[1‐Desamino]Lysinvasotocin, ein Disulfidpolypeptid mit Oxytocin‐Wirkung

Rimpler, Manfred

doi:10.1002/jlac.19717450103

Cited by 9 publications

(6 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Preparation of DOTA-dLVT and radiolabelling dLVT (Rimpler, 1971) is characterised by the presence of only one free amino group at position 8. As described above, an activated ester of DOTA obtained via the NHS/DCC system was reacted overnight with dLVT.…”

Section: Resultsmentioning

confidence: 99%

“…As a starting compound, we used dLVT (Rimpler, 1971), an OT analogue with only one potential binding site for a chelating agent: the free e-NH 2 group of the lysine residue in position 8. The lysine e-NH 2 group has been widely used to link chemical reagents to peptides (Meares et al, 1984;Terrillon et al, 2002).…”

Section: Discussionmentioning

confidence: 99%

“…To this end, we used a deaminated LVT at position 1 (dLVT) (Rimpler, 1971) (Boissonnas and Huguenin, 1960) and dLVT (MW 1007.2) (Rimpler, 1971) were resynthesised as previously described (Terrillon et al, 2002 …”

mentioning

confidence: 99%

See 2 more Smart Citations

Improved radiotracing of oxytocin receptor-expressing tumours using the new [111In]-DOTA-Lys8-deamino-vasotocin analogue

et al. 2003

View full text Add to dashboard Cite

Oxytocin receptors (OTR) have been described in a number of tumours of different origin, and represent a new target for specific radiolabelled oxytocin (OT) analogues in cancer diagnosis and therapy. By linking the DOTA chelating agent to position 8 of the deamino derivative of Lys 8 -vasotocin (dLVT), we obtained a new compound (DOTA-dLVT) with the following characteristics: (1) it forms a monomeric and stable compound that binds to OTR with an affinity comparable to that of the endogenous OT ligand; (2) it is characterised by a very good selectivity profile for the human OTR, with a low affinity binding to the closely related V1a, V1b and V2 vasopressin receptor subtypes; (3) it induces rapid and persistent receptor internalisation and (4) when radiolabelled, [ 111 In]-DOTA-dLVT is efficiently and selectively taken up by OTR-positive tumours grown in mice. These features makes radiolabelled DOTA-dLVT a very good candidate for the radiotargeting of OTR-expressing tumours.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Improved radiotracing of oxytocin receptor-expressing tumours using the new [111In]-DOTA-Lys8-deamino-vasotocin analogue

et al. 2003

View full text Add to dashboard Cite

show abstract

“…Peptides d(CH2)5[Tyr(Me) 2 ,Thr 4 ,Orn 8 ,Tyr-NH2 9 ]VT (1a) (OTA) 12 and desGly-NH2,d(CH2)5[D-Tyr 2 ,Thr 4 ,Orn 8 ]VT (2a) 13 were synthesized as previously described. 12,13 Peptides d[Lys 8 ]-VT (3a) 35,36 and d[Orn 8 ]VT (7a) 37 1) were synthesized specifically for this study. All peptides were synthesized by the Merrifield solid-phase method 38,39 as previously described [11][12][13] or with modifications previously described.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Fluorescent Antagonists and Agonists for Human Oxytocin and Vasopressin V₁_aReceptors

Terrillon

Cheng²,

Stoev³

et al. 2002

J. Med. Chem.

View full text Add to dashboard Cite

The fluoresceinyl (Flu) group has been linked by an amide bond to the side chain amino group at position 8 of (a) two oxytocin (OT) antagonists, to give d(CH(2))(5)[Tyr(Me)(2),Thr(4),Orn(8)(5/6C-Flu),Tyr-NH(2)(9)]VT (Orn(8)(5/6C-Flu)OTA) (1) and desGly-NH(2),d(CH(2))(5)[D- Tyr(2),Thr(4),Orn(8)(5/6C-Flu)]VT (2), and (b) eight Lys(8) and Orn(8) analogues of potent OT agonists, to give d[Lys(8)(5/6C-Flu)]VT (3), d[Thr(4),Lys(8)(5/6C-Flu)]VT (4), [HO(1)][Lys(8)(5/6C-Flu)]VT (5), [HO(1)][Thr(4),Lys(8)(5/6C-Flu)]VT (6), d[Orn(8)(5/6C-Flu)]VT (7), d[Thr(4),Orn(8)(5/6C-Flu)]VT (8), [HO(1)][Orn(8)(5/6C-Flu)]VT (9), and [HO(1)][Thr(4),Orn(8)(5/6C-Flu)]VT (10). The tetramethylrhodamyl (Rhm) group was attached to the precursor peptide of 9 to give [HO(1)][Orn(8)(5/6C-Rhm)]VT (11). All 11 fluorescent peptides were evaluated in human OT and vasopressin V(1a) (vasoconstrictor), V(1b) (pituitary), and V(2) (antidiuretic) receptor binding and functional assays. With K(d) = 6.24, 217, >10000, and >10000 nM for the OT, V(1a), V(1b), and V(2) receptors, peptide 1 is a potent and selective fluorescent OT antagonist and may be useful for specifically labeling OT receptors while peptide 2 exhibits low affinities for all the receptors. The fluorescent peptides 3-10 are all very potent agonists for the human OT receptor. They exhibit the following K(d) values (nM) for the human OT, V(1a), V(1b), and V(2) receptors, respectively: (3) 0.29, 57, 124, >10000; (4) 1.8, 25.5, 150, >10000; (5) 0.34, 13.7, 66, nd (not determined); (6) 0.32, 17.3, 53, >10000; (7) 0.25, 107, 393, >10000; (8) 0.40, 30, 282, >10000; (9) 0.18, 12.2, 126, nd; (10) 0.17, 11.8, 87, >1000; (11) 0.092, 7.36, nd, nd. Peptide 7 exhibits both a high affinity and a high selectivity for human OT receptors. Peptides 7 and 11 were utilized to study the internalization of the OT receptor-ligand complex. Preliminary studies indicate that this process is similar to that observed for the vasopressin V(1a) receptor and differs from that observed for vasopressin V(2) receptors. Some or all of the fluorescent OT antagonists and agonists reported here are very promising new fluorescent ligands for labeling cells which express the human OT receptor and are also useful tools to follow endocytosis of the receptor-ligand complex.

show abstract

“…cose-6-phosphate dehydrogenase (20 units). As a control an identical incubation was performed with liver homogenate which had been heated previously for 15 min in boiling water.…”

mentioning

confidence: 99%

Synthesis and some pharmacological properties of 8-L-homoarginine-vasopressin and of 1-deamino-8-L-homoarginine-vasopressin

Lindeberg¹,

Bodanszky²,

Sawyer³

1974

J. Med. Chem.

View full text Add to dashboard Cite

[1‐Desamino]Lysinvasotocin, ein Disulfidpolypeptid mit Oxytocin‐Wirkung

Cited by 9 publications

References 27 publications

Improved radiotracing of oxytocin receptor-expressing tumours using the new [111In]-DOTA-Lys8-deamino-vasotocin analogue

Improved radiotracing of oxytocin receptor-expressing tumours using the new [111In]-DOTA-Lys8-deamino-vasotocin analogue

Synthesis and Characterization of Fluorescent Antagonists and Agonists for Human Oxytocin and Vasopressin V₁_aReceptors

Synthesis and some pharmacological properties of 8-L-homoarginine-vasopressin and of 1-deamino-8-L-homoarginine-vasopressin

Contact Info

Product

Resources

About

[1‐Desamino]Lysinvasotocin, ein Disulfidpolypeptid mit Oxytocin‐Wirkung

Cited by 9 publications

References 27 publications

Improved radiotracing of oxytocin receptor-expressing tumours using the new [111In]-DOTA-Lys8-deamino-vasotocin analogue

Improved radiotracing of oxytocin receptor-expressing tumours using the new [111In]-DOTA-Lys8-deamino-vasotocin analogue

Synthesis and Characterization of Fluorescent Antagonists and Agonists for Human Oxytocin and Vasopressin V1aReceptors

Synthesis and some pharmacological properties of 8-L-homoarginine-vasopressin and of 1-deamino-8-L-homoarginine-vasopressin

Contact Info

Product

Resources

About

Synthesis and Characterization of Fluorescent Antagonists and Agonists for Human Oxytocin and Vasopressin V₁_aReceptors