Linear and cyclic kinin analogues

Rocchi, Raniero; Biondi, Laura; Cavaggion, Franco; Filira, Fernando; Gobbo, Marina; Mammi, Stefano; Scolaro, Barbara; Piek, T.

doi:10.1007/978-94-011-1474-5_140

Cited by 2 publications

(1 citation statement)

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“…Most interesting is the presence of carbohydrate moieties connected to threonine residues (33). Synthesis of some mono-and di-glycosylated analogues of the polypeptide called "carbohydrate free" vespulakinin 1 ( Figure 3) were described, (34)(35)(36). Recently the effects of these synthetic vespulakinin analogues on the synaptic transmission of the insect CNS were studied.…”

Section: Irreversible Depletion Of Cholinergic Nerve Endings By Kininsmentioning

confidence: 99%

Arthropod-Derived Neurotoxic Insecticides

Piek

1993

ACS Symposium Series

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Many hymenopteran insects incapacitate their prey by means of a neurotoxin. The glutamatergic excitatory neuromuscular transmission and the nicotinic excitatory synaptic transmission of insects is reversibly blocked by philanthotoxins, as well as by structurally related polyamine toxins isolated from spider venoms. These polyamine toxins are cation channel blockers or change at least the glutamatergic channel kinetics. They therefore are not receptor specific and are, for example, also active at the nicotinic receptors in the insect brain, albeit at higher concentrations. Poneratoxin, a 25 amino acid residue polypeptide isolated from an ant venom, is the first described hymenopteran neurotoxin affecting excitability of nerve and muscle fibres by changing the kinetics of the voltage-dependent sodium channel. The nicotinic synaptic transmission in the insect central nervous system (CNS) is presynaptically and irreversibly blocked by kinins, which probably cause transmitter depletion. Besides this delayed effect the carbohydrate-containing vespulakinins also show a direct and reversible inhibition of the synaptic transmission. Criticism on the possibilities to use venom toxins as leads in pesticide science has been, that these compounds have to be injected into the body or the CNS. For primary synthesis products the incorporation of the genetic codes into entomophilic viruses could solve this problem.Several groups of hymenopteran insects, like wasps and ants, sting their prey to a paralysis or only to a behaviourial inactivation, in order to offer the prey to the own offspring as an incapacitated, but living fresh source of food. These insects have developed venoms containing natural insecticides. The ideas of the 1980 f s included the possibility of using natural neurotoxins from arthropods as leads to new pesticides (4,(41)(42)(43).

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Section: Irreversible Depletion Of Cholinergic Nerve Endings By Kininsmentioning

confidence: 99%

Arthropod-Derived Neurotoxic Insecticides

Piek

1993

ACS Symposium Series

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Cyclic analogues of Thr⁶‐bradykinin, N⁸‐Lys‐bradykinin and endo‐Lys^8a‐vespulakinin 1

Gobbo

Biondi

Filira

et al. 1995

International Journal of Peptide and Protein Research

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Syntheses are described of the endo‐Lys8a‐vespulakinin 1 and of cyclo‐Thr6‐ and cyclo‐Nε‐Lys‐bradykinin. The linear peptides covering the entire sequences of endo‐Lys8a‐VSK‐1 and Thr6‐BK, and the decapeptide containing all residues constituting Lys‐BK, with a Arg‐Lys peptide bond involving the ε‐amino function of lysine, were prepared by the solid‐phase procedure based on Fmoc chemistry. Cyclization was carried out by the diphenylphosphorazide method. The amino‐terminal octapeptide sequence of vespulakinin 1, Fmoc‐Thr(tBu)‐Ala‐Thr(tBu)‐Thr(tBu)‐Arg(Pmc)‐Arg(Pmc)‐Arg(Pmc)‐Gly‐OH, and its Nα‐Boc‐[(Gal β)Thr3, (Gal β)Thr4]‐analogue, were used to prepare Nα‐(1–8 VSK 1)‐cyclo‐Nε‐kallidin and Nα‐[(Gal β)Thr3, (Gal β)Thr4, 1–8 VSK 1]‐cyclo‐Nε‐kallidin. Peptides and glycopeptides were characterized by amino‐acid analysis, optical rotation, analytical HPLC and FAB‐MS. Consistent with previous findings, preliminary pharmacological experiments on smooth muscle preparations showed that the cyclic, or partially cyclic, analogues were significatively less potent than the linear ones. © Munksgaard 1995.

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Linear and cyclic kinin analogues

Cited by 2 publications

References 8 publications

Arthropod-Derived Neurotoxic Insecticides

Arthropod-Derived Neurotoxic Insecticides

Cyclic analogues of Thr⁶‐bradykinin, N⁸‐Lys‐bradykinin and endo‐Lys^8a‐vespulakinin 1

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Linear and cyclic kinin analogues

Cited by 2 publications

References 8 publications

Arthropod-Derived Neurotoxic Insecticides

Arthropod-Derived Neurotoxic Insecticides

Cyclic analogues of Thr6‐bradykinin, N8‐Lys‐bradykinin and endo‐Lys8a‐vespulakinin 1

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Cyclic analogues of Thr⁶‐bradykinin, N⁸‐Lys‐bradykinin and endo‐Lys^8a‐vespulakinin 1