The effect of monocyclic and bicyclic analogs of human parathyroid hormone (hPTH)-(1-31)NH2 on bone formation and mechanical strength in ovariectomized rats
The [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2 lactam is a stronger stimulator of adenylyl cyclase activity and a better stimulator of trabecular bone in the ovariectomized (OVX) rat model of osteopenia than hPTH-(1-31)NH2. This enhanced activity is due in large part to the stabilization of the amphip...
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| Veröffentlicht in: | Calcified tissue international 2001-02, Vol.68 (2), p.95-101 |
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| creator | Morley, P Whitfield, J F Willick, G E Ross, V MacLean, S Barbier, J R Isaacs, R J Andreassen, T T |
| description | The [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2 lactam is a stronger stimulator of adenylyl cyclase activity and a better stimulator of trabecular bone in the ovariectomized (OVX) rat model of osteopenia than hPTH-(1-31)NH2. This enhanced activity is due in large part to the stabilization of the amphiphilic receptor-binding alpha-helix in the Ser17-Gln29 region. The goal of the present study was to determine whether further cyclization could produce a more active hPTH analog. To this end, we compared the relative bioactivities of the bicyclic hPTH analog [Glu17,Leu27]cyclo(Lys13-Glu17,Glu22-Lys26)-hPTH-(1-31)NH2, made by replacing Ser17 with Glu17 and introducing a second lactam linkage between Lys13 and Glu17. The relative EC50 for adenylyl cyclase stimulation by the bicyclic hPTH analog was similar to the EC50 of the monocyclic [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2, but the bicyclic analog was still more active than hPTH-(1-31)NH2. As expected from adenylyl cyclase stimulation being responsible for PTH's anabolic action, the bicyclic hPTH analog [Glu17, Leu27]cyclo(Lys13-Glu17, Glu22-Lys26)-hPTH-(1-31)NH2 was able to increase femoral trabecular volume and thickness and mechanical strength in OVX rats, but it was no more effective than [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2 when injected once daily in a dose of 0.8 nmol/100 g body weight. Thus, further constraint of the conformation of hPTH-(1-31)NH2 by introducing two lactam link-ages between Lys13-Glu17 and Glu22-Lys26 did not raise the osteogenicity above that of the monocyclic analog. |
| doi_str_mv | 10.1007/BF02678147 |
| format | Article |
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This enhanced activity is due in large part to the stabilization of the amphiphilic receptor-binding alpha-helix in the Ser17-Gln29 region. The goal of the present study was to determine whether further cyclization could produce a more active hPTH analog. To this end, we compared the relative bioactivities of the bicyclic hPTH analog [Glu17,Leu27]cyclo(Lys13-Glu17,Glu22-Lys26)-hPTH-(1-31)NH2, made by replacing Ser17 with Glu17 and introducing a second lactam linkage between Lys13 and Glu17. The relative EC50 for adenylyl cyclase stimulation by the bicyclic hPTH analog was similar to the EC50 of the monocyclic [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2, but the bicyclic analog was still more active than hPTH-(1-31)NH2. As expected from adenylyl cyclase stimulation being responsible for PTH's anabolic action, the bicyclic hPTH analog [Glu17, Leu27]cyclo(Lys13-Glu17, Glu22-Lys26)-hPTH-(1-31)NH2 was able to increase femoral trabecular volume and thickness and mechanical strength in OVX rats, but it was no more effective than [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2 when injected once daily in a dose of 0.8 nmol/100 g body weight. Thus, further constraint of the conformation of hPTH-(1-31)NH2 by introducing two lactam link-ages between Lys13-Glu17 and Glu22-Lys26 did not raise the osteogenicity above that of the monocyclic analog.</description><identifier>ISSN: 0171-967X</identifier><identifier>EISSN: 1432-0827</identifier><identifier>DOI: 10.1007/BF02678147</identifier><identifier>PMID: 11310353</identifier><language>eng</language><publisher>United States: Springer Nature B.V</publisher><subject>Adenylyl Cyclases - biosynthesis ; Animals ; Bone Development - drug effects ; Bone Development - physiology ; Bone Diseases, Metabolic - drug therapy ; Bone Diseases, Metabolic - etiology ; Cyclization ; Elasticity - drug effects ; Female ; Femur - drug effects ; Femur - pathology ; Femur - physiopathology ; Lumbar Vertebrae - drug effects ; Lumbar Vertebrae - pathology ; Lumbar Vertebrae - physiopathology ; Ovariectomy ; Parathyroid Hormone - chemistry ; Parathyroid Hormone - pharmacology ; Parathyroid Hormone - therapeutic use ; Peptide Fragments - chemistry ; Peptide Fragments - pharmacology ; Peptide Fragments - therapeutic use ; Rats ; Rats, Sprague-Dawley ; Stress, Mechanical ; Structure-Activity Relationship ; Tumor Cells, Cultured - drug effects ; Tumor Cells, Cultured - enzymology ; Weight-Bearing - physiology</subject><ispartof>Calcified tissue international, 2001-02, Vol.68 (2), p.95-101</ispartof><rights>Springer-Verlag 2001</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c311t-7765ef589cd24091aae7e2de706329b166ae205257c44c01fab63866668244a93</citedby><cites>FETCH-LOGICAL-c311t-7765ef589cd24091aae7e2de706329b166ae205257c44c01fab63866668244a93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11310353$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Morley, P</creatorcontrib><creatorcontrib>Whitfield, J F</creatorcontrib><creatorcontrib>Willick, G E</creatorcontrib><creatorcontrib>Ross, V</creatorcontrib><creatorcontrib>MacLean, S</creatorcontrib><creatorcontrib>Barbier, J R</creatorcontrib><creatorcontrib>Isaacs, R J</creatorcontrib><creatorcontrib>Andreassen, T T</creatorcontrib><title>The effect of monocyclic and bicyclic analogs of human parathyroid hormone (hPTH)-(1-31)NH2 on bone formation and mechanical strength in ovariectomized rats</title><title>Calcified tissue international</title><addtitle>Calcif Tissue Int</addtitle><description>The [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2 lactam is a stronger stimulator of adenylyl cyclase activity and a better stimulator of trabecular bone in the ovariectomized (OVX) rat model of osteopenia than hPTH-(1-31)NH2. This enhanced activity is due in large part to the stabilization of the amphiphilic receptor-binding alpha-helix in the Ser17-Gln29 region. The goal of the present study was to determine whether further cyclization could produce a more active hPTH analog. To this end, we compared the relative bioactivities of the bicyclic hPTH analog [Glu17,Leu27]cyclo(Lys13-Glu17,Glu22-Lys26)-hPTH-(1-31)NH2, made by replacing Ser17 with Glu17 and introducing a second lactam linkage between Lys13 and Glu17. The relative EC50 for adenylyl cyclase stimulation by the bicyclic hPTH analog was similar to the EC50 of the monocyclic [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2, but the bicyclic analog was still more active than hPTH-(1-31)NH2. As expected from adenylyl cyclase stimulation being responsible for PTH's anabolic action, the bicyclic hPTH analog [Glu17, Leu27]cyclo(Lys13-Glu17, Glu22-Lys26)-hPTH-(1-31)NH2 was able to increase femoral trabecular volume and thickness and mechanical strength in OVX rats, but it was no more effective than [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2 when injected once daily in a dose of 0.8 nmol/100 g body weight. Thus, further constraint of the conformation of hPTH-(1-31)NH2 by introducing two lactam link-ages between Lys13-Glu17 and Glu22-Lys26 did not raise the osteogenicity above that of the monocyclic analog.</description><subject>Adenylyl Cyclases - biosynthesis</subject><subject>Animals</subject><subject>Bone Development - drug effects</subject><subject>Bone Development - physiology</subject><subject>Bone Diseases, Metabolic - drug therapy</subject><subject>Bone Diseases, Metabolic - etiology</subject><subject>Cyclization</subject><subject>Elasticity - drug effects</subject><subject>Female</subject><subject>Femur - drug effects</subject><subject>Femur - pathology</subject><subject>Femur - physiopathology</subject><subject>Lumbar Vertebrae - drug effects</subject><subject>Lumbar Vertebrae - pathology</subject><subject>Lumbar Vertebrae - physiopathology</subject><subject>Ovariectomy</subject><subject>Parathyroid Hormone - chemistry</subject><subject>Parathyroid Hormone - pharmacology</subject><subject>Parathyroid Hormone - therapeutic use</subject><subject>Peptide Fragments - chemistry</subject><subject>Peptide Fragments - pharmacology</subject><subject>Peptide Fragments - therapeutic use</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Stress, Mechanical</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Cells, Cultured - drug effects</subject><subject>Tumor Cells, Cultured - enzymology</subject><subject>Weight-Bearing - physiology</subject><issn>0171-967X</issn><issn>1432-0827</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNpdkcFq3DAQhkVoSTZJL3mAICiEpOBWI8mSfUxD0y2ENoct9GZkeRwr2NZGsgubZ-nDViZLAz0Nw3zzMcxPyBmwj8CY_vT5lnGlC5D6gKxACp6xgus3ZMVAQ1Yq_euIHMf4yBhIpdQhOQIQwEQuVuTPpkOKbYt2or6lgx-93dneWWrGhtbuX2N6_xAXpJsHM9KtCWbqdsG7hnY-pD2kl939Zn2VXUIm4Or7mlM_0noZtAkwk0vtIh3QdmZ01vQ0TgHHh6mjbqT-twkuneEH94wNTfp4St62po_4bl9PyM_bL5ubdXb34-u3m-u7zAqAKdNa5djmRWkbLlkJxqBG3qBmSvCyBqUMcpbzXFspLYPW1EoU6ROq4FKaUpyQixfvNvinGeNUDS5a7Hszop9jpTXLC9Ayge__Ax_9HNJvYgWMSy1zIRbdhxfKBh9jwLbaBjeYsEtQtSRWvSaW4PO9cq4HbF7RfUTiL6sqj4A</recordid><startdate>20010201</startdate><enddate>20010201</enddate><creator>Morley, P</creator><creator>Whitfield, J F</creator><creator>Willick, G E</creator><creator>Ross, V</creator><creator>MacLean, S</creator><creator>Barbier, J R</creator><creator>Isaacs, R J</creator><creator>Andreassen, T T</creator><general>Springer Nature B.V</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7QP</scope><scope>7RV</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB0</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7P</scope><scope>NAPCQ</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope></search><sort><creationdate>20010201</creationdate><title>The effect of monocyclic and bicyclic analogs of human parathyroid hormone (hPTH)-(1-31)NH2 on bone formation and mechanical strength in ovariectomized rats</title><author>Morley, P ; Whitfield, J F ; Willick, G E ; Ross, V ; MacLean, S ; Barbier, J R ; Isaacs, R J ; Andreassen, T T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c311t-7765ef589cd24091aae7e2de706329b166ae205257c44c01fab63866668244a93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Adenylyl Cyclases - biosynthesis</topic><topic>Animals</topic><topic>Bone Development - drug effects</topic><topic>Bone Development - physiology</topic><topic>Bone Diseases, Metabolic - drug therapy</topic><topic>Bone Diseases, Metabolic - etiology</topic><topic>Cyclization</topic><topic>Elasticity - drug effects</topic><topic>Female</topic><topic>Femur - drug effects</topic><topic>Femur - pathology</topic><topic>Femur - physiopathology</topic><topic>Lumbar Vertebrae - drug effects</topic><topic>Lumbar Vertebrae - pathology</topic><topic>Lumbar Vertebrae - physiopathology</topic><topic>Ovariectomy</topic><topic>Parathyroid Hormone - chemistry</topic><topic>Parathyroid Hormone - pharmacology</topic><topic>Parathyroid Hormone - therapeutic use</topic><topic>Peptide Fragments - chemistry</topic><topic>Peptide Fragments - pharmacology</topic><topic>Peptide Fragments - therapeutic use</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Stress, Mechanical</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured - drug effects</topic><topic>Tumor Cells, Cultured - enzymology</topic><topic>Weight-Bearing - physiology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morley, P</creatorcontrib><creatorcontrib>Whitfield, J F</creatorcontrib><creatorcontrib>Willick, G E</creatorcontrib><creatorcontrib>Ross, V</creatorcontrib><creatorcontrib>MacLean, S</creatorcontrib><creatorcontrib>Barbier, J R</creatorcontrib><creatorcontrib>Isaacs, R J</creatorcontrib><creatorcontrib>Andreassen, T T</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>ProQuest Nursing and Allied Health Journals</collection><collection>Health & Medical Complete (ProQuest Database)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>ProQuest Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Nursing & Allied Health Database (Alumni Edition)</collection><collection>Biological Sciences</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Biological Science Database</collection><collection>Nursing & Allied Health Premium</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><jtitle>Calcified tissue international</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morley, P</au><au>Whitfield, J F</au><au>Willick, G E</au><au>Ross, V</au><au>MacLean, S</au><au>Barbier, J R</au><au>Isaacs, R J</au><au>Andreassen, T T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The effect of monocyclic and bicyclic analogs of human parathyroid hormone (hPTH)-(1-31)NH2 on bone formation and mechanical strength in ovariectomized rats</atitle><jtitle>Calcified tissue international</jtitle><addtitle>Calcif Tissue Int</addtitle><date>2001-02-01</date><risdate>2001</risdate><volume>68</volume><issue>2</issue><spage>95</spage><epage>101</epage><pages>95-101</pages><issn>0171-967X</issn><eissn>1432-0827</eissn><abstract>The [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2 lactam is a stronger stimulator of adenylyl cyclase activity and a better stimulator of trabecular bone in the ovariectomized (OVX) rat model of osteopenia than hPTH-(1-31)NH2. This enhanced activity is due in large part to the stabilization of the amphiphilic receptor-binding alpha-helix in the Ser17-Gln29 region. The goal of the present study was to determine whether further cyclization could produce a more active hPTH analog. To this end, we compared the relative bioactivities of the bicyclic hPTH analog [Glu17,Leu27]cyclo(Lys13-Glu17,Glu22-Lys26)-hPTH-(1-31)NH2, made by replacing Ser17 with Glu17 and introducing a second lactam linkage between Lys13 and Glu17. The relative EC50 for adenylyl cyclase stimulation by the bicyclic hPTH analog was similar to the EC50 of the monocyclic [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2, but the bicyclic analog was still more active than hPTH-(1-31)NH2. As expected from adenylyl cyclase stimulation being responsible for PTH's anabolic action, the bicyclic hPTH analog [Glu17, Leu27]cyclo(Lys13-Glu17, Glu22-Lys26)-hPTH-(1-31)NH2 was able to increase femoral trabecular volume and thickness and mechanical strength in OVX rats, but it was no more effective than [Leu27]cyclo(Glu22-Lys26)-hPTH-(1-31)NH2 when injected once daily in a dose of 0.8 nmol/100 g body weight. Thus, further constraint of the conformation of hPTH-(1-31)NH2 by introducing two lactam link-ages between Lys13-Glu17 and Glu22-Lys26 did not raise the osteogenicity above that of the monocyclic analog.</abstract><cop>United States</cop><pub>Springer Nature B.V</pub><pmid>11310353</pmid><doi>10.1007/BF02678147</doi><tpages>7</tpages></addata></record> |
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| subjects | Adenylyl Cyclases - biosynthesis Animals Bone Development - drug effects Bone Development - physiology Bone Diseases, Metabolic - drug therapy Bone Diseases, Metabolic - etiology Cyclization Elasticity - drug effects Female Femur - drug effects Femur - pathology Femur - physiopathology Lumbar Vertebrae - drug effects Lumbar Vertebrae - pathology Lumbar Vertebrae - physiopathology Ovariectomy Parathyroid Hormone - chemistry Parathyroid Hormone - pharmacology Parathyroid Hormone - therapeutic use Peptide Fragments - chemistry Peptide Fragments - pharmacology Peptide Fragments - therapeutic use Rats Rats, Sprague-Dawley Stress, Mechanical Structure-Activity Relationship Tumor Cells, Cultured - drug effects Tumor Cells, Cultured - enzymology Weight-Bearing - physiology |
| title | The effect of monocyclic and bicyclic analogs of human parathyroid hormone (hPTH)-(1-31)NH2 on bone formation and mechanical strength in ovariectomized rats |
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