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1985 (1)
1983 (1)
1982 (1)
1Author    Karl Folkers, CyrilY. Bowers+, WilsonB. Lutz, Klaus Friebel, Teresa Kubiak, Bernhard Schircks, Georg RampoldRequires cookie*
 Title    Synthesis and Bioassay of Antagonists of the Luteinizing Hormone Releasing Hormone Having the Azagly 10 Moiety  
 Abstract    Seven new analogs of the luteinizing hormone releasing hormone (LHRH), having an Azagly 10 moiety, and three corresponding Gly 10 -analogs were synthesized for bioassay and comparison of inhibitory potencies. This study was toward a possible advantage of the Azagly 10 moiety to minimize C-terminal degradation, in vivo. Of the three procedures which were studied to achieve Azagly 10 -peptides, the reaction of cyanate ion with hydrazides was the most favorable. Variations of substitution in position 1 were also studied. The data from the antiovulatory assay showed that an Azagly 10 moiety may not depress activity, and may allow equal or even higher activity than the Glv 10 moiety, depending on the analog. [N-Ac-D-Thr 1 , D-p-Cl-Phe 2 , D-Trp 3 -6 , Azagly 10 ] LHRH was more inhibitory than the corresponding Gly 10 -analog. Based on pairs of analogs, the following relationships appeared: (1) N-Ac-D-Thr 1 was more effective than N-Ac-jo-Cl-Phe 1 ; (2) The L-configuration of Ala as N-Ac-Ala 1 -was more effective than the D—; (3) N-Ac-Ala 1 appeared more effective than the N-Ac-D-Thr 1 ; (4) D-Trp 6 appeared more effective than D-Phe 6 . In an ultimate clinical use of an antagonist of LHRH to block ovulation, the Azagly 10 moiety may be advantageous for limitation of enzymatic degradation. 
  Reference    Z. Naturforsch. 37b, 1075—1081 (1982); received March 23 1982 
  Published    1982 
  Keywords    Antagonist, Luteinizing Hormone Releasing Hormone, Ovulation, Peptides, Azaglycine 
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 TEI-XML for    default:Reihe_B/37/ZNB-1982-37b-1075.pdf 
 Identifier    ZNB-1982-37b-1075 
 Volume    37 
2Author    Karl Folkers, CyrilY. Bowers, Teresa Kubiak, Janusz StepinskiRequires cookie*
 Title    Synthesis and Antiovulatory Activities in Rats of Analogs of the Luteinizing Hormone Releasing Hormone Having a Moiety of /?-(3-Quinolyl)-D-a-alanine in Positions 3 and 6  
 Abstract    Analogs of the luteinizing hormone releasing hormone (LHRH) having a moiety (D-Qal-) of/3-(3-quinolyl)-D-a-alanine were synthesized toward more effective inhibitors of ovulation. [N-Ac-^Cl-D-Phe 1 -2 , D-3-Pal 3 , D-3-Qal 6 , D-Ala 10 ]-LHRH was the most effective, and had an antiovulatory activity of 40% at 1 /ig/rat. D-3-Qal 6 was as effective as D-Trp 6 in combination with N-Ac-3 z1 Pro 1 , ^oF-D-Phe 2 , D-Trp 3 . D-Arg 6 was superior to D-3-Qal 6) in combination with N-Ac-^Cl-D-Phe 1 ' 2 , D-Trp 3 (or D-3-Pal 3), D-Ala 10 . The introduction of D-3-Qal 3 , D-His 3 and D-Arg 3 in comparable analogs caused sub-stantial loss of activities. Abbreviations D-3-Pal = /S-(3-pyridyl)-D-a-alanine; D-3-Qal = ß-(3-quinolyl)-D-a-alanine; BOC = fertf-butyloxy-carbonyl; ÄOC = tferf-amyloxycarbonyl; DCC = N,N'-dicyclohexylcarbodiimide; 3 ZlPro = 3,4-dehydro-L-proline; pF-D-Phe — yara-fluoro-D-phenylalanine; ^Cl-D-Phe = ^»am-ehloro-D-phenylalanine; Ac = acetyl, HPLC = high performance liquid chromato-graphy. 
  Reference    Z. Naturforsch. 38b, 1253—1256 (1983); received June 27 1983 
  Published    1983 
  Keywords    Ovulation, Hormone, Antagonist, Quinolylalanine, Luteinizing Hormone Releasing Hormone 
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 TEI-XML for    default:Reihe_B/38/ZNB-1983-38b-1253.pdf 
 Identifier    ZNB-1983-38b-1253 
 Volume    38 
3Author    Karl Folkers, CyrilY. Bowers, Yin-Zeng Liu, Xiao Shao-Bo, Hong-Ming Shieh, Chu Ji-YuRequires cookie*
 Title    Antagonists of the Luteinizing Hormone Releasing Hormone with Emphasis on Amino Acids in Position Five  
 Abstract    Seventeen analogs of the luteinizing hormone releasing hormone (LHRH) have been syn-thesized, bioassayed, and compared for antiovulatory activity (AOA) in rats. The emphasis of design was replacement of Tyr 5 of LHRH. Position 5 has not been extensively studied. [N—Ac—D-2-Nal 1 , D-pClPhe 2 , D-3-Pal 3 , D-Arg 6 , D—Ala 10 ]-LHRH was the baseline for new designs. Comparison of the AOA's of the 17 analogs with the baseline revealed the two peptides with Phe 5 and 3-Pal 5 had equivalent AOA's, and were the best of the 17, and about 45% more potent than the baseline. Analogs with pClPhe 5 , oClPhe 5 , a-MepClPhe 5 , 2-Nal 5 , Trp 5 , and His 5 were less potent than the Phe 5 -and 3-Pal 5 -analogs. Based on the Phe 5 -analog, eight other analogs were synthesized with changes in positions 1, 2, 3 and 7 and although none were better than the baseline, 5/8 showed 20—60% AOA's at 250 ng and revealed optimum positions for new designs. 
  Reference    Z. Naturforsch. 40b, 313—316 (1985); received August 20 1984 
  Published    1985 
  Keywords    Peptide, Hormone, Ovulation, Luteinizing Hormone Releasing Hormone, Antagonist 
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 TEI-XML for    default:Reihe_B/40/ZNB-1985-40b-0313.pdf 
 Identifier    ZNB-1985-40b-0313 
 Volume    40