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pTH (1-34) amide (human)

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pTH (1-34) amide (human) is a compound synthetic peptide hormone is acts as an agonist to the parathyroid hormone receptor. It is employed for the research of osteoporosis, hypoparathyroidism and various bone-related disorders.

Category

Functional Peptides

Catalog number

BAT-015313

CAS number

83139-29-1

Molecular Formula

C181H292N56O50S2

Molecular Weight

4116.79

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]amino]-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-oxobutanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]hexanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-oxopentanoic acid

Synonyms

H-Ser-Val-Ser-Glu-Ile-Gln-Leu-Met-His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu-Arg-Val-Glu-Trp-Leu-Arg-Lys-Lys-Leu-Gln-Asp-Val-His-Asn-Phe-NH2; Parathyroid hormone (1-34)amide; L-seryl-L-valyl-L-seryl-L-alpha-glutamyl-L-isoleucyl-L-glutaminyl-L-leucyl-L-methionyl-L-histidyl-L-asparagyl-L-leucyl-glycyl-L-lysyl-L-histidyl-L-leucyl-L-asparagyl-L-seryl-L-methionyl-L-alpha-glutamyl-L-arginyl-L-valyl-L-alpha-glutamyl-L-tryptophyl-L-leucyl-L-arginyl-L-lysyl-L-lysyl-L-leucyl-L-glutaminyl-L-alpha-aspartyl-L-valyl-L-histidyl-L-asparagyl-L-phenylalaninamide; hPTH (1-34)-NH2; human parathyroid hormone (1-34) amide

Appearance

White Solid

Purity

95%

Sequence

SVSEIQLMHNLGKHLNSMERVEWLRKKLQDVHNF-NH2

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C181H292N56O50S2/c1-21-96(18)146(237-161(269)114(48-53-141(251)252)213-175(283)132(84-240)233-178(286)143(93(12)13)234-148(256)103(185)82-238)179(287)217-111(45-50-134(187)242)156(264)221-120(65-90(6)7)164(272)214-116(55-62-289-20)159(267)226-125(71-100-79-197-86-204-100)168(276)229-128(74-136(189)244)171(279)219-118(63-88(2)3)149(257)202-81-138(246)206-105(39-27-30-56-182)150(258)225-124(70-99-78-196-85-203-99)167(275)223-122(67-92(10)11)165(273)227-129(75-137(190)245)172(280)232-131(83-239)174(282)215-115(54-61-288-19)158(266)211-112(46-51-139(247)248)154(262)209-109(43-34-60-200-181(194)195)160(268)235-144(94(14)15)176(284)216-113(47-52-140(249)250)157(265)224-123(69-98-77-201-104-38-26-25-37-102(98)104)166(274)222-121(66-91(8)9)162(270)210-108(42-33-59-199-180(192)193)152(260)207-106(40-28-31-57-183)151(259)208-107(41-29-32-58-184)153(261)220-119(64-89(4)5)163(271)212-110(44-49-133(186)241)155(263)230-130(76-142(253)254)173(281)236-145(95(16)17)177(285)231-126(72-101-80-198-87-205-101)169(277)228-127(73-135(188)243)170(278)218-117(147(191)255)68-97-35-23-22-24-36-97/h22-26,35-38,77-80,85-96,103,105-132,143-146,201,238-240H,21,27-34,39-76,81-84,182-185H2,1-20H3,(H2,186,241)(H2,187,242)(H2,188,243)(H2,189,244)(H2,190,245)(H2,191,255)(H,196,203)(H,197,204)(H,198,205)(H,202,257)(H,206,246)(H,207,260)(H,208,259)(H,209,262)(H,210,270)(H,211,266)(H,212,271)(H,213,283)(H,214,272)(H,215,282)(H,216,284)(H,217,287)(H,218,278)(H,219,279)(H,220,261)(H,221,264)(H,222,274)(H,223,275)(H,224,265)(H,225,258)(H,226,267)(H,227,273)(H,228,277)(H,229,276)(H,230,263)(H,231,285)(H,232,280)(H,233,286)(H,234,256)(H,235,268)(H,236,281)(H,237,269)(H,247,248)(H,249,250)(H,251,252)(H,253,254)(H4,192,193,199)(H4,194,195,200)/t96-,103-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,143-,144-,145-,146-/m0/s1

InChI Key

RRBCHMCWWOHRQL-UMXFMPSGSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CCSC)C(=O)NC(CC1=CN=CN1)C(=O)NC(CC(=O)N)C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CC2=CN=CN2)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CCSC)C(=O)NC(CCC(=O)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(C(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC(C(C)C)C(=O)NC(CC5=CN=CN5)C(=O)NC(CC(=O)N)C(=O)NC(CC6=CC=CC=C6)C(=O)N)NC(=O)C(CCC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)C)NC(=O)C(CO)N

1. Human PTH-(3-34) inhibited the effects of human parathyroid hormone-related protein on phosphate uptake in a cultured renal cell line (OK cells)

M Fukase,M Nakai,T Yamaguchi,T Fujita,N Fujii,T Tsukamoto J Bone Miner Res . 1990 Oct;5(10):995-1002. doi: 10.1002/jbmr.5650051002.

The action mechanism of hPTH and hPTHrP-(1-34) on phosphate uptake in opossum kidney (OK) cells was studied using [Nle8,18Tyr34]hPTH-(3-34)-NH2, a potent competivie inhibitor of adenylate cyclase-coupled PTH receptor. We examined the effects of hPTH-(1-34), hPTHrP-(1-34), and hPTH-(3-34) separately or in combination on the change in renal cyclic AMP production and phosphate uptake in OK cells. Both hPTH-(1-34) and hPTHrP-(1-34) stimulated intracellular cyclic AMP production to the same degree at concentrations between 10(-10) and 10(-7) M and inhibited phosphate uptake equipotently on a molar basis (27.5 +/- 2.0 and 33.2 +/- 1.2% inhibition at 10(-7) M, respectively). Both exogenous addition of (Bu)2cAMP and endogenous stimulation of cAMP by forskolin inhibited phosphate uptake in a dose-dependent manner. Cyclic AMP production induced by either hPTH-(1-34) or hPTHrP-(1-34) was inhibited by both [Nle8,18Tyr34]-hPTH-(3-34)-NH2 and [Tyr34]-hPTH-(7-34)-NH2. However, [Nle8,18Tyr34]hPTH-(3-34)-NH2 and [Tyr34]-hPTH-(7-34)-NH2 inhibited hPTH-induced cAMP production more strongly. The inhibitory action of phosphate uptake by hPTH-(1-34) and hPTHrP-(1-34) was prevented in the presence of a 100-fold greater concentration of [Nle8,18Tyr34]hPTH-(3-34)-NH2. The antagonistic action of [Nle8,18Tyr34]hPTH-(3-34)-NH2 on the inhibition of phosphate uptake induced by hPTH-(1-34) and hPTHrP-(1-34) became weaker with time (0-120 minutes), and [Nle8,18Tyr34]hPTH-(3-34)-NH2 did not antagonize the inhibition of phosphate uptake induced by hPTHrP-(1-34) at 120 minutes of incubation.(ABSTRACT TRUNCATED AT 250 WORDS)

2. Anabolic therapy for osteoporosis: parathyroid hormone

Felicia Cosman Curr Osteoporos Rep . 2005 Dec;3(4):143-9. doi: 10.1007/s11914-996-0017-2.

Recombinant human parathyroid hormone (PTH 1-34) is the only anabolic agent currently approved for the treatment of osteoporosis. The term anabolic is based on mechanism of action. PTH stimulates bone formation, in contrast to antiresorptive agents, which reduce bone resorption and formation. Recent investigations involving the PTH(1-34) and PTH(1-84) peptides, alone and in combination or sequential regimens with antiresorptive agents, have provided a greater understanding of the place of PTH in the armamentarium against osteoporosis. These studies indicate that adding a bisphosphonate to PTH in previously untreated individuals does not produce additional bone benefit; however, sequential use of PTH followed-up by an antiresorptive agent is highly effective at increasing BMD. Adding PTH after an antiresorptive agent also produces substantial bone density increments, though the magnitude of bone density increase may differ for different antiresorptive agents. PTH can repair underlying micro-architectural defects in bone, improve bone mass substantially, and perhaps change macro-architecture and geometry of bone. There are still many unanswered questions regarding PTH treatment of osteoporosis, including the optimal duration of treatment, optimal dosing regimen, mechanism of resistance to its effect after 18-24 months, and the effect of subsequent rechallenge.

3. The extracellular amino-terminal region of the parathyroid hormone (PTH)/PTH-related peptide receptor determines the binding affinity for carboxyl-terminal fragments of PTH-(1-34)

I McClure,H T Keutmann,H Jüppner,J T Potts Jr,A B Abou-Samra,H M Kronenberg,E Schipani,F R Bringhurst,G V Segre,T J Gardella Endocrinology . 1994 Feb;134(2):879-84. doi: 10.1210/endo.134.2.8299582.

The recombinant human PTH/PTH-related peptide (PTHrP) receptor, when transiently expressed in COS-7 cells, binds [Nle8,18,Tyr34] bovine PTH-(7-34)amide [PTH-(7-34)], human PTH-(10-34)amide [PTH-(10-34)], and bovine PTH-(15-34)amide [PTH-(15-34)] with at least 50-fold higher affinity than does the rat receptor homolog. In contrast, PTH-(1-34) binding affinities are similar for both receptor homologs. To map those areas of the PTH/PTHrP receptors that determine the binding specificity for carboxyl-terminal fragments of PTH-(1-34), we constructed chimeric rat/human PTH/PTHrP receptors. These bound PTH-(1-34) with normal affinity and, therefore, must have an overall conformation that resembles that of native receptors. Chimeras with the amino-terminal extracellular domain of the human PTH/PTHrP receptor have a considerably higher binding affinity for PTH-(7-34), PTH-(10-34), and PTH-(15-34) than do the reciprocal receptor constructs in which the amino-terminal region is from the rat PTH/PTHrP receptor. The opossum PTH/PTHrP receptor homolog also binds PTH-(7-34) with higher affinity than the rat receptor, and studies of rat/opossum chimeras confirm the importance of the amino-terminal extracellular domain in determining the PTH-(7-34) binding specificity. Mutant rat and human PTH/PTHrP receptors in which either residues 61-105 of the extracellular region or most of the intracellular tail were deleted have PTH-(7-34) binding characteristics indistinguishable from those of either wild-type receptor. These findings indicate that the amino-terminal extracellular region of the PTH/PTHrP receptor contains a domain(s) that largely determines the binding affinity of amino-terminally truncated PTH analogs. This region, therefore, is likely to constitute a site for ligand-receptor interaction.

4. Prevention of atrophic nonunion by the systemic administration of parathyroid hormone (PTH 1-34) in an experimental animal model

Sonya Khurana,Edward A Lin,Chuan-Ju Liu,Alexa Monroy,Kenneth A Egol J Orthop Trauma . 2012 Dec;26(12):719-23. doi: 10.1097/BOT.0b013e31826f5b9e.

Objectives:Recombinant human parathyroid hormone (PTH 1-34) has been previously shown to enhance fracture healing in animal models. Here, we sought to determine whether the systemic administration of PTH 1-34 is effective in preventing atrophic fracture nonunion in a murine, surgical nonunion model.Methods:We used an established reproducible long-bone murine fracture nonunion model by generating a midshaft femur fracture, followed by fracture distraction using an intramedullary pin and custom metallic clip to maintain a fracture gap of 1.7 mm. Mice were randomized to receive either daily intraperitoneal injections of 30 μg/kg PTH 1-34 for 14 days or saline injections. At 6 weeks after the procedure, radiographic and histologic assessment of fracture healing was performed.Results:At 6 weeks after surgery, the group treated with PTH showed higher rates of bony union (50% vs 8%; P < 0.05) as assessed by radiographic analysis. Mean gap size was also significantly lower in the PTH group (1.42 vs 0.36 mm in the control group; P < 0.05). Histologic analysis of atrophic nonunions in the control group revealed a persistent fracture gap with intervening fibrous tissue. In contrast, healed subjects in the PTH-treated group had cortical bridging with mature bone and relatively little callus, which is consistent with primary intramembranous ossification.Conclusions:Daily systemic administration of recombinant PTH 1-34 increased the rate of union in a mouse atrophic nonunion model. This may have important implications for the potential clinical role of PTH 1-34 in the treatment of atrophic fracture nonunions.