobacterial Growth: Towards a Plug‐and‐Select Ion Channel Scaffold

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Targeted Gold Nanohybrids Functionalized with Folate-Hydrophobic-Quaternized Pullulan Delivering Camptothecin for Enhancing Hydrophobic Anticancer Drug Efficacy

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Product

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Ligand Induced Cu^II Transport Restricts Cancer and Mycobacterial Growth: Towards a Plug‐and‐Select Ion Channel Scaffold

Ligand Induced Cu^II Transport Restricts Cancer and Mycobacterial Growth: Towards a Plug‐and‐Select Ion Channel Scaffold