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Helodermin

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Helodermin is a vasoactive intestinal peptide-like peptide in the salivary gland venom of the lizard Heloderma suspectum.

Category

Others

Catalog number

BAT-010732

CAS number

89468-62-2

Molecular Formula

C176H285N47O49

Molecular Weight

3843.42

Specification
Reference Reading

IUPAC Name

(3S)-4-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-5-amino-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-5-carbamimidamido-1-[[(2S,3R)-1-[[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-carbamoylpyrrolidine-1-carbonyl]pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-oxobutanoic acid

Synonyms

Exendin 2

Sequence

HSDAIFTQQYSKLLAKLALQKYLASILGSRTSPPP

InChI

InChI=1S/C176H285N47O49/c1-23-93(15)138(217-146(243)98(20)194-159(256)124(78-137(237)238)210-167(264)126(82-225)214-147(244)107(180)77-104-79-187-86-190-104)169(266)212-123(74-101-38-26-25-27-39-101)164(261)220-140(99(21)229)171(268)202-114(57-60-135(183)235)153(250)200-113(56-59-134(182)234)154(251)209-122(76-103-49-53-106(232)54-50-103)163(260)215-127(83-226)166(263)198-110(42-30-33-63-179)150(247)205-120(73-92(13)14)161(258)206-117(70-89(7)8)157(254)191-95(17)143(240)196-108(40-28-31-61-177)149(246)204-116(69-88(5)6)156(253)192-96(18)144(241)203-119(72-91(11)12)160(257)201-112(55-58-133(181)233)152(249)197-109(41-29-32-62-178)151(248)208-121(75-102-47-51-105(231)52-48-102)162(259)207-118(71-90(9)10)158(255)193-97(19)145(242)213-128(84-227)168(265)218-139(94(16)24-2)170(267)211-115(68-87(3)4)148(245)189-80-136(236)195-125(81-224)165(262)199-111(43-34-64-188-176(185)186)155(252)219-141(100(22)230)172(269)216-129(85-228)173(270)222-66-36-45-131(222)175(272)223-67-37-46-132(223)174(271)221-65-35-44-130(221)142(184)239/h25-27,38-39,47-54,79,86-100,107-132,138-141,224-232H,23-24,28-37,40-46,55-78,80-85,177-180H2,1-22H3,(H2,181,233)(H2,182,234)(H2,183,235)(H2,184,239)(H,187,190)(H,189,245)(H,191,254)(H,192,253)(H,193,255)(H,194,256)(H,195,236)(H,196,240)(H,197,249)(H,198,263)(H,199,262)(H,200,250)(H,201,257)(H,202,268)(H,203,241)(H,204,246)(H,205,247)(H,206,258)(H,207,259)(H,208,248)(H,209,251)(H,210,264)(H,211,267)(H,212,266)(H,213,242)(H,214,244)(H,215,260)(H,216,269)(H,217,243)(H,218,265)(H,219,252)(H,220,261)(H,237,238)(H4,185,186,188)/t93-,94-,95-,96-,97-,98-,99+,100+,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-,138-,139-,140-,141-/m0/s1

InChI Key

SSAAJZQUEUTACT-MDBKHZGBSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC1=CC=CC=C1)C(=O)NC(C(C)O)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CCCCN)C(=O)NC(CC3=CC=C(C=C3)O)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(CO)C(=O)NC(C(C)CC)C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)NC(C(C)O)C(=O)NC(CO)C(=O)N4CCCC4C(=O)N5CCCC5C(=O)N6CCCC6C(=O)N)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(CC7=CN=CN7)N

1. Helodermin-loaded nanoparticles: characterization and transport across an in vitro model of the follicle-associated epithelium

Anne des Rieux, et al. J Control Release. 2007 Apr 23;118(3):294-302. doi: 10.1016/j.jconrel.2006.12.023. Epub 2006 Dec 29.

M cells represent a potential portal for oral delivery of peptides and proteins due to their high endocytosis abilities. An in vitro model of human FAE (co-cultures) was used to evaluate the influence of M cells on the transport of free and encapsulated helodermin--a model peptide--across the intestinal epithelium. M cells enhanced transport of intact helodermin (18-fold, Papp=3 x 10(-6) cm s(-1)). As pegylation increased nanoparticle transport by M cells, helodermin was encapsulated in 200 nm nanoparticles containing PEG-b-PLA:PLGA 1:1. Stability of the selected formulation was demonstrated in simulated gastric and intestinal fluids. M cells increased the transport of helodermin encapsulated in these nanoparticles by a factor of 415, as compared to Caco-2 cells. Transport of free and encapsulated helodermin occurred most probably by endocytosis. In conclusion, M cells improved helodermin transport across the intestinal epithelium, confirming their high potential for oral delivery of peptides.

3. Helodermin-like peptides in thyroid C cells: stimulation of thyroid hormone secretion and suppression of calcium incorporation into bone

T Grunditz, P Persson, R Håkanson, A Absood, G Böttcher, C Rerup, F Sundler Proc Natl Acad Sci U S A. 1989 Feb;86(4):1357-61. doi: 10.1073/pnas.86.4.1357.

Helodermin is a vasoactive intestinal peptide-like peptide in the salivary gland venom of the lizard Heloderma suspectum. Helodermin-like immunofluorescence was observed in the parafollicular (C) cells in several mammals and in the C cell homologues of the chicken ultimobranchial gland. Thus, helodermin-like peptides coexist with calcitonin. The results of radioimmunoassay agreed with the immunocytochemical findings. HPLC of rat thyroid extracts revealed one major peak of helodermin-like immunoreactivity, which eluted in a position close to that of lizard helodermin. Helodermin stimulated basal thyroid hormone secretion and colloid droplet formation in conscious mice. The effect of large doses of helodermin was quite long-lasting and the maximal response occurred after 2-6 hr. In addition, helodermin suppressed the incorporation of calcium into bone in conscious rats. The findings suggest that helodermin-like peptides in C cells may be involved in the local regulation of thyroid hormone secretion and in the maintenance of calcium homeostasis.