PMID- 7612185
OWN - NLM
STAT- MEDLINE
DCOM- 19950818
LR  - 20190920
IS  - 0177-3593 (Print)
IS  - 0177-3593 (Linking)
VI  - 376
IP  - 1
DP  - 1995 Jan
TI  - New photoaffinity labelled agonists of bradykinin.
PG  - 25-32
AB  - Several photoaffinity labelled agonists of the peptide hormone bradykinin (BK) 
      were synthesized by solid phase methods. Their biological activities and binding 
      affinities were determined in both the isolated rat uterus (RUT) and guinea pig 
      ileum (GPI). As photoreactive groups p-benzoyl-phenylalanine (Bpa) and the 
      arylazides azidobenzoic acid (ABA) and azidosalicylic acid (ASA) were attached to 
      the N-terminus of the BK agonists. In addition, Bpa was incorporated at different 
      positions of the BK sequence. Three different types of BK agonists were used. 
      Firstly, the photolabels ASA and ABA were attached to BK or to Lys-BK (kallidin). 
      Secondly, tyrosine containing BK analogues, suitable for radioiodination, were 
      labelled. This series is derived from the naturally occurring analogue 
      phyllokinin [BK-Ile-Tyr(SO3H)] and from BK analogues with tyrosine at position 0 
      and 3. The third series includes several analogues with D-N-methyl-phenylalanine 
      (D-NMe-Phe) at position 7, which selectively discriminate between the RUT and GPI 
      bradykinin B2 receptors. Among the photoaffinity labelled BK agonists, the 
      iodinatable Lys(ASA)-BK (50.8% on RUT, 73.0% on GPI), ASA-BK (26.3% on RUT), 
      Bpa-BK-Ile-Tyr (13.6% on RUT, 14.0% on GPI) and the iodinated [D-Bpa-1, 
      3-I-Tyr0]-BK (15.5% on RUT, 19.0% on GPI) retained a relatively high biological 
      activity compared with BK (100%). Thus, although BK agonists are known to allow 
      only very restricted modifications without a strong reduction in biological 
      activity, these compounds should be useful candidates for receptor labelling.
FAU - Steinmetzer, T
AU  - Steinmetzer T
AD  - Friedrich-Schiller-Universitat Jena, Institut fur Biochemical und Biophysik, 
      Germany.
FAU - Schumann, C
AU  - Schumann C
FAU - Paegelow, I
AU  - Paegelow I
FAU - Liebmann, C
AU  - Liebmann C
FAU - Glasmacher, D
AU  - Glasmacher D
FAU - Brandenburg, D
AU  - Brandenburg D
FAU - Reissmann, S
AU  - Reissmann S
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - Germany
TA  - Biol Chem Hoppe Seyler
JT  - Biological chemistry Hoppe-Seyler
JID - 8503054
RN  - 0 (Affinity Labels)
RN  - S8TIM42R2W (Bradykinin)
SB  - IM
MH  - *Affinity Labels
MH  - Animals
MH  - Bradykinin/*agonists/analogs & derivatives/chemistry
MH  - Female
MH  - Guinea Pigs
MH  - Ileum/metabolism
MH  - Molecular Structure
MH  - Photochemistry
MH  - Rats
MH  - Rats, Wistar
MH  - Uterus/metabolism
EDAT- 1995/01/01 00:00
MHDA- 1995/01/01 00:01
CRDT- 1995/01/01 00:00
PHST- 1995/01/01 00:00 [pubmed]
PHST- 1995/01/01 00:01 [medline]
PHST- 1995/01/01 00:00 [entrez]
AID - 10.1515/bchm3.1995.376.1.25 [doi]
PST - ppublish
SO  - Biol Chem Hoppe Seyler. 1995 Jan;376(1):25-32. doi: 10.1515/bchm3.1995.376.1.25.